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Compare 41 Cottages in Hawley with updated reviews, rates, and availability.

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.8 out of 10, Excellent, (46)
"The cabin is cozy and sweet- we have a dog and small family and wanted to ski at Mt Snow. Cabin is short 20 minute drive to ski. Super cute town of Wilmington just a few minutes away. Go to Dots or Alpen Glow! Shaws grocery 2 minutes away. House has Pottery Barn vibes. Decent sized kitchen sitting and dining area. 2Bedroom 2 bath. This is not a house for a large crew but for a family getaway it was perfect. Street is quiet and residential. Neighbors seem really friendly. We would love to come...
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (107)
"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

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (187)
"Thank you for sharing your wonderful home! It had everything we needed including a quiet, peaceful, private, beautiful location, comfortable bed, great books!!, and a well equipped kitchen. We are very grateful you had availability for our Thanksgiving visit with family. Thank you!!"
The Clearing - Quiet - Close To Nature

Cozy Berkshire cottage with fireplace.

10.0 out of 10, Exceptional, (24)
"Very good! Enjoyed every moment once we got the thermostat set to the right temp for us. Clean and cozy!"
Cozy Berkshire cottage with fireplace.

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!

9.4 out of 10, Exceptional, (21)
"Everything was just like it was listed. We had trouble with the t.v. but other than that it was great. "
Picturesque Cottage with Sunroom on Ashmere Lake!

Rare new Home on Lake Whitingham. Semi-priv beach

10.0 out of 10, Exceptional, (1)
"This home is spectacular, built on a hillside overlooking a pond. Very tastefully built into the landscape. Inside was very well appointed and plenty of room for our family. Three bathrooms was a big plusCould have spent the entire day lookjng out the windows"
Rare new Home on Lake Whitingham. Semi-priv beach

Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We had a truly wonderful stay. The cottage and property are beautiful, peaceful and very special. Great views! Our host thought of everything, it's very comfortable and lovely. Best place to stay in Southern Vermont! Don't miss the Tiny Bread Box on Saturdays; it's just up the road. We'll defiantly be back for another visit."
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!

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

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

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!

Jacksonville Cabin w/ Wraparound Deck & Views

3.0 star property
Jacksonville Cabin w/ Wraparound Deck & Views

Luxury Vacation Rental in the Berkshires!

3.0 star property
Luxury Vacation Rental in the Berkshires!

Near Hiking & Skiing: Home in Wilmington!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Owner Brent was helpful and quick to respond to questions. The house is near Mount Snow great for skiing! Very nice place to stay, we will definitely stay again when booking for next year."
Near Hiking & Skiing: Home in Wilmington!

Wilmington Vacation Rental Near Hiking and Skiing!

3.0 star property
Wilmington Vacation Rental Near Hiking and Skiing!

Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!

3.0 star property
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!

'john's Farmhouse in Mount Snow' on 120 Acres!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful home. Great for a family get away. Hosts were top notch. I stay in rentals all the time for work and this was great. I will bring my grand kids next time. "
'john's Farmhouse in Mount Snow' on 120 Acres!

Picturesque Cottage With Sunroom on Ashmere Lake!

3.0 star property
Picturesque Cottage With Sunroom on Ashmere Lake!

Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!

3.0 star property
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!

Entire cottage in Berkshire Villiage

3.0 star property
9.4 out of 10, Exceptional, (3)
"The cottage was clean and as described. The street was very quiet."
Entire cottage in Berkshire Villiage
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 Hawley

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

9.6 out of 10, Exceptional, (127)
"A cozy spot to watch the snow come down!"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1786)
"It was very nice. Had a kitchen and 2 tvs!"
The price is AED 400
AED 476 total
includes taxes & fees
13 Mar - 14 Mar
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (925)
"Staff was exceptionally helpful and friendly."
The price is AED 547
AED 600 total
includes taxes & fees
1 Apr - 2 Apr
Jiminy Peak Mountain Resort
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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