Windsor Area, Vermont Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Windsor Area, Vermont on RentalSaver.com!

Windsor Area Rentals

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 Pricing
VRBO
From $311 per night (USD)
VRBO
Your Year-Round Mountain Escape in Ludlow—Just Minutes from Okemo
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Welcome to your perfect Vermont getaway! Located just 2.1 miles (a quick 5-minute drive) from Okemo Mountain’s main base ...
From $311 per night (USD)
VRBO
From $185 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 $185 per night (USD)
VRBO
From $569 per night (USD)
VRBO
On Okemo and steps Sachem trail!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
We are on the mountain and are perfect for a group of families that want have easy access to skiing. We're a short walk ...
From $569 per night (USD)
VRBO
From $419 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 $419 per night (USD)
VRBO
From $202 per night (USD)
VRBO
Marsh Brook is a beautiful farmhouse located in the heart of the Green Mountains
Bedrooms:
3
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 $202 per night (USD)
VRBO
From $339 per night (USD)
VRBO
Charming & Affordable Home! 1.5 miles from Okemo!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Warm and inviting ski home located in the heart of Ludlow - walk to restaurants and shops in town and then retire to our ...
From $339 per night (USD)
VRBO
From $153 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 $153 per night (USD)
VRBO
From $542 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 $542 per night (USD)
VRBO
From $1215 per night (USD)
Expedia
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 $1215 per night (USD)
Expedia
From $716 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 $716 per night (USD)
VRBO
From $318 per night (USD)
Expedia
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 $318 per night (USD)
Expedia
From $349 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 $349 per night (USD)
VRBO
From $194 per night (USD)
Expedia
109 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 $194 per night (USD)
Expedia
From $170 per night (USD)
VRBO
Queen Studio on the 2nd floor with outdoor heated pool 207
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 $170 per night (USD)
VRBO
From $336 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 $336 per night (USD)
Expedia
From $171 per night (USD)
VRBO
Deluxe One bedroom Queen Suite with outdoor heated pool 203
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 $171 per night (USD)
VRBO
From $171 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 $171 per night (USD)
Expedia
From $214 per night (USD)
VRBO
Deluxe 1 bedroom suite located on first floor with outdoor heated pool 118/120
Bedrooms:
2
Bathrooms:
1
Sleeps:
6
Welcome to Cedarbrook – Your Year-Round Mountain Escape. Tucked in the heart of Vermont's Green Mountains, Cedarbrook of ...
From $214 per night (USD)
VRBO
From $214 per night (USD)
Expedia
Cedarbrook Junior Suite 11416
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 $214 per night (USD)
Expedia
From $606 per night (USD)
VRBO
Ski-in /Out. Spacious 2BR / 2.5B Ground-Floor Condo. 4 Seasons of enchantment.
Bedrooms:
2
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 $606 per night (USD)
VRBO
From $799 per night (USD)
Expedia
Mountain-view house with hot tub, AC & amazing views, near Okemo Resort & skiing
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Ludlow Treasure Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $799 per night (USD)
Expedia
From $337 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 $337 per night (USD)
VRBO
Click For Pricing
Expedia
Secluded Rustic Home with Private Hot Tub & Huge Deck - 5 Miles to Okemo
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Andover Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
Click For Pricing
Expedia
From $271 per night (USD)
VRBO
Quaint lakefront home with a fire pit and beautiful views
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 $271 per night (USD)
VRBO
From $254 per night (USD)
Expedia
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 $254 per night (USD)
Expedia
From $160 per night (USD)
VRBO
2 Bedroom Condo in Quechee, ~VT~ - a Four Season Community!
Bedrooms:
1
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 $160 per night (USD)
VRBO
From $324 per night (USD)
Expedia
Enjoy our ski in ski out condo. Located mid-mountain at Solitude Peak!
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Newly Renovated Professional Cleaners-Linens and towels laundered off site Remote Check-In Located mid-mountain at the b ...
From $324 per night (USD)
Expedia
From $452 per night (USD)
VRBO
Ludlow-Historic Charm, Lake Rescue, Pet Friendly
Bedrooms:
2
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 $452 per night (USD)
VRBO
From $252 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 $252 per night (USD)
VRBO
From $535 per night (USD)
VRBO
Beautiful & Spacious Condo w/ Pool, Lake Access - Close to Skiing
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Birch Landing #16 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $535 per night (USD)
VRBO
From $331 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 $331 per night (USD)
Expedia
From $1606 per night (USD)
VRBO
Ski In Ski Out Renovated Trailside Condo on Sachem Trail @ Okemo Resort
Bedrooms:
2
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 $1606 per night (USD)
VRBO
From $766 per night (USD)
Expedia
Modern Farmhouse on 25 Acres / Superb Views.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This Truex Cullins designed Farmhouse is inspired by the iconic old farmsteads found throughout northern New England. Em ...
From $766 per night (USD)
Expedia
From $210 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 $210 per night (USD)
VRBO
From $342 per night (USD)
Expedia
Pet Friendly Ski House with Hot Tub
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
A ski house nestled trailside on Plymouth Notch Ski Mountain. Take in the spectacular views while you relax on the couch ...
