Windsor Area Rentals
- From $375 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 $375 per night (USD)VRBO
- From $132 per night (USD)
Expedia
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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)Expedia
- 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 $148 per night (USD)
Expedia
Condo with fireplace, W\/D & shared pool - shuttle access to Okemo Mountain
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Nana’s Nest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $148 per night (USD)Expedia
- From $293 per night (USD)
VRBO
Horses, views, updated house, skiing, hiking and shops abound!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Beautiful views in tranquil setting yet close to everything. Newly renovated and 2 minutes from town of Weston (Weston P ...
From $293 per night (USD)VRBO
- From $59 per night (USD)
Expedia
Cute Riverfront Home w\/ Free WiFi, Washer\/Dryer, & Private Deck - Close to Okemo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Green Mountain Riverside Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Sim ...
From $59 per night (USD)Expedia
- From $164 per night (USD)
VRBO
Dog-friendly & riverfront condo one mile from Okemo with wood fireplace
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The Mill #210 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $164 per night (USD)VRBO
- From $796 per night (USD)
Expedia
Picture-Perfect Vermont Mtn Cabin w\/ Hot Tub!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 15
Dive into a quintessential New England escape at this 6-bed, 3-bath vacation rental! Watch your worries fade from the mo ...
From $796 per night (USD)Expedia
- From $300 per night (USD)
VRBO
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Spacious condo located at the Castle Hill resort with access to year round outdoor heated pool and hot tub, tennis court ...
From $300 per night (USD)VRBO
- From $104 per night (USD)
Expedia
Two Double bed Standard Hotel room 218
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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 $236 per night (USD)
VRBO
Deluxe Two Bedroom Suite on the 1st floor with outdoor heated pool 10506
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $236 per night (USD)VRBO
- From $132 per night (USD)
Expedia
108 Deluxe One bedroom Queen Suite on the 1st floor w\/ outdoor heated pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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)Expedia
- From $104 per night (USD)
VRBO
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)VRBO
- From $399 per night (USD)
VRBO
Spacious, Warm, Open Floor Plan Family Home on Okemo Mt , 1 Min To Base Lodge
- Bedrooms:
- 3
- 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 $399 per night (USD)VRBO
- Click For Pricing
VRBO
Cozy Cottage near Woodstock VT and skiing!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This is a space owned by three siblings and primarily for the use of family to come and stay, so it is quirky and unique ...
Click For PricingVRBO
- From $310 per night (USD)
VRBO
Private Ludlow Village Home - 2 Miles from Okemo Base W\/Access To Okemo Shuttle
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Located 2.1 miles (-5 Min Drive) from Okemo Mountain Main Base and right off the Vermont VAST access trail for snowmobil ...
From $310 per night (USD)VRBO
- From $140 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 $140 per night (USD)VRBO
- From $165 per night (USD)
VRBO
Cozy 1BR Hilltop Getaway minutes from Okemo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Looking for an affordable escape into the beauty of Vermont? Come stay at our cozy 1 bedroom house in the woods on top o ...
From $165 per night (USD)VRBO
- From $314 per night (USD)
VRBO
Just steps to Okemo's Sachem trail!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Our townhouse at Trailside has been recently renovated and is perfect for a group of families that want have easy access ...
From $314 per night (USD)VRBO
- From $392 per night (USD)
VRBO
Beautiful Log Cabin in Weston, VT
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Looking for a quiet getaway? A mountain vibe that's cozy yet totally uncluttered? This completely renovated log cabin se ...
From $392 per night (USD)VRBO
- From $145 per night (USD)
VRBO
Marsh Brook is a beautiful farmhouse located in the heart of the Green Mountains
- Bedrooms:
- 4
- 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 $145 per night (USD)VRBO
- From $280 per night (USD)
VRBO
Charming & Affordable Home! 1.5 miles from Okemo!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
*** Please note: Winter 2024/2025 Season Rates have not been updated yet, please inquire for price quote.***** Warm an ...
From $280 per night (USD)VRBO
- From $91 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 $91 per night (USD)VRBO
- From $476 per night (USD)
Expedia
Renovated Ski House @ Okemo Mt., on Shuttle Route, Walking Distance to town!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
This is clean simple house with an open floor plan. It's warm and comfortable. 3 bedrooms, 2 full bathrooms, full kitche ...
