Windsor Area Rentals
- From $479 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 $479 per night (USD)VRBO
- From $479 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 $479 per night (USD)Expedia
- From $989 per night (USD)
VRBO
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Christmas Special: 45% off normal price for Christmas week Dec. 20-27 due to cancellation, my loss, your gain! Trim a tr ...
From $989 per night (USD)VRBO
- From $548 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 $548 per night (USD)Expedia
- From $624 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 $624 per night (USD)VRBO
- From $192 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 $192 per night (USD)Expedia
- From $240 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 $240 per night (USD)VRBO
- From $504 per night (USD)
Expedia
Ludlow Home w\/ Hot Tub, Near Okemo Resort!
- Bedrooms:
- 3
- Bathrooms:
- 6
- 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 $504 per night (USD)Expedia
- From $840 per night (USD)
VRBO
3 Level River View Home w\/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 $840 per night (USD)VRBO
- From $274 per night (USD)
Expedia
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 $274 per night (USD)Expedia
- From $576 per night (USD)
VRBO
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 $576 per night (USD)VRBO
- From $640 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 $640 per night (USD)Expedia
- From $1393 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 $1393 per night (USD)VRBO
- From $809 per night (USD)
Expedia
Okemo 6 Bedroom Chalet.
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 13
This 6 Bedroom Chalet is situated on 10+ Acres along side a beautiful river. Sleeps 13 people. Located in the Beautiful ...
From $809 per night (USD)Expedia
- From $460 per night (USD)
VRBO
Lake Rescue Vacation Home- Pets Welcome-Okemo and Killington close!!!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
1378 ROUTE 100 NORTH LUDLOW, VERMONT 05149 Waterfront home with 100 Jo feet of grassy lake frontage, complete with kaya ...
From $460 per night (USD)VRBO
- From $672 per night (USD)
VRBO
Waterfront House - Endless Lake Fun in all Seasons. 1 mile to Okemo Chairlifts!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This incredibly unique house sits hanging over the edge of Lake Rescue in Ludlow. It offers a large deep-water dock (bet ...
From $672 per night (USD)VRBO
- From $309 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 $309 per night (USD)VRBO
- From $439 per night (USD)
Expedia
Secluded Cabin w\/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Log Cabin with a View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $439 per night (USD)Expedia
- From $794 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 $794 per night (USD)VRBO
- From $1302 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 $1302 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 $502 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 $502 per night (USD)Expedia
- From $440 per night (USD)
VRBO
Killington Area Escape w\/ Deck, Views & Hot Tub!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy the incredible beauty of the Green Mountains in all 4 seasons at this versatile 3-bedroom, 2-bath Stockbridge vaca ...
From $440 per night (USD)VRBO
- From $468 per night (USD)
Expedia
Rustic lakeview cabin with fireplace, deck- near skiing
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Ludlow Comfy Cabin Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $468 per night (USD)Expedia
- From $866 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 $866 per night (USD)VRBO
- From $401 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 $401 per night (USD)Expedia
- From $430 per night (USD)
VRBO
Remodeled condo with free WiFi & shared W\/D - ski bus pickup across street
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Baggrow Unit B Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $430 per night (USD)VRBO
- From $174 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 $174 per night (USD)Expedia
- From $457 per night (USD)
VRBO
Deluxe Two Bedroom Suite on the 1st floor with outdoor heated pool 10102
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $457 per night (USD)VRBO
- From $345 per night (USD)
Expedia
Condo with fireplace, W\/D & shared pool - shuttle access to Okemo Mountain
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Nana’s Nest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $345 per night (USD)Expedia
- From $502 per night (USD)
VRBO
Magical spot w-views -3 BR home - idyllic retreat yet close to everything
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
Beautiful views in a tranquil setting yet close to everything that matters in Southern Vermont. Property itself is a 10 ...
From $502 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingExpedia
- From $353 per night (USD)
VRBO
Dog-friendly & riverfront condo one mile from Okemo with wood fireplace
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The Mill #210 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $353 per night (USD)VRBO
- From $957 per night (USD)
Expedia
Picture-Perfect Vermont Mtn Cabin w\/ Hot Tub!
