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 $202 per night (USD)
VRBO
Marsh Brook is a beautiful farmhouse located in the heart of the Green Mountains
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Marsh Brook is a beautiful farmhouse located in the heart of the Green Mountains in Central Vermont. It is surrounded by ...
From $202 per night (USD)
VRBO
From $374 per night (USD)
VRBO
Your Year-Round Mountain Escape in Ludlow—Just Minutes from Okemo
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Welcome to your perfect Vermont getaway! Located just 2.1 miles (a quick 5-minute drive) from Okemo Mountain’s main base ...
From $374 per night (USD)
VRBO
From $176 per night (USD)
VRBO
Sunset Cabin - your private romantic hideaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Your private woodlands retreat awaits. Nestled atop a beautiful 10 acre meadow with 25 acres of woods for you to enjoy; ...
From $176 per night (USD)
VRBO
From $569 per night (USD)
VRBO
On Okemo and steps Sachem trail!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
We are on the mountain and are perfect for a group of families that want have easy access to skiing. We're a short walk ...
From $569 per night (USD)
VRBO
From $441 per night (USD)
VRBO
Warm & inviting 4-bedroom home, open floor plan just steps to Okemo Mtn Resort
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Beautiful family friendly home on a "secluded" 1+ wooded acre lot with an open main floor plan that features a family ro ...
From $441 per night (USD)
VRBO
From $348 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 $348 per night (USD)
VRBO
From $741 per night (USD)
VRBO
Chic Cabin near Killington for Relaxing and Co-working
Bedrooms:
2
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 $741 per night (USD)
VRBO
From $551 per night (USD)
VRBO
Scenic South Woodstock, Vermont home
Bedrooms:
2
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 $551 per night (USD)
VRBO
From $255 per night (USD)
VRBO
Meadow View- 35 Acres outside your door
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Newly renovated in 2025! Meadow View is your home away from home. 35 acres at your fingertips including 2 trout ponds an ...
From $255 per night (USD)
VRBO
From $271 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 $271 per night (USD)
VRBO
From $494 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 $494 per night (USD)
VRBO
From $163 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 $163 per night (USD)
VRBO
From $322 per night (USD)
VRBO
Charming and Chic Vacation Rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This beautiful newly renovated apartment is conveniently located adjacent to historic Tribou Park. It is walking distan ...
From $322 per night (USD)
VRBO
$LAKESIDE LIVING\nFire Pit, Canoes, Kayaks on site. Close to many historical sites$
From $651 per night (USD)
VRBO
LAKESIDE LIVING\nFire Pit, Canoes, Kayaks on site. Close to many historical sites
Bedrooms:
2
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 $651 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 $177 per night (USD)
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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 $177 per night (USD)
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From $484 per night (USD)
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PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
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 $484 per night (USD)
VRBO
From $1304 per night (USD)
Expedia
Renovated Luxury 4 Bedroom 3.5 Bath Okemo Trailside
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Recently Renovated to the highest standing, this luxurious condo has an additional (3rd) family bathroom downstairs maki ...
From $1304 per night (USD)
Expedia
From $865 per night (USD)
VRBO
OKEMO VACATION HOUSE, HOT TUB, CENTRAL AIR 6 Bdrm (2 K, 3 Q, 1 bunk), sleeps 14
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
ATTENTION BOAT, GOLF, AND CYCLING ENTHUSIASTS, NOW WITH CENTRAL AIR FOR YEAR ROUND ENJOYMENT!! This gorgeous Lindal Ced ...
From $865 per night (USD)
VRBO
From $170 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 $170 per night (USD)
VRBO
From $549 per night (USD)
VRBO
Quechee: Fantastic Four Bedroom Home Close to Club
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Wonderful Quechee location, space and views close to Club! Renovated 4 bedroom, 3 bath cape style home on 5+ open acres ...
From $549 per night (USD)
VRBO
From $1016 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 $1016 per night (USD)
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From $433 per night (USD)
VRBO
Log Cabin home with Mt Ascutney views and pool table
Bedrooms:
4
Bathrooms:
4
Sleeps:
14
This home is located on the slopes of Mt. Ascutney, within walking distance from Mt. Ascutney Resort, the hotel, restaur ...
From $433 per night (USD)
VRBO
From $1745 per night (USD)
VRBO
Ski on/Ski off. Right on Sachem Trail. Okemo Trailside. 4bed/2bath. Sleeps 8.
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 $1745 per night (USD)
VRBO
From $352 per night (USD)
VRBO
Beautiful Vacation Home with Spectacular Views
Bedrooms:
2
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 $352 per night (USD)
VRBO
From $840 per night (USD)
VRBO
Killington Region - Sleeps 19!
