Windsor Area Rentals
From $167 per night (USD)VRBO
By the Month, Charming Guest Suite in Reading, Vermont
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stay comfortably in Reading/West Windsor, Vermont at this charming farmhouse. This two story guest suite offers a pleasa ...
From $167 per night (USD)VRBO
From $596 per night (USD)VRBO
Leaf Peepers Paradise on 10 private acres, hot tub, outdoor firepit, pool table
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Private, yet less than 10 minutes to Ludlow and Okemo, this mountain home is great for families who are looking to get a ...
From $596 per night (USD)VRBO
From $553 per night (USD)VRBO
Ski Home/Arcade Mountain Views Near Killington/Woodstock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
UNIT B side. -> Spacious newly renovated 2250 sq ft Living space. 3 large bedrooms, 2 full baths and 1 half bath -> Game ...
From $553 per night (USD)VRBO
From $383 per night (USD)Expedia
Swim, Ski & Sip: Lakefront Retreat in Plymouth
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
On Echo Lake | 5 Mi to Ski Resort | Multiple Living Spaces | 3,000 Sq Ft Tucked away in scenic Vermont, this 3-bedroom, ...
From $383 per night (USD)Expedia
From $700 per night (USD)VRBO
Whitman Brook Overlook House with Game Room
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Whitman Brook Overlook in Quechee, Vermont, offers a cozy and private retreat surrounded by the natural beauty ...
From $700 per night (USD)VRBO
From $304 per night (USD)Expedia
Tranquil 3-bedroom 2-bath Pet-Friendly condo EV charging in charming Woodstock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Get ready to relax in this 3-bedroom condo in Woodstock. This wonderful property features one king bed, one queen bed, a ...
From $304 per night (USD)Expedia
From $357 per night (USD)VRBO
Riverside Cottage on the Ottauquechee River
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Nestled right on the banks of the Ottauquechee River, Riverside Cottage offers a serene and picturesque escape ...
From $357 per night (USD)VRBO
From $1408 per night (USD)Expedia
150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 13
To the people who have seen it, Light Hill is considered one of the most beautiful properties in the Barnard area. With ...
From $1408 per night (USD)Expedia
From $349 per night (USD)VRBO
Club Access Condo near Ski Hill, Kingswood
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Experience the ultimate Vermont escape at Kingswood 1B, a spacious slope-side condo offering with breathtaking ...
From $349 per night (USD)VRBO
From $1051 per night (USD)VRBO
Renovated home in charming South Woodstock!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
The kitchen is designed to cook meals and entertain guests in an ultra-cozy barn setting. The table seats 10, with 4 bar ...
From $1051 per night (USD)VRBO
From $556 per night (USD)VRBO
Rustic cabin w/ mountain view & fireplace
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to a cozy mountain cabin in Ludlow, perfect for summer getaways with family and friends. Just a short drive from ...
From $556 per night (USD)VRBO
From $493 per night (USD)VRBO
18-Acres in Woodstock - Pet-Friendly, Trails, Brook, Fireplace, Screened Porch
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful 18-acre property less than 5 mins from center of Woodstock, VT. Brookside is a gorgeous country property wit ...
From $493 per night (USD)VRBO
From $389 per night (USD)VRBO
Charming Cabin on Lake Amherst - Private Dock, Fireplace, Firepit, Pet-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Renovated, rustic, pet-friendly cabin perched above Lake Amherst with dock and lake access. 10 minutes to Okemo's Jackso ...
From $389 per night (USD)VRBO
From $378 per night (USD)VRBO
The Okemo Cabin, Cozy 3 Bedroom Cabin minutes to Okemo and VAST Trail System
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
<p>Escape to The Okemo Cabin, nestled in the serene landscapes of Cavendish, VT. This charming 3-bedroom, 2-bathroom hav ...
