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Our top choices for Old Bennington condo rentals




1. Seasons ski-in/ski-out condo with balcony and wood-burning fireplace
Seasons ski-in/ski-out condo with balcony and wood-burning fireplaceDover
8.6 out of 10, Excellent, (37 reviews)
8.6/10
Excellent
(37 reviews)
"Location was fantastic! Great ski-in, ski-out location! Unit itself was very dated but location made up for it."
"Location was fantastic! Great ski-in, ski-out location! Unit itself was very dated but location made up for it."Evan C.
$316 nightly
The price is $357
$357 total
Nov 7 - Nov 8
Total with taxes and fees




2. Cozy 3 bedroom condo 2.5 miles to Mount Snow
Cozy 3 bedroom condo 2.5 miles to Mount SnowWest Dover
9.2 out of 10, Wonderful, (52 reviews)
9.2/10
Wonderful
(52 reviews)
"The place was absolutely relaxing, clean, and one of the best host we’ve ever had an experience with. Will come back!!"
"The place was absolutely relaxing, clean, and one of the best host we’ve ever had an experience with. Will come back!!"Scott S.
$248 nightly
The price is $280
$280 total
Nov 15 - Nov 16
Total with taxes and fees




3. Mountainside Condo - Front-Door Shuttle & Indoor Pool Complex
Mountainside Condo - Front-Door Shuttle & Indoor Pool ComplexDover
9.6 out of 10, Exceptional, (5 reviews)
9.6/10
Exceptional
(5 reviews)
"Property is very clean, beautiful condo and scenery, owner was great and communication was incredible! Highly recommend, great stay!"
"Property is very clean, beautiful condo and scenery, owner was great and communication was incredible! Highly recommend, great stay!"Douglas D.
$365 nightly
The price is $413
$413 total
Nov 8 - Nov 9
Total with taxes and fees




4. Mount Snow Fireplace Condo - 5-10 Min Walk to Sundance Lift - Sleeps 8
Mount Snow Fireplace Condo - 5-10 Min Walk to Sundance Lift - Sleeps 8Dover
9.4 out of 10, Exceptional, (23 reviews)
9.4/10
Exceptional
(23 reviews)
"Great location, comfortable and spacious living room and bedrooms. "
"Great location, comfortable and spacious living room and bedrooms. "Emma C.
$481 nightly
The price is $543
$543 total
Nov 9 - Nov 10
Total with taxes and fees




5. Expansive 2BR | Sleeps 10 | Ski-In
Expansive 2BR | Sleeps 10 | Ski-InWest Dover
$536 nightly
The price is $591
$591 total
Nov 9 - Nov 10
Total with taxes and fees




6. 2BR Loft With Views | Ski-In Access
2BR Loft With Views | Ski-In AccessWest Dover
$578 nightly
The price is $637
$637 total
Nov 9 - Nov 10
Total with taxes and fees
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.
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.
Learn more about Old Bennington
Explore attractions like Old First Congregational Church and Bennington Museum as you discover things to see and do in Old Bennington.

Photo by Justin Hunter
Open Photo by Justin Hunter
Top reviews in Old Bennington




Harwood Hill Motel
Harwood Hill MotelBennington
10/10 Excellent
We stayed here for one overnight while visiting the area. The hotel was just what we were looking for - affordable, clean, great location. There is a restaurant right next door and an apple picking orchard across the street. Easy 5-10 minute drive to a few other restaurants and about 30 minutes from Manchester with great shopping and hiking. The free breakfast in the morning was also great. I would recommend it!
We stayed here for one overnight while visiting the area. The hotel was just what we were looking for - affordable, clean, great location. There is a restaurant right next door and an apple picking orchard across the street. Easy 5-10 minute drive to a few other restaurants and about 30 minutes from Manchester with great shopping and hiking. The free breakfast in the morning was also great. I would recommend it!
Allison




Cozy Corner Motel
Cozy Corner MotelWilliamstown
10/10 Excellent
Safe, clean and quiet - everything one would wish.
And, a delicious waffle breakfast.
Safe, clean and quiet - everything one would wish.
And, a delicious waffle breakfast.
Henry




Hampton Inn Bennington
Hampton Inn BenningtonBennington
10/10 Excellent
Very impressed with evening and overnight staff. Only issue is pillows way too soft. Breakfast was good. Impressed.
Very impressed with evening and overnight staff. Only issue is pillows way too soft. Breakfast was good. Impressed.
Andrrw




Maple Terrace Motel
Maple Terrace MotelWilliamstown
10/10 Excellent
Arrived late after office closed. Easy arrangements for check in made with no issues. Light in room was on to welcome me. Room was very clean with nice appointments of water, coffee, tea, chocolates.
Arrived late after office closed. Easy arrangements for check in made with no issues. Light in room was on to welcome me. Room was very clean with nice appointments of water, coffee, tea, chocolates.
Eric




