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Browse Select New Ashford Cottages

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

2.0 star property
9.0 out of 10, Wonderful, (4)
"Cozy, serene and bucolic waterfront hideaway within driving distance of Tanglewood, Shakespeare & Company, Jacob's Pillow and all the wonderful food and cultural Berkshire gems! Julie and Russ were amazing hosts. Great communication and wonderful restaurant and museum suggestions. Definitely planning another long weekend retreat!"
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (114)
"We had a great stay- no complaints! Very close to Jiminy Peak, where we were skiing, and the house was very comfortable. Thank you!"
Charming historic cottage on scenic road to Mt. Greylock

Bennington Gem w/ Smart TV Near Historic District!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We liked staying at the place as it had good amenities (washer, dryer, dishwasher, fridge with a freezer, fan, inflatable bed, wifi, cable, free parking spots. etc) and a lot of space. Where there is no central AC, it had a window unit which worked well - we had a comfortable stay in mid-July."
Bennington Gem w/ Smart TV Near Historic District!

Entire cottage in Berkshire Villiage

3.0 star property
9.8 out of 10, Exceptional, (6)
"The cottage was clean and as described. The street was very quiet."
Entire cottage in Berkshire Villiage

Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

10.0 out of 10, Exceptional, (7)
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

Charlemont Retreat on Chickley River w/ EV Charger

3.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...
Charlemont Retreat on Chickley River w/ EV Charger

Cozy cottage with pool, walking distance to lake

10.0 out of 10, Exceptional, (15)
"The house was very convenient to anywhere we wanted to go. We even had 5 deer welcome us the first night. House was very comfortable and we loved it."
Cozy cottage with pool, walking distance to lake

Berkshires farm, 30+ guests, 50 acres

2.0 star property
The price is CA $1,477
CA $2,441 total
includes taxes & fees
Oct 1 - Oct 2
Berkshires farm, 30+ guests, 50 acres

Beachwood Cottage

9.6 out of 10, Exceptional, (5)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
Beachwood Cottage

Luxury Vacation Rental in the Berkshires!

3.0 star property
Luxury Vacation Rental in the Berkshires!

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!

Plan your Berkshires by the lake

Plan your Berkshires by the lake

Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

3.0 star property
Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

Expansive Upstate Home w/ Home Theater!

3.0 star property
Expansive Upstate Home w/ Home Theater!

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

3.0 star property
6.0 out of 10, (1)
"I tried to reach out to the contact given regarding some checkout procedures and got zero response. "
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

Modern Home Overlooking Mt. Greylock, Williamstown!

Modern Home Overlooking Mt. Greylock, Williamstown!

Cozy Berkshire cottage with fireplace.

9.8 out of 10, Exceptional, (25)
"Very nice house. Owners very helpful."
Cozy Berkshire cottage with fireplace.

Cottage in the Clouds With Mountain Views

9.4 out of 10, Exceptional, (3)
"A nice place to relax. A bit toasty on warm days but otherwise enjoyed our stay."
Cottage in the Clouds With Mountain Views

Cozy Stockbridge Cabin - Walk to Beach & Lake!

3.0 star property
2.0 out of 10, (1)
Cozy Stockbridge Cabin - Walk to Beach & Lake!

Grandparent’s Cottage 250 steps to the lake

Grandparent’s Cottage 250 steps to the lake
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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Top New Ashford Hotel Reviews

Find out more about New Ashford

Find out more about New Ashford

New Ashford Cottages information

Number of reviews
Accommodation
61 Cottages
Lowest Price
CA $1,477
Highest Price
CA $1,477

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