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

From $424 per night (USD)
VRBO
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Welcome to Blueberry Hill Escape - Discover year-round fun from skiing, mountain biking, hiking, leaf peeping, ...
From $424 per night (USD)
VRBO
From $1284 per night (USD)
Expedia
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
Bedrooms:
4
Bathrooms:
8
Sleeps:
22
A true Ski in / Ski out house on the beginner Sachem trail at Okemo mountain. This beautiful eight-bedroom chalet is ide ...
From $1284 per night (USD)
Expedia
From $1172 per night (USD)
VRBO
Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo
Bedrooms:
3
Bathrooms:
7
Sleeps:
14
Completely renovated 7 bedroom, 3 bathroom modern mountain house, located in Ludlow. Outdoor deck with BBQ, hot tub, ac ...
From $1172 per night (USD)
VRBO
From $1220 per night (USD)
Expedia
Ski Okemo! Walk to the slopes from your modern 2 bed/2 bath condo at Winterplace
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Luxurious and newly renovated and modern ski condo just steps away from the AB lift at Okemo. It's a 2 minute walk (or s ...
From $1220 per night (USD)
Expedia
From $268 per night (USD)
VRBO
Windfall @ Quechee Club VT: Cozy Updated Condo A/C, Fireplace -Ski -Golf -Renew
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Windfall - Freshly updated townhome in the heart of Quechee Lakes resort. Overlooking the Ottauquechee river, Windfall w ...
From $268 per night (USD)
VRBO
From $180 per night (USD)
Expedia
Beautiful retreat close to Okemo with free WiFi, private washer/dryer
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Proctorsville Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $180 per night (USD)
Expedia
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VRBO
Bujtin Cabin
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Spend your weekend in Quechee, an area rich with New England history, and plenty year-round activities. It makes for a s ...
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VRBO
From $299 per night (USD)
Expedia
Village Home with 15 acre backyard on the river
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Comfy family home with south facing views of the state forest and hills across the field and river. This home has a 15 A ...
From $299 per night (USD)
Expedia
From $562 per night (USD)
VRBO
The Full Vermont Experience, minutes from Okemo: Transcend to the VT Life
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Ski Okemo? Check Sledding in the back yard? Check Ice Skating on your own pond? Check Snowshoeing in your own trails? Ch ...
From $562 per night (USD)
VRBO
From $656 per night (USD)
Expedia
4bdrm Cottage central to year round fun w/fireplace
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Adventure awaits at this peaceful centrally located 4 bedroom cottage. So whatever adventure you're looking for you will ...
From $656 per night (USD)
Expedia
From $339 per night (USD)
VRBO
Mountainside Luxury 2-Level Condo at Okemo. Ski-In/Out.
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
The newest Okemo luxury mountainside ski-in, ski-out condo home with private ski locker and covered garage located in th ...
From $339 per night (USD)
VRBO
From $1233 per night (USD)
Expedia
Ski In/Ski Out Winterplace 2BR+Loft W/Fireplace, Hot Tub and Pool Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Enjoy Okemo in luxury! This top floor loft space sits in the Okemo Winterplace complex in Building C with quick access t ...
From $1233 per night (USD)
Expedia
From $309 per night (USD)
VRBO
Ludlow Village Home with Pool Table - Walk to Restaurants
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
The "Bear's Den" is conveniently located in Ludlow, VT across main street from Okemo Mountain School and Sports Odyssey ...
From $309 per night (USD)
VRBO
From $365 per night (USD)
Expedia
Ski In/Out Studio at Okemo on Sachem Trail
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Studio on the Sachem Trail at Okemo Mountain. This is a perfect location right on the Sachem Trail. The studio has a ful ...
From $365 per night (USD)
Expedia
From $100 per night (USD)
VRBO
2 Room Studio 10 minutes from Killington
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Cedarbrook is 6 miles to your favorite winter activities and Killington/Pico Mountains on the Killington access road. Fo ...
From $100 per night (USD)
VRBO
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Expedia
Your Beautiful Victorian Getaway
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
This beautiful New England Victorian, built in the 1890's, has 5 bedrooms and sits back on two private acres, situated j ...
