Old Bennington Holiday Rentals

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Holiday Rentals in Old Bennington

Classic Vermont cabin with forest views, woodstove, pools, hot tub & gym

7.0 out of 10, Good, (6)
"Dining shopping not too far, but not walkable. The amount we paid was more than double the advertised price, yet we were still asked to perform a laundry list of cleaning tasks before exiting the unit (vacuuming, folding blankets, emptying and taking out gargage, etc.). I realize there is likely a management fee, but most VRBO properties do not require anything more than making sure doors and windows are secure, sink is clear, thermostats set at certain temps, etc. The property is also in...
Classic Vermont cabin with forest views, woodstove, pools, hot tub & gym

Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

10.0 out of 10, Exceptional, (44)
"From its warmth, fireplace, chalkboard for fun with friends, lots of games and super convenient location to Mount Snow – this place is a must stay! We can’t wait to come back."
The price is AU$574
includes taxes & fees
19 Mar - 20 Mar
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

Updated Ski in ski out condo & mountain biking located at Seasons on Mt. Snow

10.0 out of 10, Exceptional, (51)
"Really loved the location of this property! Ski on/ski off was amazing! The property was great, exactly as pictured and we would love staying here again in the future!"
Updated Ski in ski out condo & mountain biking located at Seasons on Mt. Snow

SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

8.8 out of 10, Excellent, (42)
"We had a group of thirty-four people for a family vacation and had a blast. The host and the housekeeper were tremendously responsive to any small issues we had over the first few days. The kitchen was well stocked but could use more mugs for coffee/tea and additional forks for larger groups and the tea bags were past the best before date and should be replaced. Twelve bedrooms, each with their own bathroom was great. The pool, hot tubs, ping pong table, pool table, tennis court, and fire pit...
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain Den

9.4 out of 10, Exceptional, (13)
"Would have given 5-stars but the location is right below another rental and you can hear everyone walking around, which was a little annoying. After a friendly visit to the upstairs neighbors, and a cordial chat, it was a great evening. If the upstairs came with padded carpet this place would be a home run."
The price is AU$398
includes taxes & fees
10 Mar - 11 Mar
MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain Den

Perfect Country Cottage

9.6 out of 10, Exceptional, (78)
"Host was great! On top of everything involved with the trip. The house worked out great for our ski trip. "
Perfect Country Cottage

Vintage BARN Apartment-POOL-HotTub-FirePit-Hiking-Museums-Theater-Pets welcome!

9.6 out of 10, Exceptional, (28)
"We had a very peaceful and relaxing stay. The atmosphere was quiet and calming, perfect for unwinding. Everything about our time here was enjoyable, and we truly appreciated the serene environment. Highly recommend it for anyone looking for a restful getaway! "
Vintage BARN Apartment-POOL-HotTub-FirePit-Hiking-Museums-Theater-Pets welcome!

MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain House

10.0 out of 10, Exceptional, (13)
"Six of us women from Vermont golf courses stayed while playing a tournament at Haystack Country Club. The house suited us perfectly. We had some issues with the bathtub plumbing not turning off but we had prompt attention from a service person. The house had a great kitchen and tv to accommodate us."
The price is AU$590
includes taxes & fees
17 Mar - 18 Mar
MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain House

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

8.6 out of 10, Excellent, (24)
"The apartment was in a great location to get to the ski lifts. "
The price is AU$476
includes taxes & fees
27 Feb - 28 Feb
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Wilmington Vacation Rental Near Hiking and Skiing!

9.2 out of 10, Wonderful, (17)
"Perfect weekend house close to mt snow"
Wilmington Vacation Rental Near Hiking and Skiing!

Peaceful Stay at Birds of a Feather Farm & Spa

9.6 out of 10, Exceptional, (15)
"I arrived amidst freezing outdoor temperatures to a warm and cozy interior. I was visiting family and was concerned about snow and ice, Laurie had assured me that it would not be a problem and she was right. The unit was exactly as described in the ad. Laurie made sure that the snow was shoveled and I had no problems getting out in the morning! A wonderful, peaceful getaway!"
The price is AU$413
includes taxes & fees
24 Feb - 25 Feb
Peaceful Stay at Birds of a Feather Farm & Spa

Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

10.0 out of 10, Exceptional, (213)
"Our annual family ski vacation is always at Mt Snow. This year we were lucky enough to spend a week at Tony and Jeanette’s home. Which is exactly as we felt - at home. The house is beautiful and the amenities perfect. The home was clean, guest linens and towels, paper goods all provided. We loved the view and the binoculars!! We would love to stay again. "
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn

