Windsor Area Rentals
- From $85 per night (USD)
VRBO
149 upper cross unit A
- 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 $85 per night (USD)VRBO
- Click For Pricing
VRBO
Ludlow Vermont Ski Chalet
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Log construction chalet with plenty of room to relax. Large open air living room on the first floor, a brand new kitche ...
Click For PricingVRBO
- From $248 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 $248 per night (USD)VRBO
- From $453 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 $453 per night (USD)VRBO
- From $310 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 $310 per night (USD)VRBO
- From $626 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 $626 per night (USD)VRBO
- From $279 per night (USD)
VRBO
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 $279 per night (USD)VRBO
- From $177 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 $177 per night (USD)VRBO
- From $185 per night (USD)
VRBO
Relaxation Paradise
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Cozy mountain chalet. Perfect for the family to enjoy skiing, hiking, swimming. Located right between Killington and Sug ...
From $185 per night (USD)VRBO
- From $650 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 not open, but accepting online orders for next day pick up in the parking lot. Singletons in Proctorsville ...
From $650 per night (USD)VRBO
- From $360 per night (USD)
VRBO
Dog Friendly Home in S. Woodstock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
This comfortable, family-friendly home is on a quiet country road, very near boarding stables for horses. The house is ...
From $360 per night (USD)VRBO
- From $151 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 $151 per night (USD)VRBO
- From $425 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 $425 per night (USD)VRBO
- From $446 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 $446 per night (USD)Expedia
- From $752 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 $752 per night (USD)VRBO
- From $460 per night (USD)
Expedia
Fantastic Four Bedroom on 5+ Acres Close to Club with 180º Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Location, space and views close to Club! Nicely renovated 4 bedroom, 3 bath cape style home on 5+ open acres in fantast ...
From $460 per night (USD)Expedia
- From $363 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 $363 per night (USD)VRBO
- From $450 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 $450 per night (USD)VRBO
- From $245 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 $245 per night (USD)VRBO
- From $350 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 $350 per night (USD)VRBO
- From $89 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 $89 per night (USD)VRBO
- From $234 per night (USD)
VRBO
Charming and Chic Vacation Rental
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
This beautiful newly renovated apartment is conveniently located adjacent to historic Tribou Park. It is walking distan ...
From $234 per night (USD)VRBO
- From $585 per night (USD)
VRBO
Summer On The Lake - 5 minutes to Okemo\n
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
For family gatherings or a romantic getaway, this home has it all. Our house is an easy on easy off the main scenic road ...
From $585 per night (USD)VRBO
- Click For Pricing
VRBO
Vermont Country Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful country home on 9 picturesque acres on sought after Middletown Road in Andover, VT. Come enjoy the peace and ...
Click For PricingVRBO
- From $933 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 $933 per night (USD)VRBO
- From $1650 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 $1650 per night (USD)VRBO
- From $275 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 $275 per night (USD)VRBO
- From $867 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 $867 per night (USD)VRBO
- From $650 per night (USD)
VRBO
OKEMO SKI IN\/OUT and WALK TO Solitude Pool\/Hottubs, 43' North & coffee!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
WINTER 23-24 SKI SEASON!! Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $650 per night (USD)VRBO
- From $395 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 $395 per night (USD)VRBO
- From $418 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 $418 per night (USD)VRBO
- From $250 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 $250 per night (USD)VRBO
- From $180 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 $180 per night (USD)VRBO
- From $198 per night (USD)
VRBO
Flash sale! Come ski Okemo! 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 $198 per night (USD)VRBO
- From $303 per night (USD)
VRBO
Renovated Cabin Overlooking Waterfall and Pond
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cabin renovations completed in June, 2020. Many improvements are not yet captured in listing photographs. Fresh indoor ...
From $303 per night (USD)VRBO
- From $244 per night (USD)
VRBO
\"The Crooked House\" w\/ sauna on private wooded lot near Woodstock, Killington
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to the beautiful mountains of Vermont. Our four-season house is nestled on a mountainside located near Killington ...
From $244 per night (USD)VRBO
- From $428 per night (USD)
VRBO
Beautiful farmhouse minutes to Okemo. Spacious, hot tub. Weekend shuttle bus.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Quality furnishings in this spacious well-kept farmhouse minutes from Okemo base lodge. Comfortable living areas, large ...