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Expedia
From $383 per night (USD)
VRBO
1 Mile to Okemo Ski Mountains, Newly Remodeled Upstairs
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Our busy Ludlow Village is a dream come true. Visit the towns’ delicious bakeries,deli's clothing store,computer repairs ...
From $383 per night (USD)
VRBO
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Expedia
Season rental Okemo Ski Season
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
This property is 1.5 miles from Okemo Mountain and Jackson Gore, a popular ski resort. Sleeps 8. 3 bedrooms: 2 queen ...
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Expedia
From $524 per night (USD)
VRBO
Indoor Hot Tub Room/10 Miles to Okemo
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Great Central Vermont location! Private but easy to get too. Ten miles to Okemo/Jackson Gore. Skiing, golfing, hiking, s ...
From $524 per night (USD)
VRBO
From $435 per night (USD)
Expedia
Trailside Okemo Mountain House! with hot tub, firepit, and
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Your next mountain getaway awaits! This property is trailside on Okemo mountain and surrounded by trees, which creates r ...
From $435 per night (USD)
Expedia
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VRBO
Spacious and cozy single family house next to Quechee ski hill
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Single family house located right next to Quechee ski hill. Space for two families. Recently updated; three bedrooms hav ...
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VRBO
From $342 per night (USD)
Expedia
Vermont Cabin - Ski, Hike, Kayak, Leaf Peep - 5mins to Okemo, near quaint towns
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Our home is the perfect getaway, just a 5 minute drive to Okemo Mountain. This 1800s home, has one bedroom on the first ...
From $342 per night (USD)
Expedia
From $210 per night (USD)
VRBO
Getaway with a fireplace, washer/dryer, cable, pool, & golf nearby
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Brookhaven B7 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $210 per night (USD)
VRBO
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Expedia
Sunny, new centrally located condo!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Bright, open 2 bedroom, 2 bath condo centrally located in the village of Proctorsville. Across the street from the villa ...
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Expedia
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VRBO
Mountain Side Townhome at Stoney Fields
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Mountain side townhome. Fully renovated, three level townhome located in the quiet community. This three bdrm, 2.5 bath ...
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VRBO
From $194 per night (USD)
Expedia
Condo with Ski-in/Ski-Out Access + Mountain Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Find your Okemo escape in our cozy and charming ski-in/ski-out condo with mountain views! Walk out your door and experie ...
From $194 per night (USD)
Expedia
From $539 per night (USD)
VRBO
Private Mountain Sanctuary | 15 Min to Killington
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
*Winter Stays* Must have 4WD vehicle with snow tires or snow chains. We want you to make it safely up the mountain for t ...
From $539 per night (USD)
VRBO
From $887 per night (USD)
Expedia
Newly renovated! 3 BR, slopeside Winterplace condo on Okemo Mountain
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
*Newly renovated and available for rentals* - Come join the fun in this beautiful, clean 3 bedroom/2 bath condominium lo ...
From $887 per night (USD)
Expedia
From $264 per night (USD)
VRBO
Okemo Condo on Bus Route in Center of Town
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This is truly the best of Ludlow staying in a newly renovated condo in a historic mill building built in 1857. This co ...
From $264 per night (USD)
VRBO
From $751 per night (USD)
Expedia
Spacious 9-BR Downtown Residence 3-Min to Okemo
Bedrooms:
4
Bathrooms:
9
Sleeps:
17
Summary: Bring together the whole family and friend group in this expansive Downtown home, steps to dining and shopping ...
From $751 per night (USD)
Expedia
From $528 per night (USD)
VRBO
Copper Hill House - VT getaway near Ludlow & Okemo
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Copper Hill House: a three-bedroom cabin in Cavendish, VT. 10 minutes from downtown Ludlow and Okemo Mountain ...
From $528 per night (USD)
VRBO
From $253 per night (USD)
Expedia
Beautifully renovated with fireplace and coffee bar
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to our cozy, nature-inspired home, nestled in the foothills of the Green Mountains. This beautifully renovated, ...
From $253 per night (USD)
Expedia
From $338 per night (USD)
VRBO
4 BR Ranch in Proctorsville VT-Families, couples, weddings. AC; hot tub
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Enjoy our recently renovated, 1450 SF split level ranch with AC and seasonal hot tub, in the heart of the Green Mountain ...
