Windsor Area Rentals
- From $306 per night (USD)
VRBO
Mountainside Suite! Arcade, Pool, Hot Tub Access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our charming mountainside suite, located mid-mountain at the base of the Solitude Peak! Spend a fantastic day ...
From $306 per night (USD)VRBO
- From $250 per night (USD)
Expedia
Ski-In\/Ski-Out Condo with Access to Indoor Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our cozy and charming ski-in/ski-out condo at Okemo Mountain Resort! Located at the summit of the two South R ...
From $250 per night (USD)Expedia
- Click For Pricing
VRBO
Mountainside Condo w\/ Access to Pool, Ski Shuttle
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This 2-bedroom condo is in Okemo. Located near the summit of the two South Ridge Quad chairlifts, you will love to have ...
Click For PricingVRBO
- From $278 per night (USD)
Expedia
Okemo Retreat! Ski-In\/Ski-Out Condo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Come and stay in our charming ski-in/ski-out condo at Okemo Mountain Resort! Located at the summit of the two South Ridg ...
From $278 per night (USD)Expedia
- From $320 per night (USD)
VRBO
Mountainside Suite! Arcade, Pool, Hot Tub Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
When you stay at Okemo Mountain Resort, you will love to return to our cozy and charming suite, located mid-mountain at ...
From $320 per night (USD)VRBO
- From $391 per night (USD)
Expedia
Ski-in\/Ski-out Suite | Pool, Arcade, Sauna
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Come and stay in our charming ski-in/ski-out suite, located mid-mountain at the base of the Solitude Peak! Spend a fanta ...
From $391 per night (USD)Expedia
- From $286 per night (USD)
VRBO
Cozy Suite | Ski-in\/Ski-Out | Hot Tub, Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Find peace and relaxation in our cozy ski-in/ski-out suite, located mid-mountain at the base of the Solitude Peak! Spend ...
From $286 per night (USD)VRBO
- From $500 per night (USD)
Expedia
Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our three Bedroom first floor condo at Winterplace in the O building! While we wish we could get up to Okemo ...
From $500 per night (USD)Expedia
- From $140 per night (USD)
VRBO
Ski-in\/out condo with mountain views, fireplace, pool, & hot tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Winterplace H205 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $140 per night (USD)VRBO
- From $143 per night (USD)
Expedia
Ski-in\/ski-out condo with WiFi, washer\/dryer, mountain views & golf nearby
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Okemo Mountain Base Retreat C203 Our calendar is updated in real-time & our nightly rates are accurately displayed. Sim ...
From $143 per night (USD)Expedia
- From $153 per night (USD)
VRBO
Ski-in\/out condo with patio, full kitchen & high-speed WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Okemo Mountain Lodge C110 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $153 per night (USD)VRBO
- Click For Pricing
Expedia
Amazing Location! Charming Ski-in\/Ski-out Condo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Imagine an amazing mountain vacation in Okemo! When you stay in our cozy and equipped split-level unit, you will love to ...
Click For PricingExpedia
- From $250 per night (USD)
VRBO
Ski-in\/Ski-out Condo with access to Pools, Sauna
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Imagine an amazing mountain vacation in Okemo! When you stay in our charming and equipped split-level unit, you will lov ...
From $250 per night (USD)VRBO
- Click For Pricing
Expedia
Charming + Rustic Condo with Ski-in\/Ski-Out Access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Feel right at home in Okemo when you stay in our cozy and equipped Ski-in/Ski-out unit! Wonderfully located in a small s ...
Click For PricingExpedia
- From $377 per night (USD)
VRBO
2 Bedroom Mountainside Condo + nearby amenities!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This 2-bedroom mountainside condo in Okemo, Vermont is the perfect retreat for fantastic skiing and hiking, or for some ...
From $377 per night (USD)VRBO
- From $104 per night (USD)
Expedia
116 Two Double bed Standard Hotel room
- 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 $104 per night (USD)
VRBO
117 Two Double bed Standard Hotel room
- 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 $250 per night (USD)
Expedia
Village Farmhouse, mins to Okemo, Killington, Ascutney, GMHA. Pet-friendly.
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Ski dates still available! Book now for GMHA, cycling, equestrian, leaf-peeping, family events, girls getaway, romance a ...
