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

Readsboro Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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 HK$3,508
HK$6,195 total
includes taxes & fees
3 Nov - 4 Nov
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
An aerial view of a house surrounded by a forest with autumn foliage.

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)
"Great 2 family group vacation spot. Very clean and right in between great ski mountains"
United States
Jonathan
The price is HK$1,561
HK$3,997 total
includes taxes & fees
27 Oct - 28 Oct
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
8.8 out of 10, Excellent, (6 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 HK$2,855
HK$5,059 total
includes taxes & fees
27 Oct - 28 Oct
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

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 HK$2,186
HK$3,606 total
includes taxes & fees
22 Nov - 23 Nov
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 HK$3,137
HK$4,695 total
includes taxes & fees
2 Nov - 3 Nov
Bear Creek Cabin
A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

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

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (65 reviews)
"Beautiful house, amazing location, helpful and responsive hosts."
United States
Jeremy P.
The price is HK$2,415
HK$6,053 total
includes taxes & fees
27 Oct - 28 Oct
Walk To Town, Hottub, Firepit, Games, Mt Snow
A spacious living area with a stone fireplace, wooden flooring, and a cozy seating area.

7. 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 HK$2,643
HK$10,372 total
includes taxes & fees
28 Oct - 29 Oct
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

8. 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 HK$1,537
HK$4,487 total
includes taxes & fees
27 Oct - 28 Oct
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

9. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,796 reviews)
"We had an amazing stay."
United States
Luke
The price is HK$630
HK$790 total
includes taxes & fees
1 Nov - 2 Nov
Vacation Village in the Berkshires
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 HK$1,796
HK$3,776 total
includes taxes & fees
30 Oct - 31 Oct
A roomy remodeled retreat close to MassMoCA
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.

11. 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 HK$600
HK$1,424 total
includes taxes & fees
27 Oct - 28 Oct
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

12. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
The price is HK$1,145
HK$3,159 total
includes taxes & fees
4 Nov - 5 Nov
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A bedroom with a bed, a plaid sofa, and a door leading to another room.

13. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Wilmington
9.8 out of 10, Exceptional, (48 reviews)
"Great property and location. Communications with host excellent. Love the privacy and availability of firewood."
United States
Rod M.
The price is HK$831
HK$3,323 total
includes taxes & fees
4 Nov - 5 Nov
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Property grounds

14. 3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails

3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails
Halifax
10.0 out of 10, Exceptional, (1 review)
"This place was honestly amazing. All secluded and even with how far away the cabin was from the main road the cabin had everything you could imagine and everything felt perfect. 10/10 would return"
United States
Justin M.
The price is HK$1,369
HK$3,817 total
includes taxes & fees
27 Oct - 28 Oct
3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails
A two-story house with a red roof, a front porch with a railing, and a gravel driveway.

15. 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 HK$1,025
HK$3,149 total
includes taxes & fees
16 Nov - 17 Nov
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A red building with a window, surrounded by a forested area with trees and a stone wall.

16. 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 price is HK$2,833
HK$4,356 total
includes taxes & fees
8 Nov - 9 Nov
The Cottage on Mill Brook is walking distance to Berkshire East and the River.
A snow-covered wooden cabin with a balcony, surrounded by snow-covered trees.

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is HK$1,623
HK$5,082 total
includes taxes & fees
1 Nov - 2 Nov
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A rectangular pool with a brick deck, surrounded by lounge chairs and umbrellas.

18. 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 HK$525
HK$2,543 total
includes taxes & fees
2 Nov - 3 Nov
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
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
10.0 out of 10, Exceptional, (7 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 HK$946
HK$1,990 total
includes taxes & fees
2 Nov - 3 Nov
The Studio with a View. Bring your dog, too!
"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)

20. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
9.8 out of 10, Exceptional, (13 reviews)
"Great location, very clean, included washer dryer, picnic area by river, large parking space."
United States
Douglas
The price is HK$980
HK$2,223 total
includes taxes & fees
27 Oct - 28 Oct
Downtown | Waterfront | Walk to Shops
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

10/10 Excellent
"Everything was absolutely perfect! Staff was extremely friendly and the property is so clean and inviting. We loved it so much that we extended our stay!"
Angelina 7-night trip
Posted 5 hours ago
Vacation Village in the Berkshires

Find out more about Readsboro

Search for holiday rentals in Readsboro on Expedia! You can easily find your home rentals, villas, holiday apartments in Readsboro using one of the methods below:

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Look no further and take a look at our great range of rental properties in Readsboro!

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.