Hawley Holiday Rentals

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Holiday Rentals 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

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

3.0 star property
8.6 out of 10, Excellent, (1750)
"Nice and quiet family get a way"
The price is NZ$382
includes taxes & fees
1 Jan - 2 Jan 2025
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is NZ$367
includes taxes & fees
1 Jan - 2 Jan 2025
Jiminy Peak Mountain Resort

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 NZ$395
includes taxes & fees
30 Dec - 31 Dec
Berkshire Village Carriage House - Super Private!!

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

8.8 out of 10, Excellent, (43)
"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Cozy apartment located in quiet Williamsburg

9.4 out of 10, Exceptional, (47)
"Convenient location, comfortable."
The price is NZ$455
includes taxes & fees
4 Jan - 5 Jan 2025
Cozy apartment located in quiet Williamsburg

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

10.0 out of 10, Exceptional, (40)
"We enjoyed our stay at the tiny home!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Bear Creek Cabin

9.8 out of 10, Exceptional, (22)
"It was beautiful to wake up the first morning to see freshly fallen snow! Easy to get to, lots for the kids to do, wonderful place to share with my family for Thanksgiving! Only thing that I would change is having wood in the wood holder by the stove so that we didn’t have to carry it in. Would recommend to others. "
The price is NZ$1,059
includes taxes & fees
30 Dec - 31 Dec
Bear Creek Cabin

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

Berkshire Lake access

10.0 out of 10, Exceptional, (49)
"The house worked was exceptionally clean and worked great for us. The landowner was exceptionally helpful in providing suggestions. We loved visiting the Norman Rockwell Museum and walking around Lenox. Thanks for everything!"
Berkshire Lake access

Jacksonville Cabin w/ Wraparound Deck & Views

9.6 out of 10, Exceptional, (27)
"We enjoyed our stay. Everything was clean. The only thing I would suggest is checking the stairs to the basement. "
Jacksonville Cabin w/ Wraparound Deck & Views

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!

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

Mountainside Condo Ski In Ski Out

9.0 out of 10, Wonderful, (21)
"Stay at Jiminey for the 13 nights. Condo was clean and had anything you could ever need! "
The price is NZ$333
includes taxes & fees
20 Jan - 21 Jan 2025
Mountainside Condo Ski In Ski Out

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!

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

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

10.0 out of 10, Exceptional, (23)
"My partner and I really enjoyed our relaxing stay at this quaint cottage. It was clean, comfortable, and tucked away in a very quiet area. It was easy to get to restaurants and theaters in Pittsfield / Lenox / Stockbridge. The hot tub was also a great way to spend a cozy fall afternoon!"
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Spectacular Mountain views with all the amentities nearby

9.8 out of 10, Exceptional, (51)
"What a wonderful place to stay!! We were in town for my 50th high school reunion, hadn’t been back to the area in 35 years. Our accommodations enhanced a beautiful weekend, and the foliage was the cherry on top! Spacious, clean, tastefully furnished and decorated. Well equipped with every utensil, and kitchen appliance you could need! Comfy bed, great shower & good water pressure too! Secluded and quiet, but very convenient to Bernardston, Northfield and Greenfield as well as I-91. Highly...
Spectacular Mountain views with all the amentities nearby

Cozy Treetop Hideaway Near Harriman Reservoir!

9.2 out of 10, Wonderful, (12)
"Not as depicted You do not have access to the lake from The property The trees in the summer obscure the view of the lake Well equipped for bbq and games Dog friendly AC in the bedrooms would be ideal for sleeping as it was very humid this weekend"
Cozy Treetop Hideaway Near Harriman Reservoir!
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 types of properties in Hawley you may be interested in

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

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1002)
"Great check in experience. "
The price is NZ$192
includes taxes & fees
7 Jan - 8 Jan 2025
The Yankee, Trademark Collection by Wyndham

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3.0 star property
8.0 out of 10, Very good, (703)
"Staff was very accommodating. The pool area was quite nice and it was deep"
The price is NZ$196
includes taxes & fees
5 Jan - 6 Jan 2025
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
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.

Frequently asked questions

Can I find holiday rentals in Hawley?

Yes, there are holiday rentals close to the most popular sights in Hawley, or you can select a more secluded option if you're looking for a relaxing stay. Hawley is known for its parks.

What are some of the best holiday rentals that Hawley has to offer?

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort: This highly rated holiday home rental in Hawley is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Hawley?

With 5 Expedia holiday rentals, you're guaranteed to find just the right place for your Hawley stay.

What’s there to see and do in Hawley?

Mohawk Trail State Forest and Swift River are a couple of lovely local spots to get outside and enjoy nature. Hawley Bog Preserve and Zoar Outdoor/Deerfield Valley Canopy Tours are a couple of places you'll find in the wider area.

What’s a holiday rental in Hawley like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Hawley. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy front desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for a small group gathering.