Old Bennington Holiday Rentals, Bennington: Private House Rentals

A statue with outstretched arms and a tall obelisk in the background.

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Waterpark

Hot tub

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Our top choices for Old Bennington hotels

Signature Room, King plus Twin Bed, Private Bathroom, Porch, Accessible, RM-10 | Premium bedding, iron/ironing board, free WiFi, individually decorated

1. The Four Chimneys Inn

Bennington

Jeane

฿8,460

฿9,221 total

includes taxes & fees

18 Aug - 19 Aug

Desk, blackout curtains, iron/ironing board, travel cot

2. Hampton Inn Bennington

Bennington

James

฿5,674

฿6,184 total

includes taxes & fees

23 Aug - 24 Aug

In-room safe, blackout curtains, iron/ironing board

3. New Englander Inn Bennington

Bennington

"We booked for two nights at this hotel and our experiences were mixed. The free EV charging station was the best and it was convenient and right onsite. Breakfast was good. However, the hotel needed a lot of improvements in maintenance, the ice machine was out of order so we had to go to the nearby store to get ice, we saw a cockroach in the bathroom and a piece of tile was missing on the shower wall. Apparently this hotel has been operated by different names, it was Best Western, now it’s New...

William

฿3,487

฿3,801 total

includes taxes & fees

13 Sept - 14 Sept

Deluxe Room, 1 King Bed, Non Smoking, Jetted Tub | Premium bedding, desk, blackout curtains, free WiFi

Room, 2 Queen Beds, Non Smoking, Balcony | Premium bedding, desk, blackout curtains, free WiFi

Deluxe Room, 1 King Bed, Non Smoking | Premium bedding, desk, blackout curtains, free WiFi

4. Hotel Vervana, Trademark Collection by Wyndham

Bennington

John

฿3,630

฿3,957 total

includes taxes & fees

30 Aug - 31 Aug

Room, 2 Double Beds, Non Smoking | Iron/ironing board (on request), cots/infant beds, free WiFi

5. Bennington Motor Inn

Bennington

schuyler

฿3,114

฿3,394 total

includes taxes & fees

16 Aug - 17 Aug

Signature Studio | Private kitchen | Fridge, microwave

6. Knotty Pine

Bennington

Barbara

฿3,605

฿3,930 total

includes taxes & fees

17 Aug - 18 Aug

7. South Shire

Bennington

Jan

฿6,860

฿7,839 total

includes taxes & fees

16 Aug - 17 Aug

8. Starlight Inn

Bennington

Jeremia

฿3,284

฿3,579 total

includes taxes & fees

16 Aug - 17 Aug

Hypo-allergenic bedding, desk, laptop workspace, blackout curtains

9. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Victoria

฿4,635

฿5,177 total

includes taxes & fees

3 Sept - 4 Sept

10. Cozy Corner Motel

Williamstown

Jeremy

฿2,920

฿3,432 total

includes taxes & fees

13 Sept - 14 Sept

Desk, iron/ironing board (on request), cots/infant beds, free WiFi

11. Willows Motel Williamstown

Williamstown

Richard

฿3,428

฿3,829 total

includes taxes & fees

18 Aug - 19 Aug

12. The Williams Inn

Williamstown

Thomas

฿8,414

฿9,398 total

includes taxes & fees

20 Aug - 21 Aug

13. Fairfield Inn & Suites by Marriott Williamstown

Williamstown

hui

฿6,687

฿7,470 total

includes taxes & fees

7 Sept - 8 Sept

14. West Road Motel

Bennington

Creed

฿3,277

฿3,572 total

includes taxes & fees

14 Aug - 15 Aug

Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, pool loungers

15. Maple Terrace Motel

Williamstown

Christine

฿4,142

฿4,627 total

includes taxes & fees

8 Sept - 9 Sept

Double Room | Desk, iron/ironing board, rollaway beds, free WiFi

16. The Villager Motel

Williamstown

Rebecca

฿2,946

฿3,291 total

includes taxes & fees

1 Sept - 2 Sept

Desk, iron/ironing board, free cots/infant beds, free rollaway beds

17. Howard Johnson by Wyndham Williamstown

Williamstown

Donna

฿3,641

฿4,067 total

includes taxes & fees

24 Aug - 25 Aug

18. The White House Inn

Wilmington

Eleana

฿7,786

฿8,565 total

includes taxes & fees

16 Aug - 17 Aug

19. Williamstown Motel

Williamstown

Robert

฿3,608

฿4,031 total

includes taxes & fees

7 Sept - 8 Sept

Family Room | Premium bedding, free WiFi, bed sheets

Double or Twin Room - King with Deck | Premium bedding, free WiFi, bed sheets

20. Chalet 239

West Dover

Patrick

฿3,773

฿4,151 total

includes taxes & fees

23 Aug - 24 Aug

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Stay near popular Old Bennington attractions

Bennington Battle Monument

9.0/10 (202 reviews)

After visiting Bennington Battle Monument, make a plan to see the other sights and activities in Old Bennington. Discover the cafes and its art scene while you're in the area.

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Bennington Museum

9.0/10 (50 reviews)

You can spend an afternoon exploring the galleries in Bennington Museum during your travels in Old Bennington. Discover the area's mountain views and cafes.

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Old First Congregational Church

9.6/10 (12 reviews)

Find out about the history of Old Bennington when you spend time at Old First Congregational Church. In the area, take in the art scene and mountain views.

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Learn more about Old Bennington

Venture to sights like Bennington Museum and Old First Congregational Church as you discover Old Bennington.

See all hotels in Old Bennington

A tall, narrow obelisk with a pointed top, surrounded by trees and a clear blue sky.

