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

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$Ski-in\/out condo with fireplace, pool, hot tub, sauna & washer\/dryer$
From $684 per night (USD)
VRBO
Ski-in\/out condo with fireplace, pool, hot tub, sauna & washer\/dryer
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Solitude Village H102 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $684 per night (USD)
VRBO
From $532 per night (USD)
VRBO
Songbird Haven–majestic VT Timberframe, Dog-Friendly Home Along The White River
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Enjoy the Vermont countryside any time of the year on over 7 acres alongside the White River. This home offers full amen ...
From $532 per night (USD)
VRBO
From $187 per night (USD)
VRBO
Clean, Updated, & Well Appointed-Family & Dog Friendly Rental
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
We have a 2 bedroom unit available. It has 2 baths, eat-in kitchen and living room. Washer and dryer in unit. Cable TV, ...
From $187 per night (USD)
VRBO
From $368 per night (USD)
VRBO
Carriage House - 250 Private Acres; Views, Gardens, Skiing, Farm, Serenity
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
**** Before clicking "Book It," please send an inquiry to Owner**** ***Additional discounts possible for longer stays*** ...
From $368 per night (USD)
VRBO
From $464 per night (USD)
VRBO
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located at 68 Pleasant St. first floor in the village of Ludlow, Vermont on the Black River within 20 miles of 5 majo ...
From $464 per night (USD)
VRBO
From $180 per night (USD)
VRBO
Charming Log Cabin Apartment in Woodstock Village
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape to one of the prettiest towns in America. Make your vacation a quiet visit in a quintessential, charming apartmen ...
From $180 per night (USD)
VRBO
From $1438 per night (USD)
VRBO
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off!
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Christmas Special: Trim a tree! Lights, tree and decorations included for Christmas rental. Gorgeous, 3500+ square foot ...
From $1438 per night (USD)
VRBO
From $4034 per night (USD)
VRBO
Reading Farms Estate
Bedrooms:
14
Bathrooms:
18
Sleeps:
46
** 2025 season 1 week stay special pricing $17,750** please inquire **.Reading Farms Estate is an elevated lifesty ...
From $4034 per night (USD)
VRBO
From $609 per night (USD)
VRBO
Luxury 3BR Cabin 5 min Drive to Okemo and on Ski Shuttle Route
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This contemporary and upscale cabin has 3 bedrooms, 2 bathrooms, sleeps 6 people, and offers comfort, privacy, complete ...
From $609 per night (USD)
VRBO
From $470 per night (USD)
Expedia
Dog-friendly house near Okemo Mountain Resort, skiing, & heart of Ludlow Village
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Casa Okemo Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $470 per night (USD)
Expedia
From $560 per night (USD)
VRBO
Beautiful 3000 Square Foot Home
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
New 5 bedroom, 3 bath home only 8 minute drive to Okemo. This three level home has plenty of room for the entire famil ...
From $560 per night (USD)
VRBO
$Dramatic Design & Landscape 3500 Sq Ft. Farmhouse W\/Jacuzzi&Swim Pond&CentralAC!$
From $794 per night (USD)
VRBO
Dramatic Design & Landscape 3500 Sq Ft. Farmhouse W\/Jacuzzi&Swim Pond&CentralAC!
Bedrooms:
4
Bathrooms:
7
Sleeps:
28
Completely renovated by Fortune Cookie Design of Boston, this rustic modern farmhouse is one of a kind. (circa 1800's) ...
From $794 per night (USD)
VRBO
From $448 per night (USD)
VRBO
Winterplace at Okemo Mountain
Bedrooms:
2
Bathrooms:
2
Sleeps:
9
2 Bedroon, 2 Bath slopeside condo for rent. Enjoy some wonderful skiing on Okemo's groomed trails, relax by the fire, o ...
From $448 per night (USD)
VRBO
$Luxurious, Secluded, Ski Chalet, w\/ Country Decor & Hot Tub Near Okemo$
From $716 per night (USD)
Expedia
Luxurious, Secluded, Ski Chalet, w\/ Country Decor & Hot Tub Near Okemo
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
The house is decorated with a comfortable country decor. It is located within the private and secluded Farm Ridge develo ...
