Windsor Area Rentals
- From $85 per night (USD)
VRBO
Cottage Across Street from the Lake w\/ 60' Water Frontage Access, Private Dock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Sweet Pauline Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $85 per night (USD)VRBO
- From $493 per night (USD)
Expedia
Ski-In\/Ski-Out Condo w\/ Pool & Seasonal Hot Tubs - Golf & Tennis Nearby
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Winterplace G101 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $493 per night (USD)Expedia
- From $424 per night (USD)
VRBO
Secluded Rustic Home with Private Hot Tub & Huge Deck - 5 Miles to Okemo
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Andover Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $424 per night (USD)VRBO
- From $193 per night (USD)
Expedia
Quaint lakefront home with a private deck, firepit, and dock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Ludlow's Gem Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $193 per night (USD)Expedia
- From $520 per night (USD)
VRBO
Ski-in \/Out. Spacious 2BR \/ 2.5B Ground-Floor Condo. 4 Seasons of enchantment.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Spacious 2 bedroom - 2.5 bathroom condominium is located on the sunny side of Okemo in SouthFace Village, the newest dev ...
From $520 per night (USD)VRBO
- From $220 per night (USD)
Expedia
Enjoy our ski in ski out condo. Located mid-mountain at Solitude Peak!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 7
Newly Renovated Professional Cleaners-Linens and towels laundered off site Remote Check-In Located mid-mountain at the b ...
From $220 per night (USD)Expedia
- From $371 per night (USD)
VRBO
Beautiful & Spacious Condo w\/ Pool, Lake Access - Close to Skiing
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Birch Landing #16 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $371 per night (USD)VRBO
- From $166 per night (USD)
Expedia
Quaint riverfront home between Killington & Okemo with fireplace - near skiing
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Easy Living Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $166 per night (USD)Expedia
- From $255 per night (USD)
VRBO
Charming Home with Huge Deck & Game Room - Minutes to Okemo, Dog Friendly
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
In The Trees Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $255 per night (USD)VRBO
- From $359 per night (USD)
Expedia
Great Winter Getaway, 1 mile from Okemo, in the village of Ludlow.
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 14
Village mountain home in the heart of Ludlow village. Short walk to restaurants, grocery store and shops, and nearby par ...
From $359 per night (USD)Expedia
- From $232 per night (USD)
VRBO
Log Home Perfect for a Family Getaway - Five Miles from Okemo Mountain Resort
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Sherman Log House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $232 per night (USD)VRBO
- From $57 per night (USD)
Expedia
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Okemo Trailside 8E Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $57 per night (USD)Expedia
- From $402 per night (USD)
VRBO
Charming Waterfront Getaway with Yard, Firepit, Dock, Kayaks - Close to Skiing
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Lakeside Elegance Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $402 per night (USD)VRBO
- From $378 per night (USD)
Expedia
Secluded Luxury Home on Huge Property with Mountain Views - Near Slopes
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Place of Peace and Quiet Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $378 per night (USD)Expedia
- From $209 per night (USD)
VRBO
Bright, Open Home with Wraparound Deck & Mountain Views - 2 Miles to Skiing
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
South Hill Lodge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $209 per night (USD)VRBO
- From $300 per night (USD)
Expedia
Fully Renovated Ski House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
A ski house nestled trailside on Plymouth Notch Ski Mountain. Take in the spectacular views while you cozy up by the woo ...
From $300 per night (USD)Expedia
- From $120 per night (USD)
VRBO
Cozy Quechee Corner Cabin
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Quechee Cabin- 4 Season Resort Townhouse nestled in a picturesque nature setting in historic Quechee Vermont: Hike, bik ...
From $120 per night (USD)VRBO
- From $450 per night (USD)
Expedia
Mountain-view condo near Sachem Trail with pool and fireplace - walk to lifts
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 16
Okemo Trailside 5B Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $450 per night (USD)Expedia
- From $210 per night (USD)
VRBO
Dog-friendly mountain view home near Okemo & Killington with washer\/dryer
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Rivendell Home at Hawk Mountain Our calendar is updated in real-time & our nightly rates are accurately displayed. Simp ...
