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Readsboro Vacation Rentals

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Our top choices for Readsboro vacation rentals

3.0 star property
8.8 out of 10, Excellent, (2184)
"Awesome for ski"
United States
Lazar
$126 nightly
The price is $141
Jan 4 - Jan 5, 2026
Total with taxes and fees
Vacation Village in the Berkshires
9.2 out of 10, Wonderful, (17)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
$266 nightly
The price is $300
Jan 5 - Jan 6, 2026
Total with taxes and fees
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
2.0 star property
10.0 out of 10, Exceptional, (1)
"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."
United States
Anicia K.
$272 nightly
The price is $305
Dec 29 - Dec 30
Total with taxes and fees
Lake Whitingham & Mount Snow Area Village Apartment
10.0 out of 10, Exceptional, (2)
"The folks are SUPER and made me feel very welome"
United States
Mark
$227 nightly
The price is $254
Jan 19 - Jan 20, 2026
Total with taxes and fees
Wellness Getaway with a Personal Sauna, and Private River Beach!
10.0 out of 10, Exceptional, (5)
"Great stay"
United States
Chelsea D.
$200 nightly
The price is $226
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK
3.0 star property
8.4 out of 10, Very Good, (78)
"The building and the units are old and tired. Early attic decorating. And the walls are paper thin. We could hear all neighbors. I would not go back. "
United States
Doug
$420 nightly
The price is $474
Jan 5 - Jan 6, 2026
Total with taxes and fees
Long Trail House at Stratton Mountain Resort
10.0 out of 10, Exceptional, (28)
"Nice property for a quick and simple check-in. Near MassMOCA, the Clark Art Institute and much more."
United States
Mario R.
Getaway Near Mass MoCA, Great Hiking, Scenic Views
$192 nightly
The price is $215
Jan 20 - Jan 21, 2026
Total with taxes and fees
Rose wisteria 4 guests 2 bedrooms-full+queen beds
9.0 out of 10, Wonderful, (45)
"Great quiet location, kitchen had enough essentials for basic cooking to be easy. The king bed was comfortable and the living room is a great hangout spot."
United States
Franklin C.
$272 nightly
The price is $307
Jan 14 - Jan 15, 2026
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow

Vacation Home in Florida

Florida Mountain Log Cabin
2.0 star property
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
$340 nightly
The price is $366
Jan 4 - Jan 5, 2026
Total with taxes and fees
Florida Mountain Log Cabin
3.0 star property
10.0 out of 10, Exceptional, (2)
"Great location and awesome house. Owners were easy to communicate with. "
United States
Anonymous traveler
$547 nightly
The price is $601
Dec 28 - Dec 29
Total with taxes and fees
Wilmington Retreat Near Trails, Skiing & Festivals
9.6 out of 10, Exceptional, (67)
"We had a lovely stay! The studio was comfortable, clean, and just what we needed. Our hosts were friendly and helpful!"
United States
Janice L.
$188 nightly
The price is $206
Jan 1 - Jan 2, 2026
Total with taxes and fees
Cozy Rustic Apt in 18th c Berkshire Farmhouse
2.0 star property
9.6 out of 10, Exceptional, (13)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
$219 nightly
The price is $245
Jan 2 - Jan 3, 2026
Total with taxes and fees
Penthouse Apartment on Park Street
9.8 out of 10, Exceptional, (22)
"Decently-sized rooms, great lighting, plenty of space for families with kids to relax, enjoy the outdoor space, easy drive to Stratton and Wilmington. "
United States
SZU YIN C.
$359 nightly
The price is $406
Jan 5 - Jan 6, 2026
Total with taxes and fees
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
8.6 out of 10, Excellent, (27)
"We loved staying at the townhome. It was a welcome place to stay while we traveled around, enjoying fall. It was very comfortable and the village amenities were great."
United States
John N.
$433 nightly
The price is $489
Jan 15 - Jan 16, 2026
Total with taxes and fees
Lovely ski-in/out condo steps from ski lift with trails and amazing views

Vacation Home in Sunderland

Bear Pass - Mountain View by RedAwning
9.6 out of 10, Exceptional, (5)
"We loved our stay at Bear Pass! The kitchen was more than adequately stocked. The hous was great for our extended family and our 3 dogs"
United States
Megan G.
$605 nightly
The price is $678
Jan 13 - Jan 14, 2026
Total with taxes and fees
Bear Pass - Mountain View by RedAwning
9.8 out of 10, Exceptional, (100)
"Quiet and relaxing property "
United States
Michelle S.
$280 nightly
The price is $311
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
10.0 out of 10, Exceptional, (4)
"Impressively clean house! The owners were great to deal with and very responsive. Would certainly recommend to anyone traveling in the area."
United States
Kristen T.
$456 nightly
The price is $515
Jan 12 - Jan 13, 2026
Total with taxes and fees
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
9.8 out of 10, Exceptional, (38)
"Great house for family gatherings "
United Kingdom
John Paul B.
$607 nightly
The price is $678
Jan 19 - Jan 20, 2026
Total with taxes and fees
FaLL Western Mass Getaway-Airhockey-Firepit
9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
$381 nightly
The price is $430
Jan 5 - Jan 6, 2026
Total with taxes and fees
Mountain Chalet mins from Mt Snow Skiing/hiking
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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Top Readsboro Hotel Reviews

Find out more about Readsboro

Everything you need to know about Readsboro vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Readsboro vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Readsboro vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Readsboro vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Readsboro. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Readsboro in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $141 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Readsboro rentals

At Expedia, we put the best Readsboro vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Readsboro rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Readsboro vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Readsboro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Readsboro?

Yes, you can find vacation rentals near the most popular local attractions in Readsboro, or you can select a more remote option if you're looking for a relaxing stay.

What's the top vacation rental in Readsboro?

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns: Visitors like this Readsboro vacation home rental. It is located on a river and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

What’s there to see and do in Readsboro?

Deerfield River and Green Mountain National Forest are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Readsboro Town Hall and Readsboro Community Library.

What’s a vacation rental in Readsboro like?

Vacation rentals are privately owned properties where you can stay for several days or longer in Readsboro. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for small groups.