Bennington Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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, (23 reviews)
"Beautiful, clean, serene! Perfect place for a weekend anniversary getaway!"
United States
Mallory T.
The price is CA $215
CA $359 total
includes taxes & fees
Nov 24 - Nov 25
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.
The price is CA $183
CA $333 total
includes taxes & fees
Nov 10 - Nov 11
Cabin on the Ridge
A bedroom with a bed, a ceiling fan, a TV, and a small kitchenette.

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 CA $123
CA $258 total
includes taxes & fees
Nov 9 - Nov 10
Charming new tiny house-Friendship IN
A log cabin with a covered porch, wooden rocking chairs, and a potted plant.

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 CA $175
CA $334 total
includes taxes & fees
Nov 15 - Nov 16
Stoney Creek - Sit back and unwind
A wooden cabin with a porch, a staircase, and a deck.

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 CA $141
CA $241 total
includes taxes & fees
Dec 6 - Dec 7
Sassafras Woodland Cabin at Lost Trails
A covered deck with a wooden table and wicker chairs, overlooking a lake.

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 CA $157
CA $290 total
includes taxes & fees
Nov 7 - Nov 8
The River View at Esther’s
A modern kitchen with a wooden countertop, black stools, and a wall-mounted TV.

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 CA $157
CA $268 total
includes taxes & fees
Nov 16 - Nov 17
The Blue Door Place
A wooden log cabin with a dark brown door featuring a metal latch and a glass panel.

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 CA $154
CA $247 total
includes taxes & fees
Nov 9 - Nov 10
Cedar Rustic Cabin at Lost Trails
A compact kitchen with wooden cabinets, a black refrigerator, a microwave, and a coffee machine on a small shelf.

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 CA $140
CA $239 total
includes taxes & fees
Nov 8 - Nov 9
Mulberry Secluded Cabin at Lost Trails
2

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 CA $140
CA $239 total
includes taxes & fees
Nov 30 - Dec 1
Maple Cozy Cabin at Lost Trails
A wooden deck with two black rocking chairs and a small table, surrounded by a wooden railing.

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 CA $140
CA $239 total
includes taxes & fees
Nov 22 - Nov 23
Walnut Secluded Cabin at Lost Trails
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

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 CA $84
CA $145 total
includes taxes & fees
Nov 9 - Nov 10
The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
A hot tub with candles, a fire feature, and a tent in a forested area.

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 CA $224
CA $339 total
includes taxes & fees
Nov 9 - Nov 10
Romantic 1 BR Retreat on the edge of woods with private hot tub
A cozy room with a bed, a chair, a sofa, and a small table.

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 CA $131
CA $234 total
includes taxes & fees
Nov 9 - Nov 10
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
A dining area with a view of a bridge over a river, a table set with plates and cutlery, and a potted plant on the windowsill.

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 CA $296
CA $501 total
includes taxes & fees
Nov 8 - Nov 9
Downtown Riverfront Cottage
An aerial view of a swimming pool complex with multiple water slides and a surrounding area with lounge chairs and umbrellas.

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 CA $288
CA $592 total
includes taxes & fees
Nov 8 - Nov 9
207 King Suites, River Views, Deck, Downtown
Property grounds

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 CA $125
CA $227 total
includes taxes & fees
Nov 10 - Nov 11
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
A covered porch with a wooden door, potted plants, and a metal railing.

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 CA $191
CA $346 total
includes taxes & fees
Nov 8 - Nov 9
The Artist’s A-Frame
A hallway with a wooden desk, potted plants, and a window with a plant in a hanging pot.

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 CA $131
CA $147 total
includes taxes & fees
Nov 10 - Nov 11
King Bed|Non-Smoking
A covered porch with wooden beams, a welcome sign, two chairs, and a potted plant.

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 CA $409
CA $626 total
includes taxes & fees
Nov 6 - Nov 7
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

A modern bar area with a long counter, multiple stools, and a well-stocked liquor display.
Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

Fairfield Inn & Suites Madison Historic Eagle Cotton Mill
Madison Historic District

10/10 Excellent

Gorgeous facility, staff is super friendly
Canada
Patrick
Reviewed March 16, 2026
Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

Find out more about Bennington

Everything you need to know about Bennington vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Bennington vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Bennington vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Bennington vacation rentals we have selected for you start as low as CA $83 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 vacation 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 vacation.

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 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?

Red comfy cottage : Visitors like this Bennington vacation home rental. It offers an indoor pool, a patio, and a barbecue grill 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 a hot tub so you can immerse yourself in your vacation.

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.