From $716 per night (USD)
Expedia
From $375 per night (USD)
VRBO
Quechee at its Finest!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A great vacation spot awaits you and your family at this 3 bedroom, 2 bath townhouse located in the heart of Fairway Vil ...
From $375 per night (USD)
VRBO
From $151 per night (USD)
Expedia
Room in Historic Inn! 20 Minutes to Okemo!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Enjoy a private room, bathroom & shower in the historic Chester Inn, circa 1780. This charming property is conveniently ...
From $151 per night (USD)
Expedia
From $160 per night (USD)
VRBO
King & Queen Suite in Historic Inn Circa 1780
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Enjoy a private room, bathroom, shower & Fireplace in the historic Chester Inn, circa 1780. This charming property is co ...
From $160 per night (USD)
VRBO
$Ludlow Home w\/ Hot Tub, Near Okemo Resort!$
From $440 per night (USD)
Expedia
Ludlow Home w\/ Hot Tub, Near Okemo Resort!
Bedrooms:
3
Bathrooms:
6
Sleeps:
11
Escape to this secluded 4-bedroom, 3-bathroom home located in Ludlow for your next visit to Vermont. A true mountain ess ...
From $440 per night (USD)
Expedia
$Lake-view home with a private hot tub, fast WiFi, pool table, & washer\/dryer$
From $921 per night (USD)
VRBO
Lake-view home with a private hot tub, fast WiFi, pool table, & washer\/dryer
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Misty Mountain Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $921 per night (USD)
VRBO
$Quiet Modern Luxury Home w\/ Memory Foam Beds, A\/C, FAST WiFi and Full Kitchen$
From $302 per night (USD)
Expedia
Quiet Modern Luxury Home w\/ Memory Foam Beds, A\/C, FAST WiFi and Full Kitchen
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
3 Bedroom, 2 Full Baths home located 8 miles from the Killington Mountain Skyship Base Lodge. Kitchen with new applianc ...
From $302 per night (USD)
Expedia
From $569 per night (USD)
VRBO
Secluded 2600 sqft home 15 min from Okemo and Killington
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Welcome to The VT Treehouse on Hawk Mountain in Plymouth, VT. You will be able to enjoy sights and access to two of the ...
From $569 per night (USD)
VRBO
From $820 per night (USD)
VRBO
Stunning Lakeside home - ideal family getaway or work from home spot
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
*** Contact marionburch@icloud.com for current specials. This gorgeous 2,800 SF home is located right on the water (Lak ...
From $820 per night (USD)
VRBO
From $395 per night (USD)
VRBO
Ski House on Lake Rescue, 3.5 Miles from Okemo
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Charming 4 bedroom house with great lake vistas. Vaulted ceiling living room with a stone fireplace. Fully equipped ki ...
From $395 per night (USD)
VRBO
$Great 4BR\/3BA for families in village w\/ easy shuttle access. Read our reviews!$
From $729 per night (USD)
VRBO
Great 4BR\/3BA for families in village w\/ easy shuttle access. Read our reviews!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Discounted rates available for longer-term stays! Also discounts for multiple bookings! Send a message for details. ...
From $729 per night (USD)
VRBO
From $342 per night (USD)
VRBO
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This Chalet provides a nice cozy environment that makes you feel right at home. This home is being offered to travelers ...
From $342 per night (USD)
VRBO
From $683 per night (USD)
VRBO
Exquisite four bedroom, four bath single family home. Close to Quechee Club and amenities.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Excellent home for entertaining family and friends with the open concept floor plan. The main floor has 3 bedrooms and t ...
From $683 per night (USD)
VRBO
From $336 per night (USD)
VRBO
Exquisite two bedroom, 1.5 bath end unit town home near Lake Pinneo and the Quechee Club.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy convenience, comfort, and a terrific view from this stylishly decorated two-bedroom, 1.5-bath townhome (end unit). ...
From $336 per night (USD)
VRBO
From $291 per night (USD)
VRBO
New Lakeside Cottage near Okemo and Killington
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Bright, clean cottage right in the middle of the best of Vermont. Perfect for an athletic family or a couples getaway. S ...