From $476 per night (USD)Expedia
- From $757 per night (USD)
VRBO
The Cabin that brings people together
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 25
Known as 'The Cabin', this 5,000 S.F. home that is surrounded by ten private acres within brilliant wilderness, the maje ...
From $757 per night (USD)VRBO
- From $600 per night (USD)
VRBO
Winter Wonderland At Winterplace K-103!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
*K-103 is located at the top of the Main B lift. Open your door, snap into your skis from the patio ski locker and head ...
From $600 per night (USD)VRBO
- From $257 per night (USD)
VRBO
New Construction 4 season Killington VT Ski House on Lake Amherst okemo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Brand New Cozy House on Beautiful Lake Amherst. Minutes to Killington and Okemo. A perfect Vermont family getaway -- win ...
From $257 per night (USD)VRBO
- From $167 per night (USD)
Expedia
Tranquil home in a quiet neighborhood with easy access to outdoor fun
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Bear Hill Views Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $167 per night (USD)Expedia
- From $300 per night (USD)
VRBO
Renovated & immaculate. 1 block to town, 2 floors. Great monthly rates!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Tucked away on a quiet in town street, this apartment has all the warmth for a family or small group to fuel a great mo ...
From $300 per night (USD)VRBO
- From $132 per night (USD)
Expedia
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)Expedia
- From $104 per night (USD)
VRBO
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)VRBO
- From $236 per night (USD)
Expedia
Deluxe Two Bedroom Suite on the 2nd floor with outdoor heated pool 20304
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $236 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 $116 per night (USD)
Expedia
Deluxe One Bedroom Queen Suite on the 2nd floor with outdoor heated pool 202
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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)Expedia
- From $147 per night (USD)
VRBO
Deluxe 1 bedroom suite located on first floor with outdoor heated pool 11820
- 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
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 $370 per night (USD)
VRBO
Fabulous 4 bdrm\/4 bath sleeps up to 12, 1 mile from Okemo Jackson Gore
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
This Fox Run end unit townhouse has X-country/snowshoe/sledding and hiking trails directly across front door and Vermont ...
From $370 per night (USD)VRBO
- From $520 per night (USD)
Expedia
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)Expedia
- From $516 per night (USD)
VRBO
Mountain-view house with hot tub & amazing views - near Okemo Resort & skiing
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Ludlow Treasure Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $516 per night (USD)VRBO
- From $154 per night (USD)
Expedia
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 $154 per night (USD)Expedia
- From $493 per night (USD)
VRBO
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)VRBO
- From $371 per night (USD)
Expedia
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 $371 per night (USD)Expedia
- From $207 per night (USD)
VRBO
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 $207 per night (USD)VRBO
- From $138 per night (USD)
VRBO
Ski-in\/out mountainside condo close to everything with full kitchen - tranquil
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Okemo Mountain Lodge B305 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $138 per night (USD)VRBO
- From $195 per night (USD)
VRBO
2 Bedroom Condo in Quechee, ~VT~ - a Four Season Community!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Conveniently located in Quechee Vermont, we are secluded enough to provide quiet and privacy while being a stone's throw ...
From $195 per night (USD)VRBO
- From $227 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 $227 per night (USD)Expedia
- From $400 per night (USD)
VRBO
Ludlow-Historic Charm, Lake Rescue, Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Built in 1900, our charming farmhouse is the ideal location for ALL seasonal pursuits in Southern Vermont with Lake Resc ...
From $400 per night (USD)VRBO
- From $200 per night (USD)
VRBO
Peaceful Brookside North Pomfret Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy a relaxing family vacation in our brookside home that feels like you are getting away from it all, while still bei ...
From $200 per night (USD)VRBO
- From $383 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 $383 per night (USD)VRBO
- From $161 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 $161 per night (USD)Expedia
- From $1400 per night (USD)
VRBO
Ski In Ski Out Renovated Trailside Condo on Sachem Trail @ Okemo Resort
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Whether you're an avid skier that craves first tracks down to the Sunburst Six chairlift or someone who enjoys a slower ...