From $378 per night (USD)VRBO
From $371 per night (USD)VRBO
Mountainside Condo w/ Access to Pool + Ski Shuttle
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Come and stay in our cozy and charming mountainside condo at Okemo Mountain Resort! Located near the summit of the two S ...
From $371 per night (USD)VRBO
From $2386 per night (USD)Expedia
Mountain Views. Hot Tub. , 5 Wooded Acres. Private Pond
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Private Pond | Post & Beam | Nature Retreat in Plymouth, VT Welcome to your peaceful escape in the woods of Plymouth, V ...
From $2386 per night (USD)Expedia
From $414 per night (USD)VRBO
Game Room Condo, Sugar Hill, Pet-Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Please see: Other Things to Note For Area Details, please see: The Neighborhood & Getting Around • Pet Frien ...
From $414 per night (USD)VRBO
From $498 per night (USD)Expedia
Cozy 4 BR home with hot tub in Weston near 4 ski areas & many hiking trails!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Escape to picturesque Weston, home of the famous Vermont Country Store, and the perfect retreat for nature lovers and ad ...
From $498 per night (USD)Expedia
From $687 per night (USD)VRBO
Screened-Porch Home, Killington Views & Pet-Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Escape to Fox Lane Retreat, a luxurious mountain getaway in Quechee, offering breathtaking views of the Green ...
From $687 per night (USD)VRBO
From $367 per night (USD)Expedia
Condo with Fireplace, Lakeland Village, Pet-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Summary: Escape to the serene beauty of Quechee, Vermont, with this spacious 4-bedroom, 2-bath retreat featuring a stun ...
From $367 per night (USD)Expedia
From $728 per night (USD)VRBO
Large Farmhouse Steps from Downtown Ludlow & Okemo Shuttle
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Discover the perfect blend of comfort and convenience in this serene Ludlow escape. With four cozy bedrooms—featuring 2 ...
From $728 per night (USD)VRBO
From $589 per night (USD)VRBO
Spacious 4-Bedroom in Quechee VT
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy all the beauty Vermont has to offer and more in this air-conditioned 4-bedroom, 4-bath townhouse in Quechee. Walk ...
From $589 per night (USD)VRBO
From $598 per night (USD)VRBO
The Woodstead in Quechee- New Listing to VRBO!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
NEW LISTING! Very spacious, 3,000 sq. ft home with 3 floors of living, surrounded by 6+ acres of woodland and big sky vi ...
From $598 per night (USD)VRBO
From $379 per night (USD)Expedia
Sugarhouse Hideaway Cabin with Mountain Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: The ultimate Vermont escape at Sugarhouse Hideaway, where breathtaking views of Mt. Washington meet luxurious ...
From $379 per night (USD)Expedia
From $489 per night (USD)VRBO
Classic Vermont Farmhouse | Near Okemo
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Experience Vermont from this beautifully renovated farmhouse just seven minutes from Okemo Mountain. Blending ...
From $489 per night (USD)VRBO
From $571 per night (USD)Expedia
Equinox Haus: Private retreat, pool table, hot tub, game room & hiking trails
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Discover the charm of the Equinox Haus where luxury meets nature. This 4-bedroom haven boasts a unique blend of amenitie ...
From $571 per night (USD)Expedia
From $878 per night (USD)VRBO
Downtown Ludlow, walk to ski shuttle, room for multiple families, pet friendly!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to The Washburn Home of Vermont's 31st Governor, Peter Thatcher Washburn This 4-bedroom, 4.5-bathroom home is pe ...
From $878 per night (USD)VRBO
From $634 per night (USD)Expedia
Brookside Cabin + Hot Tub | Woodstock & Killington
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to Broad Brook Cabin! Nestled between picturesque Woodstock, Vermont, and Killington Ski Resort. Recon ...
From $634 per night (USD)Expedia
From $451 per night (USD)VRBO
Modern cabin oasis close to Stratton, Okemo, Bromley and Magic
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Nestled in the heart of Southern Vermont, this cozy, modern chalet offers the perfect winter getaway. The house is nea ...