From $338 per night (USD)
VRBO
From $418 per night (USD)
Expedia
Relaxing retreat in the mountains 20 min to Killington
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Welcome to Brookwood! Enjoy your stay at our peaceful 3br chalet. Come relax, hike, bike, ski, shop - whatever your hear ...
From $418 per night (USD)
Expedia
From $448 per night (USD)
VRBO
Beautiful farmhouse in Historic village
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Our beautiful and comfortable 1850s family farmhouse is modernly equipped and available for monthly stays through the se ...
From $448 per night (USD)
VRBO
From $432 per night (USD)
Expedia
Two-level vacation rental with mountain view, pellet stove, W/D & full kitchen
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The Birdhouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $432 per night (USD)
Expedia
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VRBO
Designer vacation rental - mountain view, wood stove, washer/dryer, full kitchen
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
ON-Q Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates ...
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VRBO
From $291 per night (USD)
Expedia
Cozy cabin near skiing with free WiFi, game room, deck, & wood fireplace
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Mountain View Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $291 per night (USD)
Expedia
From $321 per night (USD)
VRBO
Spacious Home w/Seasonal Lake View, Wood Stove, Washer/Dryer & Cable
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Walk to the Lakes Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $321 per night (USD)
VRBO
From $374 per night (USD)
Expedia
Charming 4-Bed Downtown Townhome 3-Min to Okemo
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Enjoy Okemo and the Green Mountains from this spacious, recently renovated townhome. The townhome features 4 be ...
From $374 per night (USD)
Expedia
From $379 per night (USD)
VRBO
Tasteful 5-BR Downtown Townhome 3-Min to Okemo
Bedrooms:
2
Bathrooms:
5
Sleeps:
9
Summary: Charming and centrally located, this 4-BR townhome is perfect for friends and families visiting Okemo. The home ...
From $379 per night (USD)
VRBO
From $317 per night (USD)
Expedia
Two-story townhome with forest/mountain view, gas fireplace, pool, gym & saunas
Bedrooms:
3
Bathrooms:
3
Sleeps:
14
Castle Hill Condos O2 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $317 per night (USD)
Expedia
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VRBO
Modernized Vermont Farmhouse
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Open, modernized, cozy farmhouse with lovely Vermont country views, wonderful kitchen, huge mudroom with laundry. 15" fr ...
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VRBO
From $284 per night (USD)
Expedia
Recently Renovated Ski-In/Out Condo w/Fireplace, Shared Pool, Hot Tub, Sauna
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Solitude Village H103 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $284 per night (USD)
Expedia
From $568 per night (USD)
VRBO
Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Rzeka Cottage! Enjoy a stylish experience at this riverfront home in the Green Mountains. Centrally located n ...
From $568 per night (USD)
VRBO
From $485 per night (USD)
Expedia
8 Mi to Okemo Mtn: Charming Ludlow Studio!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Peaceful & Secluded Location | Free WiFi | Steam Shower | Off-Street Parking Your next peaceful couple’s retreat awaits ...
From $485 per night (USD)
Expedia
From $494 per night (USD)
VRBO
Rural mountain-view home near skiing with screened porch, firepit, & game room
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
The Farmhouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $494 per night (USD)
VRBO
From $508 per night (USD)
Expedia
All-Season Ludlow Apartment: 3 Mi to Okemo Resort!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Whether you’re in the mood for a warm summer getaway or a dreamy winter vacation, you’ll find it here at this Ludlow apa ...
From $508 per night (USD)
Expedia
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VRBO
Beautifully restored 1800s farmhouse near ski slopes & steps from VAST
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Sugar House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
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VRBO
From $391 per night (USD)
Expedia
Great home near Main St - washer/dryer, fireplace, Quechee Club access available
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Dwight Road Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $391 per night (USD)
Expedia
From $422 per night (USD)
VRBO
Comfy Ludlow Apartment ~ 3 Mi to Okemo Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Transport yourself to a winter wonderland when you stay at this family-friendly apartment in Ludlow. With 2 bedrooms, 2 ...
