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Compare 451 Vacation Homes in Readsboro with updated reviews, rates, and availability.

Dog-friendly chalet cabin with valley view, deck, and private hot tub

7.6 out of 10, Good, (17)
"The cabin was the perfect weekend getaway. We had issues with connecting the projector to the internet and finally gave up on trying to connect but other then that the overall experience was great. Will be staying here again in the future. "
Dog-friendly chalet cabin with valley view, deck, and private hot tub

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

9.6 out of 10, Exceptional, (40)
"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

Cozy Home In The Berkshires, Pet Friendly with fenced in yard!

10.0 out of 10, Exceptional, (105)
"We really enjoyed our stay at Julie’s home. We will definitely to look to stay here again the next time we visit the area. Highly recommended! "
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

10.0 out of 10, Exceptional, (49)
"We loved this property with stunning foliage, hiking trails, and perfect views. The house had everything we needed to accommodate a large group and more with lots of thoughtful touches. Plenty of space, panoramic views, screened in porch, fireplace, pool table, and connected speakers throughout. We have stayed at many different rentals for our annual trip over the years and this one is our new favorite."
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Sunny Stratton Townhome ~ 1 Mi to Skiing!

10.0 out of 10, Exceptional, (4)
"Wonderful and clean townhome! Perfect location to be close to Stratton Resort. Thank you!"
Sunny Stratton Townhome ~ 1 Mi to Skiing!

New Chalet mins to Mt with Hot tub

10.0 out of 10, Exceptional, (3)
"Beautiful house with plenty of space. Very comfortable and stocked with all essentials. Great set up for kids!"
New Chalet mins to Mt with Hot tub

Walk to Ski Lift: Spacious Condo in West Dover!

2.0 star property
Walk to Ski Lift: Spacious Condo in West Dover!

West Dover Townhome Near Mount Snow Shuttle Stop!

2.0 star property
West Dover Townhome Near Mount Snow Shuttle Stop!

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

7.8 out of 10, Good, (41)
"Can't beat the location. We had a great stay."
The price is SAR 293
SAR 1,032 total
includes taxes & fees
4 Dec - 5 Dec
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

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

10.0 out of 10, Exceptional, (39)
"We had a group of nine and had a great time. There are so many wonderful features including a fully stocked kitchen, activities for kids and an awesome outdoor area to hang out and relax. Would highly recommend this house. "
The price is SAR 972
SAR 2,639 total
includes taxes & fees
16 Dec - 17 Dec
Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun

Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

10.0 out of 10, Exceptional, (209)
"Clean and well supplied with fantastic views and close proximity to town.....a wonderful fall New England experience! "
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

Shuttle or walk to village and lifts! The Powder Haus Chalet!

10.0 out of 10, Exceptional, (32)
"Great place to stay with proximity to Stratton and the walking trail. Easy to find & plenty of amenities in the house. The owners were extremely responsive of questions and provided great details of the property."
Shuttle or walk to village and lifts! The Powder Haus Chalet!

Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16

10.0 out of 10, Exceptional, (21)
"The property is exactly as described! We loved the proximity to the mountain. The house is adorable and perfectly suited for our family. The host was VERY responsive and had great customer service during our stay. We can not wait to come back again!"
Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16

Dog-friendly cabin in the woods with firepit - ski & golf at nearby mountains

9.0 out of 10, Wonderful, (67)
"My husband and i enjoyed our stay. The cabin was very clean and comfortable. We would definitely rent it again."
Dog-friendly cabin in the woods with firepit - ski & golf at nearby mountains

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. "
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat

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

1810 Brook Side Mill/House / EV Level 2 Charging on Site

10.0 out of 10, Exceptional, (68)
"This is our 3rd time staying here, we love this historic home, it is in very good condition. The home is very clean, well stocked, the layout is very good and the communication with the host is also very good. We love the brook going by. It is close to Smith College where our daughter goes to school. We also enjoy the many other places and things to do in this area. Even after our daughter graduates I can see us coming back to this home and part of Massachusetts. "
1810 Brook Side Mill/House / EV Level 2 Charging on Site

Secluded Vermont Retreat w/ 25 Acres to Explore--Dog Heaven! Mountain Views!

9.8 out of 10, Exceptional, (110)
"Every need accommodated including a back-up generator! Well appointed kitchen and bathrooms. Very cozy and spacious home inside. Very comfortable bed mattress in master bedroom. Lots of yard for dogs to run free. Nature all around. Lots of books and board games there. Laundry room was a big plus. Remote setting but lots to see and explore within reach. Very lovely stay and hosts were very responsive."
Secluded Vermont Retreat w/ 25 Acres to Explore--Dog Heaven! Mountain Views!

SPACIOUS Mountain Retreat with HOT TUB, Fire Pit & Hiking Trails

10.0 out of 10, Exceptional, (5)
"We did have a team member slip and fall on the bottom step. He was just bruised up but a safety tread might not be a bad idea"
SPACIOUS Mountain Retreat with HOT TUB, Fire Pit & Hiking Trails

Modern Mountain Retreat w/ Easy Walk to Mount Snow: Balcony-Fireplace-Loft-Pets

10.0 out of 10, Exceptional, (11)
"If you are looking for either Fall getaway along VT-100 or snow adventures this place is located with easy access to a variety of wonderful local restaurants, breweries, shopping and outdoor adventures. Bathroom and kitchen stocked with basic necessities. Great communication with hosts. Will definitely be back! "
The price is SAR 1,048
SAR 2,308 total
includes taxes & fees
24 Nov - 25 Nov
Modern Mountain Retreat w/ Easy Walk to Mount Snow: Balcony-Fireplace-Loft-Pets
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 Readsboro

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1746)
"The pool/clubhouse was a bit chaotic but the overall experience of this location was fantastic. It was lovely."
The price is SAR 634
SAR 733 total
includes taxes & fees
24 Nov - 25 Nov
Vacation Village in the Berkshires

Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill

9.6 out of 10, Exceptional, (54)
"This was our second visit to the chalet. It was just as wonderful as the first time. The chalet is incredibly cute and cozy. It's location is perfect for a quiet getaway, while also being very close to downtown Wilmington and many hiking trails. I would highly recommend!"
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very Good, (72)
"The unit was perfect for our ski race weekend. Very accessible, underground parking included (ski boxes on top of SUVs will not fit - thankfully we left ours at home), really nice place with everything we needed!"
The price is SAR 1,218
SAR 1,507 total
includes taxes & fees
25 Nov - 26 Nov
Long Trail House at Stratton 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.