Photo by Free Love Hippie

Readsboro Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Readsboro

Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1715)
"Beautiful views! "
The price is AU$283
includes taxes & fees
7 Oct - 8 Oct
Vacation Village in the Berkshires
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very good, (72)
"The unit was perfect for our ski race weekend. Very accessible, underground parking included (ski boxes on top of SUVs will not fit - thankfully we left ours at home), really nice place with everything we needed!"
Long Trail House at Stratton Mountain Resort
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
9.4 out of 10, Exceptional, (52)
"We had a fabulous time. "
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, (38)
"A friend and I stayed at this location for a few days in the autumn. Everything was as listed and it was perfect for our getaway. I would highly recommend this place for anyone I know looking for a quiet and quaint place to stay!"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
10.0 out of 10, Exceptional, (209)
"We loved our stay at the converted barn! It was completely private and super quiet. The hot tub was great, and I have never seen so many stars in my life! The house was very beautiful and felt like a home, we loved taking a look at all the decor. By the time our trip was coming to an end, we were super sad... we never wanted to leave! I would definitely return to Lars' place!! "
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Dog-friendly chalet cabin with valley view, deck, and private hot tub
7.2 out of 10, Good, (14)
"We had a great weekend staying here. The projector and hot tub were awesome amenities. There was a snow storm right before we arrived and the roads were clear and the driveway was plowed. We had a great experience and would stay here again!"
Dog-friendly chalet cabin with valley view, deck, and private hot tub
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
10.0 out of 10, Exceptional, (35)
"We read all reviews before we booked and everything said was absolutely accurate. We had a perfect get-away, walking into a beautifully designed and appointed space. Chris is a super host, readily available and responsive to all question and offering fantastic advice on local offerings. Our days started with the best breakfast sandwich ever at his country store, the days ended with extraordinary sunsets and sitting in the hot tub looking at the endless stars. We brought our couch potato dog and...
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
9.0 out of 10, Wonderful, (41)
"We had a group of thirty-four people for a family vacation and had a blast. The host and the housekeeper were tremendously responsive to any small issues we had over the first few days. The kitchen was well stocked but could use more mugs for coffee/tea and additional forks for larger groups and the tea bags were past the best before date and should be replaced. Twelve bedrooms, each with their own bathroom was great. The pool, hot tubs, ping pong table, pool table, tennis court, and fire pit...
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Bear Creek Cabin
10.0 out of 10, Exceptional, (18)
"Everything was as described, clean and comfortable with good amenities. Lots of thoughtful extras in the house that made our stay very enjoyable."
The price is AU$885
includes taxes & fees
2 Oct - 3 Oct
Bear Creek Cabin
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, (122)
"My partner and I were in MA to drop our eldest at Smith College for their first year. We chose Flight's End for the location and the fact that we were allowed to bring our pups with us. It was incredibly peaceful and just what we needed during an otherwise emotional time with such a big transition for our family. "
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
9.6 out of 10, Exceptional, (8)
"Great place. Super close to everything. Host was super helpful. Everything you need for an amazing ski weekend."
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
Green Mountain Modern House: iconic modern getaway
Green Mountain Modern House: iconic modern getaway
Walk to Mount Snow, Cozy, Clean and Comfortable!
9.6 out of 10, Exceptional, (29)
"Upon reserving the property, I sent an email to the owner and requested an early checkin, he responded very quickly and accomodated my request. The check in process was very easy, and the property was very clean. The only issue was the hot tub was not installed and functioning dury my stay, which I specifically asked for. The inside of the condo was very clean and the owner provided everything you needed. The only downside was the outside of the property was a little run down and needed some...
Walk to Mount Snow, Cozy, Clean and Comfortable!
Mount Snow's Best View - Sleeps 8-10
10.0 out of 10, Exceptional, (43)
"The property has great views of the mountain, the place was clean and offered plenty of space. It is located near plenty of restaurant's and across the street from Mt. Snow. The clubhouse is new and was a nice bonus to use. "
Mount Snow's Best View - Sleeps 8-10
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
9.6 out of 10, Exceptional, (45)
"We had a very nice stay. The house had plenty of room for our family including the living, dining, and sleeping areas. The location was great."
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
8.6 out of 10, Excellent, (20)
"Good Condo in a great location"
The price is AU$408
includes taxes & fees
3 Oct - 4 Oct
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
The Brown House. Indoor pool - Spa - Sauna - Gameroom
8.2 out of 10, Very good, (22)
"It was our yearly Guys weekend, everyone had a Great time. The house with every bedroom having a full bath was fantastic you couldn’t ask for more We spent many hours in the indoor pool and the 2 jacuzzi’s we will definitely stay there again"
The Brown House. Indoor pool - Spa - Sauna - Gameroom
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
10.0 out of 10, Exceptional, (30)
"We had a nice stay at this lovely place. It's tucked away at the end of a dirt road. We never saw another human only some wild turkeys. It was great to sit in the hot tub and look at the seasonal stream and the beautiful trees surrounding the property. "
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
9.6 out of 10, Exceptional, (39)
"My friends and I book this mansion for our annual getaway and it has become so dear to us. "
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Jacksonville Cabin w/ Wraparound Deck & Views
9.6 out of 10, Exceptional, (26)
"Very nice home on its own road, far from any neighbors, lovely location overlooking pond."
Jacksonville Cabin w/ Wraparound Deck & Views
Don't see what you're looking for?
See all available properties in Readsboro
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.
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Readsboro you may be interested in

Hotel Downstreet
3.0 star property
8.6 out of 10, Excellent, (1004)
"Convenient clean. "
The price is AU$181
includes taxes & fees
30 Sept - 1 Oct
Hotel Downstreet
The Black Bear Lodge at Stratton Mountain Resort
3.0 star property
7.4 out of 10, Good, (848)
"Liked your staff. Very helpful "
The price is AU$212
includes taxes & fees
8 Oct - 9 Oct
The Black Bear Lodge at Stratton Mountain Resort
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1715)
"Beautiful views! "
The price is AU$283
includes taxes & fees
7 Oct - 8 Oct
Vacation Village in the Berkshires
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.

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?

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub: This holiday home rental outside of Readsboro is located in the city centre, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a selection of games and 1 hot tub.

What’s there to see and do in Readsboro?

Explore the area and family-friendly sights such as Shelburne Falls Bowling Alley, or get out into nature at a spot like Deerfield River. Mount Snow and Harriman Reservoir are a couple of places you'll find in the wider area.

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.