From $291 per night (USD)
VRBO
$Ski On, Ski off Okemo Trailside Appartment, Sleeps 6\/ $550per night,$
From $644 per night (USD)
VRBO
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6\/ $550per night,
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Bright open design. Fully equipped kitchen, with dishwasher, stove, frig. and microwave. Large dinning room table with v ...
From $644 per night (USD)
VRBO
From $795 per night (USD)
VRBO
Great Location, Large Hot Tub, Wet Bar, Pool Table, Gas FP
Bedrooms:
4
Bathrooms:
6
Sleeps:
16
Moments from the entrance to Okemo, this spacious five bedroom, four bath vacation home holds up to 16 guests with all t ...
From $795 per night (USD)
VRBO
$Custom Luxury Home w\/Hot Tub on Okemo Mtn\/Family\/Group Friendly\/Shuttle Bus$
From $1794 per night (USD)
VRBO
Custom Luxury Home w\/Hot Tub on Okemo Mtn\/Family\/Group Friendly\/Shuttle Bus
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Beautiful custom-designed, spacious ski home ideal for relaxing, entertaining, cooking. Upper level sanctuary includes t ...
From $1794 per night (USD)
VRBO
From $1134 per night (USD)
VRBO
Ludlow Vermont Ski House
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Four bedroom colonial located on Ludlows prestigious South Hill. Ten minutes to Okemo and Jackson Gore, 45 minutes to Ki ...
From $1134 per night (USD)
VRBO
From $297 per night (USD)
VRBO
1794 Pioneer House - Renovated, No Cleaning Fee
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The Pioneer House is a unique survivor from Vermont’s earliest days. 100% solar powered (panels located on owner’s nearb ...
From $297 per night (USD)
VRBO
$Sunlit VT Country Home w\/Hot Tub. Ideal location near Woodstock village$
From $442 per night (USD)
VRBO
Sunlit VT Country Home w\/Hot Tub. Ideal location near Woodstock village
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Dana Road House, a welcoming 3BR/2BA Vermont country home with hot tub, king master suite & chef's kitchen! Ideally loca ...
From $442 per night (USD)
VRBO
From $232 per night (USD)
VRBO
Delightful Cozy Space in Woodstock Village
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Walking distance to everywhere in the Village and Mt Tom and Mt Peg. Parking for 2 cars, beautiful outdoor deck overlook ...
From $232 per night (USD)
VRBO
From $915 per night (USD)
VRBO
Warm and Peaceful 6 Bedroom Home in Quechee Vermont
Bedrooms:
3
Bathrooms:
6
Sleeps:
8
Come relax and stay a while in our warm and inviting, recently renovated six bedroom home in Quechee, Vermont! A peacefu ...
From $915 per night (USD)
VRBO
From $402 per night (USD)
VRBO
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
We are a licensed lodging facility in Vermont and you can find us by searching our farm name. Promotions, discounts, or ...
From $402 per night (USD)
VRBO
From $1260 per night (USD)
Expedia
Base Lodge - shuttle rte in winter - 10 BR, 5 Bath, Slp 34
Bedrooms:
5
Bathrooms:
10
Sleeps:
34
RENOVATED The Base Lodge will exceed your expectations. This beautiful 10 BR, 5 bath home with 4,000 sf is ready for yo ...
From $1260 per night (USD)
Expedia
$\The Crooked House\ with A\/C and sauna on private wooded lot near Killington$
From $369 per night (USD)
VRBO
\"The Crooked House\" with A\/C and sauna on private wooded lot near Killington
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Escape to the beautiful mountains of Vermont. Our four-season house (now with air conditioning in each bedroom and the l ...
From $369 per night (USD)
VRBO
From $880 per night (USD)
VRBO
Beautiful farmhouse minutes to Okemo. Lots of room. Spacious hot tub.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Quality furnishings in this spacious well-kept farmhouse minutes from Okemo base lodge. Comfortable living areas, large ...
From $880 per night (USD)
VRBO
From $258 per night (USD)
VRBO
School Brick House is the perfect location for a vacation
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come immerse yourself in the green mountains of Vermont. Our beautiful home is situated in the quaint town of Rochester ...
From $258 per night (USD)
VRBO
From $514 per night (USD)
VRBO
Beautiful Modern Cabin on a Vermont Farm - Stunning Panoramic Views!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
We are a licensed lodging facility in Vermont and you can find us by searching our farm name. Promotions, discounts, or ...