From $250 per night (USD)Expedia
- Click For Pricing
VRBO
Fabulous views! Brand new house!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 3
This is a brand new 2 floor home with a cathedral ceiling that takes in the west view. The upstairs has a bedroom and a ...
Click For PricingVRBO
- From $364 per night (USD)
Expedia
Historic Rideout 16m to Okemo Walk to Town
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
A @Vermont_Escapes property - Escape to Vermont with us! New Jacuzzi hot tub installed July '23. Escape to the histo ...
From $364 per night (USD)Expedia
- From $849 per night (USD)
VRBO
SKI In\/SKI Out. 4 Bedrooms, A1- Walk to Pool\/Gym, End unit with tons of sunlight
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
We are true ski in and out. We access the main Solitude lift and have direct trail access. We are a warm and inviting, ...
From $849 per night (USD)VRBO
- From $474 per night (USD)
Expedia
UNIQUE\/HISTORIC STAY IN AN 1874 ERA SCHOOLHOUSE!!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy a historic stay in this former Chester Schoolhouse recently renovated into a massive yet cozy home. Located only 1 ...
From $474 per night (USD)Expedia
- From $230 per night (USD)
VRBO
Best Location! Renovated center village Okemo 2 BR - free shuttle outside door!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Come and enjoy the fantastic skiing at Okemo! Our 2-bedroom condo is right on Main St. in the middle of dining and shop ...
From $230 per night (USD)VRBO
- From $243 per night (USD)
Expedia
5 miles to Okemo\/Ludlow, 25 Acre Playground, Great Ski or Summer Rental
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Awe-inspiring views and a peaceful vibe come together at The Big Barn Farm to serve up a fabulous vacation for any seaso ...
From $243 per night (USD)Expedia
- From $243 per night (USD)
VRBO
Great Ski or Summer Rental - 5 miles to Okemo\/Ludlow, 25 Georgeous Acres
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Awe-inspiring views and a peaceful vibe come together at The Big Barn Farm to serve up a fabulous vacation for any seaso ...
From $243 per night (USD)VRBO
- From $808 per night (USD)
Expedia
Work, Ski, Relax - Big Restored 1860s Farmhouse
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Come up solo or bring friends and family to our unique and lovingly renovated estate! Our charming 1860’s farmhouse slee ...
From $808 per night (USD)Expedia
- From $338 per night (USD)
VRBO
Ski-in\/out mountainside condo with balcony, washer\/dryer & high-speed WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Okemo Mountain Lodge B203 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $338 per night (USD)VRBO
- From $126 per night (USD)
VRBO
Alpine Farm Cottage Retreat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy our private country mountain retreat! - Beautiful farm pasture views, seasonal mountain views - 10 miles to Okemo ...
From $126 per night (USD)VRBO
- From $242 per night (USD)
VRBO
Secluded dog-friendly home amongst the trees with sauna, Wii, & 2 scenic decks
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Plymouth Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $242 per night (USD)VRBO
- Click For Pricing
Expedia
Condo with washer\/dryer, balcony, wood stove & cable - walk to slopes
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Okemo Village Vacation Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simpl ...
Click For PricingExpedia
- From $212 per night (USD)
VRBO
Country Home in Weston Vermont Welcomes You!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Pleasant surroundings with mountain views of Stratton MT, Magic MT and Bromley MT ski areas. Less than 1.5 miles from th ...
From $212 per night (USD)VRBO
- Click For Pricing
Expedia
Ski-In\/Out Condo with Electric Fireplace, Mountain Views, and Washer\/Dryer
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Okemo Trailside 22DL Shred Shack Our calendar is updated in real-time & our nightly rates are accurately displayed. Sim ...
Click For PricingExpedia
- Click For Pricing
VRBO
Mountain-view house with wood-burning fireplace, balcony, & deck - near skiing
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Okemo Clock Tower Base Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
Click For PricingVRBO
- From $233 per night (USD)
Expedia
Okemo Mountain Chalet W\/ Hot Tub and Game Room
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 15
Our Contemporary Ski House is less than 4 miles from Okemo Mountain Resort. It is situated on 10 private acres in the S ...
