A red barn with a white fence in a green field with a white RV parked in front.

Holiday Rentals in Readsboro

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Readsboro holiday rentals

A modern kitchen with large windows, a built-in dishwasher, and a refrigerator.

1. Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Whitingham
9.8 out of 10, Exceptional, (9 reviews)
"A beautiful, clean, and cozy stay. The modern space was bright and well-equipped with everything we needed, and the hot tub made it especially relaxing."
United States
Nicole H.
The price is €653
includes taxes & fees
18 Nov - 19 Nov
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
A house with a garage, surrounded by snow-covered trees and a mountain in the background.

2. Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11

Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11
Whitingham
10.0 out of 10, Exceptional, (16 reviews)
"Very peaceful backyard!! Great back deck!!"
United States
Jacqueline M.
The price is €427
includes taxes & fees
17 Nov - 18 Nov
Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11
A cozy living room with a fireplace, leather sofas, and a television mounted on the wall.

3. Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Whitingham
8.4 out of 10, Very good, (7 reviews)
"This apartment is very efficient and really wowed everyone based on the automotive inspired design. It was an impeccable space, well stocked, and the beds were even extremely comfortable. We enjoyed the bar/grill within walking distance, too. Would stay here again. "
United States
Ben B.
The price is €554
includes taxes & fees
15 Nov - 16 Nov
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
A log cabin with a balcony, surrounded by snow-covered trees and a wind turbine in the background.

4. Greylock Cabin

Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"This is a beautiful cabin on an amazing property with a great view of Mt Greylock! Clean, comfortable, great location, communication with the owner was outstanding and questions were answered quickly. It all went smoothly and we highly recommend this property!"
United States
Margaret M.
The price is €428
includes taxes & fees
14 Dec - 15 Dec
Greylock Cabin
A log cabin with a balcony, surrounded by trees.

5. Bear Creek Cabin

Bear Creek Cabin
Charlemont
9.8 out of 10, Exceptional, (55 reviews)
"We enjoyed our stay!!"
United States
Hillary S.
The price is €557
includes taxes & fees
21 Nov - 22 Nov
Bear Creek Cabin
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

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

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Wilmington
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful home and property with quick access to a clubhouse with a gym, indoor and outdoor pools, and hot tub. Great for our family trip (including two kids) and lots of games/entertainment for the kids. The house had everything we needed (including kitchenware needed for cooking and preparing food)."
United States
Natalie
The price is €470
includes taxes & fees
16 Nov - 17 Nov
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

7. Walk To Town, Hottub, Firepit, Games, Mt Snow

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (66 reviews)
"Beautiful house, amazing location, helpful and responsive hosts."
United States
Jeremy P.
Walk To Town, Hottub, Firepit, Games, Mt Snow
A spacious living area with a stone fireplace, wooden flooring, and a cozy seating area.

8. Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting
Charlemont
10.0 out of 10, Exceptional, (2 reviews)
"Our stay at the chalet was exactly what we hoped it would be! The space is in a beautiful location that is perfect for dogs. The host was very helpful and responsive and check in was a breeze. We'll be back for sure!"
United States
Georgia P.
The price is €1,094
includes taxes & fees
16 Nov - 17 Nov
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting
A wicker sofa with a floral cushion, a wicker table with magazines, and a standing fan in a room with large windows and wooden floors.

9. Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
8.0 out of 10, Very good, (2 reviews)
"Excellent accommodations. Outside patio with grill was very nice. Private parking is a plus. Would definitely rent this apartment again."
United States
Ruthie K.
The price is €251
includes taxes & fees
16 Nov - 17 Nov
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
A kitchen with white cabinets, a wooden dining table, and pendant lights.

10. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (61 reviews)
"Cute and comfy home. We enjoyed the unique decor and lack of TVs everywhere. It was a great break from all the crazy. Lots of conversation and togetherness."
United States
Diane
The price is €442
includes taxes & fees
4 Dec - 5 Dec
A roomy remodeled retreat close to MassMoCA
A wooden deck with a railing, a house with windows, and a forested area with a stream.

11. The Cottage on Mill Brook is walking distance to Berkshire East and the River.

The Cottage on Mill Brook is walking distance to Berkshire East and the River.
Charlemont
The Cottage on Mill Brook is walking distance to Berkshire East and the River.
Indoor pool

12. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,851 reviews)
"Gorgeous setting, comfortable beds and luxurious accommodations."
United States
Carol
The price is €91
includes taxes & fees
15 Nov - 16 Nov
Vacation Village in the Berkshires
A two-story house with a red roof, a front porch with a railing, and a gravel driveway.

13. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
Woodford
10.0 out of 10, Exceptional, (1 review)
"Enjoyed our stay! Very clean and comfortable."
United States
Dana W.
The price is €477
includes taxes & fees
16 Nov - 17 Nov
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A two-story house with a porch, surrounded by trees and snow.

14. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Bennington
8.6 out of 10, Excellent, (36 reviews)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
The price is €264
includes taxes & fees
15 Nov - 16 Nov
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

15. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (8 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
The price is €890
includes taxes & fees
21 Nov - 22 Nov
5BR Berkshire Home Mins To The Mountain
A rural landscape with a house surrounded by autumn foliage and a river.

16. MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is €523
includes taxes & fees
15 Nov - 16 Nov
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

17. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is €281
includes taxes & fees
16 Nov - 17 Nov
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
A wooden deck leading to a dark-colored house with a white door and windows.

18. A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST

A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
West Dover
8.8 out of 10, Excellent, (5 reviews)
"Clean, comfortable, our 2nd time staying here - very nice."
United States
Dan G.
The price is €646
includes taxes & fees
29 Nov - 30 Nov
A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
A wooden interior with a kitchen, bar area, and dining space.

19. The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
9.8 out of 10, Exceptional, (9 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
The price is €206
includes taxes & fees
18 Nov - 19 Nov
The Studio with a View. Bring your dog, too!
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"The staff were super kind and helpful, however there were some concerns. The indoor pool was closed because there were too many pool chemicals in it, which was tough since that was a primary reason for choosing this property. This meant that the families with children were relegated to the hot tub and pool table areas because the arcade area costs money to play. The staff were kind, but the lack of swimming pool and the abundance of bored children arouns changed the atmosphere. "Too many chemicals" in the pool seems like an avoidable problem. The room was lovely, but we had to take out our own trash and wash our own dishes which wasn't quite "vacation vibes" since this was listed as a hotel. Loved the gas fireplace, but it does run on by using a dial on the wall that makes a ticking sound constantly. The walls were super thin, so I could see where that would be a challenge during busy season. Honestly, I feel like the whole property would feel kind of feral during busy season with so many "first come, first served" elements, but the mountain views were gorgeous and the staff were very very kind and helpful. Also, the room was beautifully clean and cozy, which is always a nice feeling."
Johanna 1-night trip
Posted 1 hour ago
Vacation Village in the Berkshires

Find out more about Readsboro

Everything you need to know about Readsboro holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Readsboro holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Readsboro holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Readsboro holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Readsboro holiday rentals we have selected for you start as low as €91 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Readsboro rentals

At Expedia, we put the best Readsboro holiday 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 holiday.

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 holiday rentals in Readsboro?

Yes, there are holiday rentals close to the most popular sights in Readsboro, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Readsboro has to offer?

Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews: This holiday home rental outside of Readsboro is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 holiday rental in Readsboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Readsboro. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for a family getaway.