Holiday Rentals in Bennington

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Holiday Rentals in Bennington

Our top choices for Bennington holiday rentals

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!

9.8 out of 10, Exceptional, (38)
"We enjoyed the space. Had everything we needed. Great proximity to downtown shopping and entertainment. "
The price is €217
includes taxes & fees
1 Sept - 2 Sept
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

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

10.0 out of 10, Exceptional, (93)
"Perfect setting. Beautiful cabin. "
Stoney Creek - Sit back and unwind

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!"
The price is €208
includes taxes & fees
11 Sept - 12 Sept
The Artist’s A-Frame

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

9.6 out of 10, Exceptional, (9)
"Was just what i needed to stay the week after my dads passing. Safe,.comfortable and affordable "
The price is €122
includes taxes & fees
23 Sept - 24 Sept
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

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

10.0 out of 10, Exceptional, (1)
"Everything was excellent!"
Grace Woods - Private Lake | Dock | Outdoor Space

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

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.

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!

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!!

9.8 out of 10, Exceptional, (17)
"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

9.6 out of 10, Exceptional, (5)
"This property was very quaint and clean. What a cute little town in Madison Indiana. "
The price is €111
includes taxes & fees
23 Sept - 24 Sept
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.

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

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."
The price is €148
includes taxes & fees
2 Sept - 3 Sept
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

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

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

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 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 €111 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?

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!: This holiday home rental outside of Bennington 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 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.