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Compare 452 Vacation Homes in Readsboro with updated reviews, rates, and availability.

Cozy, charming mountain home.
Room
Cozy, charming mountain home.
9.8 out of 10, Exceptional, (6)
"Wonderful place to eacape to relax. "
Cozy, charming mountain home.
Dog-friendly chalet cabin with valley view, deck, and private hot tub
Dog-friendly chalet cabin with valley view, deck, and private hot tub
7.2 out of 10, Good, (15)
"We had a great weekend staying here. The projector and hot tub were awesome amenities. There was a snow storm right before we arrived and the roads were clear and the driveway was plowed. We had a great experience and would stay here again!"
Dog-friendly chalet cabin with valley view, deck, and private hot tub
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Fully stocked newly renovated Kitchen.
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
10.0 out of 10, Exceptional, (104)
"Julie was a fantastic host. She was proactive in reaching out to ensure there were no issues with our stay. The property was everything the listing had described. We enjoyed our stay and the area. It was a good point to get to the places we wanted to see. "
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Plenty of private open space to explore with the whole family!
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
10.0 out of 10, Exceptional, (48)
"The House, Lands and View of this place are all amazing. Great for big family gathering to escape and rejoice and relax. We came to explore a bit of Vermont, which we did, but we also found ourselves reluctant to go out as the house and property were so captivating all on their own!"
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Sunny Stratton Townhome ~ 1 Mi to Skiing!
Stratton Vacation Rental | 3BR | 2.5BA | 1,600 Sq Ft | Stairs Required
Sunny Stratton Townhome ~ 1 Mi to Skiing!
10.0 out of 10, Exceptional, (3)
"We loved staying in your rental! It was perfect for my wife and I and our son and his family. We stayed upstairs and they stayed downstairs. Kids loved the bunk bed. The location of the unit is perfect - close to the village area yet quiet. The area is wonderful. I golfed with my son at the Stratton Mountain course and the others explored the village and went on the gondola twice. Thank you! (We received your message regarding the issue with the downstairs bathroom. We decided we would...
Sunny Stratton Townhome ~ 1 Mi to Skiing!
New Chalet mins to Mt with Hot tub
Newly constructed cottage minutes from the mountain
New Chalet mins to Mt with Hot tub
10.0 out of 10, Exceptional, (2)
"Excellent house, very beautiful, very spacious and much better than what is seen in the photos 10 out of 10 I loved it, without a doubt I would return to this place with my family"
New Chalet mins to Mt with Hot tub
Walk to Ski Lift: Spacious Condo in West Dover!
West Dover Vacation Rental | 3BR | 3.5BA | Steps to Enter | 1,750 Sq Ft
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!
West Dover Vacation Rental | 4BR | 3.5BA | 1,800 Sq Ft | Stairs to Access
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
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 AED 272
AED 991 total
includes taxes & fees
3 Nov 2024 - 4 Nov 2024
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
Outdoor spa tub
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 AED 977
AED 2,615 total
includes taxes & fees
5 Nov 2024 - 6 Nov 2024
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
House Front. Covered Porches, Lots of sunshine Plenty of space.
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!
Exterior
Shuttle or walk to village and lifts! The Powder Haus Chalet!
10.0 out of 10, Exceptional, (31)
"Our group of 8 found the property to be a perfect accomodation while staying in town for a wedding. Check in was very convenient and communication with the host was excellent. The home was very spacious, the living area was a great space to hang out and spend time together. We had all the amenities we needed for an easy weekend while attending a friend's wedding. The location is excellent and was very convenient to the mountain. We are especially grateful for the host allowing our furry friends...
Shuttle or walk to village and lifts! The Powder Haus Chalet!
Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16
Take in stunning views from our large windows while cozied by the fire
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
Dog-friendly cabin in the woods with firepit - ski & golf at nearby mountains
9.0 out of 10, Wonderful, (65)
"We loved it and plan to return some day."
Dog-friendly cabin in the woods with firepit - ski & golf at nearby mountains
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. "
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
360 degrees of nature from within the 1 bedroom Vermont Mirror House.
Property grounds
360 degrees of nature from within the 1 bedroom Vermont Mirror House.
10.0 out of 10, Exceptional, (15)
"Great home in a peaceful location in the country. The place is perfect for a couple and has a cool basement living space."
The price is AED 1,286
AED 1,637 total
includes taxes & fees
5 Nov 2024 - 6 Nov 2024
360 degrees of nature from within the 1 bedroom Vermont Mirror House.
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
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Front of house
1810 Brook Side Mill/House / EV Level 2 Charging on Site
10.0 out of 10, Exceptional, (67)
"The house was clean and looked newly remodeled. It had everything we needed for our 3 night stay. It is a good location when visiting Western MA. We would stay there again. Western MA. "
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Secluded Vermont Retreat w/ 25 Acres to Explore--Dog Heaven! Mountain Views!
Winter wonderland!
Secluded Vermont Retreat w/ 25 Acres to Explore--Dog Heaven! Mountain Views!
9.8 out of 10, Exceptional, (109)
"It was home away from home. I loved the huge area of open land and so didn't my dogs!"
Secluded Vermont Retreat w/ 25 Acres to Explore--Dog Heaven! Mountain Views!
SPACIOUS Mountain Retreat with HOT TUB, Fire Pit & Hiking Trails
Exterior
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
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, (1737)
"The staff was very nice! And the room was spacious and clean with plenty of amenities. "
The price is AED 620
AED 717 total
includes taxes & fees
1 Nov 2024 - 2 Nov 2024
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 1,343
AED 1,663 total
includes taxes & fees
1 Dec 2024 - 2 Dec 2024
Long Trail House at Stratton Mountain Resort
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
9.4 out of 10, Exceptional, (53)
"Soup to nuts an amazing time was had by all!!"
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
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.