From $422 per night (USD)
VRBO
From $389 per night (USD)
Expedia
Hawk Mountain home with a sauna, wooded views, & washer/dryer
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Salt Ash Sanctuary Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $389 per night (USD)
Expedia
From $570 per night (USD)
VRBO
3 BR Ski-in/Ski-Out Fireplace, Pool, Full Kitchen
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Experience the pinnacle of ski-in/ski-out luxury at Winterplace. This inviting 3-bedroom, 2-bathroom condo in t ...
From $570 per night (USD)
VRBO
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Expedia
1st floor 2 Bedroom Ski in/Ski Out Condo at Okemo Winterplace
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
First floor 2 bedroom condo at Winterplace. Cozy living room with wood fireplace. Step out the back door and right ont ...
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Expedia
From $607 per night (USD)
VRBO
15 Minutes to ski Okemo - Mountain views from this magical log home on 6 acres
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This incredible log home is the perfect spot for a weekend getaway or an extended stay in Vermont. Nestled on 6 acres of ...
From $607 per night (USD)
VRBO
From $1312 per night (USD)
VRBO
Historic Farmhouse in Andover Vermont
Bedrooms:
6
Bathrooms:
11
Sleeps:
24
Situated on 20 acres in the Andover, Vermont countryside and in close driving distance to Okemo, Magic, Stratton, and Br ...
From $1312 per night (USD)
VRBO
From $930 per night (USD)
VRBO
Lovely Ludlow Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This three-bedroom home is located in the beautiful South Hill area with great access to Okemo Ski Resort, which is just ...
From $930 per night (USD)
VRBO
From $759 per night (USD)
Expedia
Minutes to Skiing/Hot Tub/Arcades
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Indulge in the ultimate mountain getaway in our stunning ski town house. Perched atop a scenic hillside, this exquisite ...
From $759 per night (USD)
Expedia
From $416 per night (USD)
VRBO
Modern Mt. Ascutney Cabin - Views, Fireplace, Chef’s Kitchen, Pets Welcome
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Wake up to sweeping Vermont views from this designer-built Mt. Ascutney cabin — with fire pit, chef’s kitchen, and cozy ...
From $416 per night (USD)
VRBO
From $660 per night (USD)
Expedia
Beautiful Green Mountain views near Killington
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Vermont getaway. Located in pretty Timber Hawk Development, this is a private location with incredible mountain/valley, ...
From $660 per night (USD)
Expedia
From $1028 per night (USD)
VRBO
Hilltop 9-BR Mountain Retreat 5-min to Okemo
Bedrooms:
7
Bathrooms:
9
Sleeps:
19
Summary: Unique, expansive, and newly-renovated retreat on a private hill overlooking Okemo & Ludlow. 5-min to the Base ...
From $1028 per night (USD)
VRBO
From $579 per night (USD)
Expedia
Contemporary 4-BR Cabin 5-min to Okemo
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Summary: Contemporary, newly-renovated cabin perched on a hill overlooking the Green Mountains, 5-minutes to Okemo Base ...
From $579 per night (USD)
Expedia
From $1286 per night (USD)
VRBO
Mountainside 5-BR Ski-In/Out Okemo Retreat
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Summary: Gather your family and friends at this ski-in, ski-out, 5-BR mountainside retreat. Located on Okemo Mountain, t ...
From $1286 per night (USD)
VRBO
From $822 per night (USD)
Expedia
Luxury Vermont Vacation Rental: Private Hot Tub!
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Your mountain escape awaits at this spacious vacation home in West Windsor, VT! Adorned with wood paneling, cathedral ce ...
From $822 per night (USD)
Expedia
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VRBO
Stunning townhome with on-site golf, pools, ski trails, and fitness center
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Windsor Village 3E Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
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VRBO
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Expedia
Luxurious Home 11 miles from Killington and Okemo
Bedrooms:
4
Bathrooms:
4
Sleeps:
6
In historic Plymouth, VT, on our stunning 10+ acre property, this country farm retreat home is the ultimate getaway for ...
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Expedia
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VRBO
Beautiful Cabins in the Mountains
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
These beautiful cabins are on a secluded property, that overlook the Vermont Green Mountains. Start your day with a refr ...
