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 $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 $364 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 $364 per night (USD)
VRBO
From $868 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 $868 per night (USD)
VRBO
From $358 per night (USD)
Expedia
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 $358 per night (USD)
Expedia
From $455 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 $455 per night (USD)
VRBO
From $466 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 $466 per night (USD)
VRBO
From $358 per night (USD)
VRBO
Leaf Peeping Flash Sale! 10 out of 10! Come 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 $358 per night (USD)
VRBO
$\The Crooked House\ with A/C and sauna on private wooded lot near Killington$
From $332 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 $332 per night (USD)
VRBO
From $517 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 $517 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 $568 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 $568 per night (USD)
VRBO
From $442 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 $442 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 $867 per night (USD)
VRBO
Peaceful & Private 6-Bedroom Retreat in Scenic Quechee, Vermont
Bedrooms:
3
Bathrooms:
6
Sleeps:
8
Welcome to your perfect Vermont getaway! Nestled in the heart of nature, escape to our warm and inviting 6-bedroom home ...
From $867 per night (USD)
VRBO
From $401 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 $401 per night (USD)
VRBO
From $734 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 $734 per night (USD)
VRBO
From $2003 per night (USD)
VRBO
Custom Luxury Home w/Hot Tub on Okemo Mtn/Family/Group Friendly/Shuttle Bus
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Beautiful custom-designed, spacious ski home ideal for relaxing, entertaining, cooking. Upper level sanctuary includes t ...
From $2003 per night (USD)
VRBO
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)
VRBO
From $271 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 $271 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 $531 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 $531 per night (USD)
VRBO
From $777 per night (USD)
VRBO
Luxury Farmhouse Retreat with Jacuzzi, Skate/Swim Pond & AC!
Bedrooms:
3
Bathrooms:
7
Sleeps:
28
“You won’t find another vacation rental with this quality, design & natural beauty. If you’re tired of bunk-bed ski hous ...
From $777 per night (USD)
VRBO
From $484 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 $484 per night (USD)
VRBO
From $920 per night (USD)
VRBO
Stunning Ski and Lake home - ideal family or friend getaway
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
*** Contact simonsburch@hotmail.com for current specials. This gorgeous 2,800 SF home is located right on the water (La ...
From $920 per night (USD)
VRBO
From $406 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 $406 per night (USD)
VRBO
From $531 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 $531 per night (USD)
VRBO
From $320 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 $320 per night (USD)
VRBO
From $570 per night (USD)
VRBO
Wood-Burning Stove, Great for Families - Z1040*
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: Exquisite four bedroom, four bath single family home located within one mile to the Quechee Club and amenities. ...
From $570 per night (USD)
VRBO
From $320 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 $320 per night (USD)
VRBO
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 $4261 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 $4261 per night (USD)
VRBO
From $175 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 $175 per night (USD)
VRBO
From $448 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 $448 per night (USD)
VRBO
From $188 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 $188 per night (USD)
VRBO
From $393 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 $393 per night (USD)
VRBO
From $170 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 $170 per night (USD)
Expedia
From $250 per night (USD)
VRBO
109 Deluxe One bedroom Queen Suite on the 1st floor w/ outdoor heated pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cedarbrook is tucked into Vermont s Green Mountains, right in the middle of the action. You re only a mile from the Kill ...
From $250 per night (USD)
VRBO
From $170 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 $170 per night (USD)
Expedia
From $228 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 $228 per night (USD)
VRBO
From $230 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 $230 per night (USD)
Expedia
From $228 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 $228 per night (USD)
VRBO
From $216 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 $216 per night (USD)
Expedia
From $210 per night (USD)
VRBO
Efficient condo near slopes with kitchenette & great location
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Ludlow Lax Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $210 per night (USD)
VRBO
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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 ...