From $514 per night (USD)
VRBO
From $840 per night (USD)
VRBO
Okemo 6 Bedroom Chalet.
Bedrooms:
2
Bathrooms:
6
Sleeps:
13
***Newly renovated kitchen and bathroom*** This 6 Bedroom Chalet is situated on 10+ Acres along side a beautiful river. ...
From $840 per night (USD)
VRBO
From $456 per night (USD)
Expedia
Lake Rescue Vacation Home- Pets Welcome-Okemo and Killington close!!!
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
1378 ROUTE 100 NORTH LUDLOW, VERMONT 05149 Waterfront home with 100 Jo feet of grassy lake frontage, complete with kaya ...
From $456 per night (USD)
Expedia
From $669 per night (USD)
VRBO
Okemo Mountain Slopeside Vacation Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Ideal Slopeside Location - Watch skiers as they come off the lift from the main base area from the living room of this f ...
From $669 per night (USD)
VRBO
From $308 per night (USD)
VRBO
Flash sale! Hike, kayak & more! Come enjoy this newly renovated, cozy home!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Turn the key and be at your home away from home at Ludlow Chalet! Welcome to our lovely, newly-renovated chalet with lot ...
From $308 per night (USD)
VRBO
From $625 per night (USD)
VRBO
Waterfront House - Endless Lake Fun in all Seasons. 1 mile to Okemo Chairlifts!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This incredibly unique house sits hanging over the edge of Lake Rescue in Ludlow. It offers a large deep-water dock (bet ...
From $625 per night (USD)
VRBO
From $302 per night (USD)
Expedia
Stay Safe! Stay strong!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to the End of the Road Stay. Convenient location to Ludlow and Okemo Ski Resort. Cross the bridge to relax and u ...
From $302 per night (USD)
Expedia
From $452 per night (USD)
VRBO
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
We are a licensed lodging facility in Vermont and you can find us by searching our farm name. Promotions, discounts, or ...
From $452 per night (USD)
VRBO
From $516 per night (USD)
Expedia
Bright, Downtown 4-BR Home 3-min to Okemo
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: This modern farmhouse style home is situated in the heart of Downtown Ludlow, just minutes away from Okemo Moun ...
From $516 per night (USD)
Expedia
From $1146 per night (USD)
VRBO
5-BR Luxury Mountain Estate 5-min to Okemo
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Summary: Escape to this deluxe estate in the foothills of Okemo Mountain for your next mountain getaway. This ornate hom ...
From $1146 per night (USD)
VRBO
From $714 per night (USD)
VRBO
Beautiful Historic 4-Season Country Estate in Okemo Valley
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Stone Walls is located on 45 acres of open meadow and a winding forest trail in the heart of the Green Mountains of sout ...
From $714 per night (USD)
VRBO
From $358 per night (USD)
VRBO
Ski, hike, swim or relax with family & friends in this nature lovers delight!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Escape year round, with family and friends, to this private 5 bedroom 2.5 bath retreat minutes from Echo lake and Plymou ...
From $358 per night (USD)
VRBO
$OKEMO SKI IN\/OUT and WALK TO Solitude Pool\/Hottubs, bar, free e-car charging!$
From $1019 per night (USD)
VRBO
OKEMO SKI IN\/OUT and WALK TO Solitude Pool\/Hottubs, bar, free e-car charging!
Bedrooms:
3
Bathrooms:
2
Sleeps:
8
WINTER 24-25 SKI SEASON!! Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $1019 per night (USD)
VRBO
$Mountainside Condo w\/ Access to Pool + Ski Shuttle$
From $605 per night (USD)
VRBO
Mountainside Condo w\/ Access to Pool + Ski Shuttle
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Come and stay in our cozy and charming mountainside condo at Okemo Mountain Resort! Located near the summit of the two S ...
From $605 per night (USD)
VRBO
$Secluded Cabin w\/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing$
From $565 per night (USD)
Expedia
Secluded Cabin w\/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Log Cabin with a View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $565 per night (USD)
Expedia
$Lux Family Retreat @ Okemo\/Bromley. Arcade Machine$
From $747 per night (USD)
VRBO
Lux Family Retreat @ Okemo\/Bromley. Arcade Machine
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
Welcome to Honeypot Farmhouse—Your family's year-round Vermont retreat. We're located under 10 miles from Okemo & Magic, ...