The Villager Motel
The Villager MotelWilliamstown
10/10 Excellent
Extremely clean room. This is not a high end room, but I would not expect that for what I paid. The room was clean, well appointed, and all of the furniture was in great shape. I was very pleased.
Extremely clean room. This is not a high end room, but I would not expect that for what I paid. The room was clean, well appointed, and all of the furniture was in great shape. I was very pleased.
Anonymous traveler




Willows Motel Williamstown
Willows Motel WilliamstownWilliamstown
10/10 Excellent
This motel is in a convenient location for visiting Williams College. Rooms are clean and the mattresses are very comfortable. They have the largest TV screens I've seen in any motel. Their Continental breakfast is extensive with a variety of pastries, breads, and beverages. The staff is kind, caring, helpful, and accommodating.
This motel is in a convenient location for visiting Williams College. Rooms are clean and the mattresses are very comfortable. They have the largest TV screens I've seen in any motel. Their Continental breakfast is extensive with a variety of pastries, breads, and beverages. The staff is kind, caring, helpful, and accommodating.
Sandra




Hotel Vervana, Trademark Collection by Wyndham
Hotel Vervana, Trademark Collection by WyndhamBennington
10/10 Excellent
Wonderful Inn. Friendly staff! Friendly Dog greets you at the door!
Wonderful Inn. Friendly staff! Friendly Dog greets you at the door!
Lisa




Inn At Mount Snow
Inn At Mount SnowWest Dover
10/10 Excellent
Our overnight stay was excellent! Spacious, clean room with a comfortable bed. Very nice breakfast choices in the morning, Keurig machine for all other hours. Large community room with a pool table, comfortable seatings and games to play; would be great for a family gathering. A deck with a view on Snow Mountain. Staff was very accommodating. Easy check-in; we are planning to return.
Our overnight stay was excellent! Spacious, clean room with a comfortable bed. Very nice breakfast choices in the morning, Keurig machine for all other hours. Large community room with a pool table, comfortable seatings and games to play; would be great for a family gathering. A deck with a view on Snow Mountain. Staff was very accommodating. Easy check-in; we are planning to return.
Peter




The Four Chimneys Inn
The Four Chimneys InnBennington
10/10 Excellent
Conveniently located. Breakfast was delicious. Extremely clean and nicely decorated.
Conveniently located. Breakfast was delicious. Extremely clean and nicely decorated.
Randall




New Englander Inn Bennington
New Englander Inn BenningtonBennington
10/10 Excellent
We enjoyed our stay at this Hotel. The experience began at check-in. The person checking in (I think his name was Dustin) was very personable, efficient and professional. During our stay he also provided helpful suggestions for restaurants in town and updates on potential ski areas. The breakfast was well provisioned and fresh. The room was clean and quiet. Nice hot and powerful shower.
We enjoyed our stay at this Hotel. The experience began at check-in. The person checking in (I think his name was Dustin) was very personable, efficient and professional. During our stay he also provided helpful suggestions for restaurants in town and updates on potential ski areas. The breakfast was well provisioned and fresh. The room was clean and quiet. Nice hot and powerful shower.
NEIL




Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection HotelNorth Adams
10/10 Excellent
Great place!
Great place!
Ann




South Shire
South ShireBennington
10/10 Excellent
Lovely place. Great room. Nice breakfast. Convenient to nearby restaurants.
Lovely place. Great room. Nice breakfast. Convenient to nearby restaurants.
Jeffrey




Brittany Motel
Brittany MotelManchester Center
10/10 Excellent
Had a lovely experience with the hotel. it was clean and tidy and ready for us when we got there. There was some issued with a neighbor on our last night that woke us up but the property managers checked in and even gave us a small refund for the trouble. Would stay here again!
Had a lovely experience with the hotel. it was clean and tidy and ready for us when we got there. There was some issued with a neighbor on our last night that woke us up but the property managers checked in and even gave us a small refund for the trouble. Would stay here again!
Heaven




Fairfield Inn & Suites by Marriott Williamstown
Fairfield Inn & Suites by Marriott WilliamstownWilliamstown
10/10 Excellent
The staff were all friendly and the hotel was clean and fresh!
The staff were all friendly and the hotel was clean and fresh!
Diane




The Porches Inn at Mass MoCA
The Porches Inn at Mass MoCANorth Adams
10/10 Excellent
Absolutely lovely. Bed was super comfortable, staff was friendly and helpful, lots of places to sit and relax. Easy walk to restaurants and across the street from the MOCA. Nice breakfast and you can even get a drink and a snack in the evening if you want. The sauna, whirlpool and heated pool at the end of October we a pleasant surprise.
Absolutely lovely. Bed was super comfortable, staff was friendly and helpful, lots of places to sit and relax. Easy walk to restaurants and across the street from the MOCA. Nice breakfast and you can even get a drink and a snack in the evening if you want. The sauna, whirlpool and heated pool at the end of October we a pleasant surprise.
Stacey
