Windsor Area, Vermont Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Windsor Area, Vermont on RentalSaver.com!

Windsor Area Rentals

$Log cabin near Okemo \/ Ludlow on 25 acres borders state forest w\/trails nearby$
From $346 per night (USD)
VRBO
Log cabin near Okemo \/ Ludlow on 25 acres borders state forest w\/trails nearby
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Beautiful hilltop cabin on 25 private acres bordering the William's River State Forest. Relax at this private retreat o ...
From $346 per night (USD)
VRBO
From $629 per night (USD)
Expedia
Okemo Modern Mountain Escape - 5 bedroom, 3 bathroom house
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
The house is tucked away off the main street in Ludlow, VT and just 1 mile away from the entrance to Okemo Mountain Reso ...
From $629 per night (USD)
Expedia
Click For Pricing
VRBO
Amazing family friendly 3+ Bedroom, 3 Full Bath in Quechee
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
If you are looking for a spacious stand-alone home with a wrap-around porch set in a picturesque VT setting, this is it! ...
Click For Pricing
VRBO
From $441 per night (USD)
Expedia
Sweet Life - Vermont Chalet - 6 person Indoor Hot Tub - 15 min to Killington
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
This cozy ski Chalet home sleeps up to 12 people- an unbeatable choice for a ski trip with friends or family for a memor ...
From $441 per night (USD)
Expedia
$Bear-Foot Lodge Killington, Private! Sauna\/Gameroom. Perfect for Large Groups!$
From $819 per night (USD)
VRBO
Bear-Foot Lodge Killington, Private! Sauna\/Gameroom. Perfect for Large Groups!
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Come enjoy the stunning scenery of Vermont's countryside while you relax in this gorgeous 5,000 sq ft. lodge. This year- ...
From $819 per night (USD)
VRBO
From $288 per night (USD)
Expedia
Circa 1868 Chester Home-Less than 20 MIN TO OKEMO
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
OVERVIEW Our historic 1868 'Elm House' is located in the picturesque town of Chester, nestled in the heart of Chester De ...
From $288 per night (USD)
Expedia
From $481 per night (USD)
VRBO
Castle Hill Resort Condo (with on-site Aveda Spa)
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Welcome home! This charming 1500 square foot 3 bedroom condo at the historical Castle Hill Resort and Spa, has everythin ...
From $481 per night (USD)
VRBO
From $171 per night (USD)
Expedia
Romantic Riverside Getaway
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Romantic Riverside Getaway. Located in the heart of Ludlow, this 1 Bedroom 1 Bath with sofa bed condo sleeps 4. Have cof ...
From $171 per night (USD)
Expedia
From $168 per night (USD)
VRBO
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This is a secluded mountainside retreat. Perfect for a getaway for two and room enough for 4 it is located on eleven pri ...
From $168 per night (USD)
VRBO
From $194 per night (USD)
Expedia
Deluxe one bedroom suite located on 2nd floor with outdoor heated pool 21820
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $194 per night (USD)
Expedia
From $398 per night (USD)
VRBO
Beautiful home offering privacy on 7 acres with private pond
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Peaceful home in Vermont’s Upper Valley. This is a beautiful three BR, two BA home offering privacy and relaxation on 7 ...
From $398 per night (USD)
VRBO
From $178 per night (USD)
Expedia
Deluxe one bedroom suite located on 2nd floor with outdoor heated pool 21517
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $178 per night (USD)
Expedia
From $186 per night (USD)
VRBO
Deluxe one bedroom suite located on 2nd floor with outdoor heated pool 21921
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $186 per night (USD)
VRBO
From $258 per night (USD)
Expedia
Updated Village Victorian on Ski Shuttle, walk to all amenties in town!
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
New to market, freshly renovated Ski Village Victorian with 4 bedrooms directly on Okemo shuttle route. Enjoy the old ...
From $258 per night (USD)
Expedia
From $156 per night (USD)
VRBO
Ludlow Village Guest House - prime location on ski shuttle, walk to restaurants
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Renovated one bedroom guest cottage in Ludlow, Vermont. Prime ski location, 12 houses down from the Mountain Road entr ...