- Bedrooms:
- 3
- Bathrooms:
- 8
- 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 $957 per night (USD)Expedia
- From $540 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 $540 per night (USD)VRBO
- From $155 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 $155 per night (USD)Expedia
- From $181 per night (USD)
VRBO
Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $181 per night (USD)VRBO
- From $457 per night (USD)
Expedia
Deluxe Two Bedroom Suite on the 1st floor with outdoor heated pool 10506
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $457 per night (USD)Expedia
- From $218 per night (USD)
VRBO
108 Deluxe One bedroom Queen Suite on the 1st floor w\/ outdoor heated pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $218 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 $538 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 $538 per night (USD)VRBO
- From $425 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 $425 per night (USD)Expedia
- From $457 per night (USD)
VRBO
Deluxe Two Bedroom Suite on the 2nd floor with outdoor heated pool 20304
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $457 per night (USD)VRBO
- From $218 per night (USD)
Expedia
Deluxe One Bedroom Queen Suite on the 2nd floor with outdoor heated pool 202
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $218 per night (USD)Expedia
- From $245 per night (USD)
VRBO
Deluxe 1 bedroom suite located on first floor with outdoor heated pool 11820
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $245 per night (USD)VRBO
- From $1161 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 $1161 per night (USD)Expedia
- From $890 per night (USD)
VRBO
Ski-In\/Ski-Out Condo w\/ Pool & Seasonal Hot Tubs - Golf & Tennis Nearby
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Winterplace G101 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $890 per night (USD)VRBO
- From $604 per night (USD)
Expedia
Secluded Rustic Home with Private Hot Tub & Huge Deck - 5 Miles to Okemo
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Andover Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $604 per night (USD)Expedia
- From $398 per night (USD)
VRBO
Quaint lakefront home with a private deck, firepit, and dock
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Ludlow's Gem Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $398 per night (USD)VRBO
- From $697 per night (USD)
Expedia
Ski-in \/Out. Spacious 2BR \/ 2.5B Ground-Floor Condo. 4 Seasons of enchantment.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Spacious 2 bedroom - 2.5 bathroom condominium is located on the sunny side of Okemo in SouthFace Village, the newest dev ...
From $697 per night (USD)Expedia
- From $669 per night (USD)
VRBO
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 $669 per night (USD)VRBO
- From $696 per night (USD)
Expedia
Beautiful & Spacious Condo w\/ Pool, Lake Access - Close to Skiing
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Birch Landing #16 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $696 per night (USD)Expedia
- From $424 per night (USD)
VRBO
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 $424 per night (USD)VRBO
- From $410 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 $410 per night (USD)Expedia
- From $237 per night (USD)
VRBO
Cozy Quechee Corner Cabin
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Quechee Cabin- 4 Season Resort Townhouse nestled in a picturesque nature setting in historic Quechee Vermont: Hike, bik ...
From $237 per night (USD)VRBO
- From $504 per night (USD)
Expedia
Condo near ski trail with fireplace, hot tub, pool, tennis & washer\/dryer
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Winterplace Q206 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $504 per night (USD)Expedia
- From $800 per night (USD)
VRBO
Home near the Bull Run Trail with fireplace, washer\/dryer & cable
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 9
Snow Lane Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $800 per night (USD)VRBO
- From $671 per night (USD)
Expedia
Mountainside condo with sauna, balcony, & walk to lifts
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Okemo Trailside 40C Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $671 per night (USD)Expedia
- From $1665 per night (USD)
VRBO
Mountainview condo with pool, hot tubs, & fireplace - 250 yards from skiing
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The Love Shack - Winterplace Q104 Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $1665 per night (USD)VRBO
- From $922 per night (USD)
Expedia
Inviting condo on Village Run Trail with a fireplace, pool, & hot tub
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Solitude Village A2 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $922 per night (USD)Expedia
- From $918 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 $918 per night (USD)VRBO
- From $554 per night (USD)
Expedia
Ski-in\/out condo with fireplace, tennis court, mountain views, & washer\/dryer
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Kettle Brook G6 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $554 per night (USD)Expedia
- From $1874 per night (USD)
VRBO
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 $1874 per night (USD)VRBO
- From $1152 per night (USD)
Expedia
Ski-in\/out condo near lifts with a fireplace, pool, hot tub, & tennis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Winterplace F101 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $1152 per night (USD)Expedia
- From $961 per night (USD)
VRBO
Ski-in\/ski-out condo with pool, hot tub, sauna, mountain view, deck, & fireplace
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Sweet Solitude G104 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $961 per night (USD)VRBO
- From $1333 per night (USD)
Expedia
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 $1333 per night (USD)Expedia
- From $550 per night (USD)
VRBO
Ski-in\/out condo with fireplace, hot tubs. pool, tennis & washer\/dryer
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Winterplace G205 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $550 per night (USD)VRBO
- From $618 per night (USD)
Expedia
Hawk Mountain retreat near Okemo with wifi, washer\/dryer & deck
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Nest at Hawk Ledges Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $618 per night (USD)Expedia
