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Our top choices for Bennington holiday rentals

1. Cabin on the Ridge: The Sequel

Cabin on the Ridge: The Sequel
Madison
10.0 out of 10, Exceptional, (23 reviews)
"Beautiful, clean, serene! Perfect place for a weekend anniversary getaway!"
United States
Mallory T.
The price is £193
includes taxes & fees
18 Nov - 19 Nov
Cabin on the Ridge: The Sequel

2. Cabin on the Ridge

Cabin on the Ridge
Madison
10.0 out of 10, Exceptional, (23 reviews)
"Super nice and cute! Would definitely stay again! "
United States
Angela G.
The price is £202
includes taxes & fees
18 Nov - 19 Nov
Cabin on the Ridge

3. Charming new tiny house-Friendship IN

Charming new tiny house-Friendship IN
Versailles
9.8 out of 10, Exceptional, (6 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 £140
includes taxes & fees
10 Nov - 11 Nov
Charming new tiny house-Friendship IN

4. Stoney Creek - Sit back and unwind

Stoney Creek - Sit back and unwind
Madison
10.0 out of 10, Exceptional, (134 reviews)
"Our family enjoyed our stay."
United States
Shanna S.
The price is £179
includes taxes & fees
15 Nov - 16 Nov
Stoney Creek - Sit back and unwind

5. Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (20 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
The price is £130
includes taxes & fees
6 Dec - 7 Dec
Sassafras Woodland Cabin at Lost Trails

6. The River View at Esther’s

The River View at Esther’s
Vevay
10.0 out of 10, Exceptional, (2 reviews)
"This is a beautiful property and lovely house. We really enjoyed the back deck and the chairs by the river. It was nice having an enclosed yard space for our dog. The coffee station was well stocked and loved the flavored Crave pods! The bed was also very comfortable. We saw some eagles diving at possibly a muskrat. The host was quickly responsive when we reached out for a very minor issue. Thank you for a wonderful stay. Shari and Jim"
United States
James F.
The price is £155
includes taxes & fees
10 Nov - 11 Nov
The River View at Esther’s

7. The Blue Door Place

The Blue Door Place
Florence
9.8 out of 10, Exceptional, (31 reviews)
"Very clean, had everything we needed! "
United States
james w.
The price is £143
includes taxes & fees
16 Nov - 17 Nov
The Blue Door Place

8. Cedar Rustic Cabin at Lost Trails

Cedar Rustic Cabin at Lost Trails
Madison
10.0 out of 10, Exceptional, (32 reviews)
"Charming, cozy cabin! Perfect for a weekend getaway!"
United States
Mollie B.
The price is £132
includes taxes & fees
9 Nov - 10 Nov
Cedar Rustic Cabin at Lost Trails

9. Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (8 reviews)
"We loved the cabin, it had everything we needed - lovely peaceful surroundings, and was very clean! Thank you."
United States
Lisa S.
The price is £129
includes taxes & fees
6 Dec - 7 Dec
Mulberry Secluded Cabin at Lost Trails

10. Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (16 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 £129
includes taxes & fees
30 Nov - 1 Dec
Maple Cozy Cabin at Lost Trails

11. 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 £129
includes taxes & fees
22 Nov - 23 Nov
Walnut Secluded Cabin at Lost Trails

12. The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102

The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
Madison Historic District
9.8 out of 10, Exceptional, (13 reviews)
"We enjoyed our visit and would recommend to others looking for a convenient location and comfortable stay."
United States
Renee M.
The price is £79
includes taxes & fees
10 Nov - 11 Nov
The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102

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
10.0 out of 10, Exceptional, (1 review)
"This was a relaxing & romantic way to celebrate our 57th wedding anniversary. Everything was clean & the host very cordial. We enjoyed the rear deck with its fireplace & hot tube as as the comfortable bed & romantic tent interior."
United States
jon h.
The price is £184
includes taxes & fees
9 Nov - 10 Nov
Romantic 1 BR Retreat on the edge of woods with private hot tub

14. 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 Historic District
9.6 out of 10, Exceptional, (9 reviews)
"Excellent location, nice deck and spa. Comfy bed large space."
United States
Zoey S.
The price is £126
includes taxes & fees
9 Nov - 10 Nov
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison

15. Downtown Riverfront Cottage

Downtown Riverfront Cottage
Madison Historic District
10.0 out of 10, Exceptional, (2 reviews)
"House was very nice, very clean. The view of the river was magnificent. Next little getaway we would return again"
United States
Curtis M.
The price is £268
includes taxes & fees
9 Nov - 10 Nov
Downtown Riverfront Cottage

16. 207 King Suites, River Views, Deck, Downtown

207 King Suites, River Views, Deck, Downtown
Madison Historic District
10.0 out of 10, Exceptional, (48 reviews)
"Loved this place, very clean and well stocked with the little extras that you always seem to need. "
United States
Matt C.
The price is £313
includes taxes & fees
9 Nov - 10 Nov
207 King Suites, River Views, Deck, Downtown

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

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Madison
9.4 out of 10, Exceptional, (20 reviews)
"Clean and cozy"
United States
Julie
The price is £122
includes taxes & fees
10 Nov - 11 Nov
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

18. The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (42 reviews)
"Great experience. Definitely recommend staying here if you’re visiting Madison. Great location to down town,"
United States
Mike H.
The price is £185
includes taxes & fees
8 Nov - 9 Nov
The Artist’s A-Frame

19. King Bed|Non-Smoking

King Bed|Non-Smoking
Aurora, IN
10.0 out of 10, Exceptional, (76 reviews)
"Found it easy to drive to nearby attractions like Versailles State Park."
United States
Anonymous traveller
The price is £78
includes taxes & fees
10 Nov - 11 Nov
King Bed|Non-Smoking

20. Quiet Indiana Getaway w/ Game Room

Quiet Indiana Getaway w/ Game Room
Moores Hill
9.4 out of 10, Exceptional, (34 reviews)
"Place was beautiful!"
United States
tracy b.
The price is £322
includes taxes & fees
6 Nov - 7 Nov
Quiet Indiana Getaway w/ Game Room
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

Find out more about Bennington

Everything you need to know about Bennington holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Bennington holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Bennington holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Bennington holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Bennington. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Bennington holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Bennington holiday rentals we have selected for you start as low as £84 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Bennington rentals

At Expedia, we put the best Bennington holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Bennington rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Bennington holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Bennington. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Bennington?

Yes, there are holiday rentals close to the most popular sights in Bennington, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Bennington has to offer?

Red comfy cottage : This holiday home rental outside of Bennington offers an indoor pool, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 wider area.

What’s a holiday rental in Bennington like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Bennington. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family trips.