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

Readsboro Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Readsboro vacation homes

An aerial view of a house surrounded by a forest with autumn foliage.

1. Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Whitingham
10.0 out of 10, Exceptional, (15 reviews)
"Great 2 family group vacation spot. Very clean and right in between great ski mountains"
United States
Jonathan
The price is CA $348
CA $804 total
includes taxes & fees
Oct 28 - Oct 29
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

2. 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 CA $412
CA $677 total
includes taxes & fees
Oct 5 - Oct 6
Greylock Cabin
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

3. 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 CA $279
CA $801 total
includes taxes & fees
Oct 26 - Oct 27
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A bedroom with a bed, bedside tables, a window, and a radiator.

4. 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
The price is CA $212
CA $605 total
includes taxes & fees
Oct 7 - Oct 8
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A wooden staircase leading to a cabin with a balcony, surrounded by trees.

5. New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly

New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly
Wilmington
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful house and a terrific central location for all things outdoors."
United States
Alex B.
The price is CA $569
CA $1,085 total
includes taxes & fees
Oct 9 - Oct 10
New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly
A kitchen with white cabinets, a wooden dining table, and pendant lights.

6. 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 CA $326
CA $691 total
includes taxes & fees
Oct 13 - Oct 14
A roomy remodeled retreat close to MassMoCA
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, (65 reviews)
"Beautiful house, amazing location, helpful and responsive hosts."
United States
Jeremy P.
The price is CA $452
CA $1,118 total
includes taxes & fees
Oct 5 - Oct 6
Walk To Town, Hottub, Firepit, Games, Mt Snow
A bedroom with a wooden headboard, a bed with patterned bedding, and a framed picture on the wall.

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is CA $359
CA $1,001 total
includes taxes & fees
Oct 27 - Oct 28
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

9. 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.
5BR Berkshire Home Mins To The Mountain
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

10. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (9 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is CA $184
CA $316 total
includes taxes & fees
Oct 19 - Oct 20
Cozy Home in Pownal VT
A bedroom with a large bed, a window with blinds, a bookshelf, and a wall-mounted ship's wheel.

11. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.6 out of 10, Exceptional, (5 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is CA $219
CA $280 total
includes taxes & fees
Oct 12 - Oct 13
The Eagles Wing at The CHM - Private Apartment
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

12. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is CA $171
CA $306 total
includes taxes & fees
Oct 6 - Oct 7
Private bed with En-suite bathroom Marigold Room
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

13. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
The price is CA $433
CA $882 total
includes taxes & fees
Oct 7 - Oct 8
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A spacious indoor area with multiple wooden tables and green chairs, large windows offering a view of a snowy mountain, and a stone fireplace with a fire.

14. Modern Mount Snow Gnarvana - Steps to Carinthia

Modern Mount Snow Gnarvana - Steps to Carinthia
Dover
10.0 out of 10, Exceptional, (26 reviews)
"Perfect for our getaway, convenient for getting to the slopes and a beautiful area to visit"
United States
Lynn B.
The price is CA $257
CA $688 total
includes taxes & fees
Oct 5 - Oct 6
Modern Mount Snow Gnarvana - Steps to Carinthia
A modern kitchen with a built-in fireplace, wine storage, and a dining area with wooden furniture.

15. Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Dover
10.0 out of 10, Exceptional, (13 reviews)
"great location easy access to the mountain and the pool was outstanding."
United States
jim f.
The price is CA $661
CA $1,680 total
includes taxes & fees
Oct 5 - Oct 6
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
A hallway with wooden flooring, white walls, and a bed in the background.

16. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
"I really enjoyed the kitchen setup and how everything I needed was there. The beds were very comfortable and having a light nearby for reading was a plus. The walk to downtown was nice. We explored Shelburne Falls out days and it did have something for everyone. I would stay here again."
United States
maureen
The price is CA $299
CA $610 total
includes taxes & fees
Oct 5 - Oct 6
Cozy private 2 bed apartment in Shelburne Falls
A house with a deck, two Adirondack chairs, a glass-top table, and a barbecue grill.

17. Spacious Vermont Farmhouse | 3 Mi to Mount Snow

Spacious Vermont Farmhouse | 3 Mi to Mount Snow
West Dover
10.0 out of 10, Exceptional, (1 review)
"All good. "
United States
ken g.
Spacious Vermont Farmhouse | 3 Mi to Mount Snow
A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

18. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (55 reviews)
"This is the second time we have stayed at this property. It is very spacious, cozy, and clean. The beds are very comfortable. It had everything we needed "
United States
Staci M.
The price is CA $576
CA $1,145 total
includes taxes & fees
Oct 15 - Oct 16
Spacious 5BR w/ Hot Tub & Games
A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.

19. Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Hoosick Falls
9.8 out of 10, Exceptional, (115 reviews)
"This is the third time we’ve stayed at this lovely home and it’s always a treat! Very clean, with a Well stocked kitchen, comfy beds and huge back yard plus a fenced in portion, your dog will love-close to Bennington and walking trails with lots to do. A home away from home! "
United States
Anita T.
The price is CA $268
CA $566 total
includes taxes & fees
Oct 5 - Oct 6
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

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

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton
The price is CA $106
CA $367 total
includes taxes & fees
Oct 5 - Oct 6
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
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

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

8/10 Good
"Accessible and a great place to stay at Stratton."
Kathy 2-night trip
Posted 1 hour ago
The Black Bear Lodge at Stratton Mountain Resort

Find out more about Readsboro

Readsboro Vacation Homes information

Number of reviews
405
Accommodation
523 Vacation Homes
Lowest Price
CA $280
Highest Price
CA $1,680

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