Bennington Vacation Rentals

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Check prices for these dates

In two weeks
Sep 19 - Sep 21
In one month
Oct 3 - Oct 5
In two months
Oct 31 - Nov 2
In three months
Nov 28 - Nov 30

Vacation Rentals in Bennington

1800’s restored log cabin on 26 private rolling wooded acres with sunset views
Property grounds

1800’s restored log cabin on 26 private rolling wooded acres with sunset views

10.0 out of 10, Exceptional, (196)
"This cabin is the perfect place to getaway and relax! It’s peaceful and beautiful!"
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
Charming 3-bedroom house in lovely downtown Madison.
Exterior

Charming 3-bedroom house in lovely downtown Madison.

2.0 star property
"Great old home and cool neighborhood. "
Charming 3-bedroom house in lovely downtown Madison.
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
Interior

Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…

10.0 out of 10, Exceptional, (47)
"Everything was really great...the property is beautiful...the amenities were amazing...and the owners so sweet and caring...the would answer a text message pronto...will stay again!"
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
Rustic cabin just outside of Madison!
4 bedrooms, free WiFi, bed sheets

Rustic cabin just outside of Madison!

10.0 out of 10, Exceptional, (44)
"This was a very nice property. The cabin was so cozy and the property was beautiful. We all enjoyed our stay."
Rustic cabin just outside of Madison!
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Fridge, microwave, oven, stovetop

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

9.8 out of 10, Exceptional, (39)
"We enjoyed the space. Had everything we needed. Great proximity to downtown shopping and entertainment. "
The price is ￥16,286
￥33,882 total
includes taxes & fees
Sep 7 - Sep 8
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
Exterior

Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

2.0 star property
9.8 out of 10, Exceptional, (9)
"Really enjoyed our stay. Super easy to find, plenty of parking. Walking distance of the shops. 10/10 would stay again."
The price is ￥11,625
￥16,783 total
includes taxes & fees
Sep 9 - Sep 10
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
Stoney Creek - Sit back and unwind
Interior

Stoney Creek - Sit back and unwind

10.0 out of 10, Exceptional, (93)
"Stayed with my Wife for a week after our wedding and it the perfect place to recharge after the rollercoaster of emotions that we had dealt with during the wedding. Would definitely recommend to anyone who is looking for a relaxing and comfortable place to stay. "
Stoney Creek - Sit back and unwind
Peaceful getaway centrally located just min. from Madison and Belterra casino.
Outdoor spa tub

Peaceful getaway centrally located just min. from Madison and Belterra casino.

9.4 out of 10, Exceptional, (26)
"We enjoyed our stay and would recommend to others."
Peaceful getaway centrally located just min. from Madison and Belterra casino.
Sunset over the city Suite 201, Sunset over the city Suite 201
Interior

Sunset over the city Suite 201, Sunset over the city Suite 201

9.6 out of 10, Exceptional, (9)
"Was just what i needed to stay the week after my dads passing. Safe,.comfortable and affordable "
The price is ￥12,140
￥20,836 total
includes taxes & fees
Sep 29 - Sep 30
Sunset over the city Suite 201, Sunset over the city Suite 201
Grace Woods - Private Lake | Dock | Outdoor Space
Exterior

Grace Woods - Private Lake | Dock | Outdoor Space

10.0 out of 10, Exceptional, (1)
"Everything was excellent!"
Grace Woods - Private Lake | Dock | Outdoor Space
Private 1 BR Home with Hot Tub,Firepit & 5 min to dwtn
Outdoor spa tub

Private 1 BR Home with Hot Tub,Firepit & 5 min to dwtn

10.0 out of 10, Exceptional, (7)
"This was such a nice place, very quiet and peaceful. The property was everything we had hoped for and the host was so nice and helpful."
The price is ￥44,415
￥66,571 total
includes taxes & fees
Sep 20 - Sep 21
Private 1 BR Home with Hot Tub,Firepit & 5 min to dwtn
Bungalow on Main!!
Exterior

Bungalow on Main!!

