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Compare 242 Vacation Homes in Bennington with updated reviews, rates, and availability.

Cozy Cabin Between Stratton Resort & Mount Snow
Stratton Vacation Rental | 3BR | 1.5BA | 1,100 Sq Ft | Stairs Required

Cozy Cabin Between Stratton Resort & Mount Snow

Cozy Cabin Between Stratton Resort & Mount Snow
Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen

Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen

Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Exterior

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

10.0 out of 10, Exceptional, (159)
"This was our second Thanksgiving at Creekside Camp. Once again, we had a wonderful stay. Not enough can be said about this charming and cozy cabin. Dan and Kellie do a phenomenal job as hosts and managing the property. We highly recommend a stay in this rustic, yet highly appointed property!"
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Miner Cottage-Historic Antique Home just steps from the Equinox Resort
Main St., Manchester, Vt.

Miner Cottage-Historic Antique Home just steps from the Equinox Resort

10.0 out of 10, Exceptional, (22)
"GREAT TIME ! GREAT HOUSE"
Miner Cottage-Historic Antique Home just steps from the Equinox Resort
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
Back of Barn

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

10.0 out of 10, Exceptional, (54)
"We rented the barn as an overflow space from the main house. The barn has everything you need and is a really cool spot to sit and view the entire property."
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton
Interior

Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton

9.8 out of 10, Exceptional, (30)
"One of the best experiences I’ve had. Communication before we arrived was as expected, and everything was better than the pictures reviews and descriptions."
The price is AED 2,016
AED 4,864 total
includes taxes & fees
23 Dec - 24 Dec
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton
Lovely Secluded Vermont Home: Stocked Pond, Trails, Ski.5 Mins to Williamstown!
Lush woodland setting is private, yet five minutes to Spring Street.

Lovely Secluded Vermont Home: Stocked Pond, Trails, Ski.5 Mins to Williamstown!

9.8 out of 10, Exceptional, (19)
"Such a gorgeous house! We loved walking the nearby trails and how close it was to Williams. Venetia was the best!"
Lovely Secluded Vermont Home: Stocked Pond, Trails, Ski.5 Mins to Williamstown!
Stylish Mountain Home Near Ski, Golf + Manchester!
Bondville Vacation Rental | 4BR | 2BA | 1,340 Sq Ft | Stairs Required

Stylish Mountain Home Near Ski, Golf + Manchester!

9.8 out of 10, Exceptional, (26)
"Starting with very friendly and hospitable owner to the house which is well maintained and comfortable, this place is great for a stay in VT. The fenced in yard was huge plus for dogs. Would definitely return. "
Stylish Mountain Home Near Ski, Golf + Manchester!
Enjoy the View from the Hot Tub!
Playful swing for indoor entertainment

Enjoy the View from the Hot Tub!

10.0 out of 10, Exceptional, (10)
"Our family loved our stay! The views are great and the house floorplan was ideal for 2 families. The main floor has a large family room that is open to the kitchen. The upper level has a nice master bedroom and the basement had a great bunk room that all the kids enjoyed! We all loved the hot tub that overlooked the beautiful mountains. The house was an easy 5 minute drive to Stratton. We look forward to coming back!"
Enjoy the View from the Hot Tub!
Three Bedroom home with loft

Three Bedroom home with loft

Three Bedroom home with loft
UNBELIEVABLE MOUNTAIN VIEWS! Convenient to Manchester,skiing,outlets
Living room as part of an open flow design. French door to deck and hot tub

UNBELIEVABLE MOUNTAIN VIEWS! Convenient to Manchester,skiing,outlets

4.0 star property
9.8 out of 10, Exceptional, (10)
"Alex was great! We had a great weekend getaway. Thanks for the firewood!"
UNBELIEVABLE MOUNTAIN VIEWS! Convenient to Manchester,skiing,outlets
Townhouse w/ hot tub, fireplace, pool, sauna, gym, tennis, shuttle, wifi, w/d

Townhouse w/ hot tub, fireplace, pool, sauna, gym, tennis, shuttle, wifi, w/d

2.0 star property
10.0 out of 10, Exceptional, (1)
Townhouse w/ hot tub, fireplace, pool, sauna, gym, tennis, shuttle, wifi, w/d
Brazer's Way Minutes to Sun Bowl & Stratton Base Lodge

Brazer's Way Minutes to Sun Bowl & Stratton Base Lodge

2.0 star property
Brazer's Way Minutes to Sun Bowl & Stratton Base Lodge
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Living room with wood-burning stove

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

10.0 out of 10, Exceptional, (213)
"Great experience "
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Your Barn!

Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont

10.0 out of 10, Exceptional, (196)
"Beautiful time of the year to enjoy this property and the surrounding woods and trails, plus Manchester. Our dogs love it here. "
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Ski In / Ski Out 4BR / 3BA Private Hot Tub and shared pool
Updated kitchen

Ski In / Ski Out 4BR / 3BA Private Hot Tub and shared pool

10.0 out of 10, Exceptional, (9)
"We had a wonderful stay. We enjoyed the home and community amenities. Location was great and our family enjoyed the convenience of having the access to ski on / ski off. We look forward to our stay next year!"
The price is AED 3,669
AED 6,397 total
includes taxes & fees
5 Jan - 6 January 2025
Ski In / Ski Out 4BR / 3BA Private Hot Tub and shared pool
Perfect for Leaf Peeping w/Bar Room, Hot Tub
Bar Room

Perfect for Leaf Peeping w/Bar Room, Hot Tub

10.0 out of 10, Exceptional, (11)
"Wonderful experience, extremely communicative and helpful management, and just a beautiful building to stay in. We wanted for nothing. Thank you!"
Perfect for Leaf Peeping w/Bar Room, Hot Tub
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
hot tub with incredible views...this is why we come to VT!

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

10.0 out of 10, Exceptional, (114)
"We have stayed here at least three times, and enjoy it every time. "
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
HUGE Private VT Mansion: 15 bedrooms, 12 bath, Sleep 34! Ski Bromley & Stratton, yoga retreats, corporate offsites, DIY weddings, family reunions, Dogs welcome
Winter_holiday_ext_closeup_Battenkill_Valley_Mansion

HUGE Private VT Mansion: 15 bedrooms, 12 bath, Sleep 34! Ski Bromley & Stratton, yoga retreats, corporate offsites, DIY weddings, family reunions, Dogs welcome

10.0 out of 10, Exceptional, (56)
"We had a wonderful time at the Battenkill Valley Mansion. The house is well equipped with everything needed for a fun family weekend with multiple generations. Melissa was super helpful with planning and check-in. The area is beautiful and we look forward to another trip."
HUGE Private VT Mansion: 15 bedrooms, 12 bath, Sleep 34! Ski Bromley & Stratton, yoga retreats, corporate offsites, DIY weddings, family reunions, Dogs welcome
Your own Private Lake - Breathtaking Views - Gym - Sauna - Hot Tub
Exterior

Your own Private Lake - Breathtaking Views - Gym - Sauna - Hot Tub

10.0 out of 10, Exceptional, (24)
"We stayed here with a group of friends and family for a weekend away in honor of my husband’s 30th birthday. This was a group of 14 adults ages 27-37 years old. I cannot say enough great things about this place. Everyone commented on how spacious the house was . Despite 14 of us being in the same house at no point did anyone feel on top of each other. There were great spaces for us to hang out as a large group and the view was beautiful. It was only a 20 minute drive into Manchester where we...
Your own Private Lake - Breathtaking Views - Gym - Sauna - Hot Tub
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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Other property types in Bennington

Perfect for Leaf Peeping w/Bar Room, Hot Tub
Bar Room

Perfect for Leaf Peeping w/Bar Room, Hot Tub

10.0 out of 10, Exceptional, (11)
"Wonderful experience, extremely communicative and helpful management, and just a beautiful building to stay in. We wanted for nothing. Thank you!"
Perfect for Leaf Peeping w/Bar Room, Hot Tub
Cross Country Ski? Downhill? Prospect and Mt Snow. Winter wonderland book now.
Skiing open now at Prospect Mountain Snowmobiling coming soon Book now before up

Cross Country Ski? Downhill? Prospect and Mt Snow. Winter wonderland book now.

9.8 out of 10, Exceptional, (132)
"Linda was amazing from beginnin'g to end to ensure a comfortable stay. This house was beautiful and so cozy to stay in. The loft bed had a gorgous view of the lake and snow. Plenty of sleeping room for my kids.They got to play in the snow too:)"
Cross Country Ski? Downhill? Prospect and Mt Snow. Winter wonderland book now.
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
Nighttime view

Two Brooks Lodge, Beautiful Waterfront Vermont Retreat

8.8 out of 10, Excellent, (27)
"In town for a long weekend and loved the location. The owner was prompt and very helpful as we made a mistake in booking. FYI, The pictures are great but it’s a bit more rustic than they make it seem. Still, it was great to sit outside and hear the brooks flowing. Very quiet street! Housecleaning was a bit lacking though as there were some huge cobwebs in the corners. That was fine for us as we spend our time in a barn anyway. "
The price is AED 632
AED 1,306 total
includes taxes & fees
25 Dec - 26 Dec
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
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.