Windsor Area Rentals
- From $122 per night (USD)
VRBO
Ski-in\/out condo with fireplace, pool, hot tub, sauna & washer\/dryer
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Solitude Village H102 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $122 per night (USD)VRBO
- From $184 per night (USD)
Expedia
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located at 68 Pleasant St. first floor in the village of Ludlow, Vermont on the Black River within 20 miles of 5 majo ...
From $184 per night (USD)Expedia
- From $392 per night (USD)
VRBO
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR\/4BA, Pool Table, Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Great Prices on Summer dates! All forthcoming rentals in May, June and July of at least (3) nights or $1,000 in rent (no ...
From $392 per night (USD)VRBO
- From $209 per night (USD)
Expedia
Dog-friendly house near Okemo Mountain Resort, skiing, & heart of Ludlow Village
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Casa Okemo Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $209 per night (USD)Expedia
- From $303 per night (USD)
VRBO
Luxurious, Secluded, Ski Chalet, w\/ Country Decor & Hot Tub Near Okemo
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
The house is decorated with a comfortable country decor. It is located within the private and secluded Farm Ridge develo ...
From $303 per night (USD)VRBO
- From $120 per night (USD)
Expedia
Room in Historic Inn! 20 Minutes to Okemo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Enjoy a private room, bathroom & shower in the historic Chester Inn, circa 1780. This charming property is conveniently ...
From $120 per night (USD)Expedia
- From $119 per night (USD)
VRBO
King & Queen Suite in Historic Inn Circa 1780
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Enjoy a private room, bathroom, shower & Fireplace in the historic Chester Inn, circa 1780. This charming property is co ...
From $119 per night (USD)VRBO
- From $400 per night (USD)
Expedia
Ludlow Home w\/ Hot Tub, Near Okemo Resort!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Escape to this secluded 4-bedroom, 3-bathroom home located in Ludlow for your next visit to Vermont. A true mountain ess ...
From $400 per night (USD)Expedia
- From $187 per night (USD)
VRBO
Lake-view home with a private hot tub, fast WiFi, pool table, & washer\/dryer
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Misty Mountain Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $187 per night (USD)VRBO
- From $109 per night (USD)
Expedia
Bigfoot Chalet, Golf-Hike-Boat-Bike-Fish-RELAX!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Calling all mountain bikers, golfers and lake lovers! Enjoy the serenity of country living while conveniently located l ...
From $109 per night (USD)Expedia
- From $360 per night (USD)
VRBO
Quiet Modern Luxury Home w\/ Memory Foam Beds, A\/C, FAST WiFi and Full Kitchen
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
3 Bedroom, 2 Full Baths home located 8 miles from the Killington Mountain Skyship Base Lodge. Kitchen with new applianc ...
From $360 per night (USD)VRBO
- From $360 per night (USD)
Expedia
Secluded 2600 sqft home 15 min from Okemo and Killington
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The VT Treehouse on Hawk Mountain in Plymouth, VT. You will be able to enjoy sights and access to two of the ...
From $360 per night (USD)Expedia
- From $219 per night (USD)
VRBO
Comfortable home with jetted tub, patio, & W\/D- near skiing
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Small Town Charm Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $219 per night (USD)VRBO
- From $550 per night (USD)
Expedia
Ski On, Ski off Okemo Trailside Appartment, Sleeps 6\/ $550per night,
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Bright open design. Fully equipped kitchen, with dishwasher, stove, frig. and microwave. Large dinning room table with v ...
From $550 per night (USD)Expedia
- From $650 per night (USD)
VRBO
Base Lodge - shuttle rte in winter - 10 BR, 5 Bath, Slp 34
- Bedrooms:
- 5
- Bathrooms:
- 10
- Sleeps:
- 34
RENOVATED The Base Lodge will exceed your expectations. This beautiful 10 BR, 5 bath home with 4,000 sf is ready for yo ...
From $650 per night (USD)VRBO
- From $400 per night (USD)
Expedia
Okemo 6 Bedroom Chalet.
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 13
***Newly renovated kitchen and bathroom*** This 6 Bedroom Chalet is situated on 10+ Acres along side a beautiful river. ...