From $156 per night (USD)
VRBO
From $202 per night (USD)
Expedia
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Our Carriage House is less than a mile to charming Chester Village-enjoy quaint restaurants and taverns, antique shops, ...
From $202 per night (USD)
Expedia
From $282 per night (USD)
VRBO
Cottage in Barnard
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Charming Vermont cottage, just up the road from Silver Lake and the Barnard General Store. Bright, warm, and welcoming, ...
From $282 per night (USD)
VRBO
From $260 per night (USD)
Expedia
Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Sportsman themed, real log cabin that has comfortable wood stove & hearth, plus backup regular heat. Bathroom with show ...
From $260 per night (USD)
Expedia
$Remodeled condo with shared washer\/dryer - walk to dining & ski lift bus pickup$
From $636 per night (USD)
VRBO
Remodeled condo with shared washer\/dryer - walk to dining & ski lift bus pickup
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Seatoller Unit C Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $636 per night (USD)
VRBO
From $571 per night (USD)
Expedia
First-floor condo with shared laundry - steps to ski bus pickup, walk to dining
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Aspatria Unit A Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $571 per night (USD)
Expedia
From $118 per night (USD)
VRBO
Hawks Mountain Farm, full apartment on a working farm.
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Hello and welcome to Hawks Mountain Farm, a working farm with gardens, chickens, two yaks, four donkeys and an 1820 farm ...
From $118 per night (USD)
VRBO
From $879 per night (USD)
Expedia
On Silver Lake & Close to Ski Areas with Sauna
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Perched on the edge of pristine Silver Lake, my country home sits on a large rolling lot overlooking the lake enjoyed by ...
From $879 per night (USD)
Expedia
From $504 per night (USD)
VRBO
Okemo LARGE home SKI DATES still available NEW Hot tub. pool table 3 full baths
Bedrooms:
3
Bathrooms:
3
Sleeps:
11
Welcome to a relaxing vacation, right in the heart of the OKEMO Valley with convenient access to major routes and only 3 ...
From $504 per night (USD)
VRBO
$Chester Home w\/ Views ~ 10 Mi to Okemo Mtn Resort!$
From $343 per night (USD)
Expedia
Chester Home w\/ Views ~ 10 Mi to Okemo Mtn Resort!
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
Rest, relax, and enjoy the tranquil surroundings when you visit this vacation rental home in Chester, Vermont! The stunn ...
From $343 per night (USD)
Expedia
From $250 per night (USD)
VRBO
Historic Ski Lodge on 112-Acre Vineyard
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
**10% discount on 7 nights or more; 25% discount on 28 nights or more. Rental Amenities: Over 900 square feet of liv ...
From $250 per night (USD)
VRBO
From $388 per night (USD)
Expedia
Killington ski house
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Recently remodeled and tastefully decorated lower level duplex located a short distance from Killington ski area (a twel ...
From $388 per night (USD)
Expedia
From $483 per night (USD)
VRBO
Sweet chalet with private hot tub, firepit, game room & minibar
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Sunny Mountainside Chalet Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $483 per night (USD)
VRBO
$Luxe Plymouth Chalet w\/ Indoor Pool & 3 Decks!$
From $1559 per night (USD)
Expedia
Luxe Plymouth Chalet w\/ Indoor Pool & 3 Decks!
Bedrooms:
6
Bathrooms:
7
Sleeps:
8
Discover one of Vermont's hidden gems when you book this Plymouth vacation rental, known as the 'Mountain Casa'. Featuri ...
From $1559 per night (USD)
Expedia
$Ski On\/Off ~ Beautiful Corner Unit ~ Well-Equipped And Perfect For Families!$
From $1624 per night (USD)
VRBO
Ski On\/Off ~ Beautiful Corner Unit ~ Well-Equipped And Perfect For Families!
Bedrooms:
4
Bathrooms:
4
Sleeps:
11
4 bedrooms, 3 and 1/2 baths. Beautifully decorated and furnished. Ski on/off townhouse located directly on the trail, ...
From $1624 per night (USD)
VRBO
From $531 per night (USD)
Expedia
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Lake Rescue Escape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $531 per night (USD)
Expedia
From $1809 per night (USD)
VRBO
Fireplace, Ski-Okemo, Apple Trees, Piano, Amazing Views, Firepit, Priory, Pool, Fields, Theatre!
