Holiday Homes in Bennington

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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

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

Peaceful Family Friendly Private Lake Waterfront Home Close to Skiing and Hiking
Bennington
10.0 out of 10, Exceptional, (16 reviews)
"Very cozy house Perfect for all family trip Very clean "
United States
Marcin W.
The price is €329
includes taxes & fees
18 Nov - 19 Nov
Peaceful Family Friendly Private Lake Waterfront Home Close to Skiing and Hiking
A hot tub with a wooden deck and a hammock in a backyard.

2. HotTub FirePit Games Huge Backyard Family Friendly

HotTub FirePit Games Huge Backyard Family Friendly
Antrim
9.4 out of 10, Exceptional, (16 reviews)
"The hot tub was great and the peace and quiet was very nice."
United States
Brian B.
The price is €266
includes taxes & fees
8 Nov - 9 Nov
HotTub FirePit Games Huge Backyard Family Friendly
A hot tub in a rustic interior with wooden beams, a staircase, and seating areas.

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

Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl
Antrim
8.8 out of 10, Excellent, (12 reviews)
"Host was communicative and helpful with some specific questions we had. The apartment was in a cute older house, nicely updated and set up for guests. Everything was nicely labeled to be easy to find. The hot tub was great as well!"
United States
Sarah H.
The price is €266
includes taxes & fees
11 Nov - 12 Nov
Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl
A hot tub in a rustic interior with wooden beams, a staircase, and seating areas.

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

16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard
Antrim
10.0 out of 10, Exceptional, (11 reviews)
"Great place to relax with a woody vibe. Excellent stay"
United States
Logan V.
The price is €573
includes taxes & fees
11 Nov - 12 Nov
16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard
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

Family Friendly, Hot Tub, King Beds Just Renovated
Hillsborough
The price is €290
includes taxes & fees
8 Nov - 9 Nov
Family Friendly, Hot Tub, King Beds Just Renovated
A red house with a stone pathway leading to it, surrounded by autumn foliage.

6. Cobb Meadow House: Cozy 5 Bedroom Retreat

Cobb Meadow House: Cozy 5 Bedroom Retreat
Dublin
10.0 out of 10, Exceptional, (27 reviews)
"Good place to stay during a wedding week"
United States
Veronique S.
Cobb Meadow House: Cozy 5 Bedroom Retreat
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

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Stoddard
10.0 out of 10, Exceptional, (6 reviews)
"Everything was perfect for our weekend stay. Host responded immediately to our questions. House had all the amenities for an enjoyable time!"
United States
Mary P.
The price is €571
includes taxes & fees
8 Nov - 9 Nov
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

8. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (27 reviews)
"Great stay, clean, accommodating and great location. Will stay again!"
United States
cody s.
The price is €313
includes taxes & fees
9 Nov - 10 Nov
Modern Downtown Escape HotTub Fire Pit Games 12ppl
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!

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
9.8 out of 10, Exceptional, (6 reviews)
"Communication with the host was easy and the house was great. I would definitely book this home again if/when I come back to Keene."
United States
Jeremy S.
The price is €423
includes taxes & fees
3 Dec - 4 Dec
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
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!

SUNAPEE RETREAT AT ENCHANTED FOREST - BRING KIDS - NEAR LAKE AND MOUNTAIN!
Newbury
9.8 out of 10, Exceptional, (21 reviews)
"Neat place, close to two ski mountains. "
United States
COLLEEN K.
The price is €959
includes taxes & fees
11 Nov - 12 Nov
SUNAPEE RETREAT AT ENCHANTED FOREST - BRING KIDS - NEAR LAKE AND MOUNTAIN!
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.

2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
Fitzwilliam
10.0 out of 10, Exceptional, (7 reviews)
"Pondlife was clean, calm, cozy, and peaceful...exactly what we wanted...fall foliage was gorgeous....rail trail hiking adjacent to the property and plenty of mountain hiking nearby. If you want to be immersed in nature's beauty, this is perfect..."
United States
Margaret
The price is €253
includes taxes & fees
15 Nov - 16 Nov
2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
A covered porch with wooden flooring, a bench, and a table with chairs.

12. Riverfront Log Home - 28 Acres - Fire Pit

Riverfront Log Home - 28 Acres - Fire Pit
Warner
The price is €855
includes taxes & fees
22 Nov - 23 Nov
Riverfront Log Home - 28 Acres - Fire Pit
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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