Holiday Rentals in Bennington

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Holiday Rentals in Bennington

Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
Interior
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
9.8 out of 10, Exceptional, (7)
"Beautiful property! Responsive and helpful hosts. Short walk into downtown Bennington. We had a blast!"
The price is €820
includes taxes & fees
2 May - 3 May
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
Great Place to get away and have clean fresh air surround you!
Exterior
Great Place to get away and have clean fresh air surround you!
9.8 out of 10, Exceptional, (120)
"The house has a beautiful view of the lake and is very clean. It is beautifully decorated, and has all the supplies that are needed for comfortable stay. The owner is very thoughtful and the house is nicely organized. We appreciated the Christmas decorations during our holiday stay, extra towels prepared for the dog and the dog treats. The house is nicely stocked with family games, and there is beautiful trail in walking distance: up the hill to vast trail, and path through the forest to Little...
Great Place to get away and have clean fresh air surround you!
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
Fridge, microwave, oven, stovetop
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
9.0 out of 10, Wonderful, (24)
"The cabin was clean and quiet and suited our needs for the weekend. The hot tub was enjoyable, although I would recommend that the owners purchase stairs to make exit and entry a bit easier."
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
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Perfect for a peaceful get away in clean fresh Vermont air!
Exterior
Perfect for a peaceful get away in clean fresh Vermont air!
10.0 out of 10, Exceptional, (66)
"Linda Jane’s place is absolutely wonderful! The house was sparkling clean and had everything we could need for a weekend ski getaway. Also situated on a scenic pond in a quiet neighborhood. About 30 minute drive to Mt. Snow. Only thing to note, the cabin is a bit open concept, so Linda Jane kindly provided a divider to allow for more privacy between the downstairs bedrooms. We had a great weekend with friends and would love to plan a trip back!"
Perfect for a peaceful get away in clean fresh Vermont air!
Victorian Home in Bennington, Vermont
Fridge, microwave, oven, stovetop
Victorian Home in Bennington, Vermont
10.0 out of 10, Exceptional, (78)
"The house fit our needs so well that we stayed an extra day. High ceilings, lots of light, more than ample room. We used it as a home base for ski slopes less than an hour away. Great work-from-home setup for a non-skier. Thank you for hosting us!"
Victorian Home in Bennington, Vermont
Lake life at Woodford Cottage
Smart TV, fireplace
Lake life at Woodford Cottage
9.6 out of 10, Exceptional, (11)
"Stayed Fri - Mon over Columbus Day weekend - overall the cabin itself was very nice. Clean, cozy and all the amenities listed. Some things to note: -There’s no dishwasher so bring paper plates and bowls to make life easier! -There’s a washer dryer combo in the kitchen but only the dryer is available for use -The front door is tricky with the lock but you’ll quickly get the hang of it -The shower is also tricky at first but you’ll also get the hang of that! -Not really any closet or drawer space...
Lake life at Woodford Cottage
Traveler Dream Space in the Center of Downtown Bennington Steps From Everything!
Fridge, microwave, oven, stovetop
Traveler Dream Space in the Center of Downtown Bennington Steps From Everything!
9.4 out of 10, Exceptional, (14)
"Great, large apartment in downtown Bennington, Vermont. Walk to restaurants and shops. Short drive to area attractions. Small amount of traffic noise did not bother us at all. We slept well each night."
Traveler Dream Space in the Center of Downtown Bennington Steps From Everything!
Meme's High Mountain Lake House
View from property
Meme's High Mountain Lake House
10.0 out of 10, Exceptional, (3)
"How was better than advertised. Really appreciated the owners leaving the essentials, including the spices and condiments. Linens, too. They really take pride in the place. Highly recommend."
Meme's High Mountain Lake House
Bennington Cabin w/ Deck & Views of 3 States!
Interior
Bennington Cabin w/ Deck & Views of 3 States!
10.0 out of 10, Exceptional, (22)
"The lodging, location and view exceeded our expectations. The owner was extremely helpful and responsive. We definitely want to return."
Bennington Cabin w/ Deck & Views of 3 States!
Two Brooks Lodge
Panoramic House | Private kitchen
Two Brooks Lodge
3.0 star property
6.0 out of 10, (2)
"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
Escape to Serenity: Cozy 3 bedroom apartment
Fridge, microwave, oven, stovetop
Escape to Serenity: Cozy 3 bedroom apartment
The price is €369
includes taxes & fees
22 May - 23 May
Escape to Serenity: Cozy 3 bedroom apartment
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
Interior
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!
Long Trail House at Stratton Mountain Resort
Condo, 2 Bedrooms | Pool
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very good, (68)
"Amazing! Cannot get a better location! So close to everything! Quick walk to village shops and slopes. Very clean. Lots more room than I was expecting for two big 17 year old boys and parents. Kids had their own bedroom, bathroom and storage area on main floor, adult had master suite with own bathroom upstairs. Plenty of room in kitchen and family room. The only complaint is that hotels hot tubs and pool were over run with too many little kids. "
The price is €351
includes taxes & fees
23 May - 24 May
Long Trail House at Stratton Mountain Resort
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Exterior
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
9.6 out of 10, Exceptional, (176)
"Third time as good as the first. We will return next year"
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
10.0 out of 10, Exceptional, (204)
"My wife and I both needed to disconnect and unwind after a very busy start to the year. We looked for cabins in Vermont. and the pictures seemed to match what we were looking for. We arrived, and found EXACTLY what the pictures and the description offered. Lars was very informative and helpful, and checked in to ensure we were ok with everything. The entire stay was exactly what we both needed. The trails around the property were really fun to explore. The one other thing I liked was the...
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Slopeside Ski-On/Off Condo on Stratton. MNT access for hiking, biking, golf.
Exterior
Slopeside Ski-On/Off Condo on Stratton. MNT access for hiking, biking, golf.
10.0 out of 10, Exceptional, (33)
"Great property. Spotless. Had everything we needed. Great information about the area. Bedroom configuration was perfect for us. Great ski on ski off location. Easy parking. Very responsive Host. Would definitely stay there again."
Slopeside Ski-On/Off Condo on Stratton. MNT access for hiking, biking, golf.
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Interior
Lovely ski-in/out condo steps from ski lift with trails and amazing views
8.4 out of 10, Very good, (17)
"We had a great stay. It's not the most modern or squeaky clean condo, but honestly worked just fine. We were comfortable and enjoyed the fireplace. And you cannot beat the location to the slopes for the price. We will be staying here again."
The price is €317
includes taxes & fees
2 May - 3 May
Lovely ski-in/out condo steps from ski lift with trails and amazing views
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
Outdoor pool, a heated pool
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
Private Tavern, Hot Tub, 8-Fireplaces, Spa Baths, Fire Pit, Baths Ensuite - Shop or Ski!
Property grounds
Private Tavern, Hot Tub, 8-Fireplaces, Spa Baths, Fire Pit, Baths Ensuite - Shop or Ski!
10.0 out of 10, Exceptional, (38)
"The house is very spacious and setup like a bed and breakfast"
Private Tavern, Hot Tub, 8-Fireplaces, Spa Baths, Fire Pit, Baths Ensuite - Shop or Ski!
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
Exterior
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
10.0 out of 10, Exceptional, (27)
"This was one of the best locations we have stayed at! We came up for a fundraiser at Stratton Mountain. Tommy was so helpful and provided great information from booking up until checkout. There is a great virtual guide that answers all important questions. The house and outdoors were exactly what we were looking for. Our dog loved running around and we enjoyed the hot tub. The house was very clean and had all the necessities we needed. Our favorite part was being cozy on the coach watching...
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
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See all available properties in 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.

