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Featured Holiday Homes in Readsboro

Charming Berkshires Retreat – Minutes to Williamstown

Charming Berkshires Retreat – Minutes to Williamstown

Williamstown
With a stay at this vacation home in Williamstown, you'll be within a 5-minute walk of Mount Greylock State Reservation and Green River Wildlife Management ...
Charming Berkshires Retreat – Minutes to Williamstown
The Jelly Mill-A Peaceful River Retreat

The Jelly Mill-A Peaceful River Retreat

Guilford
When you stay at this vacation home in Brattleboro, you'll be on the waterfront and 7 minutes by car from Green River Wildlife Management Area.
The Jelly Mill-A Peaceful River Retreat
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

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

Cummington
With a stay at this vacation home in Cummington, you'll be on the waterfront, and 8.1 mi (13 km) from Swift River and 8.3 mi (13.3 km) from Westfield River.
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft
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Contemporary Berkshire Home with Views of Taconic Golf Course

Contemporary Berkshire Home with Views of Taconic Golf Course

Williamstown
Located in Williamstown, this vacation home is within a 5-minute drive of Williams College Taconic Golf Course and Williams College.
Contemporary Berkshire Home with Views of Taconic Golf Course
Manchester,  Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

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

Sunderland
With a stay at this vacation home in Arlington, you'll be in the mountains, just steps from Green Mountain National Forest and a 4-minute drive from Mount ...
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
Private Family Estate for any Season

Private Family Estate for any Season

West Dover
With a stay at this vacation home in West Dover, you'll be in the mountains, within a 10-minute drive of Mount Snow and Green Mountain National Forest.
Private Family Estate for any Season
Shelburne Falls #1 Rated STR.  Blue on South. Style design with comfort..

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

Buckland
With a stay at this vacation home, you'll be centrally located in Shelburne Falls, just a 3-minute walk from Deerfield River and 9 minutes by foot from Lamson ...
Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

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

Whitingham
Located in Whitingham, this vacation home is on the waterfront, within a 15-minute walk of Harriman Reservoir and Green Mountain National Forest.
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!

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

Wardsboro
Located in Wardsboro, this vacation home is in the mountains, within a 15-minute drive of Green Mountain National Forest and Wardsboro Public Library.
Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Indoor Pool, Golf, Hike, Relax!
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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.

Readsboro Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Readsboro vacation homes are the perfect way for you to wing it.

Holiday houses in Readsboro let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Readsboro in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Readsboro adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Readsboro with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Readsboro vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Readsboro Holiday Homes essential information

Accommodation
575 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Charming Berkshires Retreat – Minutes to Williamstown, The Jelly Mill-A Peaceful River Retreat, Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft, Contemporary Berkshire Home with Views of Taconic Golf Course, Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing, Private Family Estate for any Season, Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort.., 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!

Top trending hotels in Readsboro

Elegant house w/ mountain views, trail to riverfront, balcony, dog-friendly, bbq

Elegant house w/ mountain views, trail to riverfront, balcony, dog-friendly, bbq

Readsboro
With a stay at this vacation home in Readsboro, you'll be on the waterfront, just steps from Green Mountain National Forest and a 5-minute drive from Readsboro ...
Elegant house w/ mountain views, trail to riverfront, balcony, dog-friendly, bbq
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
With a stay at Vacation Village in the Berkshires in Williamstown, you'll be a 3-minute drive from Jiminy Peak Mountain Resort and 5 minutes from Mountain ...
Vacation Village in the Berkshires
Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
A stay at Hotel Downstreet, Ascend Hotel Collection places you in the heart of North Adams, steps from MCLA Gallery 51 and North Adams City Hall.
Hotel Downstreet, Ascend Hotel Collection
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The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
Located in Williamstown, The Williams Inn is just steps from Williams College and 11 minutes by foot from The Clark Art Institute.
The Williams Inn
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