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Bennington Vacation Rentals

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Bennington vacation rentals

Living area

1. Cabin on the Ridge: The Sequel

Cabin on the Ridge: The Sequel
Madison
10.0 out of 10, Exceptional, (22 reviews)
"Our stay was amazing! Loved this cozy cabin in the woods! "
United States
Alison F.
$199 nightly
The price is $224
Sep 7 - Sep 8
Total with taxes and fees
Cabin on the Ridge: The Sequel
Living area

2. Cabin on the Ridge

Cabin on the Ridge
Madison
10.0 out of 10, Exceptional, (20 reviews)
"Super nice and cute! Would definitely stay again! "
United States
Angela G.
$211 nightly
The price is $237
Sep 7 - Sep 8
Total with taxes and fees
Cabin on the Ridge
Private kitchen

3. Charming new tiny house-Friendship IN

Charming new tiny house-Friendship IN
Versailles
10.0 out of 10, Exceptional, (3 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.
$173 nightly
The price is $194
Sep 7 - Sep 8
Total with taxes and fees
Charming new tiny house-Friendship IN
Exterior

4. Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (14 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.
$155 nightly
The price is $173
Sep 22 - Sep 23
Total with taxes and fees
Maple Cozy Cabin at Lost Trails
Exterior

5. Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (15 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
$146 nightly
The price is $163
Sep 22 - Sep 23
Total with taxes and fees
Sassafras Woodland Cabin at Lost Trails
Terrace/patio

6. 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.
$155 nightly
The price is $173
Sep 8 - Sep 9
Total with taxes and fees
Walnut Secluded Cabin at Lost Trails
Dining

7. The Blue Door Place

The Blue Door Place
Florence
9.8 out of 10, Exceptional, (28 reviews)
"It was great"
United States
James H.
$156 nightly
The price is $175
Sep 14 - Sep 15
Total with taxes and fees
The Blue Door Place
Exterior detail

8. Cedar Rustic Cabin at Lost Trails

Cedar Rustic Cabin at Lost Trails
Madison
10.0 out of 10, Exceptional, (31 reviews)
"Charming, cozy cabin! Perfect for a weekend getaway!"
United States
Mollie B.
$165 nightly
The price is $185
Sep 8 - Sep 9
Total with taxes and fees
Cedar Rustic Cabin at Lost Trails
Private kitchen

9. Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (8 reviews)
"Mulberry Cabin at Lost Trails was great! The cabin was cozy and felt pretty private (even though the other cabins are within view). The bed was super comfy, and they did a great job making sure the cabin had everything one might need on a trip away from home. It was also very close to all things Madison, so it felt very convenient. We would definitely stay there again!"
United States
Emily I.
$155 nightly
The price is $173
Sep 13 - Sep 14
Total with taxes and fees
Mulberry Secluded Cabin at Lost Trails
Living area

10. The River View at Esther’s

The River View at Esther’s
Vevay
$195 nightly
The price is $218
Sep 7 - Sep 8
Total with taxes and fees
The River View at Esther’s
Exterior detail

11. The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201

The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201
Madison Historic District
9.8 out of 10, Exceptional, (22 reviews)
"Our room was so cute and perfect for a couple. We loved it! The location was perfect as well!"
United States
Stee
$112 nightly
The price is $119
Sep 7 - Sep 8
Total with taxes and fees
The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201
Interior

12. King Bed|Non-Smoking

King Bed|Non-Smoking
Aurora, IN
10.0 out of 10, Exceptional, (74 reviews)
"Four nights of peace in Aurora! Quiet location close to local attractions like the Creation Museum was really handy for us."
United States
Anonymous traveler
$97 nightly
The price is $109
Sep 7 - Sep 8
Total with taxes and fees
King Bed|Non-Smoking
Property grounds

13. Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Madison
9.6 out of 10, Exceptional, (17 reviews)
"Host was very accommodating and this place was perfect for a place to stay while visiting friends. Everything was very comfortable, especially the very soft bed!! "
United States
C J.
$173 nightly
The price is $198
Sep 14 - Sep 15
Total with taxes and fees
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Interior

14. School Days

School Days
Versailles
10.0 out of 10, Exceptional, (1 review)
"The Schoolhouse was a unique experience that we enjoyed very much! We were provided with anything that we would have needed for a comfortable stay. Our host communicated promptly whenever we needed. We appreciated the cleaniless of the home. We did not realize how close in proximity we would be with the other rentals on the property, but once inside, we felt like we had privacy. This would be a great stay for a couple or small family."
United States
Lora S.
$148 nightly
The price is $166
Sep 7 - Sep 8
Total with taxes and fees
School Days
Exterior

15. The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (40 reviews)
"Very nice house and convenient to downtown, etc. If you stay here you definitely won’t be disappointed."
United States
Shirley L.
$216 nightly
The price is $243
Sep 7 - Sep 8
Total with taxes and fees
The Artist’s A-Frame
Living area

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

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Madison
9.8 out of 10, Exceptional, (72 reviews)
"Love the stay very relaxed"
United States
Steve C.
$194 nightly
The price is $223
Sep 7 - Sep 8
Total with taxes and fees
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Exterior

17. 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
$189 nightly
The price is $217
Sep 13 - Sep 14
Total with taxes and fees
Romantic 1 BR Retreat on the edge of woods with private hot tub
Living area

18. Waterfront Cabin | Near ARK | Large Family Retreat

Waterfront Cabin | Near ARK | Large Family Retreat
Warsaw
8.2 out of 10, Very Good, (12 reviews)
"Great host. Great home and an excellent stay highly recommended "
United States
Chris A.
$474 nightly
The price is $521
Sep 8 - Sep 9
Total with taxes and fees
Waterfront Cabin | Near ARK | Large Family Retreat
Interior

19. 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
10.0 out of 10, Exceptional, (5 reviews)
"The host was extremely nice and allowed us to get into the loft a little early. The loft was really nice and we enjoyed out stay. "
United States
Judi K.
$155 nightly
The price is $178
Sep 14 - Sep 15
Total with taxes and fees
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
Outdoor spa tub

20. Romantic Private Retreat 5 min from downtown with hot tub, firepit, grill

Romantic Private Retreat 5 min from downtown with hot tub, firepit, grill
Madison
10.0 out of 10, Exceptional, (19 reviews)
"Such a cute little place for my husband and I to get away for my birthday weekend! The house was adorable, well stocked for daily needs and very clean! Will definitely stay here again and recommend it to others!! "
United States
Claire S.
$282 nightly
The price is $324
Sep 23 - Sep 24
Total with taxes and fees
Romantic Private Retreat 5 min from downtown with hot tub, firepit, grill
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

Ramada by Wyndham Sparta/At Speedway

Ramada by Wyndham Sparta/At Speedway

8/10 Good
"It was good, nice and clean. The elevator is a little scary, and you only have channels to watch through but that was my fault for forgetting my laptop. Overall pretty good place!"
Michael 1-night trip
Posted 9 hours ago
Ramada by Wyndham Sparta/At Speedway

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 $178 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.

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.