- From $469 per night (USD)
VRBO
Inviting condo with a fireplace, hot tubs, pool, tennis & washer\/dryer
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Winterplace E202 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $469 per night (USD)VRBO
- From $942 per night (USD)
Expedia
Inviting condo near the Sachem Trail with wifi, washer\/dryer
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Okemo Trailside 11C Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $942 per night (USD)Expedia
- From $824 per night (USD)
VRBO
Ski-in\/out condo with mountain and lift views, hot tub, & pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Winterplace G303 - Skier's Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $824 per night (USD)VRBO
- From $668 per night (USD)
Expedia
Ski-in\/out Condo on Bull Run Trail with fireplace, & full kitchen
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Kettle Brook I4 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $668 per night (USD)Expedia
- From $450 per night (USD)
VRBO
Ski-in\/out condo with water & mountain views, private sauna & fireplace
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Kettle Brook A7 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $450 per night (USD)VRBO
- From $1406 per night (USD)
Expedia
Beautiful home near lifts with wood-burning fireplace, mountain views & cable
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Classic Log Cabin Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1406 per night (USD)Expedia
- From $476 per night (USD)
VRBO
Newly renovated ski-in\/out slope side condo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Okemo Mountain Lodge C202 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $476 per night (USD)VRBO
- From $326 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 $326 per night (USD)Expedia
- From $411 per night (USD)
VRBO
Ski-In\/Out condo with patio, mountain views, washer\/dryer, & cable
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Okemo Mountain Lodge C108 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $411 per night (USD)VRBO
- From $540 per night (USD)
Expedia
Ski-in\/out condo with a pool, tennis & fast WiFi - Sachem Trail at Okemo
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Okemo Trailside 19BL Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $540 per night (USD)Expedia
- From $634 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 $634 per night (USD)VRBO
- From $834 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 $834 per night (USD)Expedia
- From $791 per night (USD)
VRBO
Ski-in\/out condo with a fireplace, hot tub, gym, pool, washer\/dryer & cable
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Okemo Condo - Solitude Village N104 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $791 per night (USD)VRBO
- From $528 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 $528 per night (USD)Expedia
- From $484 per night (USD)
VRBO
Lovely mountain condo with pool, fireplace & cable- near skiing
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Brookhaven B1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $484 per night (USD)VRBO
- From $490 per night (USD)
Expedia
Mountain view condo with fireplace, pool, hot tub, tennis, washer\/dryer & cable
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Winter Escape - WP A202 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $490 per night (USD)Expedia
- From $759 per night (USD)
VRBO
Three-level ski-in\/out condo with sauna, 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 $759 per night (USD)VRBO
- From $478 per night (USD)
Expedia
Ski-in\/ski-out condo with pool, tennis courts, & grill
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Okemo Trailside 19BU Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $478 per night (USD)Expedia
- From $525 per night (USD)
VRBO
Ground-floor condo with fireplace, pool, hot tub, tennis, washer\/dryer & cable
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Winterplace Getaway A101 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $525 per night (USD)VRBO
- From $485 per night (USD)
Expedia
Ski-in\/out condo near ski school with washer\/dryer, fast WiFi, & mountain views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Okemo Mountain Lodge C106 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $485 per night (USD)Expedia
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- From $930 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 $930 per night (USD)Expedia
- From $648 per night (USD)
VRBO
Great Winter weekend Getaway, Village home in cul-de-sac. 1 mile to Okemo
- 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 $648 per night (USD)VRBO
- From $404 per night (USD)
Expedia
Log Home Perfect for a Family Getaway - Five Miles from Okemo Mountain Resort
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Sherman Log House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $404 per night (USD)Expedia
- From $344 per night (USD)
VRBO
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Okemo Trailside 8E Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $344 per night (USD)VRBO
- From $604 per night (USD)
Expedia
Elegantly Rustic Getaway w\/Yard, Fire Pit, Dock, Kayaks - Close to Skiing
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Lakeside Elegance Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $604 per night (USD)Expedia
- From $662 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 $662 per night (USD)VRBO
- From $516 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 $516 per night (USD)Expedia
- From $250 per night (USD)
VRBO
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 $250 per night (USD)VRBO
- From $512 per night (USD)
Expedia
Vermont Mountain Retreat: The Antler House
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 6
Welcome to the 'Antler House,' your perfect escape nestled in the scenic Vermont mountains! Located in the charming town ...
From $512 per night (USD)Expedia
- From $256 per night (USD)
VRBO
Custom-built Tiny House on forested lot near Quechee
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $256 per night (USD)VRBO
- From $1097 per night (USD)
Expedia
Mountain-view condo near Sachem Trail with pool - walk to lifts
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Okemo Trailside 5B Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1097 per night (USD)Expedia