From $747 per night (USD)
VRBO
From $887 per night (USD)
Expedia
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Situated on 12 acres with views of Okemo Mountain and direct access to VAST snowmobile trail. Minutes to charming villag ...
From $887 per night (USD)
Expedia
From $1260 per night (USD)
VRBO
The Clubhouse -11 BR Downtown, 7 Bath on shuttle
Bedrooms:
7
Bathrooms:
11
Sleeps:
34
The Clubhouse is ready to welcome your large group to Vermont! This 11 BR (sleeps 34), 7 BA home with 4,000 sq ft is re ...
From $1260 per night (USD)
VRBO
$Ronnoco Farm-Charming Brownsville\/West Windsor, VT cottage$
Click For Pricing
Expedia
Ronnoco Farm-Charming Brownsville\/West Windsor, VT cottage
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Ronnoco Farm is a small, private, and charming property conveniently located near Mt. Ascutney State Park (7.5 Miles), G ...
Click For Pricing
Expedia
From $502 per night (USD)
VRBO
The Red Bridge House. 360° of lake views.
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
The Red Bridge House is a spectacular home situated right between the hustling fun of Lake Rescue and the peaceful calm ...
From $502 per night (USD)
VRBO
$Killington Area Escape w\/ Deck, Views & Hot Tub!$
From $444 per night (USD)
Expedia
Killington Area Escape w\/ Deck, Views & Hot Tub!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Enjoy the incredible beauty of the Green Mountains in all 4 seasons at this versatile 3-bedroom, 2-bath Stockbridge vaca ...
From $444 per night (USD)
Expedia
$Ski on\/Ski off. Right on Sachem Trail. Okemo Trailside. 4bed\/2bath Sleeps 10.$
From $1897 per night (USD)
VRBO
Ski on\/Ski off. Right on Sachem Trail. Okemo Trailside. 4bed\/2bath Sleeps 10.
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Fantastic Ski-on/Ski- off location high up on Okemo mountain along Sachem Trail. Walk out the door and put your skis on ...
From $1897 per night (USD)
VRBO
From $522 per night (USD)
VRBO
Beautiful Vacation Home with Spectacular Views
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Beautiful vacation home in Quechee, Vt., designed by award winning architect. This unique home is located at one of the ...
From $522 per night (USD)
VRBO
From $1008 per night (USD)
VRBO
Killington Region - Sleeps 19!
Bedrooms:
6
Bathrooms:
7
Sleeps:
19
This historic 1840’s house has undergone a COMPLETE gut renovation and combines modern amenities with streamlined countr ...
From $1008 per night (USD)
VRBO
From $290 per night (USD)
VRBO
Between Killington and Okemo, Close to Farm & Wilderness Camp
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
House is on Plymouth Notch (formerly Roundtop Mountain), a private ski area only open on weekends. If you are skiing Ply ...
From $290 per night (USD)
VRBO
From $526 per night (USD)
VRBO
Rustic lakeview cabin with fireplace, deck- near skiing
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Ludlow Comfy Cabin Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $526 per night (USD)
VRBO
From $1106 per night (USD)
VRBO
Woodstock Village Green Location, Walk Everywhere, River Patio, Covered Bridge
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Park your car and put away your keys for your stay. 1823 Village Green Colonial. 4 bedrooms, 2 baths (both on the secon ...
From $1106 per night (USD)
VRBO
From $461 per night (USD)
VRBO
Log Cabin home with Mt Ascutney views and pool table
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
This home is located on the slopes of Mt. Ascutney, within walking distance from Mt. Ascutney Resort, the hotel, restaur ...
From $461 per night (USD)
VRBO
From $528 per night (USD)
VRBO
Killington, Left Side of Duplex ,Outside Hot Tub, Charming, Cozy, Clean
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
See Property # 104275 FOR MORE REVIEWS Note: Both Sides of the Duplex , Available For Large Groups * 8 Bedrooms, 4 Bath ...
