Bennington Vacation Homes

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Our top choices for Bennington holiday homes

A conservatory with a view of a lake surrounded by trees. Inside, there are two sofas facing the glass walls.

1. Peaceful Family Friendly Private Lake Waterfront Home Close to Skiing and Hiking

Bennington

Marcin W.

HK$2,950 total

includes taxes & fees

18 Nov - 19 Nov

A hot tub with a wooden deck and a hammock in a backyard.

2. HotTub FirePit Games Huge Backyard Family Friendly

Antrim

Brian B.

HK$2,334 total

includes taxes & fees

8 Nov - 9 Nov

A hot tub in a rustic interior with wooden beams, a staircase, and seating areas.

3. Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl

Antrim

Sarah H.

HK$2,334 total

includes taxes & fees

11 Nov - 12 Nov

4. 16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard

Antrim

Logan V.

HK$5,084 total

includes taxes & fees

11 Nov - 12 Nov

A hot tub with a view of an outdoor area with trees and a wooden structure.

5. Family Friendly, Hot Tub, King Beds Just Renovated

Hillsborough

HK$2,512 total

includes taxes & fees

18 Nov - 19 Nov

A red house with a stone pathway leading to it, surrounded by autumn foliage.

6. Cobb Meadow House: Cozy 5 Bedroom Retreat

Dublin

Veronique S.

HK$5,380 total

includes taxes & fees

8 Nov - 9 Nov

A house with a deck and a dock extending into a pond, surrounded by autumn foliage.

7. Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston

Stoddard

Mary P.

HK$4,704 total

includes taxes & fees

5 Nov - 6 Nov

A modern kitchen with a wooden countertop, dark cabinets, and a large window.

8. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Keene

cody s.

HK$2,810 total

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with granite countertops, stainless steel appliances, and a central island.

9. Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Keene

Jeremy S.

HK$3,593 total

includes taxes & fees

5 Nov - 6 Nov

A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

10. SUNAPEE RETREAT AT ENCHANTED FOREST - BRING KIDS - NEAR LAKE AND MOUNTAIN!

Newbury

COLLEEN K.

HK$8,403 total

includes taxes & fees

11 Nov - 12 Nov

A lake surrounded by trees, with a wooden deck leading to a white railing.

11. 2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.

Fitzwilliam

Margaret

HK$2,209 total

includes taxes & fees

8 Nov - 9 Nov

A covered porch with wooden flooring, a bench, and a table with chairs.

12. Riverfront Log Home - 28 Acres - Fire Pit

Warner

HK$7,325 total

includes taxes & fees

22 Nov - 23 Nov

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Top Bennington Hotel Reviews

Colby Hill Inn

8/10 Good

"Staff were very welcoming and social. Breakfast was delicious. The only unfortunate thing is because the place is so old there are no individual room thermostats so our room was extremely hot whilst trying to sleep otherwise it would get 5 stars."

Quaint Dunbarton Waterfront Cottage

10/10 Excellent

"We thoroughly enjoyed staying at this cottage. It was in a very pretty spot with a lovely view of the lake. It was so nice to just watch the scenery. The host was easy to reach. The place itself was a nice open living arrangement which was nice for visiting with other people."

Beautiful Private Lakefront new Log Home

10/10 Excellent

"The house was gorgeous! The weather as well, got to enjoy the lake with fishing and paddle boat! My sons wedding was close by at golf course, so very convenient for all of us to spend the weekend. It had everything you could possibly need and some! So happy we booked this house, will definitely use it again for special occasion to host family. Frank was extremely friendly, helpful and responsive to any questions we had."

Cozy Cabin in a rural setting #12 in Temple NH

10/10 Excellent

"The cabin was exactly as advertised. It's small - but you know that going into it! The bathroom and kitchenette were clean, the hosts were responsive, and the check in/out instructions were clear and easy to follow. The mattress is quite soft, which for some people may be excellent but we prefer firm. The property Is quite private, fairly well maintained, and in a quiet area. There are trails nearby but it's more rural so shops are 10-15 away. The space is pet friendly, but our puppy didn't join us on this trip."

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