Bennington Holiday Rentals

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Bennington

Perfect for Leaf Peeping w/Bar Room, Hot Tub

10.0 out of 10, Exceptional, (11)
"Wonderful experience, extremely communicative and helpful management, and just a beautiful building to stay in. We wanted for nothing. Thank you!"
Perfect for Leaf Peeping w/Bar Room, Hot Tub

Great Place to get away and have clean fresh air surround you!

9.8 out of 10, Exceptional, (131)
"This was one of our favorite family trips ever! So fun using the paddle boat and seeing the misty mornings and starry nights in the lake."
Great Place to get away and have clean fresh air surround you!

Two Brooks Lodge, Beautiful Waterfront Vermont Retreat

8.8 out of 10, Excellent, (27)
"In town for a long weekend and loved the location. The owner was prompt and very helpful as we made a mistake in booking. FYI, The pictures are great but it’s a bit more rustic than they make it seem. Still, it was great to sit outside and hear the brooks flowing. Very quiet street! Housecleaning was a bit lacking though as there were some huge cobwebs in the corners. That was fine for us as we spend our time in a barn anyway. "
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat

Perfect for a peaceful get away in clean fresh Vermont air!

10.0 out of 10, Exceptional, (70)
"What a lovely stay! The cabin was stocked with everything we needed and it was very clean and well organized. The photos don't quite do it justice. Peaceful lake views all day with mountains in the distance - what's not to like? We used the queen bedroom on the main floor and the bed was so very comfortable. We were there for two weeks, so we definitely used the kitchen - again, a well-planned space and well stocked. We hope to be there again!"
Perfect for a peaceful get away in clean fresh Vermont air!

Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!

8.8 out of 10, Excellent, (3)
"The property is exactly as advertised. A lot of attention to little details that make a staying experience better. I have stayed in a lot of rentals over the years, and this one is one of the best when considering what you are getting for the price. One thing to note - the rental has a very large jetted tub, however the property is on well water and has a standard home hot water tank. There really isn't enough hot water for a tub of this size unless you are careful to not use hot water during...
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!

Lake life at Woodford Cottage

9.4 out of 10, Exceptional, (13)
"Very comfortable beds! This property is what you would expect from a cottage in Vermont, but there's so much more! We were surprised by the very well equipped kitchen and the vicinity to Woodford State Park also worked out really well for us. Would definitely recommend!"
Lake life at Woodford Cottage

Meme's High Mountain Lake House

10.0 out of 10, Exceptional, (7)
"We loved this spot! From chilling by the water in the great yard and deck to explore nearby hiking spots, we couldn’t have asked for more! Jessica was very communicative as well. "
Meme's High Mountain Lake House

Stylish Rustic Retreat w/ Breathtaking Mtn Views!

10.0 out of 10, Exceptional, (25)
"My husband and I stayed here with our two dogs for 3 nights. The location is incredibly beautiful, peaceful and quiet. And the view is stunning. We had a great time exploring the incredible acreage. Based on the exact address, it took a bit longer to get into town than we thought. We ate out for all our meals, so it took a bit of coordinating to try and get everything we needed for the day to minimize the back and forth. The house was great, very spacious. Everything was nice and clean. A couple...
Stylish Rustic Retreat w/ Breathtaking Mtn Views!

Traveler Dream Space in the Center of Downtown Bennington Steps From Everything!

9.6 out of 10, Exceptional, (20)
"We had a good stay at Studio411 in Bennington. The place was as described with all we needed to be comfortable. Duane was very responsive. It’s a pretty town centrally located for tourists like us, and we would stay here again if in the area. "
Traveler Dream Space in the Center of Downtown Bennington Steps From Everything!

Victorian Home in Bennington, Vermont

10.0 out of 10, Exceptional, (86)
"The home is spacious, clean, bright, nicely decorated and well-equipped. An easy walk to shops and restaurants. It was great for our annual family gathering in southwestern Vermont."
Victorian Home in Bennington, Vermont

Two Brooks Lodge

3.0 star property
4.8 out of 10, (3)
"Strong dog smell, dirty shabby condition of interior surfaces. Obvious makeshift repairs, spongy floors, torn, flaking couch. Kitchen counter had multiple burn marks and some sticky substance, corner held down with duct tape. Screen door off tracks, laying against wall. Wife was stung by insect in the unit, had to go to hospital. We moved out after only 3 hours, and literally slept in the car rather than go back. Owner uncaring, rude and greedy. Slow to return security deposit. I've...
Two Brooks Lodge

Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The host was so kind and helpful. I will definitely cime abck here. "
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!