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VRBO
From $376 per night (USD)
Expedia
Cozy Log Cabin Short Drive to Okemo & Killington
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Get away to the Caven Cabin! Secluded quintessential Vermont log cabin nestled below a pine filled ridge. Have your mor ...
From $376 per night (USD)
Expedia
From $501 per night (USD)
VRBO
Hilltop 5-BR Carriage House 4-Min to Okemo
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Summary: Enjoy the bucolic hills overlooking Ludlow in this charming 5 bedroom converted carriage house, featuring ample ...
From $501 per night (USD)
VRBO
From $230 per night (USD)
Expedia
Reillys Rest-private home in Green Mtns, kid-pet friendly-Ski,Bike,Walk,Relax!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Reilly's Rest on Holden Hill Rd. is a private home on 6 acres located in a prime location to ski, bike, hike, walk and r ...
From $230 per night (USD)
Expedia
From $290 per night (USD)
VRBO
Riverfront, family fun, amazing rec room, close to Magic & Okemo
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Relax on the patio on the bank of the Williams River to watch the leaves turn, explore hiking trails, enjoy the outdoor ...
From $290 per night (USD)
VRBO
From $665 per night (USD)
VRBO
Luxury Barn : Hot tub, Sauna & Views
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Escape to a beautiful reinvention of an 1850s barn w/ spa amenities, panoramic Mtn views, chef's kitchen, 4 bedrms/ 4 ba ...
From $665 per night (USD)
VRBO
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VRBO
Lakeland Village steps to Quechee Club, Lake Pinneo, Golf, Mountains
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This three bedroom, two bath condo is ideal for all seasons with the Highland Golf Course a short walk away. Master bedr ...
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VRBO
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Expedia
Family Friendly Home Close to Hiking, Lakes and Restaurants
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Three levels of living space with room for everyone. The house is within walking distance to West Hill Recreation Area. ...
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Expedia
From $269 per night (USD)
VRBO
Quechee Condo | Condo in Quechee
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Quechee Condo Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $269 per night (USD)
VRBO
From $295 per night (USD)
Expedia
Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Experience the beauty of Vermont alongside modern comforts and premier amenities at this 3-bedroom, 2.5-bath vacation re ...
From $295 per night (USD)
Expedia
From $897 per night (USD)
VRBO
Luxury Ski Chalet - Okemo Killington
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Brand new house 1 mile to the Okemo lifts and 20 minutes to Killington Skyeship Base. 4 bedrooms, 2.5 baths with open li ...
From $897 per night (USD)
VRBO
From $458 per night (USD)
Expedia
Historic 150-year-old farmhouse, Jacuzzi included
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to The Farmhouse of VT - your perfect Vermont recharge spot. Step back in time in this large 1869 farmhouse, wh ...
From $458 per night (USD)
Expedia
From $426 per night (USD)
VRBO
Home with private apartment, patio, fireplace, on-site pool, gym & tennis access
Bedrooms:
6
Bathrooms:
3
Sleeps:
10
A1 at Castle Hill Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $426 per night (USD)
VRBO
From $258 per night (USD)
Expedia
Townhome with patio & on-site pool, hot tub, sauna & tennis access
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
A1 at Castle Hill - Townhome Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $258 per night (USD)
Expedia
From $179 per night (USD)
VRBO
Ground-floor apartment with pool, hot tub, tennis & gym access - near skiing
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
A1 at Castle Hill - Apartment Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $179 per night (USD)
VRBO
From $397 per night (USD)
Expedia
Weston Vacation Rental - Close to Ski Resorts!
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Private Fire Pit Surrounded by world-class ski resorts and scenic hiking trails, this 3-bedroom, 1-bath vacation rental ...
From $397 per night (USD)
Expedia
From $768 per night (USD)
VRBO
Renovated ski house near Okemo and Stratton
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
You will enjoy Vermont at this beautifully renovated house set on 12 acres in the quaint town of Chester. You can relax ...
From $768 per night (USD)
VRBO
From $410 per night (USD)
Expedia
Monthly or Seasonal rental. Sleeps 9, pet friendly! 5 mins to Okemo
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Welcome to our 3 bedroom plus den, pet friendly house on the Black River. Just a short drive to Okemo mountain and walki ...
