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

From $672 per night (USD)
VRBO
Rural mountain-view home near skiing with screened porch, firepit, & game room
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
The Farmhouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $672 per night (USD)
VRBO
From $523 per night (USD)
Expedia
All-Season Ludlow Apartment: 3 Mi to Okemo Resort!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Whether you’re in the mood for a warm summer getaway or a dreamy winter vacation, you’ll find it here at this Ludlow apa ...
From $523 per night (USD)
Expedia
From $287 per night (USD)
VRBO
Cozy Cabin near Okemo
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Cozy private cabin located just 10 minutes from Okemo! This cabin features a mud room to store all your ski gear. One be ...
From $287 per night (USD)
VRBO
$Okemo Mountain Retreat: 3BR Ski-in\/Ski-Out Condo$
From $841 per night (USD)
Expedia
Okemo Mountain Retreat: 3BR Ski-in\/Ski-Out Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Experience the ultimate ski-in/ski-out getaway at our 3 BR modern mountain retreat. This Kettlebrook condo is j ...
From $841 per night (USD)
Expedia
From $1844 per night (USD)
VRBO
Scenic 7-BR Luxury Estate 7-Min to Okemo
Bedrooms:
6
Bathrooms:
7
Sleeps:
13
Summary: Take in breath-taking views of Okemo perched on 47 private acres in the hills above Ludlow without sacrificing ...
From $1844 per night (USD)
VRBO
From $299 per night (USD)
VRBO
Charming 1700s Farm House on Beautiful 100 Acre Estate
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Illora Farm is the perfect place to disconnect from the hustle and bustle of the real world. Relax when you stay at this ...
From $299 per night (USD)
VRBO
From $867 per night (USD)
VRBO
Dog-friendly townhome at the base with mountain view & woodstove - walk to lifts
Bedrooms:
4
Bathrooms:
4
Sleeps:
11
Okemo Village B5 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $867 per night (USD)
VRBO
$Recently Renovated Ski-In\/Out Condo w\/Fireplace, Shared Pool, Hot Tub, Sauna$
From $221 per night (USD)
Expedia
Recently Renovated Ski-In\/Out Condo w\/Fireplace, Shared Pool, Hot Tub, Sauna
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Solitude Village H103 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $221 per night (USD)
Expedia
From $571 per night (USD)
VRBO
New! Hillside Farmhouse - updated 3bd cottage in heart of VT
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Experience the beauty and history of Vermont in this dog friendly, hillside farmhouse. This home has been tastefully upd ...
From $571 per night (USD)
VRBO
From $312 per night (USD)
Expedia
Newly Renovated 2-bedroom 1.75-bathroom condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Quechee, Vermont is an ideal destination in every season and has quintessential New England charm and natural beauty. Wi ...
From $312 per night (USD)
Expedia
$2bd\/2.5ba end-unit condo in the heart of Quechee$
From $343 per night (USD)
VRBO
2bd\/2.5ba end-unit condo in the heart of Quechee
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Looking for a cozy home away from home on your next Vermont vacation? Look no further than this dog friendly, 2-bedroom, ...
From $343 per night (USD)
VRBO
From $779 per night (USD)
Expedia
New! Walk to Lake Pinneo & Lakeland Golf Course! 4bd + loft
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Location, location, location! Located right across the street from Lakeland golf course with great views of the beautifu ...
From $779 per night (USD)
Expedia
Click For Pricing
VRBO
Luxurious 4-bedroom 3.5-bathroom mountain side home That sleeps 8
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
"This is not your average vacation home. This is a luxurious and exceptionally private home away from home. Whether you ...
Click For Pricing
VRBO
From $243 per night (USD)
Expedia
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dream Weaver Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $243 per night (USD)
Expedia
From $246 per night (USD)
VRBO
Condo in the heart of town near skiing - less than a mile to Okemo Mountain
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Teddy's Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $246 per night (USD)
VRBO
From $464 per night (USD)
Expedia
Mountain-view condo with skiing nearby, pool, and balcony - snowbird-friendly
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Vermont's Finest - Brookhaven F4 Our calendar is updated in real-time & our nightly rates are accurately displayed. Sim ...