9.6 out of 10, Exceptional, (4)
"We had a mixed experience during our stay at Leah's property. On the positive side, Leah was an incredibly friendly and communicative host. She was quick to respond to any questions, and the location was absolutely fantastic—very convenient and close to everything.However, upon arrival, we noticed the unit wasn’t as clean as we expected. There were stains on the rug, dust on the furniture, crumbs on the coffee table, and a dirty stovetop. The dishes appeared to have been used but weren’t...
The price is AU$794
includes taxes & fees
25 Feb - 26 Feb
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn

The Stratton Cabin | Close to Stratton & Mt Snow!

10.0 out of 10, Exceptional, (2)
"The cabin was in a great location for us and was much nicer than we thought. It had everything we needed too. I’d rent this cabin again for sure "
The Stratton Cabin | Close to Stratton & Mt Snow!

Mountain-view home near the slopes with at-home entertainment - dog-friendly

7.8 out of 10, Good, (65)
"The location was excellent. Five mins from to Mt. Snow. Nice game room but needs attention. Dartboard unusable - only 2 darts with no flights useless. Nice pool table but queues were poor and no chalk. Ping pong was almost too tight to be usable. Kitchen needs serious upgrade. Lots of pots and pans but all well aged. Overall the place could be a place we'd return to but needs upgrades."
Mountain-view home near the slopes with at-home entertainment - dog-friendly

Cozy retreat near slopes

4.4 out of 10, (7)
"Unit is a little outdated but nice.Not truly a ski in - out since you have to walk on the road about 200 yards to get to the Sachem trail.Condo does need ice cube trays since the ice maker is not working.Also the down stairs bath room heater does not work and would be nice since this is where the bath tub is located"
Cozy retreat near slopes

Dog-friendly cabin with pools, hot tub, tennis & pickleball - near Mt. Snow

8.8 out of 10, Excellent, (3)
"We had an awesome stay! Clean house"
Dog-friendly cabin with pools, hot tub, tennis & pickleball - near Mt. Snow

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

10.0 out of 10, Exceptional, (5)
"Everything was really nice! The house was great and the whole place lovely. Great location! The manager was really helpful and easy to get in touch with. He was able to help us with all of our questions. The conditions of the mountain were really good. Wonderful stay! "
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Beautiful Lodging at Mount Snow with Hot Tub on Deck

9.2 out of 10, Wonderful, (40)
"Real Vermont feel. Pretty and nice quiet neighborhood!"
Beautiful Lodging at Mount Snow with Hot Tub on Deck

Ski on Ski Off & Newly Renovated! 30 feet to covered magic carpet at Carinthia.

10.0 out of 10, Exceptional, (13)
"Amazing ski on and off house. Very responsive owner. Magical weekend."
Ski on Ski Off & Newly Renovated! 30 feet to covered magic carpet at Carinthia.
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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Other types of properties in Old Bennington you may be interested in

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.6 out of 10, Excellent, (1002)
"We love this hotel! Our room was clean and spacious, the staff members we interacted with were friendly and helpful, the lobby/common and art galleries were very interesting, and there is so much to do within easy walking distance. "
The price is AU$220
includes taxes & fees
27 Feb - 28 Feb
Hotel Downstreet, Ascend Hotel Collection

Mountaineer Inn

2.0 star property
9.0 out of 10, Wonderful, (411)
"Food choice limited for continental breakfast. staff friendly. pool table had torn felt and 2 sets of balls."
The price is AU$234
includes taxes & fees
3 Mar - 4 Mar
Mountaineer Inn

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (413)
"Very comfortable "
The price is AU$338
includes taxes & fees
16 Mar - 17 Mar
The Williams 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.

Frequently asked questions

Can I find a holiday rental in Old Bennington?

Yes, there are holiday rentals close to the most popular sights in Old 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 Old Bennington has to offer?

Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!: This holiday home rental outside of Old Bennington is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 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.

What’s there to see and do in Old Bennington?

Explore the area and cultural attractions such as Bennington Museum, or visit one of the family-friendly sights such as Sugar Shack. Other places in town to visit include Bennington Battle Monument and Old First Congregational Church.

What’s a holiday rental in Old Bennington like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Old Bennington. Holiday rentals feature extras such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and busy reception areas while still allowing you the experience of travel. 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 families.