From $451 per night (USD)VRBO
From $716 per night (USD)Expedia
Spacious 6-bedroom house with AC, WiFi in charming Springfield
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 10
Vermont is waiting for you at this 6-bedroom gorgeous antique house with all modern amenities and yesteryear charm. With ...
From $716 per night (USD)Expedia
From $655 per night (USD)VRBO
Spacious Vermont Mountain Retreat | 4BR/4BA | Near Killington & Hiking | Perfect for Groups
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Bear Foot Lodge: Spacious Vermont Mountain Chalet Near Killington Resort and Riverside Farm Discover the perfect Vermon ...
From $655 per night (USD)VRBO
From $1260 per night (USD)Expedia
8 Mi to Okemo Mountain Resort: Mtn-View Retreat!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Pets Welcome w/ Fee | Pond On-Site | 2-Level Deck Escape to the Green Mountains and stay at this spacious 4-bedroom, 3-b ...
From $1260 per night (USD)Expedia
From $576 per night (USD)VRBO
One of a Kind Farmhouse with Incredible Okemo & Sunset Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this authentic unique vintage farmhouse set on a hill amongst open fields that oozes charm! It's the perfect ...
From $576 per night (USD)VRBO
From $323 per night (USD)VRBO
All New 1-bedroom cottage on a private pond in Woodstock with WiFi, AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Get ready to relax in this all new 1-bedroom cottage in Woodstock. The full kitchen is complete with electric stove/oven ...
From $323 per night (USD)VRBO
From $407 per night (USD)VRBO
Scandinavian Serenity with A Sauna Close To Okemo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
A part of Ascutney Lofts, this home is a vacationer's dream. This stylish sanctuary is a stone’s throw from premier skii ...
From $407 per night (USD)VRBO
From $398 per night (USD)Expedia
Private 3-bedroom cabin with WiFi and backyard!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Wells cabin is our green mountain escape and we welcome it to our guests with pride. With 2,200 sq ft, our home is a pl ...
From $398 per night (USD)Expedia
From $883 per night (USD)VRBO
5BR Chalet w/ Hot Tub, Game Room & EV Charger
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: Secluded but packed with fun, this 5BR/4BA chalet is just a 5-minute drive to Okemo. Enjoy a hot tub, arcade ga ...
From $883 per night (USD)VRBO
From $881 per night (USD)Expedia
Winterplace Okemo 3BR | Perfect for Families & Ski
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Steps from the lift and packed with family-friendly comfort, this 3BR Winterplace condo at Okemo is your winte ...
From $881 per night (USD)Expedia
From $333 per night (USD)VRBO
House on Private Acres with Fire Pit, Quechee
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: The ultimate privacy & tranquility at Bayley Way Getaway, tucked away on nearly 4 acres just a mile from Quech ...
From $333 per night (USD)VRBO
From $363 per night (USD)Expedia
Charming Vermont Retreat: 2 Bedroom, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your perfect getaway in the heart of Vermont! Nestled amidst the scenic beauty of nature, our charming 2-bedr ...
From $363 per night (USD)Expedia
From $577 per night (USD)VRBO
Cheerful chalet w/sauna & hot tub - amazing location near Okemo & Killington
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
We are excited to share the Hawkie House is under new management by the owners. Come experience this sunny, well equipp ...
From $577 per night (USD)VRBO
From $543 per night (USD)Expedia
Ski-In/Out at Okemo | 3BR Ledgewood w/ Fireplace
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Ski directly to your door at this true ski-in/ski-out 3BR condo in Ledgewood, right on the Okemo slopes. With ...
From $543 per night (USD)Expedia
From $377 per night (USD)VRBO
Charming 2-Bedroom Ski-In/Ski-Out at Jackson Gore
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Enjoy year-round access to Okemo Mountain from this thoughtfully appointed 2-bedroom unit nestled in Jackson G ...
