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Bennington Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Bennington vacation rentals

A cozy wooden cabin interior with a sofa, a dining table, and a TV.

1. Cabin on the Ridge: The Sequel

Cabin on the Ridge: The Sequel
Madison
10.0 out of 10, Exceptional, (22 reviews)
"Our stay was amazing! Loved this cozy cabin in the woods! "
United States
Alison F.
The price is ￥22,606
￥40,492 total
includes taxes & fees
Sep 7 - Sep 8
Cabin on the Ridge: The Sequel
A spacious wooden cabin with a loft bedroom, a dining area, and a kitchen.

2. Cabin on the Ridge

Cabin on the Ridge
Madison
10.0 out of 10, Exceptional, (20 reviews)
"Super nice and cute! Would definitely stay again! "
United States
Angela G.
The price is ￥19,263
￥36,886 total
includes taxes & fees
Aug 30 - Aug 31
Cabin on the Ridge
A kitchen with white cabinets, a granite countertop, a stainless steel sink, a coffee maker, and a refrigerator.

3. Charming new tiny house-Friendship IN

Charming new tiny house-Friendship IN
Versailles
10.0 out of 10, Exceptional, (3 reviews)
"This tiny home was exactly what we had expected. Very clean, nice and welcoming. The owners were great and communication was excellent. We will be sure to see if it is Ava when we come to visit family again. "
United States
Randall B.
The price is ￥14,010
￥31,204 total
includes taxes & fees
Sep 24 - Sep 25
Charming new tiny house-Friendship IN
A wooden cabin with a porch, a staircase, and a deck.

4. Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (15 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
The price is ￥13,532
￥24,795 total
includes taxes & fees
Aug 30 - Aug 31
Sassafras Woodland Cabin at Lost Trails

5. Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (13 reviews)
"The overall stay was perfect for just the two of us and we loved how everything was a close drive but still felt far enough away. "
United States
Shyanne D.
The price is ￥15,920
￥27,542 total
includes taxes & fees
Sep 2 - Sep 3
Maple Cozy Cabin at Lost Trails
A wooden deck with two black rocking chairs and a small table, surrounded by a wooden railing.

6. Walnut Secluded Cabin at Lost Trails

Walnut Secluded Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful cabin. Enjoyed our stay."
United States
Jim A.
The price is ￥15,920
￥27,542 total
includes taxes & fees
Aug 30 - Aug 31
Walnut Secluded Cabin at Lost Trails
A compact kitchen with wooden cabinets, a black refrigerator, a microwave, and a coffee machine on a small shelf.

7. Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (8 reviews)
"Mulberry Cabin at Lost Trails was great! The cabin was cozy and felt pretty private (even though the other cabins are within view). The bed was super comfy, and they did a great job making sure the cabin had everything one might need on a trip away from home. It was also very close to all things Madison, so it felt very convenient. We would definitely stay there again!"
United States
Emily I.
The price is ￥15,920
￥27,542 total
includes taxes & fees
Aug 30 - Aug 31
Mulberry Secluded Cabin at Lost Trails
A modern kitchen with a wooden countertop, black stools, and a wall-mounted TV.

8. The Blue Door Place

The Blue Door Place
Florence
9.8 out of 10, Exceptional, (28 reviews)
"It was great"
United States
James H.
The price is ￥15,051
￥28,454 total
includes taxes & fees
Sep 1 - Sep 2
The Blue Door Place
A wooden log cabin with a dark brown door featuring a metal latch and a glass panel.

9. Cedar Rustic Cabin at Lost Trails

Cedar Rustic Cabin at Lost Trails
Madison
10.0 out of 10, Exceptional, (31 reviews)
"Charming, cozy cabin! Perfect for a weekend getaway!"
United States
Mollie B.
The price is ￥17,512
￥29,555 total
includes taxes & fees
Sep 1 - Sep 2
Cedar Rustic Cabin at Lost Trails
A hallway with a wooden desk, potted plants, and a window with a plant in a hanging pot.

10. King Bed|Non-Smoking

King Bed|Non-Smoking
Aurora, IN
10.0 out of 10, Exceptional, (74 reviews)
"Four nights of peace in Aurora! Quiet location close to local attractions like the Creation Museum was really handy for us."
United States
Anonymous traveler
The price is ￥15,483
￥17,341 total
includes taxes & fees
Sep 1 - Sep 2
King Bed|Non-Smoking
A covered porch with a wooden door, potted plants, and a metal railing.

11. The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (39 reviews)
"Very nice house and convenient to downtown, etc. If you stay here you definitely won’t be disappointed."
United States
Shirley L.
The price is ￥20,059
￥39,266 total
includes taxes & fees
Aug 30 - Aug 31
The Artist’s A-Frame
A modern kitchen with a central island, bar stools, and a dining area with a patterned table.

