Old Bennington Vacation Rentals from ￥22,925: Search Short-Term Rentals

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Our top choices for Old Bennington vacation rentals

1. Peaceful getaway at birds of a feather

Shaftsbury

Aidan K.

￥42,243 total

includes taxes & fees

Sep 1 - Sep 2

2. Two Brooks Lodge

Bennington

"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...

Hunter

￥60,587 total

includes taxes & fees

Sep 1 - Sep 2

3. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Bennington

Malika R.

￥51,376 total

includes taxes & fees

Sep 1 - Sep 2

Coffee/tea maker, fridge, microwave, oven

4. Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Hoosick Falls

Anita T.

￥63,633 total

includes taxes & fees

Sep 8 - Sep 9

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

Woodford

Adam a.

6. Cozy Home in Pownal VT

Pownal

Jess M.

￥31,216 total

includes taxes & fees

Sep 13 - Sep 14

7. 2-Bdr Apt In Town, By the Water

Williamstown

Thomas

￥47,369 total

includes taxes & fees

Sep 15 - Sep 16

8. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Dover

Tania J.

￥48,409 total

includes taxes & fees

Sep 1 - Sep 2

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Top Old Bennington Hotel Reviews

The Williams Inn

10/10 Excellent

"Great place. Would love to have a swimming pool for lap swimming"

Willows Motel Williamstown

10/10 Excellent

"Our one-night stay at Willows Motel was very pleasant. The staff/managers/owners were friendly and helpful, our room was comfortable and clean. We were easily able to control the temperature with up-to-date air conditioning. The free continental breakfast was healthy and generous, including a plentiful assortment of fruits, nuts, dates, etc. to accompany the cereal, breads, bagels, etc. We also appreciated the well-kept small garden areas around the property. We would choose the Willows Motel again if we are staying in the Williamstown area."

The Porches Inn at Mass MoCA

8/10 Good

"The property is on a busy road. I was glad I asked for a room on the backside of the property. It was disappointing to find there was no coffeemaker in the room. Breakfast was good. There was quite a variety of items. They had coffee, but no decaf coffee. A staff member suggested diluting the regular coffee with water. When you can’t have caffeine that’s not an option. I was glad we stayed there but probably wouldn’t go back."

Hideaway Inn Mt. Snow

10/10 Excellent

"We will definitely return to the Hideaway! We got a text before arrival with our room number and code which was very convenient. The hotel is warm and cozy and beautifully decorated. There is neat stuff to look at everywhere. The 3 floors of common spaces were really cool with a lot to offer, like a water bottle filler and coffee maker. It could use to be cleaned a little more often. When we arrived, the playroom had toys all over the floor and there were sticky drink marks on the bar and crumbs on the coffee table. Someone had crushed the chalk under the dart board and all but 1 of the darts was broken. Regardless, we had a blast playing classic Mario on the arcade game. The living room upstairs was gorgeous, next time we will be sure to use that to play games and maybe watch a movie. We didn’t use the pool because it looked green (we opted to go to the lake instead) but we did make a fire and made s’mores down at one of the fire pits on our second night which was so nice to have. The closet in the hallway to grab towels and such is super convenient and the manager was only a text away if you needed anything. Our room was beautiful and so big. We loved the balcony and the record player in the room was a cool touch my boys had fun listening to. This is a very quiet property with a lot to keep families occupied or just relax and enjoy nature. We had a wonderful stay and when we met the manager she was so sweet! We absolutely loved it and will return for future VT trips."

Find out more about Old Bennington

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Frequently asked questions

Can I find a vacation rental in Old Bennington?

Yes, you can find vacation rentals near the most popular points of interest in Old Bennington, or you can choose a more remote option if you're looking for relaxation.

What are some of the best vacation home rentals in Old Bennington?

24 Acre Southern Vermont Luxury Hilltop Retreat - Private Pool & Panoramic Views: This vacation home rental outside of Old Bennington is located in the mountains and has an outdoor pool, a patio, and air-conditioning to put you at ease in your new surroundings. Make the most of the garden in this rental home to help you unwind.

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

Explore the area and cultural attractions such as Bennington Museum, or visit a family-friendly sight such as Sugar Shack. In the larger area, you’ll find Bennington Battle Monument and Old First Congregational Church.

What’s a vacation rental in Old Bennington like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Old Bennington. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for family trips or small group gatherings.

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Check prices for these dates

Our top choices for Old Bennington vacation rentals

1. Peaceful getaway at birds of a feather

2. Two Brooks Lodge

3. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

4. Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

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

6. Cozy Home in Pownal VT

7. 2-Bdr Apt In Town, By the Water

8. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

9. New Studio In Town, By the Water

10. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

11. Downtown | Waterfront | Walk to Shops

12. Runamuk Farm Camp Tiny House near Cambridge, New York

13. Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views

14. Romantic New York Getaway near the Adirondacks

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

16. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

17. Cozy 3 bedroom condo 2.5 miles to Mount Snow

18. North Getaway Cottage

19. Spacious apartment in beautiful, historic Arlington VT

20. VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

Find vacation rentals that suit your style

Top Old Bennington Hotel Reviews

The Williams Inn

Knotty Pine

Williamstown Motel

Blue Vista Motor Lodge

Willows Motel Williamstown

The White House Inn

Hotel Vervana, Trademark Collection by Wyndham

The Porches Inn at Mass MoCA

Hideaway Inn Mt. Snow

Find out more about Old Bennington

Frequently asked questions

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