From $210 per night (USD)VRBO
- From $200 per night (USD)
Expedia
Cheerful residential home with lots of space
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Completely renovated spacious home, about 20 minutes from Okemo Mountain! 3 bedrooms, 2 1/2 bathrooms, pool table, air h ...
From $200 per night (USD)Expedia
- From $376 per night (USD)
VRBO
Upscale VT Getaway by Slopes, Lakes & Trails!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Surrounded by lakes and mountains, 'Antler House' offers easy access to year-round adventures along one of VT's most sce ...
From $376 per night (USD)VRBO
- From $202 per night (USD)
Expedia
Custom-built Tiny House on forested lot near Quechee
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This custom-built tiny house is on a two-acre forested lot, is eco-friendly, powered by solar energy, and includes a car ...
From $202 per night (USD)Expedia
- From $272 per night (USD)
VRBO
Cozy, waterfront house w\/ a deck, lake views, & a private hot tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Hall's Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $272 per night (USD)VRBO
- From $360 per night (USD)
Expedia
Okemo Modern Mountain Escape - 5 bedroom, 3 bathroom house
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
The house is tucked away off the main street in Ludlow, VT and just 1 mile away from the entrance to Okemo Mountain Reso ...
From $360 per night (USD)Expedia
- From $240 per night (USD)
VRBO
1820 Federal Style Home located on the beautiful Black River
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This spacious home will accommodate ten people comfortably. It is located within 20 minutes from Okemo Ski Resort. There ...
From $240 per night (USD)VRBO
- From $299 per night (USD)
Expedia
Log cabin near Okemo \/ Ludlow on 25 acres borders state forest w\/trails nearby
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful hilltop cabin on 25 private acres bordering the William's River State Forest. Relax at this private retreat o ...
From $299 per night (USD)Expedia
- From $70 per night (USD)
VRBO
Okemo Slopeside Ski-in\/ Ski-Out Condo - 30 Day Stay
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Seasonal Rentals Only (90 day minimum). Please message host for winter season. Great view of Okemo Mountain with conve ...
From $70 per night (USD)VRBO
- Click For Pricing
Expedia
Amazing family friendly 3+ Bedroom, 3 Full Bath in Quechee
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
If you are looking for a spacious stand-alone home with a wrap-around porch set in a picturesque VT setting, this is it! ...
Click For PricingExpedia
- From $247 per night (USD)
VRBO
Sweet Life - Vermont Chalet - 6 person Indoor Hot Tub - 15 min to Killington
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This cozy ski Chalet home sleeps up to 12 people- an unbeatable choice for a ski trip with friends or family for a memor ...
From $247 per night (USD)VRBO
- From $236 per night (USD)
Expedia
Hakuna Matata - 10 Minutes to Killington Lifts
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
"Hakuna Matata" means "no worries for the rest of your vacation." You and your pets can experience this at one of the be ...
From $236 per night (USD)Expedia
- From $801 per night (USD)
VRBO
Bear-Foot Lodge Killington, Private! Sauna\/Gameroom. Perfect for Large Groups!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Come enjoy the stunning scenery of Vermont's countryside while you relax in this gorgeous 5,000 sq ft. lodge. This year- ...
From $801 per night (USD)VRBO
- From $150 per night (USD)
Expedia
SPACIOUS VICTORIAN FARMHOUSE- 20 MIN TO OKEMO
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
OVERVIEW Our historic 1868 'Elm House' is located in the picturesque town of Chester, nestled in the heart of Chester De ...
From $150 per night (USD)Expedia
- From $400 per night (USD)
VRBO
Castle Hill Resort Condo (with on-site Aveda Spa)
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome home! This charming 1500 square foot 3 bedroom condo at the historical Castle Hill Resort and Spa, has everythin ...
From $400 per night (USD)VRBO
- From $630 per night (USD)
Expedia
Nine Bedroom, pet friendly Located between Okemo and Killington with a hot tub Chestnut Farm
- Bedrooms:
- 3
- Bathrooms:
- 9
- Sleeps:
- 15
Located on Route 100 between Okemo Ski Area and Killington Ski Area in President Calvin Coolidge`s hometown of Plymouth, ...
From $630 per night (USD)Expedia
- From $135 per night (USD)
VRBO
Romantic Riverside Getaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Romantic Riverside Getaway. Located in the heart of Ludlow, this 1 Bedroom 1 Bath with sofa bed condo sleeps 4. Have cof ...