From $377 per night (USD)VRBO
From $498 per night (USD)Expedia
Saskadena Lodge with Game Room, near Ski Hill
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Enjoy ultimate Vermont living in this beautifully renovated family home, just steps from ski slopes and featur ...
From $498 per night (USD)Expedia
From $605 per night (USD)VRBO
Terrific 3-bedroom cottage with AC in charming Cavendish
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Unwind in Cavendish at this pleasant cottage. With 3 cozy bedrooms including 2 full beds and 1 queen bed, guests can rel ...
From $605 per night (USD)VRBO
From $424 per night (USD)Expedia
Fabulous 2-bedroom house with WiFi in charming Andover
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy a peaceful stay at this lovely 2-bedroom house in Andover. The bedrooms feature 2 king beds, perfect for a comfort ...
From $424 per night (USD)Expedia
From $527 per night (USD)VRBO
Cabin on the hill Ascutney Vt - 4 bedrooms
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Nestled in the serene woods of Brownsville Vermont, this charming cabin offers a perfect retreat from everyday life. The ...
From $527 per night (USD)VRBO
From $643 per night (USD)Expedia
Lakeview Lodge • Hot Tub • Sleeps 16 • Okemo
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
Hosted by Good Day Getaways! ☆☆ HIGHLIGHTS ☆☆ ✹ Primary bedroom w/ King Sized bed + Full Ensuite bathroom ✹ Four additi ...
From $643 per night (USD)Expedia
From $505 per night (USD)VRBO
2miles to Okemo! Ski house • Hot Tub • Lake Rescue
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Hosted by Good Day Getaways! ☆☆ HIGHLIGHTS ☆☆ ✹ Primary bedroom w/ queen bed overlooking lake + Twin and trundle ✹ 2 Ad ...
From $505 per night (USD)VRBO
From $391 per night (USD)Expedia
Highland Cabin above Woodstock Village, Pets Welcome
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Escape to Highland Cabin, a sunlit Woodstock retreat, close to town yet perched on a steep, quiet hillside for ...
From $391 per night (USD)Expedia
From $566 per night (USD)VRBO
Quaint Quechee Lakes Condo - walk to Lake Pinneo & the Clubhouse!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Escape to the heart of Vermont in this recently renovated 3-bedroom, 2- bathroom condo. Featuring a modern kitchen, cozy ...
From $566 per night (USD)VRBO
From $931 per night (USD)Expedia
Direct Ski Access from J Building Okemo Winterplace
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This 2 Bedroom/2 Bath Winterplace condominium couldn`t be more convenient. The mid-mountain location boasts easy access ...
From $931 per night (USD)Expedia
From $616 per night (USD)VRBO
Private 4-BR Retreat | 10 Min to Okemo
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Escape to the peaceful countryside of Southern Vermont in this spacious four-bedroom retreat just 10 minutes f ...
From $616 per night (USD)VRBO
From $330 per night (USD)Expedia
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to your cozy luxury escape in the heart of Vermont. This thoughtfully designed tiny home is nestled in a quiet a ...
From $330 per night (USD)Expedia
From $410 per night (USD)VRBO
Live the Vermont Life in 1840 Classic Renovated Cape
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Classic 1840 farmhouse that has called home for over 40 years. We are offering a nice 2 BR- 2 bath unit on 2 floors much ...
From $410 per night (USD)VRBO
From $314 per night (USD)VRBO
Welcome to Sunrise Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sunrise Cottage is a three bedroom two bath home set atop a 2.5 acre sunny knoll in Springfield, Vermont! Relax and enjo ...
From $314 per night (USD)VRBO
From $609 per night (USD)VRBO
Okemo Mountain Lodge unit with Direct Access to Clocktower Base Area at Okemo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located on mountain at the Okemo Mountain Lodge at the Clocktower Base Area, this unit is near all the action. Assigned ...
