Bennington Area Rentals
From $423 per night (USD)VRBO
In Town Delight!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
In town and convenient to all Manchester has to offer, we are within walking distance to restaurants and shops. This is ...
From $423 per night (USD)VRBO
From $365 per night (USD)Expedia
Enjoy the views and Vermont Vibes
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Green River Escape, your peaceful getaway nestled on 8 acres of open land along the Green River and 30 acres ...
From $365 per night (USD)Expedia
From $474 per night (USD)VRBO
Charming 3-bedroom cabin in Woodford private with mountain and pond view
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Unwind in Woodford at this quaint hunting cabin. With 3 sleeping areas and 2 full bathrooms , guests can relax and recha ...
From $474 per night (USD)VRBO
From $196 per night (USD)Expedia
Converted silo apartment, peaceful grounds, two ponds, kitchenette, internet
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Red Silo Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $196 per night (USD)Expedia
From $462 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 $462 per night (USD)VRBO
From $415 per night (USD)Expedia
Cozy 2-BR Cottage on a Private Estate in Dorset
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Welcome to your own quiet corner of Green Haven. Surrounded by forest and mountain views, this charming 2-bedro ...
From $415 per night (USD)Expedia
From $462 per night (USD)VRBO
Four bedroom retreat in Vermont's Golden Triangle
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
In the heart of the Green Mountains, our newly renovated four-bedroom home blends rustic charm with modern luxury. Set o ...
From $462 per night (USD)VRBO
From $437 per night (USD)VRBO
3 Level Townhome on Private Property ~ Walk in Town ~ Spacious & Spotless
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
This terrific Townhome is on a quiet street with views looking above and beyond town. If you would like to be in town an ...
From $437 per night (USD)VRBO
From $420 per night (USD)VRBO
Private 2-bedroom condo with mountain views in charming Dorset, Vermont.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Charming Dorset Condo with Stunning Mountain Views Nestled in the quaint and historic village of Dorset, this inviting ...
From $420 per night (USD)VRBO
From $1106 per night (USD)VRBO
Quartermile Mountain Home
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Nestled just minutes away from the bustling Stratton Village on picturesque Quarter Mile Road, this stunning 5 bedroom, ...
From $1106 per night (USD)VRBO
From $390 per night (USD)VRBO
Riverfront house, dog-friendly, mountain views, a/c, porch, deck, gas stove, w/d
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Stargazing Daydreamer Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $390 per night (USD)VRBO
From $1486 per night (USD)VRBO
Spacious Suite Perfect for Relaxation in Manchester | Pool, Restaurant, Bar
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Experience historic charm and modern luxury in Vermont’s Green Mountains. Enjoy fine dining, an 18-hole golf course, and ...
From $1486 per night (USD)VRBO
From $247 per night (USD)VRBO
Updated ground floor condo w/ patio, fireplace, ski locker, door to door shuttle
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Vantage Point #7 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $247 per night (USD)VRBO
From $378 per night (USD)Expedia
Spacious New 1BR:Dorset,Equestrian,Ski & Outlets
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Green Mountain Getaway located in East Dorset | Spacious 1BR Retreat Near Vermont Summer Festival, Ski Resorts & Manches ...
From $378 per night (USD)Expedia
From $1042 per night (USD)VRBO
Top Flr Duplex 4BR 4BA - Walk to All @ Stratton Mt
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
New Rising Bear Duplex 409 at Stratton Mt-Seasonal Rental Available Spacious 3Br/4Bth Lodge With Ice Skating Pond, Heate ...
From $1042 per night (USD)VRBO
From $1237 per night (USD)VRBO
Unwind in Luxury: Elegant 4BR House for Relaxation | Pool | Bar | Restaurant
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Experience historic charm and modern luxury in Vermont’s Green Mountains. Enjoy fine dining, an 18-hole golf course, and ...
From $1237 per night (USD)VRBO
From $1237 per night (USD)VRBO
Charming 4BR Perfect for Exploring Manchester's Beauty | Pool | Bar | Restaurant
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Experience historic charm and modern luxury in Vermont’s Green Mountains. Enjoy fine dining, an 18-hole golf course, and ...
From $1237 per night (USD)VRBO
From $1486 per night (USD)VRBO
Nature Retreat: Plush House Stay w/ Spectacular Views | Near Equinox Preserve
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Experience historic charm and modern luxury in Vermont’s Green Mountains. Enjoy fine dining, an 18-hole golf course, and ...
From $1486 per night (USD)VRBO
From $1051 per night (USD)VRBO
Nature Retreat: Plush 3BR Stay w/ Spectacular Views w/ Balcony | Pool | Spa
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Experience historic charm and modern luxury in Vermont’s Green Mountains. Enjoy fine dining, an 18-hole golf course, and ...
From $1051 per night (USD)VRBO
From $2102 per night (USD)VRBO
Ultimate Comfort in 2 3BR Units w/ Stunning Mountain Setting | Onsite Pool
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
Experience historic charm and modern luxury in Vermont’s Green Mountains. Enjoy fine dining, an 18-hole golf course, and ...