From $135 per night (USD)VRBO
- From $635 per night (USD)
Expedia
Luxury Alpine Retreat: A Premier Lodge Experience Near Dartmouth & Woodstock
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Discover the epitome of luxury and adventure at our exclusive summer and ski lodge, nestled within a serene landscape th ...
From $635 per night (USD)Expedia
- From $150 per night (USD)
VRBO
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
This is a secluded mountainside retreat. Perfect for a getaway for two and room enough for 4 it is located on eleven pri ...
From $150 per night (USD)VRBO
- From $226 per night (USD)
Expedia
Beautiful home offering privacy on 7 acres with private pond
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Peaceful home in Vermont’s Upper Valley. This is a beautiful three BR, two BA home offering privacy and relaxation on 7 ...
From $226 per night (USD)Expedia
- From $147 per night (USD)
VRBO
Deluxe one bedroom suite located on 2nd floor with outdoor heated pool 21820
- Bedrooms:
- 2
- Bathrooms:
- 1
- 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 $147 per night (USD)
Expedia
Deluxe one bedroom suite located on 2nd floor with outdoor heated pool 21921
- Bedrooms:
- 2
- Bathrooms:
- 1
- 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 2nd floor with outdoor heated pool 21517
- Bedrooms:
- 2
- Bathrooms:
- 1
- 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 $195 per night (USD)
Expedia
Updated Village Victorian on Ski Shuttle, walk to all amenties in town!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
New to market, freshly renovated Ski Village Victorian with 4 bedrooms directly on Okemo shuttle route. Enjoy the old ...
From $195 per night (USD)Expedia
- From $115 per night (USD)
VRBO
Ludlow Village Guest House - prime location on ski shuttle, walk to restaurants
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Renovated one bedroom guest cottage in Ludlow, Vermont. Prime ski location, 12 houses down from the Mountain Road entr ...
From $115 per night (USD)VRBO
- From $128 per night (USD)
Expedia
1868 CARRIAGE HOUSE-QUAINT + COZY -PERFECT ESCAPE-20 MIN TO OKEMO!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Our Carriage House is less than a mile to charming Chester Village-enjoy quaint restaurants and taverns, antique shops, ...
From $128 per night (USD)Expedia
- From $357 per night (USD)
VRBO
Ski-in\/ski-out condo with WiFi, gas fireplace, and private washer\/dryer
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Tamarack 12 Archies at SouthFace Our calendar is updated in real-time & our nightly rates are accurately displayed. Sim ...
From $357 per night (USD)VRBO
- From $230 per night (USD)
Expedia
Cottage in Barnard
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Charming Vermont cottage, just up the road from Silver Lake and the Barnard General Store. Bright, warm, and welcoming, ...
From $230 per night (USD)Expedia
- From $223 per night (USD)
VRBO
Modern Home Close to Okemo w\/Private Hot Tub, Pool Table, and Free WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
The Foxhole Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $223 per night (USD)VRBO
- Click For Pricing
Expedia
Cozy & Bright Log Cabin just 8 minutes from Okemo Mountain
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Come enjoy an authentic log cabin with acres of private land located just 8 minutes from Okemo mountain. Our home sleeps ...
Click For PricingExpedia
- From $250 per night (USD)
VRBO
Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Sportsman themed, real log cabin that has comfortable wood stove & hearth, plus backup regular heat. Bathroom with show ...
From $250 per night (USD)VRBO
- From $293 per night (USD)
Expedia
Remodeled condo with shared washer\/dryer - walk to dining & ski lift bus pickup
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Seatoller Unit C Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $293 per night (USD)Expedia
- From $243 per night (USD)
VRBO
First-floor condo with shared laundry - steps to ski bus pickup, walk to dining
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Aspatria Unit A Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $243 per night (USD)VRBO
- From $111 per night (USD)
Expedia
Hawks Mountain Farm, full apartment on a working farm.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Hello and welcome to Hawks Mountain Farm, a working farm with gardens, chickens, two yaks, four donkeys and an 1820 farm ...