From $464 per night (USD)
Expedia
From $587 per night (USD)
VRBO
Cabin less than 5 mins from Jackson Gore & Okemo
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
A newly renovated private home for all seasons with a mountain view located between Okemo Mountain (5 minute drive) and ...
From $587 per night (USD)
VRBO
From $1058 per night (USD)
VRBO
Amazing Views on Music Mountain
Bedrooms:
5
Bathrooms:
4
Sleeps:
15
Create unforgettable memories at "The Views at Music Mountain". This brand new architecturally stunning modern Log and T ...
From $1058 per night (USD)
VRBO
$Okemo Ski in-Ski out @ Winterplace, 3 bdr, 2 ba Condo with Pool, Hot Tub, W\/D$
From $1221 per night (USD)
VRBO
Okemo Ski in-Ski out @ Winterplace, 3 bdr, 2 ba Condo with Pool, Hot Tub, W\/D
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Winterplace L-104 is a 3 bedroom, 2 Bath condo with Ski in-Ski out access. Walk out this first-floor unit and walk acros ...
From $1221 per night (USD)
VRBO
From $1429 per night (USD)
Expedia
Slopeside in Okemo - Beautifully Renovated Spacious Family Townhouse by RedAwning
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This property is a large, immaculate tri-level townhouse in a perfect location that offers privacy, easy parking, and a ...
From $1429 per night (USD)
Expedia
$Ski-in\/out mountainside condo with pool, hot tub, game room & washer\/dryer$
From $486 per night (USD)
VRBO
Ski-in\/out mountainside condo with pool, hot tub, game room & washer\/dryer
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
The Bear Den - Solitude Village J202 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $486 per night (USD)
VRBO
From $444 per night (USD)
Expedia
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Tiny Homes on Pleasant Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $444 per night (USD)
Expedia
From $193 per night (USD)
VRBO
10 Min to Mountains| Long Trail Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Welcome to the Long Trail Suite @ The Bridgewater Inn! We're so excited to host you. Proximity is paramount and ...
From $193 per night (USD)
VRBO
From $193 per night (USD)
Expedia
10 min to Mountains | Queen Bed | Woodstock Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Welcome to the Woodstock Suite @ The Bridgewater Inn! We're so excited to host you. Proximity is paramount and ...
From $193 per night (USD)
Expedia
From $646 per night (USD)
VRBO
Countryside, lakefront cabin with kayaks, stone fireplace, balcony, & fast WiFi
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Rescue Lake Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $646 per night (USD)
VRBO
From $156 per night (USD)
VRBO
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This is a mostly off grid cabin with total privacy. Quiet yet just 2 miles off Rt 103. If you are looking for a place ...
From $156 per night (USD)
VRBO
From $186 per night (USD)
VRBO
Minutes to Woodstock | Hiking | Ben & Jerry Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Welcome to the Ben & Jerry's Suite @ The Bridgewater Inn! We're so excited to host you. Proximity is paramount ...
From $186 per night (USD)
VRBO
From $193 per night (USD)
Expedia
2 Queens | 10 Min to Mountains | Bridgewater Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Welcome to the Ski VT Suite @ The Bridgewater Inn! We're so excited to host you. Proximity is paramount and The ...
From $193 per night (USD)
Expedia
From $1576 per night (USD)
VRBO
Okemo Ski Retreat sleeps 16 comfortably and 1 mile to the mountain
Bedrooms:
3
Bathrooms:
5
Sleeps:
16
Okemo Ski House which easily sleeps 16 guests in bedrooms! Bring your family and friends to this spacious remodeled far ...
From $1576 per night (USD)
VRBO
From $382 per night (USD)
Expedia
Renovated Farmhouse between Woodstock & Killington
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Our recently renovated farmhouse offers a comfortable and relaxing place to come home to after a full day of exploring! ...
From $382 per night (USD)
Expedia
From $381 per night (USD)
VRBO
Perfect Getaway minutes to Killington & Woodstock
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This recently updated condo offers a comfortable space to return to after a day of exploration! Located perfectly betwe ...
