Photo by Free Love Hippie

Search Vacation Homes in Readsboro

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Jul 18 - Jul 20
In two weeks
Jul 25 - Jul 27
In one month
Aug 8 - Aug 10
In two months
Sep 5 - Sep 7

Vacation Homes in Readsboro

Charming Berkshires Retreat – Minutes to Williamstown
Relax in this spacious living area with a flat-screen TV and comfortable sofa.

Charming Berkshires Retreat – Minutes to Williamstown

10.0 out of 10, Exceptional, (1)
"This was the perfect little spot for our family to stop and stay on our way to dropping our daughter at camp and enjoy Williamstown. Our hike at the Clark Institute was a highlight along with the proximity to downtown’s great restaurants.We were talking about how gorgeous it must be in the fall… when it must be even more scenic and amazing."
Charming Berkshires Retreat – Minutes to Williamstown
The Jelly Mill-A Peaceful River Retreat
Stroll up to this charming home surrounded by lush greenery and a well-manicured lawn.

The Jelly Mill-A Peaceful River Retreat

10.0 out of 10, Exceptional, (53)
"Great location, communicative and welcoming hosts, and great amenities. We loved grilling and using the firepit. The surrounding area is great to walk around in. Easy drive from here to Mt Snow."
The Jelly Mill-A Peaceful River Retreat
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft
Relax in a spacious living area with a high ceiling and large windows offering views of the surrounding greenery.

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

9.6 out of 10, Exceptional, (33)
"My wife and I had a wonderful and relaxing time celebrating our anniversary. We really enjoyed sitting by the river."
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft
Private Family Estate for any Season
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and a large window offering a view of the outdoors.

Private Family Estate for any Season

10.0 out of 10, Exceptional, (67)
"Beautiful place and great location."
Private Family Estate for any Season
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, and dishwasher, set against a sleek countertop and wooden cabinetry.

Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

10.0 out of 10, Exceptional, (118)
"We love staying in Mountain Nest! We are close enough to town and all the wonderful restaurants and shops yet we felt like we were staying in the mountains!! "
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..
Situated on a lush lawn, this charming house features a wrap-around porch and a prominent gable roof.

Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..

10.0 out of 10, Exceptional, (26)
"Beautiful property with great quality towels, furniture, and amenities. Great views and great location. Would be happy to stay again. "
Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Enjoy cooking in this well-equipped kitchen with a fireplace, large island, and flat-screen TV.

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

10.0 out of 10, Exceptional, (43)
"We enjoyed our stay at the tiny home!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Indoor Pool, Golf, Hike, Relax!
Surrounded by a forest, this serene setting features a natural waterfall cascading over rocky ledges.

Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Indoor Pool, Golf, Hike, Relax!

10.0 out of 10, Exceptional, (2)
"We had such a lovely time in this well loved cabin. Super quiet location and well stocked with everything we needed for our end of year ski trip in Stratton. The owner was very friendly and helpful. We hope we will be back soon!"
Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Indoor Pool, Golf, Hike, Relax!
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Situated in a wooded area, this cabin features a welcoming front porch and a serene, secluded environment.

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

9.6 out of 10, Exceptional, (128)
"A cozy spot to watch the snow come down!"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Home with View of Mount Snow!! Indoor-pool, spa, sauna Gym & more Sleeps 23+
Relax in a warm and inviting space with a pool view, comfortable seating, and a bookshelf.

Home with View of Mount Snow!! Indoor-pool, spa, sauna Gym & more Sleeps 23+

6.0 out of 10, (1)
"Inside property was great - house was very fun and spacious and clean . HOWEVER..the driveway clearly hadn’t been plowed for a long time when we got there and so once we pulled in our cars were stuck. We were trapped at the house for 3 days. The plow driver came to plow the neighbor and told us he hadn’t been paid by the owners so hadn’t been plowing for some time The owners finally arranged for a different plow to come but not being able to leave for 3 days really affected our ability to...
Home with View of Mount Snow!! Indoor-pool, spa, sauna Gym & more Sleeps 23+
Room for the whole family 8 minutes to Manchester
Relax in the serene mountain surroundings from this outdoor seating area, featuring Adirondack chairs around a central fire pit.

Room for the whole family 8 minutes to Manchester

10.0 out of 10, Exceptional, (3)
"Very priceable and great house with 5 bedrooms - each rooms are big and clean! Love it! Will come back again for next ski plan"
Room for the whole family 8 minutes to Manchester
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Surrounded by lush greenery, a serene forest stream flows gently over moss-covered rocks.

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

10.0 out of 10, Exceptional, (78)
"Highly recommend this charming, historic place.  Well appointed. Has everything you need for your stay.  Cozy…yet plenty of space for everyone.  Looks like it was just renovated.  Took my daughter and two granddaughters for a ski weekend.  Wouldn’t hesitate to come back here.  "
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Charlemont Retreat on Chickley River w/ EV Charger
Enjoy a serene backyard with a wooden deck, firewood, and a large tree for shade.

Charlemont Retreat on Chickley River w/ EV Charger

9.6 out of 10, Exceptional, (29)
"Great location, convenient to the ski resort. Good for a family retreat or celebration."
Charlemont Retreat on Chickley River w/ EV Charger
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Relax on the deck with a sofa, chair, and table, surrounded by large windows and a dark wood exterior.

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

10.0 out of 10, Exceptional, (12)
"We loved the house, the deck and the property amenities."
$511 nightly
The price is $545
Jul 14 - Jul 15
Total includes taxes and fees
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
North Getaway Cottage
Stunning two-story house with a central entrance and lush green surroundings.

North Getaway Cottage

9.6 out of 10, Exceptional, (20)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
$402 nightly
The price is $448
Jul 14 - Jul 15
Total includes taxes and fees
North Getaway Cottage
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes
Enjoy a serene forest view from the arched window, surrounded by lush foliage.

Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

10.0 out of 10, Exceptional, (24)
"Great location close to the slopes. Clean and comfortable. Loved the fireplace. "
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Cozy living room with a fireplace, comfortable seating, and a festive Christmas tree.

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

7.8 out of 10, Good, (49)
"Great condo in great location. Easy walk to restaurants and lifts."
$220 nightly
The price is $249
Jul 13 - Jul 14
Total includes taxes and fees
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
West Dover Home - 3 Miles to Mount Snow Resort!
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and ample cabinetry.

West Dover Home - 3 Miles to Mount Snow Resort!

9.0 out of 10, Wonderful, (21)
"Great house with so much room "
West Dover Home - 3 Miles to Mount Snow Resort!
Spyglass village- Golf & Ski
Smart TV, fireplace

Spyglass village- Golf & Ski

10.0 out of 10, Exceptional, (3)
"Great location, close to Mount Snow, ideal for skiing. Property is newly renovated, very functional and well appointed. We really enjoyed our stay."
Spyglass village- Golf & Ski
Modern Mount Snow Gnarvana - Balcony/Pet-Friendly/Walk to Lifts & Lodge
Enjoy serene views of the surrounding landscape from the large arched window.

Modern Mount Snow Gnarvana - Balcony/Pet-Friendly/Walk to Lifts & Lodge

10.0 out of 10, Exceptional, (19)
"Super nice place (very clean and modern) in a quiet area."
Modern Mount Snow Gnarvana - Balcony/Pet-Friendly/Walk to Lifts & Lodge
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free