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Compare 74 Cottages in Readsboro with updated reviews, rates, and availability.

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

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
Cross Country Ski? Downhill? Prospect and Mt Snow. Winter wonderland book now.
Skiing open now at Prospect Mountain Snowmobiling coming soon Book now before up

Cross Country Ski? Downhill? Prospect and Mt Snow. Winter wonderland book now.

9.8 out of 10, Exceptional, (132)
"Linda was amazing from beginnin'g to end to ensure a comfortable stay. This house was beautiful and so cozy to stay in. The loft bed had a gorgous view of the lake and snow. Plenty of sleeping room for my kids.They got to play in the snow too:)"
Cross Country Ski? Downhill? Prospect and Mt Snow. Winter wonderland book now.
Charming historic cottage on scenic road to Mt. Greylock
Summer

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (104)
"Great cottage, pretty much at the foot of Mount Greylock - very spacious and comfortable - in the country but close to many of the towns of the Berkshires - the hosts Cheryl and Rich were very kind and informative about the area -thank you Cheryl and Rich - I hope to return sometime -"
Charming historic cottage on scenic road to Mt. Greylock
Perfect for a peaceful get away in clean fresh Vermont air!
Newly sided entire house and garage

Perfect for a peaceful get away in clean fresh Vermont air!

10.0 out of 10, Exceptional, (71)
"Enjoyed the cozy cabin feel. Property was extremely clean and when hit with snow the plow service was totally on top of it! A lovely stay!"
Perfect for a peaceful get away in clean fresh Vermont air!
Lake life at Woodford Cottage
Livingroom - Woodburning stove and sleeper double size pull out couch.

Lake life at Woodford Cottage

9.4 out of 10, Exceptional, (13)
"Very comfortable beds! This property is what you would expect from a cottage in Vermont, but there's so much more! We were surprised by the very well equipped kitchen and the vicinity to Woodford State Park also worked out really well for us. Would definitely recommend!"
Lake life at Woodford Cottage
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Exterior

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
Cozy Falls Brook Cabin: Hike & Swim On-site!
Living area

Cozy Falls Brook Cabin: Hike & Swim On-site!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
Cozy Falls Brook Cabin: Hike & Swim On-site!
'mount Pine' Getaway Near Green Mtn Nat'l Forest!
Outdoor dining

'mount Pine' Getaway Near Green Mtn Nat'l Forest!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Amazing place! Super clean and cozy, and host was extremely nice and communicative. Highly recommend."
'mount Pine' Getaway Near Green Mtn Nat'l Forest!
Charlemont Retreat on Chickley River w/ EV Charger
Living area

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
Jacksonville Cabin w/ Wraparound Deck & Views
Terrace/patio

Jacksonville Cabin w/ Wraparound Deck & Views

3.0 star property
Jacksonville Cabin w/ Wraparound Deck & Views
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Terrace/patio

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
Living area

Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The host was so kind and helpful. I will definitely cime abck here. "
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
Cozy Treetop Hideaway Near Harriman Reservoir!
Exterior

Cozy Treetop Hideaway Near Harriman Reservoir!

3.0 star property
Cozy Treetop Hideaway Near Harriman Reservoir!
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
Exterior

Wilmington Home on 18 Acres ~ 9 Mi to Skiing!

3.0 star property
10.0 out of 10, Exceptional, (1)
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
'john's Farmhouse in Mount Snow' on 120 Acres!
Exterior

'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!
Near Hiking & Skiing: Home in Wilmington!
Living area

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!
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
Private kitchen

Peaceful Marlboro Vacation Rental w/ Sauna & Yard!

3.0 star property
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
Wilmington Vacation Rental Near Hiking and Skiing!
Living area

Wilmington Vacation Rental Near Hiking and Skiing!

3.0 star property
Wilmington Vacation Rental Near Hiking and Skiing!
West Dover Vacation Rental w/ Hot Tub Near Mt Snow
Exterior

West Dover Vacation Rental w/ Hot Tub Near Mt Snow

3.0 star property
West Dover Vacation Rental w/ Hot Tub Near Mt Snow
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
Exterior

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

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

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1752)
"So enjoyed this property and all the staff was always there to help in anyway!"
The price is AED 689
AED 792 total
includes taxes & fees
6 Jan - 7 Jan
Vacation Village in the Berkshires
Long Trail House at Stratton Mountain Resort
Living room

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very Good, (72)
"Condo was great, cozy, and clean. Has access to the pool and hot tubs from back porch and has great Mountain View’s. The village had plenty of food, little expensive, but pretty good. Overall great place to stay and enjoy the mountain. "
The price is AED 1,275
AED 1,585 total
includes taxes & fees
6 Jan - 7 Jan
Long Trail House at Stratton Mountain Resort
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

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
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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