From $381 per night (USD)
VRBO
$Hartford Escape w\/ Fire Pit ~ 3 Mi to Ski & Golf!$
From $317 per night (USD)
Expedia
Hartford Escape w\/ Fire Pit ~ 3 Mi to Ski & Golf!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to the Green Mountain State when you stay at this 2-bedroom, 1.5-bathroom vacation rental! With its fully equippe ...
From $317 per night (USD)
Expedia
$Ski-in\/Ski-out Ledgewood condo - 4 BR across 3 floors!$
From $1960 per night (USD)
VRBO
Ski-in\/Ski-out Ledgewood condo - 4 BR across 3 floors!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Right off of Ledgewood Trail, ski-in/ski-out 4 bedroom condo. Sleeps 10; ideal for 2 families! Newly renovated main fl ...
From $1960 per night (USD)
VRBO
From $450 per night (USD)
Expedia
Dog-friendly, 2-story condo at the base of Ascutney with fireplace & balcony
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Mountain's Edge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $450 per night (USD)
Expedia
From $539 per night (USD)
VRBO
Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Rzeka Cottage! Enjoy a stylish experience at this riverfront home in the Green Mountains. Centrally located n ...
From $539 per night (USD)
VRBO
$Three-story, ski-in\/out condo with mountain view & fireplace - dog-friendly$
From $1089 per night (USD)
Expedia
Three-story, ski-in\/out condo with mountain view & fireplace - dog-friendly
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Sachem Slopeside - Okemo Trailside 21B Our calendar is updated in real-time & our nightly rates are accurately displaye ...
From $1089 per night (USD)
Expedia
$Spacious 2BR Condo Ski-in\/Ski-out at Okemo w\/ pool$
From $560 per night (USD)
VRBO
Spacious 2BR Condo Ski-in\/Ski-out at Okemo w\/ pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Enjoy family-friendly ski-in/ski-out convenience at our 2-bed, 2-bath Winterplace condo. Sleeps 6 with a master ...
From $560 per night (USD)
VRBO
$Luxury Mtn. Condo w\/ 2 King Beds 4 Miles to Okemo$
From $735 per night (USD)
Expedia
Luxury Mtn. Condo w\/ 2 King Beds 4 Miles to Okemo
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: Located just minutes from Okemo Mountain, Downtown Ludlow, and the Village of Proctorsville this condo is the p ...
From $735 per night (USD)
Expedia
From $620 per night (USD)
VRBO
Valhalla!!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to Valhalla on Lake Rescue! We are a lovely four season home with plenty of options right outside our doorstep. ...
From $620 per night (USD)
VRBO
From $247 per night (USD)
Expedia
Cozy 1 king bed Apt Minutes to Okemo (Pet Friendly)
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Looking for an affordable getaway near the scenic mountains of VT? Look no further! Our cozy one-bedroom apartment is ju ...
From $247 per night (USD)
Expedia
From $537 per night (USD)
VRBO
Game Room|10 Min to Trails, Killington, Woodstock
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Escape to the historic Bridgewater House, a 2,000 sq ft home that sleeps up to 8. With a spacious kitchen, livi ...
From $537 per night (USD)
VRBO
Click For Pricing
Expedia
Tree Top Home with Hot Tub Near Killington & Okemo
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Secluded in the Green Mountains, our home is a peaceful oasis that has everything you need for an unforgettable vacation ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Ludlow Vacation Rental - Steps to Ski Lift!
Bedrooms:
3
Bathrooms:
6
Sleeps:
8
Plan your next ski trip or summer hiking excursion with family when you book this idyllic townhome nestled just 2 miles ...
Click For Pricing
VRBO
$Two Okemo condos - ski-in\/ski-out - pool, fast WiFi, washer\/dryer$
From $899 per night (USD)
Expedia
Two Okemo condos - ski-in\/ski-out - pool, fast WiFi, washer\/dryer
Bedrooms:
3
Bathrooms:
6
Sleeps:
13
Trailside 19BU & 19BL Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $899 per night (USD)
Expedia
$Andover Cabin Retreat w\/ Hot Tub & Fireplace!$
From $355 per night (USD)
VRBO
Andover Cabin Retreat w\/ Hot Tub & Fireplace!
