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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, (234)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is AED 551
AED 833 total
includes taxes & fees
12 Jan - 13 Jan
Berkshire Village Carriage House - Super Private!!
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

9.6 out of 10, Exceptional, (21)
"Our family had a wonderful stay. The house was very comfortable and the owner was very responsive. The sound of the river right outside was delightful! The bathrooms are very nicely updated - a nice perk when staying in an older home. "
Charlemont Retreat on Chickley River w/ EV Charger
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 AED 430
AED 1,062 total
includes taxes & fees
13 Jan - 14 Jan
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
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!
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, (2)
"Mid century Mod funtional house. Looks exactly as pictures. Attentive Host. Comfortable beds and furnishings. Secluded location .Must have 4x4 to get up driveway in winter!!! Yes would highly recommend and hope to be back soon!"
The price is AED 1,267
AED 2,984 total
includes taxes & fees
12 Jan - 13 Jan
The dreamiest place in Southern Vermont!
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
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, (42)
"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
Wilmington Vacation Rental Near Hiking and Skiing!
Wilmington Vacation Rental | 4BR | 2BA | 1,336 Sq Ft | Stairs Required

Wilmington Vacation Rental Near Hiking and Skiing!

9.0 out of 10, Wonderful, (16)
"Everything was as-advertised! Very happy with our stay!"
Wilmington Vacation Rental Near Hiking and Skiing!
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, (28)
"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!
Hearts Desire is a furnished whole house in a small, colorful garden center.
Exterior

Hearts Desire is a furnished whole house in a small, colorful garden center.

10.0 out of 10, Exceptional, (86)
"Simply fantastic!"
Hearts Desire is a furnished whole house in a small, colorful garden center.
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, (126)
"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
Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.
Living area

Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

9.4 out of 10, Exceptional, (6)
"Location is minutes away from town. Location was easy to find. House was very clean and had all that we needed. Perfect size for our group of 5 adults, each having our own bedroom. We found plenty to do in the area. Jane was very helpful giving us information of things to do, especially being a girl's weekend, she informed us of spas, shopping and great spots to see foliage, and nice restaurant nearby that had music. Would definitely stay here again."
Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.
Gorgeous Lake Ashmere Home with Private Hot Tub & Lake Views, Screened Porch

Gorgeous Lake Ashmere Home with Private Hot Tub & Lake Views, Screened Porch

10.0 out of 10, Exceptional, (18)
"What a great place to share the Thanksgiving holiday with love ones! The setting is beautiful and was very comfortable."
Gorgeous Lake Ashmere Home with Private Hot Tub & Lake Views, Screened Porch
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!
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Comfortable New Decor in Living Room Equipped w Smart TV and Deck

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

10.0 out of 10, Exceptional, (63)
"It was an amazing stay. The host was very proactive and helpful. "
The price is AED 1,153
AED 2,205 total
includes taxes & fees
12 Jan - 13 Jan
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
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

9.6 out of 10, Exceptional, (21)
"Our family had a wonderful stay. The house was very comfortable and the owner was very responsive. The sound of the river right outside was delightful! The bathrooms are very nicely updated - a nice perk when staying in an older home. "
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, (1754)
"We always come back to Vacation Village! We love the space and area."
The price is AED 689
AED 792 total
includes taxes & fees
12 Jan - 13 Jan
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.