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Bennington Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Bennington holiday 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)
"Beautiful, clean, serene! Perfect place for a weekend anniversary getaway!"
United States
Mallory T.
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, (23 reviews)
"Super nice and cute! Would definitely stay again! "
United States
Angela G.
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
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 NZ$341
includes taxes & fees
26 Oct - 27 Oct
Charming new tiny house-Friendship IN
A modern kitchen with a wooden countertop, black stools, and a wall-mounted TV.

4. The Blue Door Place

The Blue Door Place
Florence
9.8 out of 10, Exceptional, (30 reviews)
"Very clean, had everything we needed! "
United States
james w.
The price is NZ$324
includes taxes & fees
26 Oct - 27 Oct
The Blue Door Place
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5. Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (15 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 NZ$319
includes taxes & fees
18 Nov - 19 Nov
Maple Cozy Cabin at Lost Trails
A wooden deck with wicker furniture and a ceiling fan.

6. 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 NZ$325
includes taxes & fees
19 Nov - 20 Nov
Cedar Rustic Cabin at Lost Trails
A wooden deck with two black rocking chairs and a small table, surrounded by a wooden railing.

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.
Walnut Secluded Cabin at Lost Trails
A wooden cabin with a porch, a staircase, and a deck.

8. Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (18 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
The price is NZ$287
includes taxes & fees
9 Nov - 10 Nov
Sassafras Woodland Cabin at Lost Trails
A wall with a framed welcome message, a black metal rack with sunglasses, and a rack with colorful fabric items.

9. The River View at Esther’s

The River View at Esther’s
Vevay
10.0 out of 10, Exceptional, (1 review)
The price is NZ$380
includes taxes & fees
31 Oct - 1 Nov
The River View at Esther’s
A compact kitchen with wooden cabinets, a black refrigerator, a microwave, and a coffee machine on a small shelf.

10. Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (8 reviews)
"This is a total hidden gem! The cabin seemed brand new and was outfitted with everything you might need. We spent our 25th wedding anniversary weekend here and loved every second! Would highly recommend!"
United States
Jodi E.
The price is NZ$366
includes taxes & fees
19 Nov - 20 Nov
Mulberry Secluded Cabin at Lost Trails
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

11. The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101

The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
Madison Historic District
9.0 out of 10, Wonderful, (14 reviews)
"Very easy check in and nice location. Very comfortable stay. "
United Kingdom
Michael S.
The price is NZ$210
includes taxes & fees
16 Nov - 17 Nov
The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
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, (78 reviews)
"The place is very clean, also convenient and close to down town. Check in and everything was very smooth! I recommend this cute little place especially for young families."
United States
Kyle A.
The price is NZ$425
includes taxes & fees
15 Nov - 16 Nov
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
A cozy room with a bed, a chair, a sofa, and a small table.

13. 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, (8 reviews)
"Excellent location, nice deck and spa. Comfy bed large space."
United States
Zoey S.
The price is NZ$311
includes taxes & fees
9 Nov - 10 Nov
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
A cozy, illuminated tent-like structure with a green door, surrounded by trees and a gravel path.

14. 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.
Romantic 1 BR Retreat on the edge of woods with private hot tub
A hallway with a wooden desk, potted plants, and a window with a plant in a hanging pot.

15. 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 traveller
The price is NZ$165
includes taxes & fees
23 Oct - 24 Oct
2 Queen Beds|Non Smoking
Property grounds

16. 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, (18 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 NZ$307
includes taxes & fees
3 Nov - 4 Nov
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
A covered porch with a wooden door, potted plants, and a metal railing.

17. The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (42 reviews)
"Very cool house in a nice neighborhood. Had everything we needed and was close to anything you want to do in Madison. We will definitely stay there again!"
United States
Dean C.
The price is NZ$566
includes taxes & fees
21 Nov - 22 Nov
The Artist’s A-Frame
A hallway with a wooden floor, a brick wall, and a door with a window.

18. 604 GQ on Mulberry: 2 King Luxury Suites, Patio

604 GQ on Mulberry: 2 King Luxury Suites, Patio
Madison Historic District
10.0 out of 10, Exceptional, (1 review)
"Great property and a lot of room which was great."
United States
Kathryn B.
The price is NZ$525
includes taxes & fees
26 Oct - 27 Oct
604 GQ on Mulberry: 2 King Luxury Suites, Patio
A balcony with wicker furniture, a view of a river, and a bridge in the background.

19. Downtown Riverfront Cottage

Downtown Riverfront Cottage
Madison Historic District
10.0 out of 10, Exceptional, (1 review)
"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 NZ$624
includes taxes & fees
25 Oct - 26 Oct
Downtown Riverfront Cottage
An outdoor patio with a hot tub, a fire pit, and string lights.

20. "Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8

"Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8
Madison Historic District
10.0 out of 10, Exceptional, (22 reviews)
"This was perfect for our family of 6, the house was super clean and within walking distance to the river and many restaurants and shopping. We will definitely be staying again."
United States
George S.
The price is NZ$676
includes taxes & fees
27 Oct - 28 Oct
"Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8
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
"The motel is under a little construction. But our stay was great. It is at a peaceful location. We saw deer out the window different times. The breakfast was very good and there was always plenty of it. We will be staying there if we are that way in our travels again."
Patricia 3-night trip
Posted 1 day ago
Ramada by Wyndham Sparta/At Speedway

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, 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 NZ$252 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.