From $400 per night (USD)Expedia
- From $400 per night (USD)
VRBO
Lake Rescue Vacation Home- Pets Welcome-Okemo and Killington close!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
1378 ROUTE 100 NORTH LUDLOW, VERMONT 05149 Waterfront home with 100 feet of grassy lake frontage, complete with kayaks, ...
From $400 per night (USD)VRBO
- From $195 per night (USD)
Expedia
Cottage On Main
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Welcome to our little cottage on Main Street( was once the village library) . The house has two bedrooms one with two qu ...
From $195 per night (USD)Expedia
- From $245 per night (USD)
VRBO
Stay Safe! Stay strong!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the End of the Road Stay. Convenient location to Ludlow and Okemo Ski Resort. Cross the bridge to relax and u ...
From $245 per night (USD)VRBO
- From $153 per night (USD)
Expedia
Secluded Cabin w\/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Log Cabin with a View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $153 per night (USD)Expedia
- Click For Pricing
Expedia
Comfy Condo w\/ High-Speed WiFi, Shared Pool, Wood-Burning Fireplace, and Balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Okemo Trailside 6B Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
Click For PricingExpedia
- From $697 per night (USD)
Expedia
Okemo Mtn Retreat < 1 Mi to Jackson Gore Base!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 9
Make yourself at home in this newly remodeled 3-bedroom, 3.5-bath home in Ludlow, VT. This riverfront property sits on 1 ...
From $697 per night (USD)Expedia
- From $450 per night (USD)
VRBO
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Situated on 12 acres with views of Okemo Mountain and direct access to VAST snowmobile trail. Minutes to charming villag ...
From $450 per night (USD)VRBO
- From $650 per night (USD)
Expedia
The Clubhouse -11 BR Downtown, 7 Bath on shuttle
- Bedrooms:
- 7
- Bathrooms:
- 11
- Sleeps:
- 34
The Clubhouse is ready to welcome your large group to Vermont! This 11 BR (sleeps 34), 7 BA home with 4,000 sq ft is re ...
From $650 per night (USD)Expedia
- Click For Pricing
VRBO
Ronnoco Farm-Charming Brownsville\/West Windsor, VT cottage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Ronnoco Farm is a small, private, and charming property conveniently located near Mt. Ascutney State Park (7.5 Miles), G ...
Click For PricingVRBO
- From $420 per night (USD)
Expedia
The Red Bridge House. 360° of lake views.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
The Red Bridge House is a spectacular home situated right between the hustling fun of Lake Rescue and the peaceful calm ...
From $420 per night (USD)Expedia
- From $256 per night (USD)
VRBO
Killington Area Escape w\/ Deck & Private Hot Tub!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Enjoy the incredible beauty of the Green Mountains in all 4 seasons at this versatile 3-bedroom, 2-bath Stockbridge vaca ...
From $256 per night (USD)VRBO
- From $263 per night (USD)
Expedia
Rustic lakeview cabin with fireplace, deck- near skiing
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
Ludlow Comfy Cabin Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $263 per night (USD)Expedia
- From $750 per night (USD)
VRBO
Village House on Shuttle Route- Great Location!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Conveniently located right up the street from all restaurants, bars, shopping, and in walking distance so no car is need ...
From $750 per night (USD)VRBO
- From $346 per night (USD)
Expedia
Classic, cozy farmhouse in the 4 season playground of VT's prettiest town!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Our recently renovated1860’s farmhouse, on 95 acres abutting the banks of the Ottauquechee River, is 3 miles from histor ...
From $346 per night (USD)Expedia
- From $193 per night (USD)
VRBO
Remodeled condo with free WiFi & shared W\/D - ski bus pickup across street
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Baggrow Unit B Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $193 per night (USD)VRBO
- From $155 per night (USD)
Expedia
The Little Red Cabin! Less than 15 minutes to Okemo! Close to Everything VT!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our two bedroom one bath cabin got a refreshing renovation! Super comfy bedrooms with expansive family style living s ...