Bedrooms:
9
Bathrooms:
9
Sleeps:
17
Skiing Theatre Food Beer Farm-Cheese Music and a Monastery! This is The Apple Knoll Inn at Weston, a Gertrude Rentals pr ...
From $1809 per night (USD)
VRBO
From $1552 per night (USD)
Expedia
Fireplace, Ski-Okemo, Apple Trees, Piano, Amazing Views, Firepit, Priory, Pool, Fields, Theatre!
Bedrooms:
7
Bathrooms:
7
Sleeps:
13
Skiing Theatre Food Beer Farm-Cheese Music and a Monastery! This is The Apple Knoll Inn at Weston, a Gertrude Rentals pr ...
From $1552 per night (USD)
Expedia
From $355 per night (USD)
VRBO
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Gather with family and friends at our spacious home nestled in the Vermont woods. The Blue Moon Bungalow is your home a ...
From $355 per night (USD)
VRBO
$Perfect Home Away near Town & Skiing w\/ Private Gas Grill, Large Deck$
From $242 per night (USD)
Expedia
Perfect Home Away near Town & Skiing w\/ Private Gas Grill, Large Deck
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Ludlow Hideout Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $242 per night (USD)
Expedia
From $3095 per night (USD)
VRBO
Ski in Ski out! top of the A quad chairlift
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
2 Bed 2 Bath. Pull out sleep sofa. Sleeps 4 Adults and 4 children. Located at the top of the chairlift with a balcon ...
From $3095 per night (USD)
VRBO
From $555 per night (USD)
Expedia
Renovated Farmhouse < 1 Mile to Okemo Mountain!
Bedrooms:
2
Bathrooms:
6
Sleeps:
11
Experience the beauty of Vermont from this chic and charming farmhouse with 4 bedrooms and 2 bathrooms. The vacation ren ...
From $555 per night (USD)
Expedia
From $331 per night (USD)
VRBO
Beautifully Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Discover the best of Ludlow when you stay in our fabulously decorated updated historic home built in 1835, located in th ...
From $331 per night (USD)
VRBO
From $345 per night (USD)
Expedia
Mountain Bliss: Hot Tub, Shuttle to Okemo, Quiet Ludlow Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
MRT-11088876 Enjoy a dreamy Vermont getaway in this updated 3-bedroom condo, just 2 minutes from the Clock Tower Base at ...
From $345 per night (USD)
Expedia
From $293 per night (USD)
VRBO
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Our year round cottage is located on Lake Pauline in Ludlow Vermont, with 900 ft of lake frontage! Just 1.5 miles from O ...
From $293 per night (USD)
VRBO
From $277 per night (USD)
Expedia
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Hi, we are using Homeaway/VRBO for renters who love the slopes, the outdoors and places like Okemo. We are always open ...
From $277 per night (USD)
Expedia
Click For Pricing
VRBO
Newly Renovated Cottage with hot tub, fire place, and 5min to Killington Gondola
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Stone’s Throw Vermont is a charming 3bed 1.5 bath cottage with hot tub, fireplace, outdoor covered dinning space, and mo ...
Click For Pricing
VRBO
From $666 per night (USD)
Expedia
Your Vermont Vacation Awaits!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Mountain View Retreat is truly your home away from home for "Your Vermont Vacation". This bright, airy and comfortable f ...
From $666 per night (USD)
Expedia
From $377 per night (USD)
VRBO
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Discover the best of Ludlow when you stay in our fabulously decorated updated historic home built in 1835, located in th ...
From $377 per night (USD)
VRBO
$Ski-in Ski-Out Okemo Oasis w\/ Deck + Mtn View!$
From $597 per night (USD)
Expedia
Ski-in Ski-Out Okemo Oasis w\/ Deck + Mtn View!
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Boasting easy access to the slopes and local hiking trails, this 3-bedroom, 2-bathroom vacation rental is great for fami ...
From $597 per night (USD)
Expedia
From $410 per night (USD)
VRBO
Ski Chalet with Hot Tub on Okemo Mountain
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Newly renovated in fall 2023, this 3-level, 1700+ sq. ft. ski chalet is just a 4 min drive to Okemo Mountain Resort and ...