12. 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!
Madison
9.8 out of 10, Exceptional, (72 reviews)
"Great house just outside of historic Madison. Easy access to the river . Home is beautifully decorated and great place for a getaway. Many shops to visit in Madison ."
United States
John H.
The price is ￥17,050
￥35,902 total
includes taxes & fees
Sep 1 - Sep 2
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

13. Romantic 1 BR Retreat on the edge of woods with private hot tub

Romantic 1 BR Retreat on the edge of woods with private hot tub
Madison
The price is ￥26,507
￥34,878 total
includes taxes & fees
Sep 13 - Sep 14
Romantic 1 BR Retreat on the edge of woods with private hot tub

14. Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Madison
9.6 out of 10, Exceptional, (17 reviews)
"Very close to downtown restaurants and shopping. The trails out back were nice and relaxing to walk on. The property was quiet and relaxing. Perfect size for my wife and I and our 12 pound dog. The dog loved the trails and kept us busy on his walks."
United States
Dean
The price is ￥15,481
￥28,793 total
includes taxes & fees
Sep 1 - Sep 2
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
A hallway with a wooden desk, potted plants, and a window with a plant in a hanging pot.

15. King Bed|Smoking|Aurora

King Bed|Smoking|Aurora
Aurora, IN
10.0 out of 10, Exceptional, (70 reviews)
"Room offered great privacy which is important when traveling with family, would definitely come back next time we're in town!"
United States
Anonymous traveler
The price is ￥15,483
￥17,341 total
includes taxes & fees
Sep 1 - Sep 2
King Bed|Smoking|Aurora
A hallway with a wooden desk, potted plants, and a window with a plant in a hanging pot.

16. 2 Queen Beds|Non Smoking

2 Queen Beds|Non Smoking
Aurora, IN
10.0 out of 10, Exceptional, (76 reviews)
"Nice little room with all the basics covered,just what we wanted for our stay!"
United States
Anonymous traveler
The price is ￥16,675
￥18,676 total
includes taxes & fees
Sep 1 - Sep 2
2 Queen Beds|Non Smoking
A Hillcrest Motel sign with a 'NO VACANCY' sign below it.

17. 2 Queen Bed Smoking | Hillcrest

2 Queen Bed Smoking | Hillcrest
Aurora, IN
10.0 out of 10, Exceptional, (72 reviews)
"Great spot near local attractions. Clean rooms and easy parking."
United States
Anonymous traveler
The price is ￥16,675
￥18,676 total
includes taxes & fees
Sep 1 - Sep 2
2 Queen Bed Smoking | Hillcrest
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

18. The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201

The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201
Madison
9.8 out of 10, Exceptional, (22 reviews)
"Our room was so cute and perfect for a couple. We loved it! The location was perfect as well!"
United States
Stee
The price is ￥13,214
￥22,577 total
includes taxes & fees
Sep 1 - Sep 2
The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201
A modern living room with a black sofa, a wooden coffee table, and a brick accent wall.

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

The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Madison
10.0 out of 10, Exceptional, (44 reviews)
"Loved the whole place and all the little touches. It was super cozy and location wise is close to everything. We will definitely be stay again. "
United States
Hannah S.
The price is ￥17,050
￥34,072 total
includes taxes & fees
Aug 30 - Aug 31
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
A cozy room with a bed, a chair, a sofa, and a small table.

20. Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison

Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
Madison
10.0 out of 10, Exceptional, (4 reviews)
"Excellent location, nice deck and spa. Comfy bed large space."
United States
Zoey S.
The price is ￥14,478
￥27,638 total
includes taxes & fees
Sep 1 - Sep 2
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
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

8/10 Good
"Several choices for dining, from coffee take-out to sit-down. Quality and quantity of food was good; price was not. It is a casino resort hotel, so there are no bargains to be had."
Rod 1-night trip
Posted 11 hours ago
Belterra Casino Resort

Find out more about Bennington

Search for holiday rentals in Bennington on Expedia! You can easily find your home rentals, villas, holiday apartments in Bennington using one of the methods below:

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Look no further and take a look at our great range of rental properties in Bennington!

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?

The Wadsworth in National Historic District of Madison, Indiana. : Visitors like this Bennington vacation home rental. It is located on a river and has a patio, a garden, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

What’s there to see and do in Bennington?

Explore the area and family-friendly sights such as Madison Railroad Station Museum, or get out into nature at a spot like General Butler State Resort Park. Belterra Casino and Versailles State Park 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.