From $155 per night (USD)Expedia
- From $236 per night (USD)
VRBO
Deluxe Two Bedroom Suite on the 1st floor with outdoor heated pool 10102
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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
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
- From $142 per night (USD)
VRBO
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 $142 per night (USD)VRBO
- From $293 per night (USD)
Expedia
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)Expedia
- From $62 per night (USD)
VRBO
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 $62 per night (USD)VRBO
- From $117 per night (USD)
Expedia
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 $117 per night (USD)Expedia
- From $786 per night (USD)
VRBO
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 $786 per night (USD)VRBO
- From $300 per night (USD)
Expedia
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)Expedia
- From $104 per night (USD)
VRBO
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)VRBO
- From $236 per night (USD)
Expedia
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)Expedia
- From $132 per night (USD)
VRBO
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)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $444 per night (USD)
VRBO
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 $444 per night (USD)VRBO
- From $147 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 $147 per night (USD)Expedia
- From $236 per night (USD)
VRBO
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)VRBO
- From $132 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 $132 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 $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 $93 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 $93 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
- From $292 per night (USD)
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 ...
From $292 per night (USD)VRBO
- From $143 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 $143 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 $403 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 $403 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 $74 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 $74 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 $433 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 $433 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 $269 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 $269 per night (USD)Expedia
- From $803 per night (USD)
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 ...
From $803 per night (USD)VRBO
- 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 $135 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 $135 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 $140 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 $140 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 $161 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 $161 per night (USD)Expedia
- From $138 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 $138 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 $103 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 $103 per night (USD)VRBO
- From $423 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 $423 per night (USD)Expedia
- From $162 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 $162 per night (USD)VRBO
- From $125 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 $125 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
- From $146 per night (USD)
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 ...
From $146 per night (USD)Expedia
- From $175 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 $175 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
- From $326 per night (USD)
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 ...
From $326 per night (USD)VRBO
- From $199 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 $199 per night (USD)Expedia
- From $170 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 $170 per night (USD)VRBO
- From $174 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 $174 per night (USD)Expedia
- From $207 per night (USD)
VRBO
Lovely mountain condo with pool, fireplace & cable- near skiing
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Brookhaven B1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $207 per night (USD)VRBO
- From $141 per night (USD)
Expedia
Mountain view condo with fireplace, pool, hot tub, tennis, washer\/dryer & cable
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Winter Escape - WP A202 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $141 per night (USD)Expedia
- From $891 per night (USD)
VRBO
Mountain condo with fireplace, deck, washer\/dryer & shuttle to ski rail
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Okemo Trailside 48A Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $891 per night (USD)VRBO
- From $227 per night (USD)
Expedia
Three-level ski-in\/out condo with sauna, fireplace, washer\/dryer & mountain view
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Okemo Trailside 32C Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $227 per night (USD)Expedia
- Click For Pricing
VRBO
Ski-in\/ski-out condo with pool, wood-burning fireplace, tennis courts, & grill
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 7
Okemo Trailside 19BU Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
Click For PricingVRBO
- From $191 per night (USD)
Expedia
Ground-floor condo with fireplace, pool, hot tub, tennis, washer\/dryer & cable
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 9
Winterplace Getaway A101 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $191 per night (USD)Expedia
- From $208 per night (USD)
VRBO
Ski-in\/out condo near ski school with washer\/dryer, fast WiFi, & mountain views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Okemo Mountain Lodge C106 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $208 per night (USD)VRBO
- From $188 per night (USD)
Expedia
Ski-in\/out condo near trails with fireplace, pool, hot tub, sauna, mountain view
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
Solitude Village M302 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $188 per night (USD)Expedia
- From $101 per night (USD)
VRBO
Ski-in\/out condo with a pool, hot tub, sauna, fireplace, & washer\/dryer
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Solitude Retreat L104 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $101 per night (USD)VRBO
- From $255 per night (USD)
Expedia
Ski-in\/out home with a hot tub, fireplace, cable & golf nearby
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Wood Lantern Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $255 per night (USD)Expedia
- Click For Pricing
VRBO
Inviting condo with fireplace, pool, hot tubs, tennis, washer\/dryer - near lifts
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Eagle's Nest - WP P103 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
Click For PricingVRBO
- From $552 per night (USD)
Expedia
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 $552 per night (USD)Expedia