Other types of properties in Bennington you may be interested in

Hampton Inn Bennington
Exterior
Hampton Inn Bennington
2.5 star property
8.6 out of 10, Excellent, (865)
"Excellent Inn. Knowledgable and helpful Staff."
The price is €155
includes taxes & fees
7 May - 8 May
Hampton Inn Bennington
Best Western Bennington
In-room safe, blackout curtains, iron/ironing board
Best Western Bennington
2.5 star property
7.8 out of 10, Good, (699)
"Nice and clean "
The price is €121
includes taxes & fees
7 May - 8 May
Best Western Bennington
The Autumn Inn
Front of property
The Autumn Inn
2.0 star property
7.8 out of 10, Good, (490)
"The host was very charming and kind. "
The price is €87
includes taxes & fees
1 Jun - 2 Jun
The Autumn Inn
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.

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 €317 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 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?

Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms: This highly rated holiday home rental in Bennington is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. Other favourite homes for rent in Bennington are Victorian Home in Bennington, Vermont 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 Woodford State Park and Harmen Hills Trail, or simply take in cultural attractions like Bennington Museum and Robert Frost Stone House Museum. While here, Old First Congregational Church and Bennington Battle Monument 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.

Recent reviews of Bennington properties
Expedia verified reviews

South Shire

South Shire

5/5 Excellent
"Old world charm - this beautiful Victorian mansion is the perfect remedy for the sterile and soulless beige."
A verified traveller stayed at South Shire
Posted 5 days ago
South Shire