Bedrooms:
5
Bathrooms:
7
Sleeps:
19
This historic 1840’s house has undergone a COMPLETE gut renovation and combines modern amenities with streamlined countr ...
From $840 per night (USD)
VRBO
From $1064 per night (USD)
VRBO
OKEMO SKI IN/OUT. WALK TO Solitude Lifts, Pool/Hottubs,bar,free e-car charging
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
WINTER 24-25 SKI SEASON!! Solitude and Jackson Gore lifts OPEN. 43' North Open! Solitude Pool/Hottubs open!! Our cal ...
From $1064 per night (USD)
VRBO
From $458 per night (USD)
VRBO
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
We are a licensed lodging facility in Vermont and you can find us by searching our farm name. Promotions, discounts, or ...
From $458 per night (USD)
VRBO
From $521 per night (USD)
VRBO
Beautiful Modern Cabin on a Vermont Farm - Stunning Panoramic Views!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
We are a licensed lodging facility in Vermont and you can find us by searching our farm name. Promotions, discounts, or ...
From $521 per night (USD)
VRBO
From $571 per night (USD)
Expedia
Beautiful Historic Country Estate – Modern Comfort in Okemo Valley
Bedrooms:
3
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 $571 per night (USD)
Expedia
From $313 per night (USD)
VRBO
Ski, hike, swim or relax with family & friends in this nature lovers delight!
Bedrooms:
1
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 $313 per night (USD)
VRBO
From $304 per night (USD)
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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 $304 per night (USD)
VRBO
From $323 per night (USD)
VRBO
Spring Sale- Okemo- hike, kayak, golf, repeat! Enjoy this newly renovated 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 $323 per night (USD)
VRBO
$\The Crooked House\ with A/C and sauna on private wooded lot near Killington$
From $317 per night (USD)
VRBO
\"The Crooked House\" with A/C and sauna on private wooded lot near Killington
Bedrooms:
2
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 $317 per night (USD)
VRBO
From $462 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 $462 per night (USD)
VRBO
From $343 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 $343 per night (USD)
VRBO
From $555 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 $555 per night (USD)
VRBO
From $399 per night (USD)
Expedia
Sunlit VT Country Home w/Hot Tub. Ideal location near Woodstock village
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Dana Road House, a welcoming 3BR/2BA Vermont country home with hot tub, king master suite & chef's kitchen! Ideally loca ...
From $399 per night (USD)
Expedia
From $277 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 $277 per night (USD)
VRBO
From $869 per night (USD)
VRBO
Peaceful private escape in our spacious 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 6 bedroom home in Quechee, Vermont! A peaceful ...
From $869 per night (USD)
VRBO
From $406 per night (USD)
VRBO
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
We are a licensed lodging facility in Vermont and you can find us by searching our farm name. Promotions, discounts, or ...
From $406 per night (USD)
VRBO
From $722 per night (USD)
VRBO
Great Location, Large Hot Tub, Wet Bar, Pool Table, Gas FP
Bedrooms:
4
Bathrooms:
5
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 $722 per night (USD)
VRBO
From $1923 per night (USD)
VRBO
Custom Luxury Home w/Hot Tub on Okemo Mtn/Family/Group Friendly/Shuttle Bus
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
Beautiful custom-designed, spacious ski home ideal for relaxing, entertaining, cooking. Upper level sanctuary includes t ...
From $1923 per night (USD)
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From $1144 per night (USD)
VRBO
Ludlow Vermont Ski House
Bedrooms:
2
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 $1144 per night (USD)
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From $273 per night (USD)
VRBO
1794 Pioneer House - Renovated, No Cleaning Fee
Bedrooms:
1
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 $273 per night (USD)
VRBO
From $470 per night (USD)
VRBO
Spacious, Updated Lake House Near Okemo Ski Area
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
This newly-renovated year round waterfront home is located on a quiet cove with 100 feet of lake frontage. The home offe ...
From $470 per night (USD)
VRBO
From $457 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 $457 per night (USD)
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From $603 per night (USD)
VRBO
Dramatic Design & Landscape 3500 Sq Ft. Farmhouse W/Jacuzzi&Swim Pond&CentralAC!
Bedrooms:
3
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 $603 per night (USD)
VRBO
From $264 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 $264 per night (USD)
VRBO
From $734 per night (USD)
VRBO
Stunning Ski and Lake home - ideal family or friend getaway
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
*** Contact marionburch@icloud.com for current specials. This gorgeous 2,800 SF home is located right on the water (Lak ...