From $609 per night (USD)VRBO
From $413 per night (USD)Expedia
Elegant 4BR Retreat•3–5 Min to Okemo•Walk to Town
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your thoughtfully curated Ludlow retreat — a refined four-bedroom home designed for comfort in every season. ...
From $413 per night (USD)Expedia
From $496 per night (USD)VRBO
Luxe Condo with Cathedral Ceilings & Pond, Snow Village
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Experience timeless Vermont elegance! A spacious retreat with soaring ceilings, a cozy fireplace, and private ...
From $496 per night (USD)VRBO
From $542 per night (USD)Expedia
180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Unwind at this Hartford home with tall windows highlighting breathtaking mountain views. It's the perfect tranquil spot ...
From $542 per night (USD)Expedia
From $703 per night (USD)VRBO
3-Bedroom Townhome Overlooking 12th Hole in Quechee, VT Recently Renovated!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Stay comfortably in Quechee at this 3-bedroom townhome. Each bedroom features a king bed, ensuring a good night's sleep ...
From $703 per night (USD)VRBO
From $742 per night (USD)Expedia
Saskadena Lodge & Little House, Full Property
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Summary: Experience the ultimate Vermont escape with our exclusive dual listing, combining a spacious 4-bedroom lodge a ...
From $742 per night (USD)Expedia
From $317 per night (USD)VRBO
Little House at Saskadena, right at the base of Ski Hill
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Escape to this bright and private studio cottage at Saskadena Peak, where sweeping mountain and meadow views, ...
From $317 per night (USD)VRBO
From $607 per night (USD)Expedia
2BR Winterplace Ski Condo w/ Fireplace + Hot Tubs
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Enjoy mountain fun with the family at this 2BR Winterplace condo at Okemo. A short walk puts you on the slopes ...
From $607 per night (USD)Expedia
From $1839 per night (USD)VRBO
New construction: 4-bed, 4-bath house at Okemo Ski Mountain in Ludlow, VT
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Your Vermont getaway awaits at this 4-bedroom house. With 1 king bed, 3 queen beds, and 1 full bed, this peaceful retrea ...
From $1839 per night (USD)VRBO
From $1023 per night (USD)Expedia
Walk to Trail and Amenities at this Solitude Village Condo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
This ski home is convenient and comfortable. Get cozy by the woodburning fireplace after a long day on the slopes. Unwi ...
From $1023 per night (USD)Expedia
From $972 per night (USD)VRBO
Luxury Barn w/ Panoramic Okemo Views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Experience one of Southern Vermont's most remarkable homes. Set on nearly 14 private acres, this custom timber ...
From $972 per night (USD)VRBO
From $296 per night (USD)Expedia
Unplug, Unwind & Explore: Remote Vermont Cabin
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Tranquil Escape | Pet Friendly w/ Fee | Near Hiking & Skiing Experience the perfect blend of peaceful relaxation and ou ...
From $296 per night (USD)Expedia
From $1096 per night (USD)VRBO
Three Bedroom Country home with private hot tub and 5 min drive to Okemo Mountain
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to this quintessential Vermont farmhouse, where rustic character meets modern comfort. Just five minutes from Oke ...
From $1096 per night (USD)VRBO
From $204 per night (USD)VRBO
Quaint Queen room at the Chester Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy a private room & bathroom with tub in the historic Chester Inn, circa 1780. This charming property is conveniently ...
From $204 per night (USD)VRBO
From $216 per night (USD)VRBO
Spacious 4-bedroom house in charming Springfield with AC, fitness room
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Vermont Ski and Stay. Get ready to relax in this 4-bedroom house in Springfield. The bedrooms feature 1 king bed, 2 quee ...