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Enjoy a peaceful Vermont escape at this charming Andover home. This 3-bedroom, 1-bathroom vacation rental boasts an invi ...
From $355 per night (USD)
VRBO
From $906 per night (USD)
Expedia
Birch Lodge - mountain views, hottub, minutes to Okemo!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Located in a private development, this home sits surrounded by the lush forest with a clearing exposing the face of Okem ...
From $906 per night (USD)
Expedia
$Condo on Quechee Golf Course 3bd\/2bt Private Feel$
From $513 per night (USD)
VRBO
Condo on Quechee Golf Course 3bd\/2bt Private Feel
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
<p>Located next to a golf course, this 3-bedroom, 2-bathroom condo brings all of Quechee within your reach. Fans of natu ...
From $513 per night (USD)
VRBO
$Steps from Sachem trail, hot tub, 2 master suits, total 5 bed\/bath, build 2022$
From $2893 per night (USD)
VRBO
Steps from Sachem trail, hot tub, 2 master suits, total 5 bed\/bath, build 2022
Bedrooms:
5
Bathrooms:
5
Sleeps:
13
Walking distance to sachem trail (600feet), custom build in 2022, private hot tub, spacious, 5 bedroom, 5 bathroom, easi ...
From $2893 per night (USD)
VRBO
From $1007 per night (USD)
VRBO
Cozy Ludlow Home: 2 Mi to Okemo Mountain Resort!
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
- MRT-11153470-001 - Dog Friendly w/ Fee - Walk to Ski Trails - Mountain Views - Fireplace Ensure your ski trip goes of ...
From $1007 per night (USD)
VRBO
From $512 per night (USD)
Expedia
Lakefront home with large yard, firepit, canoe, and fireplace
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Lake House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $512 per night (USD)
Expedia
From $438 per night (USD)
VRBO
Mountain Getaway
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy the splendor of a classic Vermont getaway in our welcoming home nestled privately in the Green Mountains of Vermo ...
From $438 per night (USD)
VRBO
From $697 per night (USD)
Expedia
Log cabin on Macintosh Pond access to VAST trail system snowmobile trails.
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Post and beam log cabin on 40 acres is completely private on a dead end road with a large flat lawn to enjoy. Less than ...
From $697 per night (USD)
Expedia
$Hot Tub w\/views! Minutes to the Mountain!$
From $422 per night (USD)
VRBO
Hot Tub w\/views! Minutes to the Mountain!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Looking for a summer retreat in a picturesque ski town? Look no further! Our cozy summer house is nestled in the heart o ...
From $422 per night (USD)
VRBO
From $461 per night (USD)
Expedia
New! The Gathering Place - hot tub and sauna, a perfect vacation home getaway!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
The Gathering Place Perched atop Willard Road in Quechee VT, this lovingly updated 4-bedroom 3 bath contemporary style h ...
From $461 per night (USD)
Expedia
$Okemo Ski in \/Ski out from the Sachem Trail$
From $1939 per night (USD)
VRBO
Okemo Ski in \/Ski out from the Sachem Trail
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Be the first on the trail ski from this wonderful 3 bedroom townhome on top of the sachem trail. Comfortably sleeps 8 t ...
From $1939 per night (USD)
VRBO
$New! 3bd\/2.5ba with Sauna - a Vacationers Dream!$
From $483 per night (USD)
Expedia
New! 3bd\/2.5ba with Sauna - a Vacationers Dream!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to this beautiful condominium in Quechee, Vermont overlooking the stunning Highland Golf Course! This is your pe ...
From $483 per night (USD)
Expedia
From $477 per night (USD)
VRBO
Inviting Vermont Home On Mount Ascutney!
Bedrooms:
2
Bathrooms:
6
Sleeps:
8
Bundle up for alpine activities or curl up and get cozy at this 4-bedroom, 2-bath home. Situated just a short walk from ...
From $477 per night (USD)
VRBO
Click For Pricing
Expedia
Less than 5 mi. to Killington Skyeship Gondola
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Private, soundproofed, high-tech security, hard-wired fire/heat/smoke/carbon monoxide, fire doors, keyless entry, FOB se ...