From $734 per night (USD)
VRBO
From $402 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 $402 per night (USD)
VRBO
From $381 per night (USD)
Expedia
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 $381 per night (USD)
Expedia
From $312 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 $312 per night (USD)
VRBO
From $617 per night (USD)
VRBO
Wood-Burning Stove, Great for Families | Z1040*
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Summary: Exquisite four bedroom, four bath single family home located within one mile to the Quechee Club and amenities. ...
From $617 per night (USD)
VRBO
From $318 per night (USD)
VRBO
Golf, Lake Pinneo & The Club | Windsor Village 4A
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Enjoy convenience, comfort, and a terrific view from this stylishly decorated two-bedroom, 1.5-bath townhome (e ...
From $318 per night (USD)
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From $291 per night (USD)
VRBO
New Lakeside Cottage near Okemo and Killington
Bedrooms:
2
Bathrooms:
2
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
From $4341 per night (USD)
VRBO
Reading Farms Estate
Bedrooms:
13
Bathrooms:
15
Sleeps:
46
** 2026 season 1 week stay special pricing $19,750** please inquire **.Reading Farms Estate is an elevated lifesty ...
From $4341 per night (USD)
VRBO
From $225 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 $225 per night (USD)
VRBO
From $431 per night (USD)
VRBO
Songbird Haven–majestic VT Timberframe, Dog-Friendly Home Along The White River
Bedrooms:
3
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 $431 per night (USD)
VRBO
From $169 per night (USD)
VRBO
Clean, Updated, & Well Appointed-Family & Dog Friendly Rental
Bedrooms:
2
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 $169 per night (USD)
VRBO
From $361 per night (USD)
VRBO
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This exceptionally nice, renovated converted carriage house sits on a private 280 acre estate 2 miles from downtown Wood ...
From $361 per night (USD)
VRBO
From $152 per night (USD)
Expedia
107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool
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 $152 per night (USD)
Expedia
From $216 per night (USD)
VRBO
109 Deluxe One bedroom Queen Suite on the 1st floor w/ outdoor heated pool
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 $216 per night (USD)
VRBO
From $157 per night (USD)
Expedia
Queen Studio on the 2nd floor with outdoor heated pool 207
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 $157 per night (USD)
Expedia
From $246 per night (USD)
VRBO
Cedarbrook Junior Suite 11416
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 $246 per night (USD)
VRBO
From $192 per night (USD)
Expedia
Deluxe One bedroom Queen Suite with outdoor heated pool 203
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 $192 per night (USD)
Expedia
From $217 per night (USD)
VRBO
Deluxe one bedroom suite located on first floor with outdoor heated pool 11517
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Cedarbrook – Your Year-Round Mountain Escape. Tucked in the heart of Vermont's Green Mountains, Cedarbrook of ...
From $217 per night (USD)
VRBO
From $157 per night (USD)
Expedia
Cozy Studio Condo with Great Location, WiFi & Kitchenette
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Sweet Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $157 per night (USD)
Expedia
From $140 per night (USD)
VRBO
Efficient condo near slopes with kitchenette & great location
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Ludlow Lax Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $140 per night (USD)
VRBO
From $135 per night (USD)
Expedia
Riverfront studio with river view, full kitchen, & free WiFi
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Vermont Farm Studio Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $135 per night (USD)
Expedia
From $208 per night (USD)
VRBO
Woodstock Suite | 10 Min to Mountains |A/C| Hiking
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 $208 per night (USD)
VRBO
From $423 per night (USD)
Expedia
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 $423 per night (USD)
Expedia
From $156 per night (USD)
VRBO
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Bedrooms:
0
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 $209 per night (USD)
Expedia
Ben & Jerry Suite | Minutes to Woodstock | Hiking
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 $209 per night (USD)
Expedia
From $237 per night (USD)
VRBO
2 Queens | 10 Mins to the Mountains | A/C | Hiking
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 $237 per night (USD)
VRBO
From $1590 per night (USD)
Expedia
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 $1590 per night (USD)
Expedia
From $1103 per night (USD)
VRBO
Scenic 7-BR Luxury Estate 7-Min to Okemo
Bedrooms:
5
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 $1103 per night (USD)
VRBO
From $467 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 $467 per night (USD)
Expedia
From $413 per night (USD)
VRBO
Ski-in/out mountainside condo with pool, hot tub, game room & washer/dryer
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
The Bear Den - Solitude Village J202 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $413 per night (USD)
VRBO
From $194 per night (USD)
Expedia
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Tiny Homes on Pleasant Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $194 per night (USD)
Expedia
From $309 per night (USD)
VRBO
Hartford Escape w/ Fire Pit ~ 3 Mi to Ski & Golf!