From $233 per night (USD)Expedia
- From $358 per night (USD)
VRBO
\"The Arched Chalet\" Stunning Green Mountain views close to Killington and Okemo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the Arched Chalet, one of the last arched ski homes in the area located on Plymouth Notch ski mountain. The ...
From $358 per night (USD)VRBO
- Click For Pricing
Expedia
Dog-Friendly Cottage with High-Speed WiFi, Firepit, and Washer\/Dryer
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
Little Yellow Bungalow Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
Click For PricingExpedia
- From $217 per night (USD)
VRBO
Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
The Pond House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $217 per night (USD)VRBO
- Click For Pricing
Expedia
Come Home to Vermont
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Lake frontage on the only natural lake between Okemo Mt and Killington Mt. Ski the best 2 mountains, snow mobile, cross ...
Click For PricingExpedia
- From $79 per night (USD)
VRBO
Downtown Condo w\/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Cozy Ludlow Escape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $79 per night (USD)VRBO
- From $999 per night (USD)
Expedia
Stunning Log Home, 7 Bed\/4 Bath. Mountain View!
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 16
Authentic, custom crafted, log home. Amazing natural light throughout the house. 2-person jacuzzi tub, game room with pi ...
From $999 per night (USD)Expedia
- From $179 per night (USD)
VRBO
Bright Condo w\/ Community Perks: Near Ski Quechee!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 7
Follow days skiing Vermont’s top resorts with leisurely afternoons and home-cooked meals at this 2-bedroom, 2.5-bath con ...
From $179 per night (USD)VRBO
- Click For Pricing
Expedia
Large 4 bedroom one mile from Okemo Base. Walk to downtown Ludlow
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Bring the whole family to this great place with lots of room for fun. Located approx. 1 mile from Okemo base lodge and o ...
Click For PricingExpedia
- From $558 per night (USD)
VRBO
The Quechee Haus: VT Retreat with Outdoor Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Relax, rejuvenate, and restore at The Quechee Haus. Located just 10 minutes from downtown Woodstock, 30 minutes from Kil ...
From $558 per night (USD)VRBO
- From $399 per night (USD)
Expedia
Quiet Modern Luxury Home w\/ Memory Foam Beds, FAST WiFi and Full Kitchen
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
3 Bedrooms, 2 Full Bathrooms, Sleeps up to 8, Washer/Dryer, Radiant Floor Heat 3 Bedroom, 2 Full Baths home located 8 mi ...
From $399 per night (USD)Expedia
- From $261 per night (USD)
VRBO
Lakefront home with amazing views, fireplace, firepit, & gas grill
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Lake Rescue Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $261 per night (USD)VRBO
- From $309 per night (USD)
Expedia
~ Fire Pit, Pool Table ~ Private Classic VT Ski Chalet WALK TO OKEMO SKI LIFT
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
PLEASE NOTE: No Saturday arrivals or departures without owner approval BEFORE booking. Recommended local activities and ...
From $309 per night (USD)Expedia
- From $85 per night (USD)
VRBO
Whimsical Room & Private Bathroom in Historic Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Enjoy a private room & bathroom with tub in the historic Chester Inn, circa 1780. This charming property is conveniently ...
From $85 per night (USD)VRBO
- From $70 per night (USD)
Expedia
Honeymoon Suite with Jacuzzi Tub in Historic Inn
- 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 $70 per night (USD)Expedia
- From $133 per night (USD)
VRBO
Okemo Mountain, Family Affordable 2 fl village location walk to town, Dogs OK.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Linens not provided!! Located in the village of Ludlow, Vermont on the Black river with in 20 miles of 5 major ski area’ ...
From $133 per night (USD)VRBO
- From $490 per night (USD)
Expedia
5 Bedroom Home with Views of Quechee
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Spacious 5 bedroom home in Quechee lakes. 1/2 mile from Quechee clubhouse for Dining, Golf, Skiing, Tennis. 20 minutes f ...
From $490 per night (USD)Expedia
- From $400 per night (USD)
VRBO
Escape To Quechee For Ski, Golf, Swimming! Family & Pet Friendly!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
A three bedroom condo in a private courtyard setting, surrounded by beautiful grounds and gorgeous mountains. Convenien ...