From $410 per night (USD)
VRBO
From $577 per night (USD)
Expedia
Private Home on Okemo with HOT TUB. WALK TO SKI TRAIL OR DRIVE 2 MIN TO LODGE
Bedrooms:
3
Bathrooms:
6
Sleeps:
14
This Okemo Mountain home is the perfect Vermont getaway within walking distance (400 yards) of the slopes! PLEASE NOTE ...
From $577 per night (USD)
Expedia
$Renovated condo w\/ shared seasonal pool & tennis - walk to trail$
From $226 per night (USD)
VRBO
Renovated condo w\/ shared seasonal pool & tennis - walk to trail
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Okemo Trailside 6A Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $226 per night (USD)
VRBO
$Vermont Farmhouse Getaway Near the Slopes W\/ Mtn Views, Free WiFi, Full Kitchen$
From $217 per night (USD)
Expedia
Vermont Farmhouse Getaway Near the Slopes W\/ Mtn Views, Free WiFi, Full Kitchen
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Vermont Mountain Farmhouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $217 per night (USD)
Expedia
$Walk to Okemo Base Lodge & Lifts. Private On Mountain Home with Hot Tub\/Fire Pit$
From $354 per night (USD)
VRBO
Walk to Okemo Base Lodge & Lifts. Private On Mountain Home with Hot Tub\/Fire Pit
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
PLEASE NOTE: No Saturday arrivals or departures, no pets, no smoking, no parties. Recommended local activities and floor ...
From $354 per night (USD)
VRBO
From $295 per night (USD)
Expedia
Cozy 3br cabin 5 minutes (1.5 miles) from Okemo Mountain Base
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
1,050 square foot 3 BR cabin: Bedroom 1 and 2 have queen-size beds. Bedroom 3 has a twin size trundle bed. There is al ...
From $295 per night (USD)
Expedia
From $1363 per night (USD)
VRBO
Winterplace E building - top of the Quad
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This wonderful condo is in the PERFECT location. Hiking, mountain biking or skiing we have the best location. Located ju ...
From $1363 per night (USD)
VRBO
From $386 per night (USD)
Expedia
Lake Rescue Summers, Ski Okemo Winters
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Views of and Direct Access to Lake Rescue. 3 BR + Loft with 2.5 Baths. 4 min to Okemo. Newly renovated home perfect for ...
From $386 per night (USD)
Expedia
$Coveted Ski-In\/Ski-Out Winterplace Condo with Hot Tubs, Indoor Pool & Fireplace$
From $345 per night (USD)
VRBO
Coveted Ski-In\/Ski-Out Winterplace Condo with Hot Tubs, Indoor Pool & Fireplace
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Winterplace K102 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $345 per night (USD)
VRBO
From $528 per night (USD)
Expedia
Vermont life at Hill Top Gardens
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Three story Vermont Homestead with five bedrooms exquisitely designed with an open floor concept. Large chef kitchen and ...
From $528 per night (USD)
Expedia
From $467 per night (USD)
VRBO
Okemo Family Friendly Getaway
Bedrooms:
4
Bathrooms:
4
Sleeps:
14
Private family friendly mountain retreat with open floor plan, wood detailing with bright spacious rooms, fireplace, coo ...
From $467 per night (USD)
VRBO
From $117 per night (USD)
VRBO
Village Ski Apartment
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
You would be renting a very nice ski apartment with fully equipped kitchen, large living room and large bedroom. Also a ...
From $117 per night (USD)
VRBO
From $328 per night (USD)
VRBO
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
Bedrooms:
2
Bathrooms:
6
Sleeps:
10
Welcome to 'Smokeshire Hilltop Farmhouse!' This lovely 5-bedroom, 2-bathroom vacation rental sits on a plateau above the ...
From $328 per night (USD)
VRBO
From $264 per night (USD)
Expedia
Ski on, ski off trailside condo at Okemo
Bedrooms:
3
Bathrooms:
4
Sleeps:
13
We’d love to welcome you to our home away from home. Located steps from Sachem trail, our townhome at the Okemo Trailsi ...