From $111 per night (USD)Expedia
- From $680 per night (USD)
VRBO
Heavenly Lakeside Country House Close to Ski Areas w\/ Sauna
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Perched on the edge of pristine Silver Lake, my country home sits on a large rolling lot overlooking the lake enjoyed by ...
From $680 per night (USD)VRBO
- From $359 per night (USD)
Expedia
Okemo LARGE home.few ski dates left at discount.Book summer adventure now! Lakes
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 11
Welcome to a relaxing vacation, right in the heart of the OKEMO Valley with convenient access to major routes and only 3 ...
From $359 per night (USD)Expedia
- From $258 per night (USD)
VRBO
Chester Home w\/ Views ~10 Mi to Okemo Mtn Resort!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Rest, relax, and enjoy the tranquil surroundings when you visit this vacation rental home in Chester, Vermont! The stunn ...
From $258 per night (USD)VRBO
- From $176 per night (USD)
VRBO
Historic Ski Lodge on 112-Acre Vineyard
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
**10% discount on 7 nights or more; 30% discount on 28 nights or more. Rental Amenities: Over 900 square feet of liv ...
From $176 per night (USD)VRBO
- From $240 per night (USD)
VRBO
Lori and Dean's Killington Ski House with Wi-Fi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Recently remodeled and tastefully decorated lower level duplex located a short distance from Killington ski area (a twel ...
From $240 per night (USD)VRBO
- From $308 per night (USD)
Expedia
Huge Home with Private Pond - Ideal Remote Getaway for Family, Friends & More
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
HUGE 4 BD 3.5 BA HOME FOR LONG TERM STAYS & FAMILY GATHERINGS. 2 TV ROOMS, WORKING FIREPLACES, WIFI, INCREDIBLE VIEWS, S ...
From $308 per night (USD)Expedia
- From $331 per night (USD)
VRBO
Sweet chalet with private hot tub, firepit, game room & minibar
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Sunny Mountainside Chalet Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $331 per night (USD)VRBO
- From $819 per night (USD)
Expedia
Luxe Plymouth Chalet w\/ Indoor Pool & 3 Decks!
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
Discover one of Vermont's hidden gems when you book this Plymouth vacation rental, known as the 'Mountain Casa'. Featuri ...
From $819 per night (USD)Expedia
- From $1400 per night (USD)
VRBO
Ski On\/Off ~ Beautiful Corner Unit ~ Well-Equipped And Perfect For Families!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
4 bedrooms, 3 and 1/2 baths. Beautifully decorated and furnished. Ski on/off townhouse located directly on the trail, ...
From $1400 per night (USD)VRBO
- From $274 per night (USD)
Expedia
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Lake Rescue Escape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $274 per night (USD)Expedia
- From $645 per night (USD)
VRBO
Silver Lake Country House Close to Woodstock & Ski Areas
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Perched on the edge of pristine Silver Lake, my country home sits on a large rolling lot overlooking the lake enjoyed by ...
From $645 per night (USD)VRBO
- From $600 per night (USD)
Expedia
Fireplace, Ski-Okemo, Apple Trees, Piano, Amazing Views, Firepit, Priory, Pool, Fields, Theatre!
- Bedrooms:
- 9
- Bathrooms:
- 8
- Sleeps:
- 17
Skiing Theatre Food Beer Farm-Cheese Music and a Monastery! This is The Apple Knoll Inn at Weston, a Gertrude Rentals pr ...
From $600 per night (USD)Expedia
- From $489 per night (USD)
VRBO
Fireplace, Ski-Okemo, Apple Trees, Piano, Amazing Views, Firepit, Priory, Pool, Fields, Theatre!
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 13
Skiing Theatre Food Beer Farm-Cheese Music and a Monastery! This is The Apple Knoll Inn at Weston, a Gertrude Rentals pr ...
From $489 per night (USD)VRBO
- From $403 per night (USD)
Expedia
Ski Okemo, Killington, Magic & Bromley
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Gather with family and friends at our spacious home nestled in the Vermont woods. The Blue Moon Bungalow is your home a ...