Top Old Bennington Hotel Reviews

Inn At Mount Snow

10/10 Excellent

"This was such a delightful treat. The property is renovated and every room is beautifully decorated yet unique. The common areas are beautiful and offer every small detail you could want. From fresh cookies, s'mores kits, bonfire kits, board games and a record player with plenty of musical choices. This property offers free breakfast daily. The breakfast was delicious with fresh granola, muffins, cereal, fruit, and yogurt. The innkeepers are friendly and helpful. They live on the property and are available if you need anything. The views from the property are spectacular. I would highly recommend this property and look forward to staying here again."

Hideaway Inn Mt. Snow

8/10 Good

"The rooms are small."

Howard Johnson by Wyndham Williamstown

10/10 Excellent

"All good"

New Englander Inn Bennington

8/10 Good

"Stairwell needs cleaning, but very comfortable and good value for the price."

Fairfield Inn & Suites by Marriott Williamstown

8/10 Good

"We have stayed before and will stay again!"

Brittany Motel

10/10 Excellent

"We enjoyed our stay at this hotel. It is a little older but still in good condition. It was very clean! The staff was extremely responsive to any questions or needs that we had. We loved the little snack book and having coffee in the morning was great."

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Nice!"

The Williams Inn

10/10 Excellent

"The dinner we had was very good, excellent bar, great wait staff. On the whole it was very satisfying. "

The Porches Inn at Mass MoCA

10/10 Excellent

"Great & comfortable place, good staff. Free (simple) breakfast! A pool, hot tub. And the incredible Mass Moca right there. Our second time here, & we’ll be back."

More cheap stays in Old Bennington

Brittany Motel

1056 Main Street/Historic Route 7A Manchester Center VT

฿3,013

฿3,314 total

24 Aug - 25 Aug

includes taxes & fees

New Englander Inn Bennington

220 Northside Drive Bennington VT

฿3,487

฿3,801 total

13 Sept - 14 Sept

includes taxes & fees

7.6/10 Good! (989 reviews)

Willows Motel Williamstown

480 Main St Williamstown MA

฿3,428

฿3,829 total

18 Aug - 19 Aug

includes taxes & fees

9/10 Wonderful! (1,000 reviews)

Knotty Pine

130 Northside Dr Bennington VT

฿3,605

฿3,930 total

17 Aug - 18 Aug

includes taxes & fees

Hotel Vervana, Trademark Collection by Wyndham

141 West Main Street Bennington VT

฿3,630

฿3,957 total

30 Aug - 31 Aug

includes taxes & fees

8.2/10 Very good! (1,000 reviews)

Howard Johnson by Wyndham Williamstown

213 Main St Williamstown MA

฿3,641

฿4,067 total

24 Aug - 25 Aug

includes taxes & fees

6.6/10 (931 reviews)

Frequently asked questions

Where is the best place for a stay in Old Bennington?

Based on our traveller data, The Four Chimneys Inn is one of the top choices for your stay. This B&B is a short 1-minute walk from Green Mountain National Forest, and it offers free breakfast and free parking. Other good choices for your visit to the area are Hotel Vervana, Trademark Collection by Wyndham and Hotel Downstreet, an Ascend Collection Hotel. See all available top hotels, or vacation rentals in Old Bennington.

If I need to cancel my hotel reservation in Old Bennington, will I receive a refund?

Yes! The majority of room reservations are refundable provided that you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If your reservation is non-refundable, it might still be possible to cancel it and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Old Bennington.

How is it staying in Old Bennington?

Visitors will definitely enjoy all that Old Bennington has to offer. There are 1006 hotels and other accommodation options in the surrounding area. Find out more about Old Bennington.

What are the top places to visit in Old Bennington?

A couple of favourite places to visit are Bennington Museum and Old First Congregational Church. You'll also find Hemmings Motor News Car Lover's Convenience Store & Vehicle Display and Prospect Mountain Nordic Ski Center in the area. Take a look at what more there is to see and do in Expedia's Old Bennington guide.

What's the weather like in Old Bennington?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Old Bennington are January, March, February and December, with each month seeing an average of 21 cm of snowfall.

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Book Hotels in Old Bennington on Expedia.com

Find hotels in Old Bennington, VT from ฿3,291

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Old Bennington

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Old Bennington hotels

1. The Four Chimneys Inn

2. Hampton Inn Bennington

3. New Englander Inn Bennington

4. Hotel Vervana, Trademark Collection by Wyndham

5. Bennington Motor Inn

6. Knotty Pine

7. South Shire

8. Starlight Inn

9. Hotel Downstreet, an Ascend Collection Hotel

10. Cozy Corner Motel

11. Willows Motel Williamstown

12. The Williams Inn

13. Fairfield Inn & Suites by Marriott Williamstown

14. West Road Motel

15. Maple Terrace Motel

16. The Villager Motel

17. Howard Johnson by Wyndham Williamstown

18. The White House Inn

19. Williamstown Motel

20. Chalet 239

Stay near popular Old Bennington attractions

Bennington Battle Monument

Bennington Museum

Old First Congregational Church

Learn more about Old Bennington

Top Old Bennington Hotel Reviews

Inn At Mount Snow

Hideaway Inn Mt. Snow

Howard Johnson by Wyndham Williamstown

New Englander Inn Bennington

Fairfield Inn & Suites by Marriott Williamstown

Brittany Motel

Hotel Downstreet, an Ascend Collection Hotel

The Williams Inn

The Porches Inn at Mass MoCA

More cheap stays in Old Bennington

Brittany Motel

New Englander Inn Bennington

Willows Motel Williamstown

Knotty Pine

Hotel Vervana, Trademark Collection by Wyndham

Howard Johnson by Wyndham Williamstown

Frequently asked questions

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