Click For Pricing
Expedia
Click For Pricing
VRBO
New! 4 Bedroom, Pet Friendly House on Main!
Bedrooms:
4
Bathrooms:
4
Sleeps:
7
Welcome to this stunning newly restored, dog friendly, home located in the heart of Quechee Village! This oasis offers e ...
Click For Pricing
VRBO
$Farmhouse w\/ mountain views close to skiing. Includes outdoor sauna EV CHRGR$
From $557 per night (USD)
Expedia
Farmhouse w\/ mountain views close to skiing. Includes outdoor sauna EV CHRGR
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Experience 180 degrees mountain views at this quaint farmhouse. World Class Skiing at Okemo Mountain is just 23 mins, B ...
From $557 per night (USD)
Expedia
From $485 per night (USD)
VRBO
Ski Chalet in Ludlow, VT
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Large Chalet; with 3 full bedrooms and a 2 set bunk bedroom room. Located just minutes from Okemo Mountain Resort and a ...
From $485 per night (USD)
VRBO
From $733 per night (USD)
Expedia
Greydon Cabin ~ Rustic Luxury in Woodstock VT
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Greydon Cabin ~ This classic Vermont log home will gives a whole new meaning to the word, "cabin." Top of the ...
From $733 per night (USD)
Expedia
$Mountainside 5-BR Ski-In\/Out Okemo Estate$
From $1272 per night (USD)
VRBO
Mountainside 5-BR Ski-In\/Out Okemo Estate
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Summary: Enjoy the pinnacle of Okemo Mountain living in this top-of-market ski-in, ski-out, 5-BR home. Property features ...
From $1272 per night (USD)
VRBO
From $529 per night (USD)
Expedia
Peaceful, mountain-view home with large deck, & grill - dog-friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Valkyrie Run Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $529 per night (USD)
Expedia
From $539 per night (USD)
VRBO
New! End unit steps from Ski Quechee 4-bedroom 3.5 bath
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to the perfect mountain retreat! This stunningly renovated end-unit condo is located just steps away from the Qu ...
From $539 per night (USD)
VRBO
From $564 per night (USD)
Expedia
Morey Mountain Retreat - 4 BR 2BA Secluded Getaway!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Experience the beauty of Quechee, Vermont in this unique 4-bedroom 2 bath, dog friendly, home in the serene Quechee Lake ...
From $564 per night (USD)
Expedia
From $136 per night (USD)
VRBO
Run, ride, hike and swim in Central Vermont
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy the winter in beautiful Vermont. The guest area is the entire main floor of a large house with my quiet second hom ...
From $136 per night (USD)
VRBO
From $864 per night (USD)
Expedia
Luxury Four Bedroom Modern Log Home
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Welcome to your Vermont getaway! Picture yourself in this exquisite four bedroom, three full and two-half bath log home, ...
From $864 per night (USD)
Expedia
From $3967 per night (USD)
VRBO
Totally Restored Grand Mansion & Estate overlooking the CT River
Bedrooms:
19
Bathrooms:
16
Sleeps:
39
Perched atop Juniper Hill, the Windsor Mansion Inn spans over 14 acres in the historic hamlet of Windsor, Vermont, the t ...
From $3967 per night (USD)
VRBO
From $197 per night (USD)
VRBO
Cabin in the Orchard near Silver Lake
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Charming Studio Cabin with wood-burning stone fireplace, kitchenette with toaster oven/air fryer, coffee maker, mini-ref ...
From $197 per night (USD)
VRBO
Click For Pricing
VRBO
Private wing of the Largest Colonial Revival Mansion in the US
Bedrooms:
4
Bathrooms:
3
Sleeps:
7
Built in 1902 and comprehensively renovated in late 2016, the Windsor Mansion is an incredibly well preserved example of ...
Click For Pricing
VRBO
$5br\/ 2bath Family Vacation Home, Shuttle at door+short walk to Restaurants$
Click For Pricing
Expedia
5br\/ 2bath Family Vacation Home, Shuttle at door+short walk to Restaurants
Bedrooms:
2
Bathrooms:
5
Sleeps:
15
This home has 5 bedrooms plus a den that has a futon. The home sleeps 13 to 15 persons very comfortably. The home is loc ...