From $403 per night (USD)Expedia
- From $181 per night (USD)
VRBO
Perfect Home Away near Town & Skiing w\/ Private Gas Grill, Large Deck
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Ludlow Hideout Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $181 per night (USD)VRBO
- Click For Pricing
Expedia
Slopeside condo in the desired South Face Village at Okemo Mountain
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Full kitchen, washer/dryer located in the unit. There is a ski lift waiting just outside your door. Amenities include: a ...
Click For PricingExpedia
- Click For Pricing
VRBO
Spacious home with WiFi, Private Pool, & Hot Tub - Near Slopes & Lake
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Ludlow Landing Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
Click For PricingVRBO
- From $800 per night (USD)
Expedia
Ski in Ski out! top of the A quad chairlift
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
2 Bed 2 Bath. Pull out sleep sofa. Sleeps 4 Adults and 4 children. Located at the top of the chairlift with a balcon ...
From $800 per night (USD)Expedia
- From $296 per night (USD)
VRBO
Ski in\/out @Base Lodge at Clock tower,Okemo. Building B Ground Level sleeps 6
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Ski in/out 1 bd condo in Building B at Okemo clock tower. walk or ski to magic carpet and Quad A/B lift. Cozy One bedr ...
From $296 per night (USD)VRBO
- From $436 per night (USD)
Expedia
Renovated Farmhouse < 1 Mile to Okemo Mountain!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 11
Experience the beauty of Vermont from this chic and charming farmhouse with 4 bedrooms and 2 bathrooms. The vacation ren ...
From $436 per night (USD)Expedia
- From $195 per night (USD)
VRBO
Beautifully Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Discover the best of Ludlow when you stay in our fabulously decorated updated historic home built in 1835, located in th ...
From $195 per night (USD)VRBO
- From $198 per night (USD)
Expedia
Mountain Bliss: Hot Tub, Shuttle to Okemo, Quiet Ludlow Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Okemo Westwood Condo - a SkyRun Vermont Property SkyRun Vermont prides itself in providing you the best experience dur ...
From $198 per night (USD)Expedia
- From $260 per night (USD)
VRBO
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Our year round cottage is located on Lake Pauline in Ludlow Vermont, with 900 ft of lake frontage! Just 1.5 miles from O ...
From $260 per night (USD)VRBO
- From $208 per night (USD)
Expedia
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Hi, we are using Homeaway/VRBO for renters who love the slopes, the outdoors and places like Okemo. We are always open ...
From $208 per night (USD)Expedia
- Click For Pricing
VRBO
Newly Renovated Cottage with hot tub, fire place, and 5min to Killington Gondola
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stone’s Throw Vermont is a charming 3bed 1.5 bath cottage with hot tub, fireplace, outdoor covered dinning space, and mo ...
Click For PricingVRBO
- From $379 per night (USD)
Expedia
Ski-in Ski-Out Okemo Oasis w\/ Deck + Mtn View!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Boasting easy access to the slopes and local hiking trails, this 3-bedroom, 2-bathroom vacation rental is great for fami ...
From $379 per night (USD)Expedia
- From $283 per night (USD)
VRBO
Ski Chalet with Hot Tub on Okemo Mountain
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
New kitchen & large living area. Renovated bedrooms. New deck and exterior as of Fall, 2023! Relax in this 3-level (170 ...
From $283 per night (USD)VRBO
- From $453 per night (USD)
Expedia
Your Vermont Vacation Awaits!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Mountain View Retreat is truly your home away from home for "Your Vermont Vacation". This bright, airy and comfortable f ...
From $453 per night (USD)Expedia
- From $99 per night (USD)
VRBO
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Discover the best of Ludlow when you stay in our fabulously decorated updated historic home built in 1835, located in th ...
From $99 per night (USD)VRBO
- From $189 per night (USD)
Expedia
Vermont Farmhouse Getaway Near the Slopes W\/ Mtn Views, Free WiFi, Full Kitchen
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Vermont Mountain Farmhouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $189 per night (USD)Expedia
- From $523 per night (USD)
VRBO
Private Home on Okemo with HOT TUB. WALK TO SKI TRAIL OR DRIVE 2 MIN TO LODGE
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
This Okemo Mountain home is the perfect Vermont getaway within walking distance (400 yards) to the slopes! PLEASE NOTE ...