From $1400 per night (USD)VRBO
- From $574 per night (USD)
VRBO
Modern Farmhouse on 25 Acres \/ Superb Views.
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
This Truex Cullins designed Farmhouse is inspired by the iconic old farmsteads found throughout northern New England. Em ...
From $574 per night (USD)VRBO
- From $185 per night (USD)
VRBO
Cozy Historic Hilltop Cottage with Mount Ascutney View
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This exceedingly charming cottage on a wooded hilltop just outside of Brownsville has great views of Mt Ascutney and a b ...
From $185 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 $163 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 $163 per night (USD)VRBO
- From $983 per night (USD)
VRBO
Charming Ski Chalet Minutes From Okemo Mountain!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 15
Less than 3 miles to Okemo mountain. It is a 4-5 minute drive, we clocked it! Located in the South Hills neighborhood ...
From $983 per night (USD)VRBO
- From $258 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 $258 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 $224 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 $224 per night (USD)VRBO
- From $56 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 $56 per night (USD)Expedia
- From $382 per night (USD)
VRBO
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 $382 per night (USD)VRBO
- From $375 per night (USD)
Expedia
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 $375 per night (USD)Expedia
- From $198 per night (USD)
VRBO
Condo near ski trail with fireplace, hot tub, pool, tennis & washer\/dryer
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Winterplace Q206 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $198 per night (USD)VRBO
- From $981 per night (USD)
Expedia
Home near the Bull Run Trail with fireplace, washer\/dryer & cable
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Snow Lane Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $981 per night (USD)Expedia
- Click For Pricing
VRBO
Mountainside condo with sauna, wood-burning fireplace, balcony, & walk to lifts
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Okemo Trailside 40C Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
Click For PricingVRBO
- From $217 per night (USD)
Expedia
Charming ski-in\/ski-out condo with fireplace, washer\/dryer, tennis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Kettle Brook J1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $217 per night (USD)Expedia
- From $498 per night (USD)
VRBO
Mountainview condo with pool, hot tubs, & fireplace - 250 yards from skiing
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
The Love Shack - Winterplace Q104 Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $498 per night (USD)VRBO
- From $405 per night (USD)
Expedia
Inviting condo on Village Run Trail with a fireplace, pool, & hot tub
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 9
Solitude Village A2 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $405 per night (USD)Expedia
- Click For Pricing
VRBO
Top-floor condo with ski-in\/out access, hot tubs, pool, washer\/dryer
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Winterplace K306 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
Click For PricingVRBO
- Click For Pricing
Expedia
Condo with fireplace, pool, hot tubs, washer\/dryer - walk to skiing
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Winterplace C101 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
Click For PricingExpedia
- From $463 per night (USD)
VRBO
Beautiful mountain home at Okemo Resort with wood stoves, kitchen & kitchenette
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Doc's Folly Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $463 per night (USD)VRBO
- From $91 per night (USD)
Expedia
Ski-in\/out condo with fireplace, tennis court, mountain views, & washer\/dryer
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Kettle Brook G6 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $91 per night (USD)Expedia
- Click For Pricing
Expedia
Beautiful lakefront home with hot tub, fireplace, washer\/dryer, firepit & cable
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
Gone Fishing Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
Click For PricingExpedia
- From $467 per night (USD)
Expedia
Birch Hills
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
This is the perfect Vermont outdoor playground property. With 84.4 acres, beautiful stone walls, and spacious lawns whic ...
From $467 per night (USD)Expedia
- From $111 per night (USD)
VRBO
Ski-in\/out condo with mountain views, fireplace, hot tub, pool, & tennis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Winterplace J103 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $111 per night (USD)VRBO
- From $1282 per night (USD)
Expedia
Mountain-view house near Okemo base with gas fireplace, & deck - walk to lifts
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Chalet at the Base of Okemo Mountain Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $1282 per night (USD)Expedia
- From $632 per night (USD)
VRBO
Ski-in\/out condo near lifts with a fireplace, pool, hot tub, & tennis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Winterplace F101 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $632 per night (USD)VRBO
- From $386 per night (USD)
Expedia
Ski-in\/ski-out condo with pool, hot tub, sauna, mountain view, deck, & fireplace
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 9
Sweet Solitude G104 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $386 per night (USD)Expedia
- Click For Pricing
VRBO
Private lakefront home with private hot tub, WiFi, central AC, & fireplace
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Hillside House at Lakeshore Drive Our calendar is updated in real-time & our nightly rates are accurately displayed. Si ...