Bedrooms:
1
Bathrooms:
2
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 $309 per night (USD)
VRBO
From $1960 per night (USD)
Expedia
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)
Expedia
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VRBO
Dog-friendly, 2-story condo at the base of Ascutney with fireplace & balcony
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Mountain's Edge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
Click For Pricing
VRBO
From $363 per night (USD)
Expedia
Three-story, ski-in/out condo with mountain view - dog-friendly
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Sachem Slopeside - Okemo Trailside 21B Our calendar is updated in real-time & our nightly rates are accurately displaye ...
From $363 per night (USD)
Expedia
From $556 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 $556 per night (USD)
VRBO
From $451 per night (USD)
Expedia
The Bridgewater House | Game Room | Hiking | Porch
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: Welcome to the historic Bridgewater House, a 2,000 sq ft home that sleeps up to 8. With a spacious kitchen, liv ...
From $451 per night (USD)
Expedia
From $997 per night (USD)
VRBO
Walk to Ski Trails: Ludlow Home on Okemo Mountain!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Dog Friendly w/ Fee | Walk to Ski Trails | Mountain Views | Fireplace Ensure your ski trip goes off without a hitch at ...
From $997 per night (USD)
VRBO
From $674 per night (USD)
Expedia
Log cabin on Macintosh Pond access to VAST trail system snowmobile trails.
Bedrooms:
4
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 $674 per night (USD)
Expedia
From $301 per night (USD)
VRBO
Andover Cabin Retreat w/ Hot Tub & Fireplace!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Enjoy a peaceful Vermont escape at this charming Andover home. This 3-bedroom, 1-bathroom vacation rental boasts an invi ...
From $301 per night (USD)
VRBO
From $477 per night (USD)
Expedia
Inviting Vermont Home On Mount Ascutney!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bundle up for alpine activities or curl up and get cozy at this 3-bedroom, 2-bath home. Situated just a short walk from ...
From $477 per night (USD)
Expedia
From $357 per night (USD)
VRBO
3 bdrm Stillwater Farmhouse near 4 ski resorts
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Have you ever wanted to live back in the 1800s in an old farmhouse on 30 acres? We did! Here’s your chance! This is our ...
From $357 per night (USD)
VRBO
From $199 per night (USD)
Expedia
Okemo | Spacious Executive Room w Amenities Nearby
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in a picturesque studio condo that offers a seamless blend of convenience and elegance, providing an idyllic retr ...
From $199 per night (USD)
Expedia
From $249 per night (USD)
VRBO
Okemo | Charming Room & Amenities Nearby | Pools
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Step into a charming room for 4, where convenience meets beauty to create the ultimate getaway. Indulge in the nearby am ...
From $249 per night (USD)
VRBO
From $675 per night (USD)
Expedia
Log manor on 65 private acres of land with entertaining amenities & hot tub
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Spruce Moose Lodge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $675 per night (USD)
Expedia
From $264 per night (USD)
VRBO
Okemo's Jackson Gore-1 Bedroom Condo /Direct Ski Access. Walk to Pool & hot tubs
Bedrooms:
2
Bathrooms:
1
Sleeps:
6
Luxury one bedroom condo with kitchen and living room at Jackson Gore on Okemo Mountain Resort. STEPS TO THE OKEMO SKI ...
From $264 per night (USD)
VRBO
Click For Pricing
Expedia
Sunny 1850 farm house and pond
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Close to the towns of Norwich (VT) and Hanover (NH) our house is peaceful, spacious and cozy. It's south facing with a b ...
Click For Pricing
Expedia
From $499 per night (USD)
VRBO
Farmhouse w/ mountain views close to skiing. Includes outdoor sauna EV CHRGR
Bedrooms:
2
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 $499 per night (USD)
VRBO
From $644 per night (USD)
VRBO
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 $644 per night (USD)
VRBO
From $354 per night (USD)
VRBO
3-story dog-friendly home with private hot tub, firepit, grill, wood stove, EVC
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Spacious Mountain Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $354 per night (USD)
VRBO
From $651 per night (USD)
Expedia
17-Acre Vermont Escape w/ Panoramic Mountain Views
Bedrooms:
2
Bathrooms:
6
Sleeps:
14
Built in 1892, this classic yet modern Cavendish vacation rental exudes old-world charm and elegance! Every window in th ...
From $651 per night (USD)
Expedia

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