Holiday Rentals in Bennington

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Holiday Rentals in Bennington

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
9.8 out of 10, Exceptional, (41)
"We enjoyed the space. Had everything we needed. Great proximity to downtown shopping and entertainment. "
The price is €197
includes taxes & fees
22 Oct - 23 Oct
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, (52)
"Great property, great location, and amazing hosts. Incredible attention to detail and service. It would take too long to describe everything that impressed us so I'll just say it's all perfect and if this place is available when you're visiting Madison, stop searching and just book it."
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
Peaceful getaway centrally located just min. from Madison and Belterra casino.
9.4 out of 10, Exceptional, (29)
"Very nice place!"
Peaceful getaway centrally located just min. from Madison and Belterra casino.
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
9.8 out of 10, Exceptional, (8)
"Super comfortable, clean little apartment in a quiet area off the main strip. We loved out stay!"
The price is €111
includes taxes & fees
3 Nov - 4 Nov
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
Sunset over the city Suite 201, Sunset over the city Suite 201
9.6 out of 10, Exceptional, (10)
"Was just what i needed to stay the week after my dads passing. Safe,.comfortable and affordable "
The price is €119
includes taxes & fees
3 Nov - 4 Nov
Sunset over the city Suite 201, Sunset over the city Suite 201
Rustic cabin just outside of Madison!
10.0 out of 10, Exceptional, (47)
"Great day, we loved the cabin!"
Rustic cabin just outside of Madison!
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
10.0 out of 10, Exceptional, (206)
"This place checks all of our boxes for the things we look for in a rental cabin. "
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
KY log home close to The Ark Encounter on private 14 acres private seasonal pool
9.2 out of 10, Wonderful, (30)
"Great secluded location with an awesome large pool! We had a blast and would highly recommend. I do think a pull out couch or something on the landing at the top of the stairs, or even in the basement, would be a nice addition for more sleeping space. "
KY log home close to The Ark Encounter on private 14 acres private seasonal pool
Rustic Private Cabin on 30 acres w/Loft/Firepit/Secluded/Trails
9.8 out of 10, Exceptional, (33)
"Quiet, peaceful stay. Enjoyed the setting!Cabin was clean!"
Rustic Private Cabin on 30 acres w/Loft/Firepit/Secluded/Trails
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
9.6 out of 10, Exceptional, (19)
"Perfect little cozy cabin for an amazing getaway! We were able to just relax and enjoy our time together with zero distractions. 10/10 would definitely stay here again! "
The price is €256
includes taxes & fees
15 Oct - 16 Oct
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
2.0 star property
10.0 out of 10, Exceptional, (12)
"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
15 Oct - 16 Oct
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
Stoney Creek - Sit back and unwind
10.0 out of 10, Exceptional, (96)
"Stayed with my Wife for a week after our wedding and it the perfect place to recharge after the rollercoaster of emotions that we had dealt with during the wedding. Would definitely recommend to anyone who is looking for a relaxing and comfortable place to stay. "
Stoney Creek - Sit back and unwind
Madison's Only YURT Experience
9.2 out of 10, Wonderful, (11)
"This place is adorable and has so much potential. The beds were comfortable and the Yurt was cozy. "
Madison's Only YURT Experience
Bungalow on Main!!
9.8 out of 10, Exceptional, (22)
"Great location to walk around town or to the river. House is charming with nice updates and bigger than it looks from the outside. Great stay. "
Bungalow on Main!!
Rustic Cabin at Lost Trails
10.0 out of 10, Exceptional, (15)
"It was a great peaceful getaway for my wife and I. Quiet and clean. "
Rustic Cabin at Lost Trails
Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
9.4 out of 10, Exceptional, (8)
"Very easy check in and nice location. Very comfortable stay. "
The price is €125
includes taxes & fees
3 Nov - 4 Nov
Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath
9.6 out of 10, Exceptional, (21)
"Very nice house good accommodations would stay again !!!"
Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath
Livery Loft: our other BEST downtown location! Award winning! Come see why.
10.0 out of 10, Exceptional, (17)
"Beautiful property with THE BEST host! We will definitely stay here again!"
Livery Loft: our other BEST downtown location! Award winning! Come see why.
The Wadsworth in National Historic District of Madison, Indiana.
10.0 out of 10, Exceptional, (58)
"Super cute and great location"
The Wadsworth in National Historic District of Madison, Indiana.
Unique Secluded Cabin with Loft on Classified Forest
9.6 out of 10, Exceptional, (42)
"Had a wonderful time. Great place to just get away from it all. The dogs had a blast. Would definitely recommend staying here."
Unique Secluded Cabin with Loft on Classified Forest
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

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.