Click For PricingVRBO
- Click For Pricing
Expedia
Ski-in\/ski-out condo with fireplace, AC, WiFi, & shared pool, hot tubs, & tennis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Winterplace J306 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
Click For PricingExpedia
- From $149 per night (USD)
VRBO
Ski-in\/out condo with fireplace, hot tubs. pool, tennis & washer\/dryer
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Winterplace G205 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $149 per night (USD)VRBO
- From $301 per night (USD)
Expedia
Hawk Mountain retreat near Okemo with fireplace, washer\/dryer & deck
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Ledges 19 at Hawk Mountain Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $301 per night (USD)Expedia
- From $171 per night (USD)
VRBO
Inviting condo with a fireplace, hot tubs, pool, tennis & washer\/dryer
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Winterplace E202 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
Ski-in\/out condo with a fireplace, hot tub, pool, washer\/dryer & sauna
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Slopeside Getaway - Winterplace F102 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
Click For PricingExpedia
- Click For Pricing
VRBO
Inviting condo near the Sachem Trail with a fireplace, washer\/dryer
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Okemo Trailside 11C Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
Click For PricingVRBO
- From $328 per night (USD)
Expedia
Ski-in\/out condo with mountain and lift views, hot tub, & pool
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
Winterplace G303 - Skier's Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $328 per night (USD)Expedia
- From $147 per night (USD)
VRBO
Ski-in\/out Condo on Bull Run Trail with fireplace, & full kitchen
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Kettle Brook I4 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $147 per night (USD)VRBO
- Click For Pricing
Expedia
Luxury home near Sachem Trail & Lifts with sauna, washer\/dryer, & fireplace
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 13
Upper Loop Escape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
Click For PricingExpedia
- From $135 per night (USD)
VRBO
Ski-in\/out condo with water & mountain views, private sauna & fireplace
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Kettle Brook A7 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $135 per night (USD)VRBO
- From $432 per night (USD)
Expedia
Beautiful home near lifts with wood-burning fireplace, mountain views & cable
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Classic Log Cabin Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $432 per night (USD)Expedia
- From $199 per night (USD)
VRBO
Newly renovated ski-in\/out slope side condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Okemo Mountain Lodge C202 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $199 per night (USD)VRBO
- From $106 per night (USD)
Expedia
Ski-in\/ski-out condo with pool, hot tub, sauna, fireplace, W\/D, & central AC
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Jackson Gore Bixby 844 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $106 per night (USD)Expedia
- From $53 per night (USD)
VRBO
Ski-In\/Out condo with patio, mountain views, washer\/dryer, & cable
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Okemo Mountain Lodge C108 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $53 per night (USD)VRBO
- Click For Pricing
Expedia
Ski-in\/out condo with a pool, fireplace & fast WiFi - Sachem Trail at Okemo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Okemo Trailside 19BL Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
Click For PricingExpedia
- From $259 per night (USD)
VRBO
Ultimate ski-in\/out condo with mountain views, hot tub, & fireplace
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Ledgewood E3 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $259 per night (USD)VRBO
- Click For Pricing
Expedia
Beautiful home with pond views, tennis court, fireplace, hot tub, & washer\/dryer
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
East Hill Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
Click For PricingExpedia
- Click For Pricing
VRBO
Condo near the slopes with a fireplace, mountain views, washer\/dryer, & cable
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Ledgewood B4 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
Click For PricingVRBO
- From $253 per night (USD)
Expedia
Classic ski home with hot tub, washer\/dryer, mountain views, fireplace, & cable
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 13
Tannen Spitz Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $253 per night (USD)Expedia
- From $257 per night (USD)
VRBO
Ski-in\/out condo with a fireplace, hot tub, gym, pool, washer\/dryer & cable
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Okemo Condo - Solitude Village N104 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $257 per night (USD)VRBO
- From $211 per night (USD)
Expedia
Rustic home with a private hot tub, fireplace, cable, & washer\/dryer
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Hawk Spur Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $211 per night (USD)Expedia