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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 54 Cottages in New Ashford with updated reviews, rates, and availability.

Family-Friendly Richmond Cottage w/ Private Yard
Property grounds

Family-Friendly Richmond Cottage w/ Private Yard

2.0 star property
10.0 out of 10, Exceptional, (4)
"Excellent property: would have liked to stay longer. "
Family-Friendly Richmond Cottage w/ Private Yard
Cozy cottage with pool, walking distance to lake
Outdoor pool

Cozy cottage with pool, walking distance to lake

10.0 out of 10, Exceptional, (14)
"We spent the weekend for a nearby wedding. Great area. The house was clean and had everything you would want. Good communication with the host. Thanks!"
Cozy cottage with pool, walking distance to lake
Charming historic cottage on scenic road to Mt. Greylock
Outdoor dining

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (107)
"It was a very quiet unique place to stay! You get a beautiful place with a lot of history and Good feel! I sent a picture to my dad and he Remembered using those same desks when he was a kid. Very nice weekend."
Charming historic cottage on scenic road to Mt. Greylock
Beachwood Cottage
Beach nearby

Beachwood Cottage

10.0 out of 10, Exceptional, (3)
"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
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
Fridge, microwave, stovetop, dishwasher

4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!

2.0 star property
10.0 out of 10, Exceptional, (1)
"This property was exactly as advertised and was in a safe and private location. The hosts perfectly accommodated our stay and we cannot be more thankful to them for a fully-functional house that was suitable for the adults and children. It was truly a pleasure to stay at this home."
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
Lake Cottage - 15 Minutes to Jiminy Peak Ski Resort, Albany, Troy
Beach nearby, sun loungers

Lake Cottage - 15 Minutes to Jiminy Peak Ski Resort, Albany, Troy

10.0 out of 10, Exceptional, (10)
"Kelly was an amazing host. She was incredibly inviting and friendly. If we needed anything, Kelly was there, ready to help. The house was beautiful and was perfect for a wedding weekend with our bridal party. We highly recommend Kelly and her wonderful house for anyone who wants a relaxing getaway or for a wedding party to stay and get ready for their big day on this beautiful lake."
Lake Cottage - 15 Minutes to Jiminy Peak Ski Resort, Albany, Troy
Lake Views & Dock Access - Pittsfield Cottage!
Outdoor dining

Lake Views & Dock Access - Pittsfield Cottage!

10.0 out of 10, Exceptional, (1)
"This house was more than we could ask for it’s right on the water and has everything you could possibly forget handy! A all around, great place to enjoy nature and spend time with family and friends. Super straightforward didn’t need to ask the host any questions Will be booking here again! "
Lake Views & Dock Access - Pittsfield Cottage!
Picturesque Cottage with Sunroom on Ashmere Lake!
Interior

Picturesque Cottage with Sunroom on Ashmere Lake!

9.4 out of 10, Exceptional, (21)
"Beautiful lake house and ideal for our group of 4 women celebrating our 45th high school reunion. Beautiful lake view and Love that Ozzie’s is just a few miles away. "
Picturesque Cottage with Sunroom on Ashmere Lake!
Cozy Berkshire cottage with fireplace.
Fridge, microwave, oven, stovetop

Cozy Berkshire cottage with fireplace.

10.0 out of 10, Exceptional, (24)
"Very nice house. Owners very helpful."
Cozy Berkshire cottage with fireplace.
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
Dining

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

2.0 star property
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
Plan your Berkshires by the lake
Exterior

Plan your Berkshires by the lake

Plan your Berkshires by the lake
Cottage in the Clouds With Mountain Views
Miscellaneous

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
Bennington Gem w/ Smart TV Near Historic District!
House (1 Bedroom) | Private kitchen | Microwave, oven, stovetop, dishwasher

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!
Charlemont Retreat on Chickley River w/ EV Charger
Interior

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

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
Luxury Vacation Rental in the Berkshires!
TV, fireplace, books

Luxury Vacation Rental in the Berkshires!

3.0 star property
Luxury Vacation Rental in the Berkshires!
Spacious Historic Home in the Berkshires!
TV, fireplace, books

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
Stockbridge Home: Walk to Town Beach!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Stockbridge Home: Walk to Town Beach!

3.0 star property
Stockbridge Home: Walk to Town Beach!
Berkshire Hideaway w/ Fire Pit & Playground!
Interior

Berkshire Hideaway w/ Fire Pit & Playground!

3.0 star property
Berkshire Hideaway w/ Fire Pit & Playground!
Picturesque Cottage With Sunroom on Ashmere Lake!
Interior

Picturesque Cottage With Sunroom on Ashmere Lake!

3.0 star property
Picturesque Cottage With Sunroom on Ashmere 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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Other property types in New Ashford

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1802)
"The property was clean and the staff very accommodated."
The price is AED 418
AED 507 total
includes taxes & fees
6 May - 7 May
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (928)
"Staff was exceptionally helpful and friendly."
The price is AED 493
AED 550 total
includes taxes & fees
4 May - 5 May
Jiminy Peak Mountain Resort
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
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.