From $342 per night (USD)
Expedia
From $203 per night (USD)
VRBO
Cozy Quechee Corner Cabin
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Quechee Cabin, an authentic Vermont offering - 4 Season Resort Townhouse nestled in a picturesque nature setting in hist ...
From $203 per night (USD)
VRBO
From $1074 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 $1074 per night (USD)
VRBO
From $658 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 $658 per night (USD)
VRBO
From $478 per night (USD)
Expedia
Log Home Perfect for a Family Getaway - Five Miles from Okemo Mountain Resort
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Sherman Log House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $478 per night (USD)
Expedia
From $263 per night (USD)
VRBO
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 $263 per night (USD)
VRBO
From $505 per night (USD)
Expedia
Elegantly Rustic Getaway w/Yard, Fire Pit, Dock, Kayaks - Close to Skiing
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Lakeside Elegance Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $505 per night (USD)
Expedia
From $640 per night (USD)
VRBO
Secluded Luxury Home on Huge Property with Mountain Views - Near Slopes
Bedrooms:
3
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 $640 per night (USD)
VRBO
From $568 per night (USD)
Expedia
Bright, Open Home with Wraparound Deck & Mountain Views - 2 Miles to Skiing
Bedrooms:
2
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 $568 per night (USD)
Expedia
From $334 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 $334 per night (USD)
VRBO
From $1186 per night (USD)
Expedia
Home near the Bull Run Trail with fireplace, washer/dryer & cable
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Snow Lane Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1186 per night (USD)
Expedia
From $926 per night (USD)
VRBO
Mountainside condo with sauna, balcony, & walk to lifts
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Okemo Trailside 40C Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $926 per night (USD)
VRBO
From $523 per night (USD)
Expedia
Inviting condo on Village Run Trail with a fireplace, pool, & hot tub
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Solitude Village A2 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $523 per night (USD)
Expedia
From $669 per night (USD)
VRBO
Inviting Okemo ski mountain home, two house walk to ski slope!
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
Doc's Folly Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $669 per night (USD)
VRBO
From $284 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 $284 per night (USD)
Expedia
From $1609 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 $1609 per night (USD)
VRBO
From $836 per night (USD)
Expedia
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 $836 per night (USD)
Expedia
From $354 per night (USD)
VRBO
Ski-in/ski-out condo with pool, hot tub, sauna, mountain view, deck, & fireplace
Bedrooms:
2
Bathrooms:
2
Sleeps:
9
Sweet Solitude G104 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $354 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
From $388 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 $388 per night (USD)
VRBO
From $582 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 $582 per night (USD)
Expedia
From $293 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 $293 per night (USD)
VRBO
From $724 per night (USD)
Expedia
Inviting condo near the Sachem Trail with wifi, washer/dryer
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Okemo Trailside 11C Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $724 per night (USD)
Expedia
From $385 per night (USD)
VRBO
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 $385 per night (USD)
VRBO
From $391 per night (USD)
Expedia
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 $391 per night (USD)
Expedia
From $272 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 $272 per night (USD)
VRBO
From $615 per night (USD)
Expedia
Beautiful home near lifts with wood-burning fireplace, mountain views & cable
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Classic Log Cabin Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $615 per night (USD)
Expedia
From $261 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 $261 per night (USD)
VRBO
From $220 per night (USD)
Expedia
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 $220 per night (USD)
Expedia
From $402 per night (USD)
VRBO
Ski-in/out condo with a pool, tennis & 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 $402 per night (USD)
VRBO
Click For Pricing
Expedia
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 Pricing
Expedia
From $317 per night (USD)
VRBO
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 $317 per night (USD)
VRBO
From $419 per night (USD)
Expedia
Ski-in/out condo with a fireplace, hot tub, gym, pool, washer/dryer & cable
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Okemo Condo - Solitude Village N104 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $419 per night (USD)
Expedia
From $323 per night (USD)
VRBO
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 $323 per night (USD)
VRBO
From $323 per night (USD)
Expedia
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 $323 per night (USD)
Expedia
From $194 per night (USD)
VRBO
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 $194 per night (USD)
VRBO
From $371 per night (USD)
Expedia
Three-level ski-in/out condo with sauna, washer/dryer & mountain view
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Okemo Trailside 32C Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $371 per night (USD)
Expedia
From $475 per night (USD)
VRBO
Ski-in/ski-out condo with pool, 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 ...
From $475 per night (USD)
VRBO
From $390 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 $390 per night (USD)
Expedia
From $472 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 $472 per night (USD)
VRBO
From $595 per night (USD)
Expedia
Ski-in/out home with a hot tub, fireplace, cable & golf nearby
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Wood Lantern Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $595 per night (USD)
Expedia
From $1056 per night (USD)
VRBO
Family, Pet Friendly Bridgewater/Killington/Woodstock Area Rental
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Located on the Ottoquechee River 6 miles from Killington Skyship high speed quad, 20 minutes from Okemo Mountain, and 6 ...