From $428 per night (USD)VRBO
- From $450 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 $450 per night (USD)VRBO
- From $627 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 $627 per night (USD)VRBO
- From $990 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 $990 per night (USD)VRBO
- From $1000 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 $1000 per night (USD)VRBO
- From $244 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 $244 per night (USD)VRBO
- From $301 per night (USD)
VRBO
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 $301 per night (USD)VRBO
- From $217 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 $217 per night (USD)VRBO
- From $743 per night (USD)
VRBO
Warm and inviting 6 Bedroom Home in Quechee Vermont
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
Come relax and stay a while in our warm and inviting, recently renovated six bedroom home in Quechee, Vermont! Ideal for ...
From $743 per night (USD)VRBO
- From $350 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 $350 per night (USD)VRBO
- From $316 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 $316 per night (USD)VRBO
- From $305 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 $305 per night (USD)VRBO
- From $450 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 $450 per night (USD)VRBO
- From $654 per night (USD)
VRBO
Stunning Lakeside home - ideal family getaway or work from home spot
- Bedrooms:
- 3
- 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 $654 per night (USD)VRBO
- From $223 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 $223 per night (USD)VRBO
- From $246 per night (USD)
Expedia
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 $246 per night (USD)Expedia
- From $247 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 $247 per night (USD)VRBO
- From $330 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 $330 per night (USD)VRBO
- From $325 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 $325 per night (USD)VRBO
- From $675 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 $675 per night (USD)VRBO
- Click For Pricing
VRBO
Lake Rescue Chalet - 6-Bedroom Lake & Ski House with Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 12
Spring skiing is here & conditions are great! Reserve 2 or more nights til 4/15 for 25% off! Use code SPRING25. Lake R ...
Click For PricingVRBO
- From $210 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 $210 per night (USD)VRBO
- From $3569 per night (USD)
VRBO
Reading Farms Estate
- Bedrooms:
- 14
- Bathrooms:
- 15
- Sleeps:
- 46
Reading Farms Estate is an elevated lifestyle vacation property and lies in the heart of Vermont now an official ...
From $3569 per night (USD)VRBO
- From $222 per night (USD)
VRBO
IT'S FOLIAGE SEASON!
- 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 $222 per night (USD)VRBO
- From $325 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 $325 per night (USD)VRBO
- From $195 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 $195 per night (USD)VRBO
- From $410 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 $410 per night (USD)VRBO
- From $104 per night (USD)
Expedia
107 Deluxe Studio Queen, w\/ Sleeper sofa w\/ outdoor heated pool
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 4
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $104 per night (USD)Expedia
- From $132 per night (USD)
VRBO
109 Deluxe One bedroom Queen Suite on the 1st floor w\/ outdoor heated pool
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 4
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $132 per night (USD)VRBO
- From $104 per night (USD)
Expedia
Queen Studio on the 2nd floor with outdoor heated pool 207
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 4
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $104 per night (USD)Expedia
- From $116 per night (USD)
VRBO
Deluxe One bedroom Queen Suite with outdoor heated pool 203
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 4
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $116 per night (USD)VRBO
- From $147 per night (USD)
Expedia
Cedarbrook Junior Suite 11416
- Bedrooms:
- 2
- Bathrooms:
- 0
- Sleeps:
- 6
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $147 per night (USD)Expedia
- From $147 per night (USD)
VRBO
Deluxe one bedroom suite located on first floor with outdoor heated pool 11517
- Bedrooms:
- 2
- Bathrooms:
- 0
- Sleeps:
- 6
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $147 per night (USD)VRBO
- From $56 per night (USD)
Expedia
Cozy Studio Condo with Great Location, WiFi & Kitchenette
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 4
Sweet Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $56 per night (USD)Expedia
- From $324 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 $324 per night (USD)VRBO
- From $572 per night (USD)
Expedia
Modern 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 $572 per night (USD)Expedia
- From $1500 per night (USD)
VRBO
Hop on\/off Sachem trail! Townhouse just across parking lot from trail
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Family friendly! 3 floor townhouse just a quick walk across the parking lot from Sachem Trail. After a day of skiing r ...
