Bennington Vacation Rentals

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Nov 4 - Nov 5
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Nov 5 - Nov 6
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Nov 7 - Nov 9
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Nov 14 - Nov 16

Vacation Rentals in Bennington

Interior
Sunset over the city Suite 201, Sunset over the city Suite 201
Sunset over the city Suite 201, Sunset over the city Suite 201
9.6 out of 10, Exceptional, (10)
"Had a great time hanging out in Madison. The Madison Inn, specifically room 201 worked out well for us. The place was clean, well furnished, and felt comfortable. The only downside is there isn't much counter space in the kitchen or bathroom, so inevitably any getting-ready routines spread across the room a bit. For a brief getaway to visit the town or to hike Clifty Falls, I would highly recomend giving this property a shot. I'm sure we'll return again soon!"
United States
Justin B.
The price is ￥11,087
￥20,025 total
includes taxes & fees
Nov 18 - Nov 19
Sunset over the city Suite 201, Sunset over the city Suite 201
4 bedrooms, free WiFi, bed sheets
Rustic cabin just outside of Madison!
Rustic cabin just outside of Madison!
10.0 out of 10, Exceptional, (49)
"Our place was comfortable and had everything we needed. Plenty of places to rest after busy days. The boys had fun playing in the creek, we had fun relaxing on the front porch. The beds were comfortable and it was close to town. One of our favorite VRBO's. "
United States
Kimberly H.
Rustic cabin just outside of Madison!
Interior
Stoney Creek - Sit back and unwind
Stoney Creek - Sit back and unwind
10.0 out of 10, Exceptional, (100)
"It’s was amazing! The listing was completely accurate! Communication was a breeze!"
United States
Bobbie R.
Stoney Creek - Sit back and unwind
Interior
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
10.0 out of 10, Exceptional, (58)
"Great property, great location, and amazing hosts. Incredible attention to detail and service. It would take too long to describe everything that impressed us so I'll just say it's all perfect and if this place is available when you're visiting Madison, stop searching and just book it."
United States
John S.
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
Fridge, microwave, oven, stovetop
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
9.8 out of 10, Exceptional, (45)
"We were able to check in early. The house is very cute and we enjoyed using the golf cart to explore around town. We enjoyed hanging out in the evening in the house. It had everything we needed and it was very clean. We would definitely stay there again,"
United States
Karen W.
The price is ￥16,169
￥34,532 total
includes taxes & fees
Nov 10 - Nov 11
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Property grounds
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
9.8 out of 10, Exceptional, (9)
"Nice new property in a great location!"
United States
John B.
The price is ￥9,239
￥17,400 total
includes taxes & fees
Nov 24 - Nov 25
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
TV, fireplace
Cozy Cabin Madison Indiana
Cozy Cabin Madison Indiana
10.0 out of 10, Exceptional, (17)
"Cabin was relatively secluded, in a pretty location and exactly as described. 5 minutes from downtown Madison Indiana which is a beautiful old river town. Host was exceedingly accommodating and gracious and the property has everything you need. Will definitely book again. "
United States
Clay G.
Cozy Cabin Madison Indiana
Fridge, microwave, oven, stovetop
The Wadsworth in National Historic District of Madison, Indiana.
The Wadsworth in National Historic District of Madison, Indiana.
10.0 out of 10, Exceptional, (62)
"Decorating was very nice. Loved the back patio. The whole experience was just perfect. I highly recommend this property. "
United States
Patricia H.
The Wadsworth in National Historic District of Madison, Indiana.
Fridge, microwave, oven, stovetop
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
9.6 out of 10, Exceptional, (19)
"Very clean and cozy"
United States
Susie I.
The price is ￥14,475
￥27,272 total
includes taxes & fees
Nov 5 - Nov 6
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
Outdoor spa tub
Peaceful getaway centrally located just min. from Madison and Belterra casino.
Peaceful getaway centrally located just min. from Madison and Belterra casino.
9.4 out of 10, Exceptional, (29)
"We enjoyed our stay and would recommend to others."
United States
JoAnna and Jordan J.
Peaceful getaway centrally located just min. from Madison and Belterra casino.
Dining
Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath
Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath
9.4 out of 10, Exceptional, (22)
"Very nice house good accommodations would stay again !!!"
United States
Henry C.
Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath
Dining
Madison's Only YURT Experience
Madison's Only YURT Experience
9.2 out of 10, Wonderful, (11)
"This place is adorable and has so much potential. The beds were comfortable and the Yurt was cozy. "
United States
Nicole E.
Madison's Only YURT Experience
Outdoor dining
Secluded Country Home in Historic Hoosier Hills
Secluded Country Home in Historic Hoosier Hills
10.0 out of 10, Exceptional, (122)
"Great property, very peaceful. "
United States
Theresa G.
Secluded Country Home in Historic Hoosier Hills
Smart TV
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
10.0 out of 10, Exceptional, (15)
"Great downtown location in a peaceful little town. "
United States
Megan M.
The price is ￥17,878
￥34,550 total
includes taxes & fees
Nov 6 - Nov 7
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Property grounds
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
10.0 out of 10, Exceptional, (208)
"This place checks all of our boxes for the things we look for in a rental cabin. "
United States
Brian and Holly w.
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
Fridge, microwave, oven, coffee/tea maker
Rustic Private Cabin on 30 acres w/Loft/Firepit/Secluded/Trails
Rustic Private Cabin on 30 acres w/Loft/Firepit/Secluded/Trails
9.8 out of 10, Exceptional, (34)
"Very nice cabin tucked away in the hills of southern Indiana. Very well appointed cabin, on a quiet dead end street."
United States
Timothy D.
Rustic Private Cabin on 30 acres w/Loft/Firepit/Secluded/Trails
Exterior
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
2.0 star property
10.0 out of 10, Exceptional, (12)
"Nice location! Walking distance to lots of shops and restaurants. Very clean! "
United States
Sara D.
The price is ￥19,403
￥25,855 total
includes taxes & fees
Nov 5 - Nov 6
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
2 bedrooms, free WiFi, bed sheets
Unique Secluded Cabin with Loft on Classified Forest
Unique Secluded Cabin with Loft on Classified Forest
9.6 out of 10, Exceptional, (45)
"Had a wonderful time. Great place to just get away from it all. The dogs had a blast. Would definitely recommend staying here."
United States
Stephanie F.
Unique Secluded Cabin with Loft on Classified Forest
1 bedroom, WiFi, bed sheets
Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
8.8 out of 10, Excellent, (10)
"Very easy check in and nice location. Very comfortable stay. "
United Kingdom
Michael S.
The price is ￥12,372
￥21,399 total
includes taxes & fees
Nov 18 - Nov 19
Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
3 bedrooms, iron/ironing board, WiFi, bed sheets
Alterra:Slees 8,Steps to Main St,Serene
Alterra:Slees 8,Steps to Main St,Serene
10.0 out of 10, Exceptional, (1)
"Home is beautiful. Great stay."
United States
Ben M.
Alterra:Slees 8,Steps to Main St,Serene
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

Red Roof Inn Carrollton

Red Roof Inn Carrollton

10/10 Excellent
"The staff is extremely friendly, kind, and helpful! "
Eden 1-night trip
Posted 1 day ago
Red Roof Inn Carrollton

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.