Bennington Vacation Rentals

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Dec 4 - Dec 5
Tomorrow
Dec 5 - Dec 6
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Vacation Rentals in Bennington

4 bedrooms, free WiFi, bed sheets
Rustic cabin just outside of Madison!

Cabin in Madison

10.0 out of 10, Exceptional, (53)
"Great day, we loved the cabin!"
United States
Mark C.
Rustic cabin just outside of Madison!
Interior
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…

Apartment in Madison

10.0 out of 10, Exceptional, (61)
"This was the best place I have ever stayed. The place was amazing and the hospitality exceeded expectations. I would definitely recommend staying here. "
United States
Adam K.
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
Fridge, microwave, oven, stovetop
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

Vacation Home in Madison

9.8 out of 10, Exceptional, (50)
"It is a nice place. We were able to walk to the river and main street fairly easy. "
United States
Paul W.
$216 nightly
The price is $248
Dec 7 - Dec 8
Total with taxes and fees
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Smart TV
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

Apartment in Madison

10.0 out of 10, Exceptional, (21)
"Great downtown location in a peaceful little town. "
United States
Megan M.
$185 nightly
The price is $213
Dec 7 - Dec 8
Total with taxes and fees
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Interior
Stoney Creek - Sit back and unwind

Cabin in Madison

10.0 out of 10, Exceptional, (102)
"Close enough to be convenient to local attractions, out enough to be mostly quiet. "
United States
Garry B.
Stoney Creek - Sit back and unwind
Dining
Madison's Only YURT Experience

Vacation Home in Madison

9.2 out of 10, Wonderful, (11)
"One if the most relaxing vacations that I have ever had. Very private, quiet and no traffic. The bed was very comfortable the space of the entire yurt was amazing. My little dogs loved the goats, and running lease free. We were not looking forward to leaving. The host is wonderful too!! We highly recommend staying here!!"
United States
Sharon N.
Madison's Only YURT Experience
Exterior
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

Apartment in Madison

2.0 star property
10.0 out of 10, Exceptional, (14)
"We could not have been happier with this cute little place. Wonderful location with easy walking access to both the riverfront and all Madison had to offer with shops and dining options. We would not hesitate to stay here again!"
United States
Gary W.
$146 nightly
The price is $168
Dec 8 - Dec 9
Total with taxes and fees
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
Property grounds
Sonshine Cabin is your own private park. With wildlife or a hike to the creek.

Cabin in Madison

10.0 out of 10, Exceptional, (312)
"My family and I have been staying here for years, and love it! Quiet, clean, and plenty to do nearby. "
United States
J B.
Sonshine Cabin is your own private park. With wildlife or a hike to the creek.
Property grounds
1800’s restored log cabin on 26 private rolling wooded acres with sunset views

Cabin in Madison

10.0 out of 10, Exceptional, (209)
"Francine's Cabin is such a peaceful and private place to stay. We love it and have stayed there several times. "
United States
Tammy C.
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
Terrace/patio
Riverview Home Near Creation Museum/Ark/Ski/Bikes/Cincinnati/Hot Tub-Sleeps 11

Vacation Home in Aurora

10.0 out of 10, Exceptional, (50)
"We had a great visit— thank you!!!"
United States
Amy D.
$444 nightly
The price is $498
Dec 7 - Dec 8
Total with taxes and fees
Riverview Home Near Creation Museum/Ark/Ski/Bikes/Cincinnati/Hot Tub-Sleeps 11
Interior
#207 King Suites, River Views, Deck, Downtown

Vacation Home in Madison

10.0 out of 10, Exceptional, (36)
"This is a beautiful historic house. Everything was neat, clean and perfect working order. Will definitely stay there again."
United States
Rick M.
$369 nightly
The price is $434
Dec 7 - Dec 8
Total with taxes and fees
#207 King Suites, River Views, Deck, Downtown
Microwave, oven, stovetop
Charming 2-bedroom house with a river view in wonderful Madison

Vacation Home in Madison

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great spot walkable to downtown Madison & the river area. Appreciated how well-stocked the kitchen, bathroom, and laundry were. And being able to bring a pet was a big plus."
United States
Chelsea C.
Charming 2-bedroom house with a river view in wonderful Madison
Exterior
The Artist’s A-Frame

Vacation Home in Madison

10.0 out of 10, Exceptional, (25)
"Wonderful place to stay "
United States
Susan H.
$212 nightly
The price is $244
Dec 18 - Dec 19
Total with taxes and fees
The Artist’s A-Frame
2 bedrooms, free WiFi, bed sheets
Unique Secluded Cabin with Loft on Classified Forest

Cabin in Florence

9.6 out of 10, Exceptional, (45)
"beautiful cabin. picture perfect very secluded "
United States
Deborah P.
Unique Secluded Cabin with Loft on Classified Forest
Property grounds
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102

Apartment in Madison

9.8 out of 10, Exceptional, (10)
"Super comfortable, clean little apartment in a quiet area off the main strip. We loved out stay!"
United States
Courtney G.
$126 nightly
The price is $129
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
Outdoor spa tub
Peaceful getaway centrally located just min. from Madison and Belterra casino.

Vacation Home in Vevay

9.4 out of 10, Exceptional, (29)
"Such a cute, comfortable home away from home! The hot tub was so nice. We were so relaxed. "
United States
Theresa H.
Peaceful getaway centrally located just min. from Madison and Belterra casino.
Exterior
Charming 3-bedroom house in lovely downtown Madison.

Vacation Home in Madison

2.0 star property
9.4 out of 10, Exceptional, (11)
"Great old home and cool neighborhood. "
United States
Randy S.
Charming 3-bedroom house in lovely downtown Madison.
Fridge, microwave, oven, stovetop
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS

Vacation Home in Madison

10.0 out of 10, Exceptional, (16)
"Perfect location for a long weekend getaway! Cute place and right on the river. Place was clean and cozy, host was great. "
United States
Toni N.
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS
Fridge, microwave, oven, stovetop
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill

Vacation Home in Madison

10.0 out of 10, Exceptional, (12)
"Madison Manor II was perfect for our annual girls trip. We were comfortable, location was great, the home was very clean."
United States
Carissa N.
$315 nightly
The price is $362
Dec 7 - Dec 8
Total with taxes and fees
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill
Fridge, microwave, oven, stovetop
#209 Kings, River View, Deck, Bicentennial Park

Vacation Home in Madison

10.0 out of 10, Exceptional, (62)
"Amazing stay in an beautiful town. Easy access to charming shops and restaurants. "
United States
Kyle L.
$369 nightly
The price is $434
Dec 7 - Dec 8
Total with taxes and fees
#209 Kings, River View, Deck, Bicentennial Park
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

Hillside Inn

Hillside Inn

10/10 Excellent
"We had a wonderful time in Madison. The hotel is quite charming and the history behind it is so fascinating. There are some minor updates that need to be repaired in Room 104, but overall, it's fine. Merry Christmas! "
Thomas 2-night trip
Posted 3 days ago
Hillside Inn

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Bennington in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $129 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

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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?

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!: Visitors like this Bennington vacation home rental. It offers a patio, a selection of games, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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. The Ridge Winery Tasting Room and Belterra Casino 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.