Bennington Vacation Rentals

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Vacation Rentals in Bennington

Our top choices for Bennington vacation rentals

1800’s restored log cabin on 26 private rolling wooded acres with sunset views
Property grounds

1800’s restored log cabin on 26 private rolling wooded acres with sunset views

10.0 out of 10, Exceptional, (195)
"This cabin is the perfect place to getaway and relax! It’s peaceful and beautiful!"
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Fridge, microwave, oven, stovetop

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

9.8 out of 10, Exceptional, (38)
"We enjoyed the space. Had everything we needed. Great proximity to downtown shopping and entertainment. "
$215 nightly
The price is $247
Sep 1 - Sep 2
Total with taxes and fees
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
Interior

Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…

10.0 out of 10, Exceptional, (47)
"Everything was really great...the property is beautiful...the amenities were amazing...and the owners so sweet and caring...the would answer a text message pronto...will stay again!"
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
Stoney Creek - Sit back and unwind
Interior

Stoney Creek - Sit back and unwind

10.0 out of 10, Exceptional, (93)
"Perfect setting. Beautiful cabin. "
Stoney Creek - Sit back and unwind
The Artist’s A-Frame
Exterior

The Artist’s A-Frame

10.0 out of 10, Exceptional, (19)
"I can't say enough about our stay at the Artist's A-Frame. The hosts are exceptional, the location is ideal, and the space is beautiful! I highly recommend and am anxious to return!"
$206 nightly
The price is $237
Sep 11 - Sep 12
Total with taxes and fees
The Artist’s A-Frame
Rustic cabin just outside of Madison!
4 bedrooms, free WiFi, bed sheets

Rustic cabin just outside of Madison!

10.0 out of 10, Exceptional, (42)
"This was a very nice property. The cabin was so cozy and the property was beautiful. We all enjoyed our stay."
Rustic cabin just outside of Madison!
Sunset over the city Suite 201, Sunset over the city Suite 201
Interior

Sunset over the city Suite 201, Sunset over the city Suite 201

9.6 out of 10, Exceptional, (9)
"Was just what i needed to stay the week after my dads passing. Safe,.comfortable and affordable "
$129 nightly
The price is $138
Sep 23 - Sep 24
Total with taxes and fees
Sunset over the city Suite 201, Sunset over the city Suite 201
KY log home close to The Ark Encounter on private 14 acres private seasonal pool
Outdoor pool

KY log home close to The Ark Encounter on private 14 acres private seasonal pool

9.2 out of 10, Wonderful, (30)
"We enjoyed the space the cabin had to offer and had a great time."
KY log home close to The Ark Encounter on private 14 acres private seasonal pool
Grace Woods - Private Lake | Dock | Outdoor Space
Exterior

Grace Woods - Private Lake | Dock | Outdoor Space

10.0 out of 10, Exceptional, (1)
"Everything was excellent!"
Grace Woods - Private Lake | Dock | Outdoor Space
Cozy Cabin Madison Indiana
TV, fireplace

Cozy Cabin Madison Indiana

10.0 out of 10, Exceptional, (16)
"The cabin was just as described online it's very quiet and was the perfect getaway "
Cozy Cabin Madison Indiana
Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St
Fridge, microwave, oven, stovetop

Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St

10.0 out of 10, Exceptional, (7)
"My husband and I came to celebrate our anniversary and his retirement and to go hiking- our favorite activity together! This place was perfect! Location! Location! Location! Near everything- walked downtown to shops and restaurants! The place itself was clean, nicely decorated, and very welcoming We will e back! "
Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St
Peaceful getaway centrally located just min. from Madison and Belterra casino.
Outdoor spa tub

Peaceful getaway centrally located just min. from Madison and Belterra casino.

9.4 out of 10, Exceptional, (26)
"We enjoyed our stay and would recommend to others."
Peaceful getaway centrally located just min. from Madison and Belterra casino.
Candlelit Comfort: Hot Tub, Firepit, Massage Chair-Romantic Getaway!
Outdoor spa tub

Candlelit Comfort: Hot Tub, Firepit, Massage Chair-Romantic Getaway!

10.0 out of 10, Exceptional, (7)
"This was such a nice place, very quiet and peaceful. The property was everything we had hoped for and the host was so nice and helpful."
Candlelit Comfort: Hot Tub, Firepit, Massage Chair-Romantic Getaway!
Bungalow on Main!!
Exterior

Bungalow on Main!!

9.8 out of 10, Exceptional, (18)
"Wonderful accommodations, beautifully decorated and very clean! We will be back!"
Bungalow on Main!!
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
Property grounds

Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102

9.6 out of 10, Exceptional, (5)
"This property was very quaint and clean. What a cute little town in Madison Indiana. "
$122 nightly
The price is $125
Sep 23 - Sep 24
Total with taxes and fees
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
Sonshine Cabin is your own private park. With wildlife or a hike to the creek.
Property grounds

Sonshine Cabin is your own private park. With wildlife or a hike to the creek.

10.0 out of 10, Exceptional, (307)
"My family and I truly enjoyed our stay. We love coming here it has all the amenities that added to our comfort. Hosts were very accommodating which was really appreciated. "
Sonshine Cabin is your own private park. With wildlife or a hike to the creek.
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
Exterior

Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

2.0 star property
9.8 out of 10, Exceptional, (8)
"Really enjoyed our stay. Super easy to find, plenty of parking. Walking distance of the shops. 10/10 would stay again."
$146 nightly
The price is $168
Sep 2 - Sep 3
Total with taxes and fees
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
Unique Secluded Cabin with Loft on Classified Forest
2 bedrooms, free WiFi, bed sheets

Unique Secluded Cabin with Loft on Classified Forest

9.6 out of 10, Exceptional, (41)
"Beautiful, secluded cabin!! Loved seeing the deer each evening. If we are in this area again, we would definitely stay here!"
Unique Secluded Cabin with Loft on Classified Forest
Charming 2-bedroom house in Devil's Elbow Osgood, IN
Smart TV

Charming 2-bedroom house in Devil's Elbow Osgood, IN

10.0 out of 10, Exceptional, (2)
"House is as pictured and stated. Beds were comfortable, well stocked kitchen, nice keurig selection of coffee, beautiful outdoor setting behind house backs up to woods,very peaceful. Great place would stay again."
Charming 2-bedroom house in Devil's Elbow Osgood, IN
Madison's Only YURT Experience
Dining

Madison's Only YURT Experience

9.4 out of 10, Exceptional, (9)
"This place is adorable and has so much potential. The beds were comfortable and the Yurt was cozy. "
Madison's Only YURT Experience
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

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 $125 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

While you're exploring the area, General Butler State Resort Park and Vevay Island are a couple of picturesque spots to get outside and enjoy nature. 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.