From $528 per night (USD)
VRBO
From $267 per night (USD)
VRBO
Savage Hart Farm Is A Small Sheep Farm With Guest Accommodations.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
On the border of Vermont and New Hampshire, Savage Hart Farm is a perfect place to stay for a memorable visit to the hea ...
From $267 per night (USD)
VRBO
From $588 per night (USD)
VRBO
Mountain Top Cabin With Incredible Okemo Views And Sunsets
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
The cabin is 2017 construction decorated with a comfortable, rustic, country decor. It is located at the end of a priva ...
From $588 per night (USD)
VRBO
From $426 per night (USD)
VRBO
149 Upper Crossroad Unit B
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Renovated in the Summer of 2018, the Townhomes at Clock Tower are a beautiful, spacious year-mountain retreat. It sleeps ...
From $426 per night (USD)
VRBO
From $903 per night (USD)
Expedia
Village House on Shuttle Route- Great Location!
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Conveniently located right up the street from all restaurants, bars, shopping, and in walking distance so no car is need ...
From $903 per night (USD)
Expedia
From $447 per night (USD)
VRBO
Classic, cozy farmhouse in the 4 season playground of VT's prettiest town!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Our recently renovated1860’s farmhouse, on 95 acres abutting the banks of the Ottauquechee River, is 3 miles from histor ...
From $447 per night (USD)
VRBO
From $187 per night (USD)
VRBO
Secluded and Serene - GET AWAY FROM IT ALL! Barnard, VT
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Lovely country cabin on private and secluded 6 acres in Barnard, VT! Minutes from Silver Lake, Woodstock, Quechee, Roy ...
From $187 per night (USD)
VRBO
From $513 per night (USD)
VRBO
PRIVATE & AFFORDABLE charming custom ranch in South Woodstock ! AC and WIFI.
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Sunny 4 bedroom 2 bath home sleeps 7 in beds. Located on 4 lush acres of rolling fields, mature trees and streams, this ...
From $513 per night (USD)
VRBO
From $1413 per night (USD)
Expedia
Renovated Luxury 4 Bedroom 3.5 Bath Okemo Trailside
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Recently Renovated to the highest standing, this luxurious condo has an additional (3rd) family bathroom downstairs maki ...
From $1413 per night (USD)
Expedia
From $1309 per night (USD)
VRBO
OKEMO VACATION HOUSE, HOT TUB, CENTRAL AIR 6 Bdrm (2 K, 3 Q, 1 bunk), sleeps 14
Bedrooms:
5
Bathrooms:
7
Sleeps:
14
ATTENTION BOAT, GOLF, AND CYCLING ENTHUSIASTS, NOW WITH CENTRAL AIR FOR YEAR ROUND ENJOYMENT!! This gorgeous Lindal Ced ...
From $1309 per night (USD)
VRBO
From $162 per night (USD)
VRBO
Cozy 2 bedroom minutes from Okemo base lodge - Inquire about seasonal rental
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Cozy chalet located on Okemo Mountain Resort within a mile of the base lodge and a half mile from The VAST. Located on ...
From $162 per night (USD)
VRBO
From $550 per night (USD)
VRBO
Fantastic Four Bedroom on 5+ Acres Close to Club with 180º Views
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Location, space and views close to Club! Nicely renovated 4 bedroom, 3 bath cape style home on 5+ open acres in fantast ...
From $550 per night (USD)
VRBO
$Remodeled condo with free WiFi & shared W\/D - ski bus pickup across street$
From $430 per night (USD)
Expedia
Remodeled condo with free WiFi & shared W\/D - ski bus pickup across street
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Baggrow Unit B Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $430 per night (USD)
Expedia
From $348 per night (USD)
VRBO
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Woodward Grove Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $348 per night (USD)
VRBO
From $320 per night (USD)
VRBO
Charming and Chic Vacation Rental
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This beautiful newly renovated apartment is conveniently located adjacent to historic Tribou Park. It is walking distan ...
From $320 per night (USD)
VRBO
$5 minutes to Okemo- Skihouse On The Lake\n$
From $792 per night (USD)
VRBO
5 minutes to Okemo- Skihouse On The Lake\n
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
For ski trips, lakeside vacation and family gatherings or a romantic getaway, this home has it all. Within 5 minutes to ...
