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Compare 187 Vacation Homes in Hawley with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (232)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is SAR 548
SAR 839 total
includes taxes & fees
30 Dec - 31 Dec
Berkshire Village Carriage House - Super Private!!
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
The house was originally built in 1864 and completely updated in 2009

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

9.8 out of 10, Exceptional, (41)
"This property is stunning. It fit our group of 14 perfectly. There are so many unique details and beautiful furniture. The kitchen was well-stocked for pots/pans/utensils/cleaning supplies which I always appreciate - makes group meals so much easier to manage. Quiet area, would be great all year round depending on what activities you like. Hot tub was a major highlight!"
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
The Jelly Mill-A River Retreat
Green River Cottage. Walk up ramp to enter patio area, lockbox on inside door.

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (43)
"It is a beautiful home with a ton of space (we only had 3 people, but it easily sleeps 6), very clean and well-kept. Our hosts provided everything we needed to make our stay perfect. I also like that the hosts were not overboard with all the rules, as with some other rentals. The hosts were beyond friendly and had excellent communication throughout the whole process. If you are looking for a lovely home with a ton of space to stay while exploring Vermont and Massachusetts, I highly recommend...
The Jelly Mill-A River Retreat
Charlemont Retreat on Chickley River w/ EV Charger
Charlemont Vacation Rental | 4BR | 2BA | 3,000 Sq Ft | Stairs Required

Charlemont Retreat on Chickley River w/ EV Charger

9.4 out of 10, Exceptional, (20)
"We loved the property! Our family, which included 2 very young grandchildren all felt comfortable in this historic home with 2 modern bathrooms. I loved the open kitchen and family rooms, and the original wide plank floors. Plus, we were happy to find toys to entertain the 3 year old. The owners were very gracious and responsive. Visitors should just be aware that the owners' unit shares a common wall with the house. Dog barking and sounds of their kitchen preparation were evident through the...
Charlemont Retreat on Chickley River w/ EV Charger
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Marina

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (10)
"As advertised "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Lovely Secluded Vermont Home: Stocked Pond, Trails, Ski.5 Mins to Williamstown!
Lush woodland setting is private, yet five minutes to Spring Street.

Lovely Secluded Vermont Home: Stocked Pond, Trails, Ski.5 Mins to Williamstown!

9.8 out of 10, Exceptional, (19)
"Such a gorgeous house! We loved walking the nearby trails and how close it was to Williams. Venetia was the best!"
Lovely Secluded Vermont Home: Stocked Pond, Trails, Ski.5 Mins to Williamstown!
Outdoor Enthusiasts Paradise in Beautiful Vermont!
Main Living room - First Floor

Outdoor Enthusiasts Paradise in Beautiful Vermont!

10.0 out of 10, Exceptional, (3)
"This rental property was very clean and spacious. There is air conditioning upstairs and ceiling fans (which is hard to come by in this area). Great location. Highly recommend."
Outdoor Enthusiasts Paradise in Beautiful Vermont!
Plainfield House in a 10,000 acre state forest and private pond
Front lawn for sledding

Plainfield House in a 10,000 acre state forest and private pond

9.6 out of 10, Exceptional, (84)
"Very nice place, clean, great communication. "
Plainfield House in a 10,000 acre state forest and private pond
The dreamiest place in Southern Vermont!
Interior

The dreamiest place in Southern Vermont!

10.0 out of 10, Exceptional, (1)
"This was a great property! Only wish there was a larger fridge/ freezer and ice maker! Otherwise great! We did not get to use the fire pit as we were hardly there but it was great for what we needed."
The price is SAR 1,296
SAR 3,052 total
includes taxes & fees
5 Jan - 6 January 2025
The dreamiest place in Southern Vermont!
Cozy apartment located in quiet Williamsburg
Exterior

Cozy apartment located in quiet Williamsburg

9.4 out of 10, Exceptional, (47)
"Convenient location, comfortable."
The price is SAR 563
SAR 960 total
includes taxes & fees
27 Dec - 28 Dec
Cozy apartment located in quiet Williamsburg
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
View of house as seen from road near the brook

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
Chic Pittsfield Home With A View!

Chic Pittsfield Home With A View!