From $216 per night (USD)VRBO
From $628 per night (USD)Expedia
Hidden Kingdom | Near Echo Lake, Private Retreat w/ Outdoor Space
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Hidden Kingdom – Your Four-Season Vermont Escape Brought to you by GetAway Tucked away on scenic Kingdom Road in Plymou ...
From $628 per night (USD)Expedia
From $1028 per night (USD)VRBO
Luxury Okemo Lodge | 0.5 Mi to Slopes | Sleeps 14
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Summary: Escape to this luxury mountain lodge just 0.5 miles from Okemo's base area, where spacious gathering spaces, a ...
From $1028 per night (USD)VRBO
From $464 per night (USD)Expedia
Modern Ski-in/Ski-Out Winterplace Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience true ski-in/ski-out living at Winterplace in this modern Okemo condo with direct access to the A&B Quads. One ...
From $464 per night (USD)Expedia
From $375 per night (USD)VRBO
Cozy, Private Dog-Friendly A-Frame Cabin: Mins to Hiking + Adorable Towns
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
NEW to VRBO! 40+ 5-star reviews on other booking sites. Tucked beneath Vermont pines, our cozy A-frame is a peaceful esc ...
From $375 per night (USD)VRBO
From $1388 per night (USD)Expedia
Ski In/Out condo close to everything with modern kitchen, balcony and views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Ski on/ski off convenience doesn't get better than this at the Clocktower Base. Mere steps from the lifts, ski school, a ...
From $1388 per night (USD)Expedia
From $476 per night (USD)VRBO
12 Min to Okemo MTN/Ludlow, 4 bd/2 bath, game room, hot tub, fireplace, fire pit
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Make yourself at home in this 4-bedroom Cavendish retreat. Quick drive to Okemo Mtn Ludlow Vermont. This beautiful hous ...
From $476 per night (USD)VRBO
From $891 per night (USD)Expedia
Ludlow Treasure | Okemo, Hot Tub, Game Room, Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Wake each morning to sweeping mountain views and fresh Vermont air in this stunning Ludlow retreat, where unforgettable ...
From $891 per night (USD)Expedia
From $332 per night (USD)VRBO
Soothing 2-bedroom cottage in charming Rochester perfect for relaxing getaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover this 2-bedroom charming cottage in Rochester. Guests find a cozy retreat featuring one queen bed and two twin b ...
From $332 per night (USD)VRBO
From $887 per night (USD)Expedia
Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to Pine & Plaid, a sun-filled designer cabin in Quechee with exclusive access to the Quechee Club—offering golf, ...
From $887 per night (USD)Expedia
From $535 per night (USD)VRBO
The Grange — Updated Village Home Near Okemo
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the Grange - a thoughtfully updated Vermont home located right in Ludlow Village. With a comfortable layout, ...
From $535 per night (USD)VRBO
From $525 per night (USD)Expedia
Lovely Chalet atop Vermont’s Green Mountains - perfect for a cozy getaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Retreat into the wild heart of Vermont's Green Mountains with easy access to both Woodstock and Killington. Our thoughtf ...
From $525 per night (USD)Expedia
From $850 per night (USD)VRBO
Stunning Views, 10 Mins from Woodstock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Just under 10 minutes from Woodstock Village, this 2023 home offers dramatic views and a thoughtfully-appointe ...
From $850 per night (USD)VRBO
From $2452 per night (USD)Expedia
Historic 1789 Luxury Farmhouse near Dartmouth College
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Twin Meadow Farm - 6 mi from Dartmouth College. The ultimate private sanctuary for Big Green sport weekends, family gat ...
From $2452 per night (USD)Expedia
From $585 per night (USD)VRBO
Fabulous Luxury Log Home, 6BR/4BA Hot Tub, 3 Min Drive to Base
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Brand new Hot Springs Hot Tub Fall 2026! Long driveway with dramatic stone walls lead you to a spacious, beautifully la ...