From $1056 per night (USD)
VRBO
From $665 per night (USD)
Expedia
Mountain-view condo near Sachem Trail with pool - walk to lifts
Bedrooms:
2
Bathrooms:
3
Sleeps:
16
Okemo Trailside 5B Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $665 per night (USD)
Expedia
Click For Pricing
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 ...
Click For Pricing
VRBO
From $230 per night (USD)
VRBO
Cheerful residential home with lots of space
Bedrooms:
2
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 $230 per night (USD)
VRBO
Click For Pricing
VRBO
Vermont Mountain Retreat: The Antler House
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Welcome to the 'Antler House,' your perfect escape nestled in the scenic Vermont mountains! Located in the charming town ...
Click For Pricing
VRBO
From $256 per night (USD)
Expedia
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)
Expedia
From $379 per night (USD)
VRBO
Little Cabin On The Ridge Andover Vt
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Recently built classic Vermont cabin. This cozy home is perfect for singles, couples and families. The well-designed spa ...
From $379 per night (USD)
VRBO
From $630 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 $630 per night (USD)
Expedia
Click For Pricing
VRBO
A distinctive family retreat for an epic ski vacation!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Our Ski house is nestled on Main Street in the small town of Proctorsville just 4.5 miles from the base of Okemo Mountai ...
Click For Pricing
VRBO
From $309 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 $309 per night (USD)
VRBO
From $355 per night (USD)
VRBO
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 $355 per night (USD)
VRBO
$\Whispering Pines\ Ski House in the heart of the Green Mountains$
From $691 per night (USD)
VRBO
\"Whispering Pines\" Ski House in the heart of the Green Mountains
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Fantastic 5BR ski house located in private neighborhood in prime location in the heart of the Green Mountains. Enjoy tru ...
From $691 per night (USD)
VRBO
From $523 per night (USD)
VRBO
Amherst Lake Views - Minutes To Okemo And Killington - 5 Bedrooms
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Relax and enjoy stunning views of beautiful Amherst Lake and surrounding mountains from the house and deck. Located just ...
From $523 per night (USD)
VRBO
From $347 per night (USD)
VRBO
Beautiful Mountain Getaway for Skiing
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Mountain getaway with beautiful views , minutes from Okemo & Killington . Private home at Hawk Resort 8 mi to Okemo and ...
From $347 per night (USD)
VRBO
From $218 per night (USD)
VRBO
Vermont Charm in the 1840 Gideon Lee House
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Sunshine, flowers, Farmers' Markets, hikes and starry nights are here. Scents fill the air and the birds are calling. S ...
From $218 per night (USD)
VRBO
From $828 per night (USD)
Expedia
Resort on a Farm
Bedrooms:
4
Bathrooms:
0
Sleeps:
0
Gorgeous estate on a 23 acre farm with resort amenities available for monthly occupancy. Located just a few minutes from ...
From $828 per night (USD)
Expedia
From $1160 per night (USD)
VRBO
Gorgeous Slopeside Winterplace/Okemo Vail Resorts Available Feb holiday/March!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Newly Renovated, Winterplace at Okemo Vail Resorts Slope Side: This Top Floor, End Unit, Front Line Winterplace condo fe ...
From $1160 per night (USD)
VRBO
From $532 per night (USD)
Expedia
Kettle Brook 2 BR & 2 BA ski in/out condo on Okemo Mountain
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Kettle Brook is scenic ski in/out complex between the Bull Run and Kettle Brook trails on Okemo Mountain. Direct ski a ...
From $532 per night (USD)
Expedia
Click For Pricing
VRBO
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 Pricing
VRBO
From $461 per night (USD)
VRBO
Long Range Mountain Views in West Windsor
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Thistle Hill, a beautiful private property on 17 acres. Home is located 12 miles from Woodstock in the heart ...
From $461 per night (USD)
VRBO
From $1122 per night (USD)
VRBO
Ski house. Okemo Ludlow Vermont
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Large timber frame family style ski home with a spectacular veiw of the mountain Professional kitchen,Games, Hot Tub, s ...
From $1122 per night (USD)
VRBO
From $432 per night (USD)
Expedia
Sweet Life - Vermont Chalet - 6 person Indoor Hot Tub - 15 min to Killington
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
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 $432 per night (USD)
Expedia
From $3124 per night (USD)
VRBO
Havenwood, a beautiful private, gated estate in Woodstock, Vermont
Bedrooms:
7
Bathrooms:
7
Sleeps:
14
This secluded 125 acre estate is aptly named. A few nights at Havenwood will leave one feeling both relaxed and energiz ...
From $3124 per night (USD)
VRBO
From $990 per night (USD)
VRBO
The Cottage on private gated 400 acre Reading Farms Estate
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
This home is one of 3 on a 400 gated acre estate . It has a kitchen, 3 bedroom, 1.5 bathrooms. Main floor bedroom has a ...
From $990 per night (USD)
VRBO

Search Your Destination Now!

Windsor Area Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 1,000 Rentals