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Expedia
From $397 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 $397 per night (USD)
VRBO
From $519 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 $519 per night (USD)
Expedia
From $1484 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 $1484 per night (USD)
VRBO
From $353 per night (USD)
Expedia
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 $353 per night (USD)
Expedia
From $260 per night (USD)
VRBO
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 $260 per night (USD)
VRBO
From $301 per night (USD)
Expedia
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 $301 per night (USD)
Expedia
From $426 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 $426 per night (USD)
VRBO
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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 ...
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Expedia
From $367 per night (USD)
VRBO
Beautiful ski in-ski out condo at Okemo Mountain
Bedrooms:
1
Bathrooms:
1
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 $367 per night (USD)
VRBO
From $627 per night (USD)
Expedia
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 $627 per night (USD)
Expedia
From $668 per night (USD)
VRBO
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 $668 per night (USD)
VRBO
From $297 per night (USD)
Expedia
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 $297 per night (USD)
Expedia
From $785 per night (USD)
VRBO
Waterfront retreat with dock, sauna, & firepit - near Woodstock & ski areas
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Turtle Grove Lakehouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $785 per night (USD)
VRBO
From $446 per night (USD)
Expedia
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 $446 per night (USD)
Expedia
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VRBO
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 ...
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VRBO
From $605 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 $605 per night (USD)
Expedia
From $1002 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 $1002 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 $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 $264 per night (USD)
Expedia
2 Queens | 10 Mins to the Mountains | Foliage
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 $264 per night (USD)
Expedia
From $1590 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 $1590 per night (USD)
VRBO
From $310 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 $310 per night (USD)
VRBO
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
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Expedia
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 ...
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Expedia
From $732 per night (USD)
VRBO
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 $732 per night (USD)
VRBO
From $498 per night (USD)
Expedia
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 $498 per night (USD)
Expedia
From $341 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 $341 per night (USD)
VRBO
From $511 per night (USD)
VRBO
Inviting Vermont Home On Mount Ascutney!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Whether you're bundling up for alpine adventures or unwinding in style, this freshly updated 3-bed, 2-bath Windsor retre ...
From $511 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 $317 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 $317 per night (USD)
Expedia
From $353 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 $353 per night (USD)
VRBO
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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 ...
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Expedia
From $249 per night (USD)
VRBO
Updated Main St Condo in downtown Ludlow!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
First floor unit located on Main St. Easily take a stroll through the town. Short walk to restaurants and shops. On Okem ...
From $249 per night (USD)
VRBO
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Expedia
Main St Studio - Newly Updated!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy easy access to everything from this perfectly located home base, right on Main St. Take a stroll through the town ...
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Expedia
From $560 per night (USD)
VRBO
Charming Okemo Home: Hot Tub, Fireplace, Sleeps 9
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Summary: Experience Ludlow's enchanting charm at this inviting home! Unwind in the private hot tub, gather by the wood-b ...
From $560 per night (USD)
VRBO
From $432 per night (USD)
Expedia
Charming condo in a resort community with pool access, tennis, a sauna & golf
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Lakeland Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $432 per night (USD)
Expedia
From $565 per night (USD)
VRBO
Inviting three-story condo with decks - near the Quechee Club
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Sugar Hill Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $565 per night (USD)
VRBO
From $713 per night (USD)
Expedia
3-BR Winterplace Ski-In/Out Okemo Condo w/ Loft
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: Embrace the tranquility of Okemo Mountain in this charming 3-BR ski-in/out loft. Featuring three bedrooms, two ...
From $713 per night (USD)
Expedia
From $812 per night (USD)
VRBO
Okemo Ski-In/Ski-Out: Modern, Cozy 2-BR Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: We are excited to share this newly renovated slopeside condominium in Kettlebrook Village on Okemo Mountain! Th ...
From $812 per night (USD)
VRBO
From $168 per night (USD)
Expedia
The Creek Cabin at Sky Hollow, The Creek Cabin at Sky Hollow
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cozy cabin located in the woods by a creek on a quiet hilltop farm. Ideal for a relaxing retreat or a couples getaway. S ...