From $264 per night (USD)
Expedia
From $409 per night (USD)
VRBO
Vermont get-away end unit townhouse nestled in the trees
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
We welcome you to a wonderfully located Vermont getaway The Vermont Sugar Maple. Comfortably nestled in the trees, surro ...
From $409 per night (USD)
VRBO
From $177 per night (USD)
Expedia
Vermont Retreat
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This is a non-smoking one-bedroom apartment with a queen-sized bed. Located just minutes off Route 4 between Woodstock ...
From $177 per night (USD)
Expedia
Click For Pricing
VRBO
Quaint cabin with Lake Pauline views
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Two bedroom, 1 bath unit steps away from Jackson Gore and 5 minute drive to Okemo main base. The town of Ludlow has grea ...
Click For Pricing
VRBO
From $215 per night (USD)
Expedia
Mountainside Suite! Arcade, Pool, Hot Tub Access
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to our charming mountainside suite, located mid-mountain at the base of the Solitude Peak! Spend a fantastic day ...
From $215 per night (USD)
Expedia
$Ski-In\/Ski-Out Condo with Access to Indoor Pool$
From $223 per night (USD)
VRBO
Ski-In\/Ski-Out Condo with Access to Indoor Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to our cozy and charming ski-in/ski-out condo at Okemo Mountain Resort! Located at the summit of the two South R ...
From $223 per night (USD)
VRBO
$Mountainside Condo w\/ Access to Pool, Ski Shuttle$
Click For Pricing
Expedia
Mountainside Condo w\/ Access to Pool, Ski Shuttle
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This 2-bedroom condo is in Okemo. Located near the summit of the two South Ridge Quad chairlifts, you will love to have ...
Click For Pricing
Expedia
$Okemo Retreat! Ski-In\/Ski-Out Condo$
From $253 per night (USD)
VRBO
Okemo Retreat! Ski-In\/Ski-Out Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Come and stay in our charming ski-in/ski-out condo at Okemo Mountain Resort! Located at the summit of the two South Ridg ...
From $253 per night (USD)
VRBO
From $238 per night (USD)
Expedia
Mountainside Suite! Arcade, Pool, Hot Tub Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
When you stay at Okemo Mountain Resort, you will love to return to our cozy and charming suite, located mid-mountain at ...
From $238 per night (USD)
Expedia
$Ski-in\/Ski-out Suite | Pool, Arcade, Sauna$
From $338 per night (USD)
VRBO
Ski-in\/Ski-out Suite | Pool, Arcade, Sauna
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Come and stay in our charming ski-in/ski-out suite, located mid-mountain at the base of the Solitude Peak! Spend a fanta ...
From $338 per night (USD)
VRBO
$Cozy Suite | Ski-in\/Ski-Out | Hot Tub, Pool$
From $219 per night (USD)
Expedia
Cozy Suite | Ski-in\/Ski-Out | Hot Tub, Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Find peace and relaxation in our cozy ski-in/ski-out suite, located mid-mountain at the base of the Solitude Peak! Spend ...
From $219 per night (USD)
Expedia
From $592 per night (USD)
VRBO
Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to our three Bedroom first floor condo at Winterplace in the O building! While we wish we could get up to Okemo ...
From $592 per night (USD)
VRBO
$Ski-in\/out condo with mountain views, fireplace, pool, & hot tub$
From $148 per night (USD)
Expedia
Ski-in\/out condo with mountain views, fireplace, pool, & hot tub
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Winterplace H205 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $148 per night (USD)
Expedia
$Ski-in\/ski-out condo with WiFi, washer\/dryer, mountain views & golf nearby$
From $215 per night (USD)
VRBO
Ski-in\/ski-out condo with WiFi, washer\/dryer, mountain views & golf nearby
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Okemo Mountain Base Retreat C203 Our calendar is updated in real-time & our nightly rates are accurately displayed. Sim ...
From $215 per night (USD)
VRBO
$Ground Floor ski-in\/out condo, full kitchen & high-speed WiFi$
From $228 per night (USD)
Expedia
Ground Floor ski-in\/out condo, full kitchen & high-speed WiFi
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Okemo Mountain Lodge C110 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $228 per night (USD)
Expedia
$Ski-in\/Ski-out Condo at Okemo$
From $167 per night (USD)
VRBO
Ski-in\/Ski-out Condo at Okemo
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape to our cozy and charming condo in an amazing Okemo location! Walk out your door and experience the best of this l ...