From $523 per night (USD)VRBO
- From $181 per night (USD)
Expedia
Renovated condo w\/ shared seasonal pool & tennis - walk to trail
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Okemo Trailside 6A Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $181 per night (USD)Expedia
- From $278 per night (USD)
VRBO
Hot Tub+Fire Pit- Walk to Okemo Base Lodge & Lifts. Private On Mountain home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
PLEASE NOTE: No Saturday arrivals or departures, no pets, no smoking, no parties. Recommended local activities and floor ...
From $278 per night (USD)VRBO
- From $1170 per night (USD)
Expedia
Winterplace condo E building - top of the Quad
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This wonderful condo is in the perfect location. Located just steps to the top of the A/B lift with your private ski loc ...
From $1170 per night (USD)Expedia
- From $246 per night (USD)
VRBO
Cozy 3br cabin 5 minutes (1.5 miles) from Okemo Mountain Base
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
1,050 square foot 3 BR cabin: Bedroom 1 and 2 have queen-size beds. Bedroom 3 has a twin size trundle bed. There is al ...
From $246 per night (USD)VRBO
- From $350 per night (USD)
Expedia
Lake Rescue Summers, Ski Okemo Winters
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Views of and Direct Access to Lake Rescue. 3 BR + Loft with 2.5 Baths. 4 min to Okemo. Newly renovated home perfect for ...
From $350 per night (USD)Expedia
- From $185 per night (USD)
VRBO
Coveted Ski-In\/Ski-Out Winterplace Condo with Hot Tubs, Indoor Pool & Fireplace
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Winterplace K102 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $185 per night (USD)VRBO
- From $147 per night (USD)
Expedia
Downtown Home with High-Speed WiFi, Wood Stove, Deck, and Private Washer\/Dryer
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Downtown Ludlow Home Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $147 per night (USD)Expedia
- From $494 per night (USD)
VRBO
Vermont life at Hill Top Gardens
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Three story Vermont Homestead with five bedrooms exquisitely designed with an open floor concept. Large chef kitchen and ...
From $494 per night (USD)VRBO
- From $350 per night (USD)
Expedia
Okemo Family Friendly Getaway
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Private family friendly mountain retreat with open floor plan, wood detailing with bright spacious rooms, fireplace, coo ...
From $350 per night (USD)Expedia
- From $105 per night (USD)
VRBO
Village Ski Apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
You would be renting a very nice ski apartment with fully equipped kitchen, large living room and large bedroom. Also a ...
From $105 per night (USD)VRBO
- From $276 per night (USD)
Expedia
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to 'Smokeshire Hilltop Farmhouse!' This lovely 5-bedroom, 2-bathroom vacation rental sits on a plateau above the ...
From $276 per night (USD)Expedia
- From $299 per night (USD)
VRBO
Inviting Ski-In Ski-Out Condo at Okemo Mtn Resort!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Glide out your front door into blissful days on the slopes at this lovely 1-bedroom, 1-bath vacation rental in Ludlow. B ...
From $299 per night (USD)VRBO
- From $700 per night (USD)
Expedia
Ski on, ski off trailside condo at Okemo
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
We’d love to welcome you to our home away from home. Located steps from Sachem trail, our townhome at the Okemo Trailsi ...
From $700 per night (USD)Expedia
- From $282 per night (USD)
VRBO
Vermont get-away end unit townhouse nestled in the trees
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
We welcome you to a wonderfully located Vermont getaway The Vermont Sugar Maple. Comfortably nestled in the trees, surro ...
From $282 per night (USD)VRBO
- From $449 per night (USD)
Expedia
Cozy Log Cabin, 5 Min to Ski, Great for Groups, Oversized Deck, Dog-friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 13
Also available for long-term rent. Please inquire for more details. A 3-minute drive from downtown Ludlow & Okemo Moun ...
From $449 per night (USD)Expedia
- From $144 per night (USD)
VRBO
Vermont Retreat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This is a non-smoking one-bedroom apartment with a queen-sized bed. It is convenient to mountains, lakes, and more. A ...
From $144 per night (USD)VRBO
- Click For Pricing
Expedia
Quaint cabin with Lake Pauline views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Two bedroom, 1 bath unit steps away from Jackson Gore and 5 minute drive to Okemo main base. The town of Ludlow has grea ...
Click For PricingExpedia