From $168 per night (USD)
Expedia
From $113 per night (USD)
VRBO
The Pond Cabin at Sky Hollow, The Hunter Cabin at Sky Hollow
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Welcome to our beautiful 120 acre homestead! The pond cabin is the perfect serene and private getaway. Enjoy a cup of co ...
From $113 per night (USD)
VRBO
From $123 per night (USD)
Expedia
The Apartment at Sky Hollow, The Apartment at Sky Hollow
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A charming one bedroom apartment attached to the main farm house, the guest suite at Sky Hollow Farm boasts stunning mou ...
From $123 per night (USD)
Expedia
From $178 per night (USD)
VRBO
The Guest House at Sky Hollow, The Guest House at Sky Hollow
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Quiet hilltop house on an 1800's farm at the end of a dirt road offering high speed internet, direct access to miles of ...
From $178 per night (USD)
VRBO
From $238 per night (USD)
Expedia
Red Barn Cabin
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Our cozy modern cabin is anything but ordinary, nestled amidst the pastoral landscapes of Brownsville, Vermont. Moments ...
From $238 per night (USD)
Expedia
Click For Pricing
VRBO
Slopeside 4-BR Lodge At The Base of Okemo Mountain
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Summary: Nestled at the base of Okemo Mountain's iconic clock tower, this slopeside retreat offers four bedrooms and fou ...
Click For Pricing
VRBO
From $566 per night (USD)
VRBO
Peaceful Cavendish Retreat w/ Hot Tub & Fireplace!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Discover the serenity of Cavendish and make lasting memories at this 3-bedroom, 2.5-bath vacation rental. Nestled in the ...
From $566 per night (USD)
VRBO
From $297 per night (USD)
VRBO
The Carol - 10 minutes to Okemo & Newly Renovated
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Carol — Charming, Historic & Renovated+ Sauna Access! A unique stay with a style all its own, just 10 minutes to Oke ...
From $297 per night (USD)
VRBO
From $401 per night (USD)
Expedia
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
At Sugar Maple Mountain Retreat our beautiful light-filled cabins are set deep in the woods and surrounded by hundreds o ...
From $401 per night (USD)
Expedia
From $858 per night (USD)
VRBO
Amazing Views and Sunsets in a fully remodeled VT home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Gather around the fireplace in the living room with massive wall to wall windows or relax on the second story deck under ...
From $858 per night (USD)
VRBO
From $445 per night (USD)
Expedia
Sprawling Riverbend Farmhouse Close to Mountains with Hot Tub
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Welcome to the Riverbend, a designer Southern Vermont farmhouse <10 minutes from Magic Mountain! This newly renovated hi ...
From $445 per night (USD)
Expedia
Click For Pricing
VRBO
Kettlebrook ski-in/out condo w/ a newly updated kitchen and fully renovated bath
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
• This ski in/out two bedroom/one bathroom condo is located in the Kettlebrook community on Okemo Mountain. This condo i ...
Click For Pricing
VRBO
From $129 per night (USD)
Expedia
Beautiful 3 Bedroom Condo in Ludlow VT
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Recently renovated 3 bedroom condo at Okemo Mountain in Ludlow, VT (4 hrs from NYC). Enjoy the green mountains and retr ...
From $129 per night (USD)
Expedia
From $386 per night (USD)
VRBO
Golf Views, Walk to Club - Lakeland Village 4B
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Summary: Explore the trails or hit the slopes during the day, and return to the comfort of your cozy retreat in the even ...
From $386 per night (USD)
VRBO
From $396 per night (USD)
Expedia
Ski-in/out, dog-friendly condo with prime location for skiing & hiking
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Ascutney Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $396 per night (USD)
Expedia
From $435 per night (USD)
VRBO
Charming farmhouse, dog friendly, Appalachian trail access
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Starry Plough Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $435 per night (USD)
VRBO
From $507 per night (USD)
Expedia
Mountain View 3-BR Retreat 10-Min to Okemo
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: Nestled in the serene landscape of Ludlow, Vermont, this charming mountain view 3-BR house offers the perfect r ...
From $507 per night (USD)
Expedia

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