Holiday Homes in Bennington

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Holiday Homes in Bennington

Mountain Sanctuary Dome Rustic Solitude 5BR
Interior

Mountain Sanctuary Dome Rustic Solitude 5BR

9.8 out of 10, Exceptional, (6)
"We had an awesome stay at Nate’s place! The stone architecture and wood oven fireplace gave a truly unique experience, and the house was very spacious. The fully equipped kitchen made for anxenjoyable cooking experience. Nate was also flexible and responsive. Definitely recommend this for your weekend getaway home!"
Mountain Sanctuary Dome Rustic Solitude 5BR
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Interior

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

7.8 out of 10, Good, (50)
"Great condo in great location. Easy walk to restaurants and lifts."
The price is AU$390
includes taxes & fees
24 Aug - 25 Aug
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
Exterior detail

Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

10.0 out of 10, Exceptional, (63)
"We had a "
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
UNBELIEVABLE MOUNTAIN VIEWS! Convenient to Manchester,skiing,outlets
Outdoor spa tub

UNBELIEVABLE MOUNTAIN VIEWS! Convenient to Manchester,skiing,outlets

4.0 star property
10.0 out of 10, Exceptional, (17)
"We had a wonderful stay, the property was perfect for our family. The view was especially nice. Very quick & easy to get to Manchester and ski mountains."
UNBELIEVABLE MOUNTAIN VIEWS! Convenient to Manchester,skiing,outlets
Sleep 20. Pool. Tennis. Dogs loved. Private home on #1 resort on TripAdvisor.
Terrace/patio

Sleep 20. Pool. Tennis. Dogs loved. Private home on #1 resort on TripAdvisor.

9.8 out of 10, Exceptional, (17)
"Spacious house and beautiful grounds."
Sleep 20. Pool. Tennis. Dogs loved. Private home on #1 resort on TripAdvisor.
Luxury 4-BR Mountain Estate 10-min to Manchester
Interior

Luxury 4-BR Mountain Estate 10-min to Manchester

2.0 star property
10.0 out of 10, Exceptional, (2)
"This property is amazing: the grounds, the gardens and of course an exceptional, well equipped house. The architecture, the views and the many bedrooms and bathrooms made it so comfortable for our group of nine. The kitchen is well organized and has every convenience for cooking in."
Luxury 4-BR Mountain Estate 10-min to Manchester
Cozy 3-BR Retreat Near Stratton & Manchester
Dining

Cozy 3-BR Retreat Near Stratton & Manchester

Cozy 3-BR Retreat Near Stratton & Manchester
Luxury Post and Beam Barn Set On 10 Acres
Fridge, microwave, oven, stovetop

Luxury Post and Beam Barn Set On 10 Acres

10.0 out of 10, Exceptional, (86)
"Amazing property and host. Would love to stay again next time in the area. "
Luxury Post and Beam Barn Set On 10 Acres
Stylish Mountain Home Near Ski, Golf + Manchester!
Outdoor spa tub

Stylish Mountain Home Near Ski, Golf + Manchester!

9.8 out of 10, Exceptional, (33)
"Relaxing weekend just a few miles from the ski mountain. Hot tub was great."
Stylish Mountain Home Near Ski, Golf + Manchester!
Vermont Summer Escape - Sleeps 8 with FirePit, Hot Tub, and Pet Friendly!
Exterior

Vermont Summer Escape - Sleeps 8 with FirePit, Hot Tub, and Pet Friendly!

10.0 out of 10, Exceptional, (6)
"We loved staying at the Sloane School! It was modern yet so cozy. It had everything we needed, there were only three of us but there was plenty of room for more. The hot tub was delightful, the bathrooms were beautiful, the kitchen was so nice and everything was immaculate! I would stay there again in a heartbeat! "
Vermont Summer Escape - Sleeps 8 with FirePit, Hot Tub, and Pet Friendly!
Cozy ski home with amazing views of Stratton & Bromley Mountains.
Property grounds

Cozy ski home with amazing views of Stratton & Bromley Mountains.

9.4 out of 10, Exceptional, (30)
"The convenient near-mountain location and living room views are hard to beat; the hot tub was a great touch as well! It was perfect for our large group over a holiday weekend."
Cozy ski home with amazing views of Stratton & Bromley Mountains.
Gather Together – Stratton Mtn Luxury & Comfort with a View
Exterior

Gather Together – Stratton Mtn Luxury & Comfort with a View

8.0 out of 10, Very good, (5)
"Lots of Room, Clean, 5 min to the Slopes, we will stay here again!"
Gather Together – Stratton Mtn Luxury & Comfort with a View
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Fridge, microwave, oven, stovetop

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

8.6 out of 10, Excellent, (32)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
The price is AU$483
includes taxes & fees
24 Aug - 25 Aug
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
8-bedroom vacation home just 16 minutes from Golf Club at Equinox
Dining

8-bedroom vacation home just 16 minutes from Golf Club at Equinox

9.6 out of 10, Exceptional, (17)
"Happy experience and plenty of room. Everyone enjoyed the lake and sounding places."
8-bedroom vacation home just 16 minutes from Golf Club at Equinox
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

10.0 out of 10, Exceptional, (226)
"Beautiful property. Very relaxing, secluded. "
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
Fridge, microwave, oven, stovetop

Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

10.0 out of 10, Exceptional, (120)
"House was accurately described. Kitchen was well-equipped. Village of Manchester is just a short drive away. Deck and hot tub were awesome!"
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
Secluded Mountain Retreat: Gorgeous Views, 5 Mins to Stratton, Sauna, Firepit
Property grounds

Secluded Mountain Retreat: Gorgeous Views, 5 Mins to Stratton, Sauna, Firepit

2.0 star property
9.2 out of 10, Wonderful, (9)
"No hassles great place as described in listing. Clean and has all necessary amenities. Would happily stay there again "
Secluded Mountain Retreat: Gorgeous Views, 5 Mins to Stratton, Sauna, Firepit
Spacious village house, dog-friendly, patio, fireplace, a/c, air hockey, w/d
Fridge, microwave, oven, stovetop

Spacious village house, dog-friendly, patio, fireplace, a/c, air hockey, w/d

8.4 out of 10, Very good, (5)
"We really enjoyed our stay. The house is beautiful and in such a great location. The host was great! I would definitely stay there again."
Spacious village house, dog-friendly, patio, fireplace, a/c, air hockey, w/d
Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.
4 bedrooms, iron/ironing board, WiFi, bed sheets

Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.

2.0 star property
10.0 out of 10, Exceptional, (7)
"Awesome."
The price is AU$2,247
includes taxes & fees
26 Aug - 27 Aug
Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.
Perfect Reunion House w/pool, tennis, fireplace & piano. Dogs welcome.
Fridge, microwave, oven, stovetop

Perfect Reunion House w/pool, tennis, fireplace & piano. Dogs welcome.

9.8 out of 10, Exceptional, (24)
"Great location near Bromley and Stratton for skiing. Our group of 16 had plenty of room and were very comfortable. Melissa was very accommodating and responsive. Would definitely recommend this property."
Perfect Reunion House w/pool, tennis, fireplace & piano. Dogs welcome.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Bennington Hotel Reviews

The Four Chimneys Inn

The Four Chimneys Inn

10/10 Excellent
"What an absolutely amazing stay!! Everything was perfect. Highly recommend having dinner onsite. "
Jon 1-night trip
Posted 1 day ago
The Four Chimneys Inn