9.0 out of 10, Wonderful, (9)
"This property was just as shown in the listing and met our needs very well. It was well appointed and had many inviting areas to gather and relax in. The kitchen was well equipped and easy to use. Some very nice touches with closets and bathroom storage areas that made staying there user friendly. "
Chic Pittsfield Home With A View!
Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun
Outdoor spa tub

Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun

10.0 out of 10, Exceptional, (41)
"We stayed for Thanksgiving week. The house was more than big enough for our group of nine. The open kitchen/living room/dining room worked great for preparing and eating Thanksgiving dinner together. My wife identified an issue with the outdoor gas grill; the hosts had the grill replaced quickly and we were able to use it as planned. The hosts were very responsive and helpful. We would definitely stay here again."
Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun
Secluded, Cozy Cabin on 10 Acres of Woods ~16 mi to Slopes & Pet Friendly!
Welcome to our Whitingham Wonderland. Enjoy gas fireplace, smart tv, cozy throws

Secluded, Cozy Cabin on 10 Acres of Woods ~16 mi to Slopes & Pet Friendly!

10.0 out of 10, Exceptional, (26)
"The house was perfect for a group of five of us. The kitchen and grill were great for our culinary needs. Thanks for letting us stay!"
Secluded, Cozy Cabin on 10 Acres of Woods ~16 mi to Slopes & Pet Friendly!
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
Nighttime view

Two Brooks Lodge, Beautiful Waterfront Vermont Retreat

8.8 out of 10, Excellent, (27)
"In town for a long weekend and loved the location. The owner was prompt and very helpful as we made a mistake in booking. FYI, The pictures are great but it’s a bit more rustic than they make it seem. Still, it was great to sit outside and hear the brooks flowing. Very quiet street! Housecleaning was a bit lacking though as there were some huge cobwebs in the corners. That was fine for us as we spend our time in a barn anyway. "
The price is SAR 620
SAR 1,303 total
includes taxes & fees
26 Dec - 27 Dec
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
Charming home with fireplace, game room, full kitchen, gas grill, & balcony

Charming home with fireplace, game room, full kitchen, gas grill, & balcony

7.4 out of 10, Good, (3)
Charming home with fireplace, game room, full kitchen, gas grill, & balcony
Dancing Horse Lodge
Dancing Horse Lodge - Entrance View

Dancing Horse Lodge

9.4 out of 10, Exceptional, (38)
"We had a great stay with our family. Clean and close to where my daughter lives."
Dancing Horse Lodge
Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow
Wonderful place to gather!

Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow

10.0 out of 10, Exceptional, (125)
"We enjoyed living in this beautiful house and spent an amazing vacation! The club house is also great with all the facilities!"
Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow
Beautiful Modern A-Frame in Southern Vermont is The Place To BE!
Welcome! Plenty of space to yourselves to relax and soak in great outdoors!

Beautiful Modern A-Frame in Southern Vermont is The Place To BE!

10.0 out of 10, Exceptional, (76)
"Very cute and quiet location! Cabin has everything ine would need! Plenty of parking, and there are trails throughout the property. Its in the perfect spot, only 18 minutes from town. "
Beautiful Modern A-Frame in Southern Vermont is The Place To BE!
Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..
A full kitchen with almost everything you need to cook your favorite dishes.

Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..

10.0 out of 10, Exceptional, (20)
"Beautiful property with great quality towels, furniture, and amenities. Great views and great location. Would be happy to stay again. "
Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..
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
View of house as seen from road near the brook

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
Charlemont Retreat on Chickley River w/ EV Charger
Charlemont Vacation Rental | 4BR | 2BA | 3,000 Sq Ft | Stairs Required

Charlemont Retreat on Chickley River w/ EV Charger

9.4 out of 10, Exceptional, (20)
"We loved the property! Our family, which included 2 very young grandchildren all felt comfortable in this historic home with 2 modern bathrooms. I loved the open kitchen and family rooms, and the original wide plank floors. Plus, we were happy to find toys to entertain the 3 year old. The owners were very gracious and responsive. Visitors should just be aware that the owners' unit shares a common wall with the house. Dog barking and sounds of their kitchen preparation were evident through the...
Charlemont Retreat on Chickley River w/ EV Charger
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1750)
"Nice and quiet family get a way"
The price is SAR 704
SAR 810 total
includes taxes & fees
5 Jan - 6 January 2025
Vacation Village in the Berkshires
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.