Click For Pricing
Expedia
$New! Updated 3 BR w\/ Sauna, access to Pool$
From $490 per night (USD)
VRBO
New! Updated 3 BR w\/ Sauna, access to Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Enjoy a truly unforgettable vacation experience at this updated family friendly 3 bed, 3 bath end unit condo located in ...
From $490 per night (USD)
VRBO
$Spacious retreat with private hot tub, game room, deck, fireplace, & W\/D$
Click For Pricing
Expedia
Spacious retreat with private hot tub, game room, deck, fireplace, & W\/D
Bedrooms:
3
Bathrooms:
5
Sleeps:
13
Okemo Valley Chalet Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
Click For Pricing
Expedia
From $384 per night (USD)
VRBO
Beautiful ski in-ski out condo at Okemo Mountain
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A true ski in/ski out condo located at the base of the beautiful Okemo Mountain! Within steps of the chalet and near the ...
From $384 per night (USD)
VRBO
From $1904 per night (USD)
VRBO
Perfect 6 BR Mountain House on Okemo across from Suncatcher lift
Bedrooms:
5
Bathrooms:
6
Sleeps:
22
Our 6 BR / 4.5 home is ideal for multi-generational families or multiple families - can sleep 22. House is on Okemo Moun ...
From $1904 per night (USD)
VRBO
From $416 per night (USD)
VRBO
New! South Woodstock Cottage - restored, modern luxury
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Step into history and luxury with this beautifully restored antique farmhouse in South Woodstock! From its charming hist ...
From $416 per night (USD)
VRBO
$New! 2bd\/2ba Tastefully Updated, Golf course View Condo!$
From $417 per night (USD)
Expedia
New! 2bd\/2ba Tastefully Updated, Golf course View Condo!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy a peaceful getaway in this adorable, newly renovated Fairway Village condo situated on the beautiful Highland Golf ...
From $417 per night (USD)
Expedia
From $673 per night (USD)
VRBO
Stunning Views in Ludlow Vermont Minutes to Okemo Resort
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
MRT-11088876 This fabulous home overlooks the Okemo Valley and is less than a five-minute drive to Okemo Resort. Stunnin ...
From $673 per night (USD)
VRBO
$New! 3BR\/3.5BA Pristine Fox Hollow Condo$
From $589 per night (USD)
Expedia
New! 3BR\/3.5BA Pristine Fox Hollow Condo
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Perfectly designed for your lifestyle. Nestled in the picturesque Quechee Lakes golf community, this stunning 3 bedroom, ...
From $589 per night (USD)
Expedia
From $796 per night (USD)
VRBO
3-story dog-friendly home with private hot tub, firepit, grill, wood stove, EVC
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Spacious Mountain Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $796 per night (USD)
VRBO
$17-Acre Vermont Escape w\/ Panoramic Mountain Views$
From $566 per night (USD)
Expedia
17-Acre Vermont Escape w\/ Panoramic Mountain Views
Bedrooms:
2
Bathrooms:
8
Sleeps:
14
Built in 1892, this classic yet modern Cavendish vacation rental exudes old-world charm and elegance! Every window in th ...
From $566 per night (USD)
Expedia
From $331 per night (USD)
VRBO
2nd-floor condo near Okemo Mtn with streaming, WiFi, partial AC, & full kitchen
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Hidden Gem Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $331 per night (USD)
VRBO
$Spacious & renovated condo with balcony, fireplace, jetted tub, desk, W\/D, & AC$
From $499 per night (USD)
Expedia
Spacious & renovated condo with balcony, fireplace, jetted tub, desk, W\/D, & AC
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Castle Hill Condos G4 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $499 per night (USD)
Expedia
From $761 per night (USD)
VRBO
Waterfront retreat with dock, sauna, & firepit - near Woodstock & ski areas
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Turtle Grove Lakehouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $761 per night (USD)
VRBO
From $400 per night (USD)
Expedia
Updated 3 bdrm golf course condo
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
A Golf Lover's Dream Vacation Spot in Vermont! Escape the hustle and bustle of daily life and unwind in this stunningly ...