From $410 per night (USD)
Expedia
From $364 per night (USD)
VRBO
Two-story condo with forest views, Echo Lake beach access, pool, dock & tennis
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Birch Landing #1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $364 per night (USD)
VRBO
From $345 per night (USD)
Expedia
4-BR Timeless Farmhouse 3-min to Okemo
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Enjoy the charm and convenience of Ludlow Village in this newly-renovated 4-BR farmhouse, located on Main Stree ...
From $345 per night (USD)
Expedia
From $858 per night (USD)
VRBO
Okemo Mountain View Retreat
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Welcome to this spacious 5-bedroom, 3 ½ bathroom home, prefect for accommodating large groups of up to 12 people. Locate ...
From $858 per night (USD)
VRBO
From $300 per night (USD)
Expedia
Historical home overlooking the river, walk to the village & covered bridge
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Maple's Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $300 per night (USD)
Expedia
From $880 per night (USD)
VRBO
Skiers Paradise, 15 min to Okemo and Killington
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to the perfect Ski getaway nestled in the heart of VT - just a stone's throw (15 min drive) away from the Killin ...
From $880 per night (USD)
VRBO
From $568 per night (USD)
Expedia
Tree-lined home with firepit, open interior & washer/dryer - near skiing
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Knoll Perch Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $568 per night (USD)
Expedia
From $472 per night (USD)
VRBO
Family-Friendly Condo at Okemo w/ Fireplace
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: This mountain community offers guests direct access to the slopes, especially at this on-trail unit sitting rig ...
From $472 per night (USD)
VRBO
From $218 per night (USD)
Expedia
Remote Escape: Vermont Cabin w/ Mountaintop Views!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Ever feel nostalgic for a cozy cabin, a fire pit, and a scenic view? Discover the beauty of those 'little things' at thi ...
From $218 per night (USD)
Expedia
From $575 per night (USD)
VRBO
Newly Renovated 4-BR Country Retreat 5-Min to Okemo
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Enjoy the scenery, tranquility, and recreation of the Green Mountains in this newly renovated 4-BR home, minute ...
From $575 per night (USD)
VRBO
From $1012 per night (USD)
Expedia
Alpine 6-BR Estate On Okemo Mountain
Bedrooms:
5
Bathrooms:
6
Sleeps:
15
Summary: Experience elevated Green Mountain living in this 6-BR, expansive timber-frame chalet on the mountainside of Ok ...
From $1012 per night (USD)
Expedia
From $741 per night (USD)
VRBO
OKEMO WINTERPLACE Best Location, Ski-In/Ski-Out 4BR/3BATH + LOFT. Spacious.
Bedrooms:
3
Bathrooms:
5
Sleeps:
11
Winterplace is a perfect escape for summer, fall or winter relaxation or adventure. Best Location SKI-IN/SKI-OUT⛷ with ...
From $741 per night (USD)
VRBO
From $293 per night (USD)
Expedia
Modern Chalet w/ Serene Views and Jacuzzi Hot Tub- 15 Minutes to Okemo Mountain
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Ideal to host up to 6 guests, this home on 2 acres of land is a perfect retreat for anyone looking to be in the heart of ...
From $293 per night (USD)
Expedia
From $370 per night (USD)
VRBO
Secluded farmhouse with private inground pool!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Escape to Your Vermont dream vacation… Nestled in the heart of Vermont’s picturesque countryside, this charming farmhou ...
From $370 per night (USD)
VRBO
Click For Pricing
Expedia
Spruce Moose Cottage | Tiny House on 65 private acres
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Spruce Moose Cabin Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
Click For Pricing
Expedia
From $477 per night (USD)
VRBO
Okemo | 2BR + Loft Condo + Close to All Amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to a delightful 2-bedroom + loft condo for 8, where convenience and aesthetics come together to create the ultim ...
From $477 per night (USD)
VRBO
From $495 per night (USD)
Expedia
Okemo | 3BR + Loft Condo & Close to All Amenities
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Your dreamy 3-bedroom + loft condo for 12 awaits, offering the perfect blend of convenience and charm. With amenities, s ...
From $495 per night (USD)
Expedia

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