From $2102 per night (USD)VRBO
From $2102 per night (USD)VRBO
Green Mountain Retreat – Golf | Spa | Heated Pool | Hiking & Minutes to Bromley
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
Experience historic charm and modern luxury in Vermont’s Green Mountains. Enjoy fine dining, an 18-hole golf course, and ...
From $2102 per night (USD)VRBO
From $1052 per night (USD)VRBO
2 Units | Relaxing 3BR Retreat Perfect for Your Green Mountain Escape | Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Experience historic charm and modern luxury in Vermont’s Green Mountains. Enjoy fine dining, an 18-hole golf course, and ...
From $1052 per night (USD)VRBO
From $134 per night (USD)VRBO
Cozy motel suite in charming Woodford with WiFi, AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
You won’t want to leave this charming, one-of-a-kind place. Our centrally located private suite is perfect for the outdo ...
From $134 per night (USD)VRBO
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Cottage in East Dorset on Deming Pond, AC, WiFi Washer Dryer
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Unwind in Dorset at this charming cottage. With 2 cozy bedrooms - one with a full bed and the other with two twin beds, ...
Click For PricingVRBO
From $482 per night (USD)VRBO
Cozy 3-BR Retreat Near Stratton & Manchester
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: A reimagined Vermont escape just minutes from Stratton, where natural textures, thoughtful design, and mountain ...
From $482 per night (USD)VRBO
From $261 per night (USD)Expedia
Historic Home with Colonial Charm in Manchester
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Experience timeless elegance at Manchester's 1812 House. This duplex home, nestled in a picturesque meadow and surrounde ...
From $261 per night (USD)Expedia
From $206 per night (USD)VRBO
Red Country Escape with Mountain Views
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Enjoy our 3 bedroom, 1 bath red farmhouse home sitting on 16 acres in upstate New York. Amazing views of the Taconic Mou ...
From $206 per night (USD)VRBO
From $376 per night (USD)Expedia
Modern Mountain Retreat w/ Chef’s Kitchen
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience comfort, style, and warmth in this beautifully appointed open-concept home, perfect for families or groups se ...
From $376 per night (USD)Expedia
From $523 per night (USD)VRBO
Secluded 4 bedroom home with sweeping mountain views in Williamstown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Your cozy getaway awaits in Williamstown at this lovely home with sweeping mountain views. With 4 bedrooms including a k ...
From $523 per night (USD)VRBO
From $731 per night (USD)Expedia
1812 House, 2 Stays, 1 home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Experience the bucolic charm of Vermont at 1812 House! This colonial gem has been converted into two distinctive apartme ...
From $731 per night (USD)Expedia
From $224 per night (USD)VRBO
Modern, Stylish apartment on Stunning Horse Farm in Shaftsbury Vermont.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy a peaceful stay at this elegant 1-bedroom apartment in Shaftsbury. The Zen bedroom features a comfortable queen be ...
From $224 per night (USD)VRBO
From $708 per night (USD)VRBO
Ski in Ski Out newly renovated Slopeside G2
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Book your stay today and start planning your dream vacation! This newly renovated townhome is the perfect blend of adven ...
From $708 per night (USD)VRBO
From $315 per night (USD)VRBO
Charming 2-bedroom Stratton Mountain Condo with shuttle service
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience the Charm of Stratton in This Cozy 2-Bedroom Condo Escape to the beauty of Stratton with a stay in this invi ...
From $315 per night (USD)VRBO
From $346 per night (USD)VRBO
Charming 3 BR Barn House in Landgrove overlooking the valley and near Bromley
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience small town Vermont at it's finest in this quaint 3-bedroom post and beam barn house in Landgrove. Relax on th ...
From $346 per night (USD)VRBO
From $422 per night (USD)VRBO
Enchanting 5-bedroom farmhouse in Landgrove
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Lovely 1840s farmhouse available for preferred two week/monthly or seasonal rentals! Located on a dirt road along a bab ...
From $422 per night (USD)VRBO
From $693 per night (USD)Expedia
Tranquil farmhouse in Manchester - perfect for ski or summer fun!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Whether summer or winter, stay comfortably in Manchester at our charming 5-bedroom farmhouse. The bedrooms feature 2 ful ...
From $693 per night (USD)Expedia
From $348 per night (USD)VRBO
Tranquil Brookside Retreat w/hot tub & fireplace - pet friendly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Discover a serene escape that is perfect for memory-making family trips, friend getaways, or restful retreats. This inv ...
From $348 per night (USD)VRBO
From $361 per night (USD)Expedia
LUXURY CONDO l 2 EN SUITES l FALL FOLIAGE l POOL & HOT TUB
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
LUXURY @ STRATTON Your Perfect Vermont Escape Plan your perfect fall getaway at this newly upgraded, beautifully desig ...
From $361 per night (USD)Expedia