Luxury Living High Above the Center of Town.

9.8 out of 10, Exceptional, (10)
"Wonderful condo in the heart of Bennington. Great restaurants within walking distance. Easy drive to Prospect Mountain, Mt Snow, Stratton, Bromley, and Magic. We went to them all."
Luxury Living High Above the Center of Town.

Beautifully renovated 2 bedroom condo in Stratton VT - walk to Village/Lifts!

Beautifully renovated 2 bedroom condo in Stratton VT - walk to Village/Lifts!

5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio

9.6 out of 10, Exceptional, (8)
"Great place. Super close to everything. Host was super helpful. Everything you need for an amazing ski weekend."
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (200)
"Of all the rental cabons I've enjoyed over many years, ths one was at the top. Private, quiet and relaxing,,,so much so that I chose to forgo a day of fishing just to enjoy a warm peaceful fire. My thanks to the property manager for his welcoming, helpful & accommodating efforts. Thank you! Richard"
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Luxury Oasis w/Serene Views! Close to Ski Slopes w/Shuttle. Gameroom. Golf. WiFi

10.0 out of 10, Exceptional, (43)
"Brad was a wonderful host and the home and area had so much for us to do. It was the perfect place to get away and be with friends. "
Luxury Oasis w/Serene Views! Close to Ski Slopes w/Shuttle. Gameroom. Golf. WiFi

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very good, (72)
"The unit was perfect for our ski race weekend. Very accessible, underground parking included (ski boxes on top of SUVs will not fit - thankfully we left ours at home), really nice place with everything we needed!"
The price is AU$711
includes taxes & fees
3 Dec - 4 Dec
Long Trail House at Stratton Mountain Resort

Stratton South Long Trail Studio Adjacent to the Village and Lifts

9.4 out of 10, Exceptional, (56)
"Right across the road from Stratton Mountain. Check in was easy. Place was clean and comfortable. Much nicer and roomier than a typical hotel room. Highly recommended"
Stratton South Long Trail Studio Adjacent to the Village and Lifts

Modern Ski In / Ski Out 4BR / 3BA Smart Home w/ Private Hot Tub and shared pool

10.0 out of 10, Exceptional, (9)
"We had a wonderful stay. We enjoyed the home and community amenities. Location was great and our family enjoyed the convenience of having the access to ski on / ski off. We look forward to our stay next year!"
Modern Ski In / Ski Out 4BR / 3BA Smart Home w/ Private Hot Tub and shared pool
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.
Don't see what you're looking for?
See all available properties in Bennington
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Bennington you may be interested in

Hampton Inn Bennington

2.5 star property
8.6 out of 10, Excellent, (931)
"Pet friendly and clean!"
The price is AU$242
includes taxes & fees
8 Dec - 9 Dec
Hampton Inn Bennington

Best Western Bennington

2.5 star property
7.8 out of 10, Good, (782)
"Breakfast was okay, but not great"
The price is AU$173
includes taxes & fees
3 Dec - 4 Dec
Best Western Bennington

The Hotel Vervana at Bennington

2.5 star property
8.2 out of 10, Very good, (1040)
"God price, easy check in, comfortable bed"
The price is AU$174
includes taxes & fees
28 Nov - 29 Nov
The Hotel Vervana at Bennington
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental 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. Tourists who visit Bennington speak highly of the ski slopes and array of shops. While you're in the area, you can also enjoy the majestic mountain landscape and museums.

What are some of the best holiday rentals that Bennington has to offer?

Victorian Home in Bennington, Vermont: This highly rated holiday home rental in Bennington is located near skiing, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of books. Other favourite homes for rent in Bennington are Perfect for Leaf Peeping w/Bar Room, Hot Tub and Two Brooks Lodge, Beautiful Waterfront Vermont Retreat.

How many holiday rentals will I find in Bennington?

With 13 Expedia holiday rentals, you're guaranteed to find just the right place for your Bennington stay.

What’s there to see and do in Bennington?

Enjoy the outdoors at Green Mountain National Forest and Woodford State Park, or simply take in cultural attractions like Bennington Museum and Robert Frost Stone House Museum. While here, Bennington Battle Monument and Hemmings Motor News Car Lover's Convenience Store & Vehicle Display are other places worth a visit.

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 feature extras such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a family getaway.