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Bennington Vacation Rentals

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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Bennington vacation rentals

TV, fireplace

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 AED 444
AED 833 total
includes taxes & fees
18 Aug - 19 Aug
Cabin on the Ridge: The Sequel
TV, fireplace, DVD player

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 AED 444
AED 876 total
includes taxes & fees
19 Aug - 20 Aug
Cabin on the Ridge
Private kitchen

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 AED 323
AED 716 total
includes taxes & fees
18 Aug - 19 Aug
Charming new tiny house-Friendship IN
Exterior

4. 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 AED 367
AED 635 total
includes taxes & fees
18 Aug - 19 Aug
Maple Cozy Cabin at Lost Trails
Exterior

5. 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 AED 312
AED 572 total
includes taxes & fees
18 Aug - 19 Aug
Sassafras Woodland Cabin at Lost Trails
Coffee/tea maker, fridge, microwave, oven

6. 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 AED 367
AED 635 total
includes taxes & fees
18 Aug - 19 Aug
Mulberry Secluded Cabin at Lost Trails
Terrace/patio

7. 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 AED 367
AED 635 total
includes taxes & fees
1 Sep - 2 Sep
Walnut Secluded Cabin at Lost Trails
Exterior detail

8. Cedar Rustic Cabin at Lost Trails

Cedar Rustic Cabin at Lost Trails
Madison
10.0 out of 10, Exceptional, (30 reviews)
"Charming, cozy cabin! Perfect for a weekend getaway!"
United States
Mollie B.
The price is AED 404
AED 682 total
includes taxes & fees
1 Sep - 2 Sep
Cedar Rustic Cabin at Lost Trails
Interior

9. 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 AED 251
AED 281 total
includes taxes & fees
11 Sep - 12 Sep
King Bed|Non-Smoking
Exterior detail

10. The Madison Inn, Historic woodside view suite 205, Historic woodside view suite 205

The Madison Inn, Historic woodside view suite 205, Historic woodside view suite 205
Madison
9.8 out of 10, Exceptional, (7 reviews)
"Cozy, peaceful, wonderful with great location. "
United Kingdom
Ed E.
The price is AED 463
AED 703 total
includes taxes & fees
1 Sep - 2 Sep
The Madison Inn, Historic woodside view suite 205, Historic woodside view suite 205
Exterior

11. Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River

Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
Madison
The price is AED 430
AED 853 total
includes taxes & fees
18 Aug - 19 Aug
Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
Property grounds

12. 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, (16 reviews)
"Host was very accommodating and this place was perfect for a place to stay while visiting friends. Everything was very comfortable, especially the very soft bed!! "
United States
C J.
The price is AED 374
AED 683 total
includes taxes & fees
15 Sep - 16 Sep
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Outdoor dining

13. Charming 2-bedroom house with a river view in wonderful Madison

Charming 2-bedroom house with a river view in wonderful Madison
Madison
9.4 out of 10, Exceptional, (6 reviews)
"The place was indeed charming. The host was wonderful and available for all questions! "
United States
Amy W.
Charming 2-bedroom house with a river view in wonderful Madison
Exterior

14. 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 AED 463
AED 881 total
includes taxes & fees
24 Aug - 25 Aug
The Artist’s A-Frame
Smart TV

15. 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, (71 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 AED 413
AED 860 total
includes taxes & fees
23 Aug - 24 Aug
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Interior

16. 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 AED 347
AED 653 total
includes taxes & fees
1 Sep - 2 Sep
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
Smart TV

17. 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 AED 437
AED 841 total
includes taxes & fees
26 Aug - 27 Aug
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Interior

18. 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 AED 251
AED 281 total
includes taxes & fees
11 Sep - 12 Sep
King Bed|Smoking|Aurora
Microwave, oven, stovetop, dishwasher

19. The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St

The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St
Madison
9.8 out of 10, Exceptional, (23 reviews)
"Great stay and beautiful house. The location was really outstanding and many restaurants, boutiques, and coffee shops were within walking distance. "
United States
Stephanie B.
The price is AED 493
AED 1,758 total
includes taxes & fees
30 Aug - 31 Aug
The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St
Interior

20. 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 AED 278
AED 311 total
includes taxes & fees
11 Sep - 12 Sep
2 Queen Beds|Non Smoking
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

Ramada by Wyndham Sparta/At Speedway

Ramada by Wyndham Sparta/At Speedway

10/10 Excellent
"Everything was great"
Tommy 4-night trip
Posted 1 day ago
Ramada by Wyndham Sparta/At Speedway

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.