From $167 per night (USD)
VRBO
$Amazing Location! Charming Ski-in\/Ski-out Condo$
Click For Pricing
Expedia
Amazing Location! Charming Ski-in\/Ski-out Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Imagine an amazing mountain vacation in Okemo! When you stay in our cozy and equipped split-level unit, you will love to ...
Click For Pricing
Expedia
$Ski-in\/Ski-out Condo with access to Pools, Sauna$
From $208 per night (USD)
VRBO
Ski-in\/Ski-out Condo with access to Pools, Sauna
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Imagine an amazing mountain vacation in Okemo! When you stay in our charming and equipped split-level unit, you will lov ...
From $208 per night (USD)
VRBO
$Charming + Rustic Condo with Ski-in\/Ski-Out Access$
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Expedia
Charming + Rustic Condo with Ski-in\/Ski-Out Access
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Feel right at home in Okemo when you stay in our cozy and equipped Ski-in/Ski-out unit! Wonderfully located in a small s ...
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Expedia
From $412 per night (USD)
VRBO
2 Bedroom Mountainside Condo + nearby amenities!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This 2-bedroom mountainside condo in Okemo, Vermont is the perfect retreat for fantastic skiing and hiking, or for some ...
From $412 per night (USD)
VRBO
From $157 per night (USD)
Expedia
116 Two Double bed Standard Hotel room
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $157 per night (USD)
Expedia
From $178 per night (USD)
VRBO
117 Two Double bed Standard Hotel room
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $178 per night (USD)
VRBO
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Expedia
Fabulous views! Brand new house!
Bedrooms:
2
Bathrooms:
1
Sleeps:
3
This is a brand new 2 floor home with a cathedral ceiling that takes in the west view. The upstairs has a bedroom and a ...
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Expedia
From $604 per night (USD)
VRBO
Historic Rideout 16m to Okemo Walk to Town
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
A @Vermont_Escapes property - Escape to Vermont with us! New Jacuzzi hot tub installed July '23. Escape to the histo ...
From $604 per night (USD)
VRBO
From $928 per night (USD)
Expedia
A1 Solitude. 4 Bedrooms, ski in and out to main Solitude lift, pool & gym access
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
We are true ski in and out. We access the main Solitude lift and have direct trail access. We are a warm and inviting, ...
From $928 per night (USD)
Expedia
$UNIQUE\/HISTORIC STAY IN AN 1874 ERA SCHOOLHOUSE!!$
From $577 per night (USD)
VRBO
UNIQUE\/HISTORIC STAY IN AN 1874 ERA SCHOOLHOUSE!!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Enjoy a historic stay in this former Chester Schoolhouse recently renovated into a massive yet cozy home. Located only 1 ...
From $577 per night (USD)
VRBO
From $421 per night (USD)
Expedia
Best Location! Renovated center village Okemo 2 BR - free shuttle outside door!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Come and enjoy the fantastic skiing at Okemo! Our 2-bedroom condo is right on Main St. in the middle of dining and shop ...
From $421 per night (USD)
Expedia
$5 miles to Okemo\/Ludlow, 25 Acre Playground, Great Ski or Summer Rental$
From $290 per night (USD)
VRBO
5 miles to Okemo\/Ludlow, 25 Acre Playground, Great Ski or Summer Rental
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Awe-inspiring views and a peaceful vibe come together at The Big Barn Farm to serve up a fabulous vacation for any seaso ...
From $290 per night (USD)
VRBO
$Great Ski or Summer Rental - 5 miles to Okemo\/Ludlow, 25 Gorgeous Acres$
From $290 per night (USD)
Expedia
Great Ski or Summer Rental - 5 miles to Okemo\/Ludlow, 25 Gorgeous Acres
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Awe-inspiring views and a peaceful vibe come together at The Big Barn Farm to serve up a fabulous vacation for any seaso ...
From $290 per night (USD)
Expedia
From $1019 per night (USD)
VRBO
Work, Ski, Relax - Big Restored 1860s Farmhouse
Bedrooms:
5
Bathrooms:
7
Sleeps:
12
Come up solo or bring friends and family to our unique and lovingly renovated estate! Our charming 1860’s farmhouse slee ...