From $1500 per night (USD)VRBO
- From $1012 per night (USD)
Expedia
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 $1012 per night (USD)Expedia
- From $171 per night (USD)
VRBO
Spacious dog-friendly home with two decks, fireplace, home office, pools & golf
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Decks and Dreams Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $171 per night (USD)VRBO
- Click For Pricing
Expedia
Beautiful home with fireplace, W\/D & AC - near Main Street & Simon Pearce
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Chester Arthur Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
Click For PricingExpedia
- From $213 per night (USD)
VRBO
Ski-in\/out mountainside condo with pool, hot tub, game room & washer\/dryer
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
The Bear Den - Solitude Village J202 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $213 per night (USD)VRBO
- From $96 per night (USD)
Expedia
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
- Bedrooms:
- 2
- Bathrooms:
- 0
- Sleeps:
- 4
Tiny Homes on Pleasant Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $96 per night (USD)Expedia
- From $86 per night (USD)
VRBO
10 min to Mountains | Queen Bed | Woodstock Suite
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Summary: Welcome to the Woodstock Suite @ The Bridgewater Inn! We're so excited to host you. Proximity is paramount and ...
From $86 per night (USD)VRBO
- Click For Pricing
VRBO
Largest Colonial Revival Mansion less than 15 minutes to Woodstock
- Bedrooms:
- 15
- Bathrooms:
- 15
- Sleeps:
- 32
Built in 1902 and comprehensively renovated in late 2016, the Windsor Mansion is an incredibly well preserved example of ...
Click For PricingVRBO
- From $183 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 $183 per night (USD)VRBO
- Click For Pricing
Expedia
Dog-friendly mountain-view home with private 7-person hot tub, fireplace, & deck
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Hardy-Silva Vermont Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
Click For PricingExpedia
- From $110 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 $110 per night (USD)VRBO
- From $80 per night (USD)
Expedia
Ben & Jerry Themed Suite | 10 Min to Killington
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Summary: Welcome to the Ben & Jerry's Suite @ The Bridgewater Inn! We're so excited to host you. Proximity is paramount ...
From $80 per night (USD)Expedia
- From $81 per night (USD)
VRBO
2 Queens | 10 Min to Mountains | Bridgewater Inn
- Bedrooms:
- 1
- Bathrooms:
- 0
- 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 $81 per night (USD)VRBO
- From $1350 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 $1350 per night (USD)Expedia
- Click For Pricing
Expedia
Briggs Ski House | Group Ski Fun | Newly Remodeled
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
The Briggs Ski House was originally built in 1905 as a two family home, but as of December 2022, it has been remodeled a ...
Click For PricingExpedia
- From $222 per night (USD)
Expedia
Cozy Hartford Escape w\/ Fire Pit, Near Golfing!
- Bedrooms:
- 2
- 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 $222 per night (USD)Expedia
- From $1700 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 $1700 per night (USD)VRBO
- From $52 per night (USD)
Expedia
Efficient condo near slopes with kitchenette & great location
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 4
Ludlow Lax Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $52 per night (USD)Expedia
- From $58 per night (USD)
VRBO
Riverfront studio with river view, full kitchen, & free WiFi
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 3
Vermont Farm Studio Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $58 per night (USD)VRBO
- From $486 per night (USD)
Expedia
Stunning Views in Ludlow Vermont Minutes to Okemo Resort
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summit Cabin in Ludlow - a SkyRun Vermont Property SkyRun Vermont prides itself in providing you the best experience d ...
From $486 per night (USD)Expedia
- From $238 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 $238 per night (USD)VRBO
- From $587 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 $587 per night (USD)Expedia
- From $131 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 $131 per night (USD)VRBO
- From $206 per night (USD)
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 ...
From $206 per night (USD)Expedia
- From $249 per night (USD)
VRBO
23-24 ski season is here! Beautiful ski In\/ski out condo at Okemo Mountain
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
2023-24 Ski Season is here, come enjoy this premier spot! A true ski in/ski out condo located at the base of the beautif ...
From $249 per night (USD)VRBO
- Click For Pricing
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 familes - can sleep 22. House is on Okemo Mount ...
Click For PricingVRBO
- Click For Pricing
Expedia
Modern mountain living with a hot tub, decks, fireplaces, & ski access - dogs ok
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The Red Roof Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
Click For PricingExpedia
- From $103 per night (USD)
Expedia
Ski-In\/Ski-Out Condo with Lift View, Fireplace & Shared Hot Tubs\/Pool\/Tennis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
The Great Escape - WP G104 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $103 per night (USD)Expedia