9.8 out of 10, Exceptional, (18)
"Wonderful accommodations, beautifully decorated and very clean! We will be back!"
Bungalow on Main!!
The Artist’s A-Frame
Exterior

The Artist’s A-Frame

10.0 out of 10, Exceptional, (19)
"I can't say enough about our stay at the Artist's A-Frame. The hosts are exceptional, the location is ideal, and the space is beautiful! I highly recommend and am anxious to return!"
The price is ￥17,914
￥34,903 total
includes taxes & fees
Sep 11 - Sep 12
The Artist’s A-Frame
Unique Secluded Cabin with Loft on Classified Forest
2 bedrooms, free WiFi, bed sheets

Unique Secluded Cabin with Loft on Classified Forest

9.6 out of 10, Exceptional, (41)
"Beautiful, secluded cabin!! Loved seeing the deer each evening. If we are in this area again, we would definitely stay here!"
Unique Secluded Cabin with Loft on Classified Forest
KY log home close to The Ark Encounter on private 14 acres private seasonal pool
Outdoor pool

KY log home close to The Ark Encounter on private 14 acres private seasonal pool

9.2 out of 10, Wonderful, (30)
"We enjoyed the space the cabin had to offer and had a great time."
KY log home close to The Ark Encounter on private 14 acres private seasonal pool
Charming 2-bedroom house in Devil's Elbow Osgood, IN
Smart TV

Charming 2-bedroom house in Devil's Elbow Osgood, IN

10.0 out of 10, Exceptional, (3)
"Great accommodations. Highly recommend. Will definitely rebook. "
Charming 2-bedroom house in Devil's Elbow Osgood, IN
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill
Fridge, microwave, oven, stovetop

"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill

10.0 out of 10, Exceptional, (8)
"We thought the house was great and the location was perfect! We would definitely stay there again. "
The price is ￥20,579
￥50,226 total
includes taxes & fees
Sep 30 - Oct 1
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Smart TV

The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

10.0 out of 10, Exceptional, (8)
"Clean, spacious, nicely decorated, comfortable bed. For us it was also nostalgic - from the windows on Main we could see the home where my husband’s mother was raised and the location of his grandparents’ grocery (in the latter 1930s- 1971).. now the Attic, a coffee, pastry, sandwich shop. "
The price is ￥17,618
￥33,711 total
includes taxes & fees
Sep 14 - Sep 15
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
Fridge, microwave, oven, stovetop

Peaceful Cozy Cabin 10 minutes from Historic downtown Madison

9.6 out of 10, Exceptional, (17)
"Perfect little cozy cabin for an amazing getaway! We were able to just relax and enjoy our time together with zero distractions. 10/10 would definitely stay here again! "
The price is ￥26,649
￥42,905 total
includes taxes & fees
Sep 8 - Sep 9
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
Carol’s Cabin in the Woods in Historic Hoosier Hills
Exterior

Carol’s Cabin in the Woods in Historic Hoosier Hills

10.0 out of 10, Exceptional, (37)
"My small group wanted to relax in a quiet setting and Carol’s cabin was perfect. Extremely clean, well-provisioned, quiet and private with a beautiful property to stroll around. Would definitely come back!"
Carol’s Cabin in the Woods in Historic Hoosier Hills
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

Belterra Casino Resort

Belterra Casino Resort

10/10 Excellent
"Beautiful resort. Lobby and restaurants were conveniently located and the staff were friendly and welcoming. The rooms were spacious and comfortable. "
Saad 1-night trip
Posted 2 weeks ago
Belterra Casino Resort

Find out more about Bennington

Find out more about Bennington

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Frequently asked questions

Can I find vacation rentals in Bennington?

Yes, we have vacation rentals close to popular local attractions in Bennington, or you can choose a more remote option if you're looking for a relaxing stay.

What are some of the best vacation home rentals in Bennington?

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!: Visitors like this Bennington vacation home rental. It offers a patio, a selection of games, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What’s there to see and do in Bennington?

While you're exploring the area, General Butler State Resort Park and Vevay Island are a couple of picturesque spots to get outside and enjoy nature. The Ridge Winery Tasting Room and Belterra Casino are a couple of places you'll find in the larger area.

What’s a vacation rental in Bennington like?

A vacation rental is a private property you can book for short or long periods in Bennington. Vacation rentals feature extras such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family trips or small group gatherings.