From $400 per night (USD)
Expedia
From $316 per night (USD)
VRBO
Newly Renovated 2-bedroom 1.5-bathroom condo unit NEW INVENTORY
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape the everyday and come stay at this Mill Run retreat! Nestled away near Quechee Main Street, you'll be close to al ...
From $316 per night (USD)
VRBO
From $407 per night (USD)
Expedia
3 Bedroom condo with beautiful golf course views sleeps 6
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Welcome to your perfect getaway in the beautiful Quechee Lakes area! This stunning 3-bedroom end condo unit offers all t ...
From $407 per night (USD)
Expedia
From $384 per night (USD)
VRBO
2 Bedroom with Hot Tub - 1 Minute from Gondola - Skyeship House
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to your private getaway in the middle of Vermont’s most active recreational region. Skiing, mountain biking, hik ...
From $384 per night (USD)
VRBO
$Camp Amherst: Ski and Lakeside Retreat. Killington\/Okemo, Firepit, private dock!$
From $483 per night (USD)
Expedia
Camp Amherst: Ski and Lakeside Retreat. Killington\/Okemo, Firepit, private dock!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Our newly renovated lakeside "camp" is the perfect place for an active yet relaxing Summer/Fall getaway or a fun-filled ...
From $483 per night (USD)
Expedia
$Ski-in\/Ski-out 3-level Townhouse at the Top of Trailside Village -Okemo Mountain$
From $1540 per night (USD)
VRBO
Ski-in\/Ski-out 3-level Townhouse at the Top of Trailside Village -Okemo Mountain
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
Located at the highest point in the popular Trailside Village at Okemo Mountain Resort, this 3-level four-bedroom end un ...
From $1540 per night (USD)
VRBO
$Peaceful mountain setting w\/private hot tub, 5 minutes to Okemo. Pet friendly!$
From $536 per night (USD)
Expedia
Peaceful mountain setting w\/private hot tub, 5 minutes to Okemo. Pet friendly!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
A lovely upscale 3 bedroom, 2 bathroom mountain home located 5 minutes from downtown Ludlow and Okemo Mountain Resort. ...
From $536 per night (USD)
Expedia
From $415 per night (USD)
VRBO
Spacious July 4th Getaway by Woodstock Killington
Bedrooms:
2
Bathrooms:
3
Sleeps:
11
WELCOME to this charming Vermont family home, located just a stone's throw from the historic town of Woodstock, Vermont' ...
From $415 per night (USD)
VRBO
From $301 per night (USD)
Expedia
Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Experience the beauty of Vermont alongside modern comforts and premier amenities at this 3-bedroom, 2.5-bath vacation re ...
From $301 per night (USD)
Expedia
Click For Pricing
VRBO
Rockledge Farm country living
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Rockledge Farm is in a beautiful rural river valley overlooking fields and mountains, only about 15 scenic miles from Wo ...
Click For Pricing
VRBO
From $866 per night (USD)
Expedia
Luxury Vermont Vacation Rental: Private Hot Tub!
Bedrooms:
4
Bathrooms:
7
Sleeps:
12
Your mountain escape awaits at this spacious vacation home in West Windsor, VT! Adorned with wood paneling, cathedral ce ...
From $866 per night (USD)
Expedia
From $373 per night (USD)
VRBO
Stunning townhome with on-site golf, pools, ski trails, and fitness center
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Windsor Village 3E Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $373 per night (USD)
VRBO
From $447 per night (USD)
Expedia
Remodeled downtown home with private hot tub, grill, deck - dogs OK
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
The Greene House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $447 per night (USD)
Expedia
Click For Pricing
VRBO
Luxurious Home 11 miles from Killington and Okemo
Bedrooms:
4
Bathrooms:
4
Sleeps:
6
In historic Plymouth, VT, on our stunning 10+ acre property, this country farm retreat home is the ultimate getaway for ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Beautiful Cabins in the Mountains
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
These beautiful cabins are on a secluded property, that overlook the Vermont Green Mountains. Start your day with a refr ...
Click For Pricing
Expedia

Search Your Destination Now!

Windsor Area Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 1,000 Rentals