From $400 per night (USD)VRBO
- From $178 per night (USD)
Expedia
Vermont Trailside Getaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Enjoy our trailside, ski in ski out condo. Located At the top of the A&B lifts. Skip the crowds at the Base! After an ...
From $178 per night (USD)Expedia
- From $231 per night (USD)
VRBO
Woodstock Village Carriage House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Carriage house to historic 1861 home. One bedroom, queen bed with en suite bathroom. Full kitchen, open-plan living roo ...
From $231 per night (USD)VRBO
- From $139 per night (USD)
Expedia
Renovated condo, walk to dining, on bus route to ski slopes
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Depot Street Condo Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $139 per night (USD)Expedia
- From $304 per night (USD)
VRBO
Mountain Top Townhome Near Okemo and Killington
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Mountain top getaway home with beautiful views located off of Vermont Rt 100 Scenic Byway. Only 8 miles from Okemo and 1 ...
From $304 per night (USD)VRBO
- From $268 per night (USD)
Expedia
Ski-in\/out gem with balcony, fast WiFi, modern decor & full kitchen
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Okemo Mountain Lodge C306: Aspen in Okemo Our calendar is updated in real-time & our nightly rates are accurately displ ...
From $268 per night (USD)Expedia
- Click For Pricing
VRBO
Solitude Village Stunner!
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 11
Best location on Okemo? Many say so, you can skate across parking lot to ski on spot & ski off at same. Fully outfitted, ...
Click For PricingVRBO
- From $293 per night (USD)
Expedia
Dog-friendly house near skiing with mountain view, game room, fireplace, & grill
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Misty Maple Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $293 per night (USD)Expedia
- From $229 per night (USD)
VRBO
Mountain-view lodge with deck, fireplace, pool table, W\/D & fast WiFi
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Tranquility in VT Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $229 per night (USD)VRBO
- From $168 per night (USD)
Expedia
Mountain view home with deck, wood fireplace, washer\/dryer, and high-speed WiFi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Mountain View Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $168 per night (USD)Expedia
- Click For Pricing
Expedia
⚜Luxury Home⚜Private Pond⚜25 Acres of Privacy⚜5 Min Downtown Woodstock⚜Spa⚜BBQ
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
⚜ Gorgeous family home on a 25-acre estate in a picturesque natural setting. ⚜ Large, lush house that sleeps up to 8 ad ...
Click For PricingExpedia
- From $350 per night (USD)
Expedia
Killington Skiers\/Snowmobilers\/MountainBikers Dream with Outdoor Jacuzzi + Wi-Fi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Recently updated, tastefully decorated upper level duplex located only seven miles to the Killington Access Road. This c ...
From $350 per night (USD)Expedia
- From $160 per night (USD)
VRBO
Dog-friendly riverfront home with washer\/dryer, partial A\/C, river views, & wifi
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Vermont Farmhouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $160 per night (USD)VRBO
- From $326 per night (USD)
Expedia
2-Story riverfront home + studio with washer\/dryer, river views, & free WiFi
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Vermont Farm House and Studio Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $326 per night (USD)Expedia
- From $199 per night (USD)
VRBO
Home located 5 minutes to Okemo Mountain, Lake Rescue, and nearby Fox Run Golf.
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Comfortable and close to amenities, perfect for two families to share for a weekend if interested in skiing, hiking or k ...
From $199 per night (USD)VRBO
- Click For Pricing
Expedia
Classic home with private hot tub, deck, & wood stove - near Okemo Mountain
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 13
Cozy in Cavendish Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
Click For PricingExpedia
- Click For Pricing
Expedia
Vermont charm 8 minutes to Okemo Mountain!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Eight minutes to Okemo mountain, the little house is a step back to simpler times. Everything you need with space to bre ...
Click For PricingExpedia
- From $315 per night (USD)
Expedia
Après Chalet: A Modern Ski-In\/Out condo at Okemo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience the ultimate ski-in/ski-out convenience just steps from the lift. This fully renovated condo offers modern co ...
From $315 per night (USD)Expedia
- From $175 per night (USD)
VRBO
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Ludlow when you stay in our fabulously renovated historic condo built in 1857. The Mill Place cond ...