From $1019 per night (USD)
VRBO
$Ski-in\/out mountainside condo with balcony, washer\/dryer & high-speed WiFi$
From $559 per night (USD)
Expedia
Ski-in\/out mountainside condo with balcony, washer\/dryer & high-speed WiFi
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Okemo Mountain Lodge B203 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $559 per night (USD)
Expedia
From $296 per night (USD)
VRBO
Secluded dog-friendly home amongst the trees with sauna, Wii, & 2 scenic decks
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Plymouth Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $296 per night (USD)
VRBO
$Ski-In\/Out Condo with Mountain Views, and Washer\/Dryer$
From $376 per night (USD)
Expedia
Ski-In\/Out Condo with Mountain Views, and Washer\/Dryer
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Okemo Trailside 22DL Shred Shack Our calendar is updated in real-time & our nightly rates are accurately displayed. Sim ...
From $376 per night (USD)
Expedia
$Okemo Mountain Chalet W\/ Hot Tub and Game Room$
From $619 per night (USD)
VRBO
Okemo Mountain Chalet W\/ Hot Tub and Game Room
Bedrooms:
3
Bathrooms:
4
Sleeps:
15
Our Contemporary Ski House is less than 4 miles from Okemo Mountain Resort. It is situated on 10 private acres in the S ...
From $619 per night (USD)
VRBO
$\The Arched Chalet\ Stunning Green Mountain views close to Killington and Okemo$
From $489 per night (USD)
Expedia
\"The Arched Chalet\" Stunning Green Mountain views close to Killington and Okemo
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Welcome to the Arched Chalet, one of the last arched ski homes in the area located on Plymouth Notch ski mountain. The ...
From $489 per night (USD)
Expedia
$Downtown Condo w\/ Electric Fireplace, WiFi & Shuttle Stop Across the Street$
From $231 per night (USD)
VRBO
Downtown Condo w\/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cozy Ludlow Escape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $231 per night (USD)
VRBO
From $252 per night (USD)
Expedia
Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
The Pond House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $252 per night (USD)
Expedia
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VRBO
Come Home to Vermont
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Lake frontage on the only natural lake between Okemo Mt and Killington Mt. Ski the best 2 mountains, snow mobile, cross ...
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VRBO
$Stunning Log Home, 7 Bed\/4 Bath. Mountain View!$
From $1119 per night (USD)
Expedia
Stunning Log Home, 7 Bed\/4 Bath. Mountain View!
Bedrooms:
4
Bathrooms:
7
Sleeps:
16
Authentic, custom crafted, log home. Amazing natural light throughout the house. 2-person jacuzzi tub, game room with pi ...
From $1119 per night (USD)
Expedia
$Bright Condo w\/ Community Perks: Near Ski Quechee!$
From $295 per night (USD)
VRBO
Bright Condo w\/ Community Perks: Near Ski Quechee!
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Follow days skiing Vermont’s top resorts with leisurely afternoons and home-cooked meals at this 2-bedroom, 2.5-bath con ...
From $295 per night (USD)
VRBO
Click For Pricing
Expedia
Large 4 bedroom one mile from Okemo Base. Walk to downtown Ludlow
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Bring the whole family to this great place with lots of room for fun. Located approx. 1 mile from Okemo base lodge and o ...
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Expedia
From $684 per night (USD)
VRBO
The Quechee Haus: VT Retreat with Outdoor Hot Tub
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Relax, rejuvenate, and restore at The Quechee Haus. Located just 10 minutes from downtown Woodstock, 30 minutes from Kil ...
From $684 per night (USD)
VRBO
$Quiet Modern Luxury Home w\/ Memory Foam Beds, FAST WiFi and Full Kitchen$
From $251 per night (USD)
Expedia
Quiet Modern Luxury Home w\/ Memory Foam Beds, FAST WiFi and Full Kitchen
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
3 Bedrooms, 2 Full Bathrooms, Sleeps up to 8, Washer/Dryer, Radiant Floor Heat 3 Bedroom, 2 Full Baths home located 8 mi ...
From $251 per night (USD)
Expedia

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