From $792 per night (USD)
VRBO
From $249 per night (USD)
VRBO
Relaxation Paradise
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Cozy mountain chalet. Perfect for the family to enjoy skiing, hiking, swimming. Located right between Killington and Sug ...
From $249 per night (USD)
VRBO
From $707 per night (USD)
VRBO
Farm House located 1 mile from Okemo's Jackson Gore base lodge!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
*** Shaw’s is NOW open!!*** Enjoy 2,400 sq ft, conveniently located 1 mile from Okemo's Jackson Gore base lodge, 4 miles ...
From $707 per night (USD)
VRBO
From $504 per night (USD)
Expedia
TRAILSIDE, Huge, Newly Renovated, 6 bedroom condo ski-on ski-off, sleeps 18
Bedrooms:
4
Bathrooms:
6
Sleeps:
18
Wonderfully located off of Sachem Trail, within the Trailside Condominium Community, Ski on, Ski off. One of the most ...
From $504 per night (USD)
Expedia
From $221 per night (USD)
VRBO
Meadow View- 35 Acres outside your door
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Meadow View is your home away from home. 35 acres at your fingertips including 2 trout ponds and 25 acres of wooded trai ...
From $221 per night (USD)
VRBO
From $176 per night (USD)
Expedia
The Little Red Cabin! Less than 15 minutes to Okemo! Close to Everything VT!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Our two bedroom one bath cabin got a refreshing renovation! Super comfy bedrooms with expansive family style living s ...
From $176 per night (USD)
Expedia
$Lakefront Vacation House w\/ quiet, sandy beach\/boats -$
From $364 per night (USD)
VRBO
Lakefront Vacation House w\/ quiet, sandy beach\/boats -
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Great location 10 minutes from Ludlow, VT (Okemo), 20 minutes from Killington area, and 30 minutes from Rutland, Spring ...
From $364 per night (USD)
VRBO
From $825 per night (USD)
VRBO
Chic Cabin near Killington for Relaxing and Co-working
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
The Hide(OOO)ut is the best place to truly be Out of Office! Built-in 1978, this 5-bed log cabin was recently renovated ...
From $825 per night (USD)
VRBO
From $344 per night (USD)
VRBO
Deluxe Two Bedroom Suite on the 1st floor with outdoor heated pool 10102
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $344 per night (USD)
VRBO
From $498 per night (USD)
VRBO
Scenic South Woodstock, Vermont home
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Nestled on a hillside above the scenic village of S. Woodstock, Apple Hill is a cozy year-round home with a large deck o ...
From $498 per night (USD)
VRBO
From $205 per night (USD)
VRBO
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $205 per night (USD)
VRBO
$Condo with fireplace, W\/D & shared pool - shuttle access to Okemo Mountain$
From $340 per night (USD)
Expedia
Condo with fireplace, W\/D & shared pool - shuttle access to Okemo Mountain
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Nana’s Nest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $340 per night (USD)
Expedia
From $502 per night (USD)
VRBO
Fall Foliage Paradise - 3 BR Private Home - Weston, Vermont
Bedrooms:
1
Bathrooms:
4
Sleeps:
7
Beautiful views in a tranquil setting yet close to everything that matters in Southern Vermont. Property itself is a 10 ...
From $502 per night (USD)
VRBO
$Cute Riverfront Home w\/ Free WiFi, Washer\/Dryer, & Private Deck - Close to Okemo$
Click For Pricing
Expedia
Cute Riverfront Home w\/ Free WiFi, Washer\/Dryer, & Private Deck - Close to Okemo
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Green Mountain Riverside Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Sim ...
Click For Pricing
Expedia
From $317 per night (USD)
VRBO
Dog-friendly & riverfront condo one mile from Okemo with wood fireplace
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
The Mill #210 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $317 per night (USD)
VRBO
$Picture-Perfect Vermont Mtn Cabin w\/ Hot Tub!$
From $1163 per night (USD)
Expedia
Picture-Perfect Vermont Mtn Cabin w\/ Hot Tub!
Bedrooms:
3
Bathrooms:
8
Sleeps:
15
Dive into a quintessential New England escape at this 6-bed, 3-bath vacation rental! Watch your worries fade from the mo ...
From $1163 per night (USD)
Expedia

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