From $175 per night (USD)VRBO
- From $341 per night (USD)
Expedia
Private Chester Home w\/ Deck, Mins to Skiing!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Spacious, private and fully outfitted for a group getaway to Vermont, this 3-bedroom, 3-bath vacation rental is ready fo ...
From $341 per night (USD)Expedia
- From $915 per night (USD)
VRBO
Best Location SKI-ON\/SKI-OFF⛷ with hot tubs, pool, fireplace
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
-PREMIUM 2-story apartment unit with a loft- 1 master bedroom (King bed) + 2nd bedroom (Queen bed_ 3rd bedroom (Two prem ...
From $915 per night (USD)VRBO
- From $280 per night (USD)
Expedia
Slopeside townhome on Okemo Ski Mountain! Summer Pool, Tennis & Air Conditioning
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Prime location for this cozy 4 bedroom townhome steps from Sachem ski trail! Walk out and be on the slopes in 1-2 minute ...
From $280 per night (USD)Expedia
- From $433 per night (USD)
VRBO
Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Secluded ski chalet with centralized location to Okemo Mt., Killington Mt. (around 15 minutes to each), Woodstock and lo ...
From $433 per night (USD)VRBO
- Click For Pricing
Expedia
Quiet Vermont Winter Getaway
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Cozy and secluded describes this VT home. It's the perfect place for a group of friends or family to enjoy some time awa ...
Click For PricingExpedia
- From $150 per night (USD)
VRBO
Gorgeous Vermont sunrises
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Chris and Tammy’s Mountain View getaway. The apartment is located in lovely rural Vermont on a quiet dirt r ...
From $150 per night (USD)VRBO
- From $187 per night (USD)
VRBO
Skyeship House Condo with Hot Tub! - 1 Minute from Gondola - Sleeps 12 Easily
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to your private getaway in the middle of Vermont’s most active recreational region. Skiing, mountain biking, hik ...
From $187 per night (USD)VRBO
- From $135 per night (USD)
VRBO
Gateway to Adventure
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Located in the heart of Ludlow, this 2 Bedroom 1 Bath condo sleeps 6. Wake up and have coffee on the deck right on the ...
From $135 per night (USD)VRBO
- From $700 per night (USD)
Expedia
Artisan Ski House for Groups! Killington + Okemo in Minutes. Walk to Long Trail
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 18
NO SATURDAY CHECK-IN OR OUT! NO FRIDAY CHECK OUT. Fantastic ski house location, where you can be on the Skyeship Gondola ...
From $700 per night (USD)Expedia
- From $454 per night (USD)
VRBO
Dog-friendly lakefront home w/ balcony, dock access, kayaks, snowshoes & woodstove
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Lakeview Chalet Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $454 per night (USD)VRBO
- Click For Pricing
Expedia
Peaceful, mountain-view home with large deck, & grill - dog-friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Valkyrie Run Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
Click For PricingExpedia
- From $115 per night (USD)
VRBO
Run, ride, hike and swim in Central Vermont
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy the winter in beautiful Vermont. The guest area is the entire main floor of a large house with my quiet second hom ...
From $115 per night (USD)VRBO
- From $380 per night (USD)
Expedia
Okemo Trailside Extension #29C | Condo in Ludlow
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Okemo Trailside Extension #29C Our calendar is updated in real-time & our nightly rates are accurately displayed. Simpl ...
From $380 per night (USD)Expedia
- From $914 per night (USD)
VRBO
Okemo Escape: Premier Condo Steps to the Slopes
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience the ultimate ski-in/ski-out retreat at our 3-bedroom Winterplace condo at Okemo. Nestled in one of the best s ...
From $914 per night (USD)VRBO
- From $523 per night (USD)
Expedia
Slopeside Fun at Winterplace: Sleeps 10 on Okemo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Discover Winterplace at Okemo – Your Perfect Slopeside Getaway! Direct trail access, a heated pool, and stunning mountai ...
From $523 per night (USD)Expedia
- From $814 per night (USD)
VRBO
Alpine Adventure Awaits: 3-BR Sleeps 10 at Okemo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to your dream winter getaway at Winterplace on Okemo! This top-floor condo offers 3 warm bedroom suites, a fun l ...
