Windham Rentals
From $597 per night (USD)VRBO
Winter Getaway at the Octagon w/ 3 Fireplaces!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
WE GOT THE SNOW! Perfectly situated between Stratton (15mi), Okemo (15mi), Bromley (12mi) and Magic Mountain (2mi) resor ...
From $597 per night (USD)VRBO
From $181 per night (USD)Expedia
Single-Level Duplex with Fast WiFi & a Full Kitchen - Close to Magic Mountain
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Magic Birch Lodge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $181 per night (USD)Expedia
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
From $345 per night (USD)Expedia
Londonderry Chalet w/ Deck, Fire Pit & Views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Indulge in a blissful trip to the mountains at this timeless and elegant 3-bedroom, 2-bath log cabin. With a quiet-yet-c ...
From $345 per night (USD)Expedia
From $234 per night (USD)VRBO
Cozy 3BR Vermont Artistic Retreat w/ Trails
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Discover this cozy 3-bedroom artistic retreat in Windham, VT’s serene countryside, perfect for spring and summer adventu ...
From $234 per night (USD)VRBO
From $426 per night (USD)VRBO
Charming Farmhouse 5 minutes from Magic Mountain & close to 5 other Ski Resorts
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Centrally located home for all of your year-round outdoor activities! Come enjoy all Vermont has to offer on this 3-acre ...
From $426 per night (USD)VRBO
From $228 per night (USD)VRBO
Mountain chalet
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Our chalet was built in 2020 with all new furnishings and amenities. It is nestled in the woods of Powder Mill. Several ...
From $228 per night (USD)VRBO
From $366 per night (USD)VRBO
1830's Recently Renovated Rustic Farmhouse, Windham Vermont
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Our 1830s rustic and comfortable familyfarmhouse, Blue Flyer Farm, is available for rent through the seasons. The Summe ...
From $366 per night (USD)VRBO
From $325 per night (USD)VRBO
3+ - bedroom chalet with loft just 10 minutes from Magic Mountain Ski Resort
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to our cozy 3-bedroom chalet with loft nestled in the heart of Windham! Situated near Magic Mountain and a 20 mi ...
From $325 per night (USD)VRBO
From $326 per night (USD)Expedia
Historic Farmhouse, Quaint Vermont Experience
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Come, enjoy this historic (circa 1810) farmhouse set on 12+ acres. Listed on the Vermont historic register, our 4 bedroo ...
From $326 per night (USD)Expedia
From $2828 per night (USD)VRBO
Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.
- Bedrooms:
- 6
- Bathrooms:
- 11
- Sleeps:
- 30
This is a picturesque, rustic contemporary 7000 sq. ft. home on 15 acres with gorgeous views, and comes with great ameni ...
From $2828 per night (USD)VRBO
From $302 per night (USD)Expedia
Vermont Ski Chalet ~ 5 Mi to Magic Mountain
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Outdoor adventure awaits at this chic 4-bedroom, 3-bath vacation rental in Windham! Complete with a cozy interior space ...
From $302 per night (USD)Expedia
From $447 per night (USD)VRBO
Minutes to a Magical Apres Ski! 3 Beds, EV Charger, Mins to 4 Ski Mtns
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Convenient location minutes from multiple renowned ski resorts and picture-perfect state parks, this house affords easy ...
From $447 per night (USD)VRBO
Click For PricingExpedia
The Windham Hill A-Frame - Close to 3 Ski Resorts!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Welcome to our cozy A-Frame, nestled in scenic Vermont. Perfect for skiers, we're just 20 mins from Bromley, 8 ...
Click For PricingExpedia
From $408 per night (USD)VRBO
Near Magic Mtn &Stratton Mtn ski resorts, outdoor is fun and great leaf peeping.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Newly Remodeled! The Snowflake Hideaway is a great house for all seasons. Located off Rt 30 in Southern Vermont, it is c ...
From $408 per night (USD)VRBO
From $1088 per night (USD)VRBO
New! Cozy private Chalet with incredible views, close to Mountains!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 15
Views, views, views! This lovely Vermont home is centrally located and close to everything a group needs for a fantastic ...
From $1088 per night (USD)VRBO
From $548 per night (USD)VRBO
Tranquil Mountain Chalet- fireplace, deck, sauna, hiking trails, close to skiing
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy every season in this classic Vermont Chalet, located in a quiet wooded neighborhood in the Green Mountains. The op ...
From $548 per night (USD)VRBO
From $496 per night (USD)Expedia
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy a peaceful stay at this marvelous 2-bedroom barn in Londonderry. This charming property features two comfortable q ...
From $496 per night (USD)Expedia
From $646 per night (USD)VRBO
Cozy 2-bedroom cabin in enjoyable Londonderry with AC with hot tub and sauna
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Make yourself at home in this adorable 2-bedroom retreat. Nestled in the charming town of Londonderry, this cabin is the ...
From $646 per night (USD)VRBO
From $471 per night (USD)Expedia
Welcome to The Aster Chalet
- Bedrooms:
- 3
- Bathrooms:
- 1
- Sleeps:
- 10
Welcome to The Aster Chalet! Our mid-century getaway has been thoughtfully updated with modern-day amenities for the ut ...
From $471 per night (USD)Expedia
From $269 per night (USD)VRBO
Charming gingerbread A-frame situated on 3 acres, woodstove, A/C, deck
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Koliba Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $269 per night (USD)VRBO
From $534 per night (USD)Expedia
Beautiful house w/ mountain & pond views, hot tub, pool table, bbq, firepit, w/d
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Wish Upon A Star Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $534 per night (USD)Expedia
From $321 per night (USD)VRBO
Peaceful chalet near Bromley, Magic, Okemo, Mount Snow, and Stratton
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
This quiet mountain get away is the perfect place for your friends and family to enjoy beautiful southern Vermont. Our ...
From $321 per night (USD)VRBO
From $969 per night (USD)Expedia
Play & Relax in Windham – Spacious Bedrooms, Hot Tub, Fire Pit & Basement Den
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 15
Get ready to relax in this 5-bedroom house in Windham - perfect for families or groups of friends looking for a place to ...
From $969 per night (USD)Expedia
From $513 per night (USD)VRBO
Peaceful 5-BR Escape Near Stratton
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: Tucked away on a quiet stretch of Windham’s scenic countryside, this spacious 5-bedroom getaway offers the perf ...
From $513 per night (USD)VRBO