From $585 per night (USD)VRBO
From $1330 per night (USD)Expedia
Riverfront 1800s Farmhouse, Sleeps 12+, Minutes from Killington + Woodstock
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
Your Vermont Getaway Between Killington & Woodstock Escape to a beautifully renovated 1800s Vermont farmhouse on 6 priv ...
From $1330 per night (USD)Expedia
From $231 per night (USD)VRBO
Bridgewater Living - Long Trail Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stay close to Vermont’s best outdoor adventures at the Long Trail Suite, a private studio suite just 10 minutes from Kil ...
From $231 per night (USD)VRBO
From $629 per night (USD)Expedia
Mountain Retreat near Okemo | Spectacular Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Perched on a quiet knoll in Plymouth’s Green Mountains, this three-level retreat offers magical mountain and sunset view ...
From $629 per night (USD)Expedia
From $231 per night (USD)VRBO
Bridgewater Living - Woodstock Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stay close to skiing, dining, and Vermont charm at the Woodstock Suite, a private studio suite just 10 minutes from Kill ...
From $231 per night (USD)VRBO
From $232 per night (USD)Expedia
Bridgewater Living - Ben&Jerry Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stay close to Vermont’s best skiing at the Ben & Jerry’s Suite, a fun, themed private suite just 10 minutes from the Kil ...
From $232 per night (USD)Expedia
From $231 per night (USD)VRBO
Bridgewater Living - Ski VT Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Private studio with two queen beds just 10 minutes from Killington Skyeship Lodge. The Ski VT Suite is ideal for ski bud ...
From $231 per night (USD)VRBO
From $198 per night (USD)Expedia
Near Killington & Woodstock | Game Room, Fireplace
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Designed for gathering after a day of adventure, the home combines warm wood finishes with comfortable, modern living sp ...
From $198 per night (USD)Expedia
From $525 per night (USD)VRBO
Lakefront Cottage w/ Hot Tub & Dock on Lake Rescue
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Lakefront Cottage w/ Hot Tub & Dock in Ludlow This renovated lakefront cottage in Ludlow, VT offers the perfect blend o ...
From $525 per night (USD)VRBO
From $435 per night (USD)VRBO
Private 2BR Cottage in Bridgewater, near Killington & Woodstock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to a private 2BR Vermont cottage perfectly located between Killington Resort and Woodstock Village. Sleeping up t ...
From $435 per night (USD)VRBO
From $344 per night (USD)VRBO
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Coolidge Barn is a two-bedroom, two-bath Plymouth home on a large country property with gardens, woods, and mountain ...
From $344 per night (USD)VRBO
From $1415 per night (USD)Expedia
Large Luxury 6br Okemo Home | Hot Tub | Mtn View
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
Welcome to Mountainside Retreat. This large Vermont mountain home has 6 bedrooms, and 4.5 bathrooms, with 2 queen bedro ...
From $1415 per night (USD)Expedia
From $431 per night (USD)VRBO
Cozy 3-bedroom lake cottage w/ Harry Potter dorm near Woodstock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Live your Nancy Meyers, Gilmore Girls, and Harry Potter dreams at this peaceful cottage across the street from Silver La ...
From $431 per night (USD)VRBO
Click For PricingExpedia
Sunny Condo with Golf Views, Windsor Village
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Bright, inviting end-unit condo with extra windows and peaceful golf course views in the heart of Quechee. Enj ...
Click For PricingExpedia
From $1015 per night (USD)VRBO
Resort-Style Community! Quechee Chalet w/ Deck
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
2,264 Sq Ft | Large Wooded Lot | Family-Friendly Layout This isn't your average cabin in the woods! Think elevated int ...
From $1015 per night (USD)VRBO
From $308 per night (USD)Expedia
2-BD short drive to DHMC & Dartmouth College
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy the best of both worlds — a quiet and relaxing Vermont setting while remaining conveniently connected to the Upper ...
From $308 per night (USD)Expedia