Top Villas in Bennington County in 2026

A house on a grassy hill surrounded by autumn-colored trees.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Top Cities in Bennington County

A white building with black shutters, a sign for Covey & NY, and an American flag.

Our top choices for Bennington County villas

1. Vermont Vacation Villa—Grapevine Getaway

Pownal

Tim A.

2. Gorgeous Victorian-Style House w/ Hilltop Pool!

Rupert

"We spent a week here with four adults and four kids. We had ample room for everyone and enjoyed the property. This is an old rustic house and has some quirks, but the house is in great shape and the property is fantastic. If you are looking for a remote getaway this is nice, as the property has plenty of outdoor options to keep busy. The kitchen has a lot of utensils, pots and pans for use and there is outdoor equipment available as well. "

Bradley P.

3. Mountain Haven for Families | Deck | Shuttle | Views

Winhall

Laura B.

4. Gorgeous Victorian-style House w/ Hilltop Pool!

Rupert

5. Spacious Piper Ridge Townhome Near Stratton

Winhall

View all properties

Find vacation rentals that suit your style

Cabins

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Top Bennington County Hotel Reviews

Knotty Pine

10/10 Excellent

"The property was quaint and provided what I needed for my stay. Staff was very helpful. Could not use pool as it was raining the whole time I was there. I will definitely use that property again."

Aspen At Manchester

10/10 Excellent

"The motel was very nice and the location is perfect and very close to all of the restaurants and shops. The landscaping was beautiful and the view was amazing. My girls loved the free use of the Mountain Bikes and we enjoyed the fire pits at night. The room was clean and the beds were very comfortable. The pool was nice but it just had regular and Adirondack chairs but no actual lounge chairs which would have been a nice touch. The lobby was very nice and we played some of the Board Games Provided. They have a popcorn machine and smores kit which was really nice. Also, well stocked with extra towels, toiletries and bath tissues if needed. Things to improve on would be the pool and providing lounge chairs, water pressure in the shower was terrible but probably not much they can do about that. I would definitely stay here again as it was perfect for our travel needs and the price was great for everything offered. I also brought my dogs and they loved it too!!!"

The Equinox Golf Resort And Spa

8/10 Good

"We have been staying at the Equinox for years when in town for a horse show. Unfortunately, the property declines in condition and management every year. Walking in through the back of the hotel to check in, you're immediately hit with the smell of mold. The front desk staff weren't overly helpful or friendly. This year we had a very odd room requiring us to carry our luggage up a couple flights of stairs both in the hallway and once we opened the door to our room. I imagine that room being difficult for many. The room itself was fine. Relatively clean. Very comfortable beds. Nice, crisp white linens. The bathroom/vanity area are large but VERY dark making it super challenging to get ready. On a positive note, the air conditioning worked well - other years they have had to put in window units. In the year 2026, the rooms should also have smart TVs that allow for streaming. Positives..... Beautiful location. Easy drive to the horse show. The back deck/fire pit are a perfect spot to grab dinner/drinks. The absolute star of the show was the bartender Jayden. He could not have been more accommodating. 100% service with a smile. Helped us get seating for a large party on a Saturday night and provided superior service - to include offering to fill our water bottles as the hotel/resort doesn't offer filling stations. He truly made our stay!!"

Frequently asked questions

Why book your villa in Bennington County with Expedia?

Booking a villa in Bennington County is as easy as working out your travel dates and picking a place that meets your requirements. Seeking something upscale or budget friendly, or a property that also has WiFi and a hot tub? Use Expedia's search filters to narrow your results and find the perfect fit.

How can I find cheap villas in Bennington County?

Expedia is here to help you look for cheap villas in Bennington County. Use our handy filter tool to choose star rating, amenities and budget to refine your search and find a great place to stay in just a few keystrokes.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Top Cities in Bennington County

Manchester

Our top choices for Bennington County villas

1. Vermont Vacation Villa—Grapevine Getaway

2. Gorgeous Victorian-Style House w/ Hilltop Pool!

3. Mountain Haven for Families | Deck | Shuttle | Views

4. Gorgeous Victorian-style House w/ Hilltop Pool!

5. Spacious Piper Ridge Townhome Near Stratton

Find vacation rentals that suit your style

Top Bennington County Hotel Reviews

Knotty Pine

Hotel Vervana, Trademark Collection by Wyndham

Aspen At Manchester

Toll Road Inn

Hampton Inn and Suites Manchester

The Manchester View

The Equinox Golf Resort And Spa

The Palmer House Resort, an Ascend Collection Hotel

New Englander Inn Bennington

Frequently asked questions

Explore a world of travel with Expedia