From $814 per night (USD)VRBO
- From $140 per night (USD)
Expedia
Cozy Cavendish Bunk minutes to Okemo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy a stylish & relaxing experience at this centrally-located guest home. Newly renovated with local interior designer ...
From $140 per night (USD)Expedia
- From $241 per night (USD)
VRBO
Renovated lakefront cottage with deep-water dock, swim platform, & firepit
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Bon Vie Chalet Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $241 per night (USD)VRBO
- From $617 per night (USD)
VRBO
Spacious 3BR Ski In\/Ski Out Okemo Condo w\/Hot Tub & Amenities
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Top floor slopeside location with all of the best features including in-unit full kitchen, washer & dryer, 2 gas firepla ...
From $617 per night (USD)VRBO
- From $805 per night (USD)
VRBO
3-Story Chalet on Okemo Mtn, 0.4 mi to Lodge w\/ 2 Fireplaces, Game Room, Firepit
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 16
Get away to the Treehouse, a quintessential Vermont ski and vacation home located on Okemo Mountain. Just a two-minute d ...
From $805 per night (USD)VRBO
- From $582 per night (USD)
Expedia
Ski-in\/ski-out condo with private hot tub, amazing deck & huge view
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Okemo Mountain Vista Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $582 per night (USD)Expedia
- From $750 per night (USD)
VRBO
Cozy trailside ski retreat on Okemo Mountain
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy the ease of Ski in/Ski out living at Trailside on Okemo Mountain. Our three bedroom, three bathroom condo aka "Don ...
From $750 per night (USD)VRBO
- From $345 per night (USD)
VRBO
Cozy Pet-Friendly Log Cabin, 1\/2 mile to Okemo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
OVERVIEW: Welcome to Black Bear Cabin! Enjoy your getaway in a modern 3-bedroom log cabin! Located in downtown Ludlow, ...
From $345 per night (USD)VRBO
- From $295 per night (USD)
VRBO
Jewel Brook Cottage- 4BR house on a tranquil flowing brook!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This newly renovated 4 bedroom 2 bath Ski Cottage on Jewel Brook is the perfect family retreat. Listen to the sound of f ...
From $295 per night (USD)VRBO
- Click For Pricing
VRBO
Holiday Inn Club Vacation Resort, an IHG Property - 3BD\/3BA at Mount Ascutney
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
From the Mt. Ascutney resort, you are within driving distance of three well-known ski resorts - , Okemo (34 mins), and M ...
Click For PricingVRBO
- Click For Pricing
VRBO
Sleek 2BR Condo with Fireplace, Ski-in\/Ski-out
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Looking for an effortless slopeside ski vacation? Stay in our charming, fully updated, and perfectly inviting ski condom ...
Click For PricingVRBO
- From $237 per night (USD)
Expedia
Mountain View Retreat! Cozy Vermont Cottage Near Many Major Ski Resorts.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Tranquil RIVERFRONT Home In The Vermont Countryside. Enjoy the new fenced-in backyard **CLOSE TO BIG SKI RESORTS** 5 m ...
From $237 per night (USD)Expedia
- From $451 per night (USD)
VRBO
The Ole Magic Magnificent Mansion near Okemo
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 10
Discover the enchanting charm of Springfield, Vermont, and immerse yourself in a retreat that seamlessly blends historic ...
From $451 per night (USD)VRBO
- From $423 per night (USD)
VRBO
Cozy Lakeview Lake Rescue Chalet btw Okemo and Killington. Perfect for Families
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Cozy, chic lakefront chalet 3 minutes to Okemo, 17 minutes to Killington, and Fox Run Golf Course. Woodburning fireplace ...
From $423 per night (USD)VRBO
- From $377 per night (USD)
VRBO
Lakefront cabin with dock, hot tub, fire pit!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Better to wake….. at the lake! Have your morning coffee or tea out on the private dock. Fish, kayak, swim and hike as so ...
From $377 per night (USD)VRBO
- From $586 per night (USD)
VRBO
Mountain 4-BR Haven Retreat 2-min to Okemo
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 13
Summary: Gather your entire family and group of friends at this spacious home nestled at the foothills of Okemo Mountain ...
From $586 per night (USD)VRBO