A coastal landscape with a river flowing into the sea, surrounded by forested hills and a cloudy sky.

Colebrook Holiday Rentals

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Colebrook holiday rentals

Property grounds

River Overlook - What a view from your deck!

River Overlook - What a view from your deck!
Collinsville
10.0 out of 10, Exceptional, (25 reviews)
"I only did a short stay (2 nights) but it was super adorable! I will definitely stay again when I'm back in the area."
United States
Mary S.
River Overlook - What a view from your deck!
Dining

Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
10.0 out of 10, Exceptional, (2 reviews)
"Place was perfectly located for where we needed to be. The host was amazing, would stay again. Unit was comfy and cozy with perfect little homey touches. "
United States
Brittany M.
The price is HK$1,103
HK$3,366 total
includes taxes & fees
5 Jul - 6 Jul
Art House 3 Beds Close to Warner Theater
Property grounds

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (147 reviews)
"Great location"
United States
Will G.
The price is HK$1,341
HK$2,612 total
includes taxes & fees
16 Jul - 17 Jul
Big farmhouse in the foothills of the Berkshires
Exterior

Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.2 out of 10, Wonderful, (5 reviews)
"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."
United States
Rhonda H.
The price is HK$684
HK$2,144 total
includes taxes & fees
5 Jul - 6 Jul
Cozy Attic 10 min to Llitchfield
Terrace/patio

Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.2 out of 10, Wonderful, (47 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Exterior

Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is HK$847
HK$1,598 total
includes taxes & fees
6 Jul - 7 Jul
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Exterior

The Old Avon Village

The Old Avon Village
Avon
6.2 out of 10, (10 reviews)
"Great location. Alexander was very responsive to any requests. Met our needs. "
United States
Deborah S.
The price is HK$635
HK$2,222 total
includes taxes & fees
5 Jul - 6 Jul
The Old Avon Village
1 bedroom, desk, iron/ironing board, WiFi

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
The price is HK$1,013
HK$3,170 total
includes taxes & fees
5 Jul - 6 Jul
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Interior

The Historic Hideaway

The Historic Hideaway
Avon
6.0 out of 10, (4 reviews)
"Once we found the house it was very warm & cozy. The mini- muffins on the counter was a bonus. House mailbox was 87 but address was 89 that you only see if door is closed which it wasn't on 1st 2 passes. Limited exterior lights made coming back at night a challenge. "
United States
Kim C.
The price is HK$635
HK$2,183 total
includes taxes & fees
5 Jul - 6 Jul
The Historic Hideaway
Property grounds

Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (23 reviews)
"Great location, quite country yet close to MA and airport."
United States
Todd R.
The price is HK$973
HK$1,758 total
includes taxes & fees
3 Aug - 4 Aug
Peaceful Meadow Retreat
Outdoor spa tub

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is HK$1,638
HK$3,555 total
includes taxes & fees
6 Jul - 7 Jul
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (18 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is HK$1,588
HK$2,484 total
includes taxes & fees
7 Jul - 8 Jul
Cozy Riverside Berkshires Retreat
Terrace/patio

The Old Avon 1800 Manor

The Old Avon 1800 Manor
Avon
10.0 out of 10, Exceptional, (1 review)
"Wonderful place and host very responsive and friendly!"
United States
Anonymous traveller
The price is HK$1,514
HK$3,712 total
includes taxes & fees
5 Jul - 6 Jul
The Old Avon 1800 Manor
Property grounds

Sun Filled Lake House Living

Sun Filled Lake House Living
Avon
6.0 out of 10, (3 reviews)
"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"
United States
Joseph C.
The price is HK$839
HK$2,422 total
includes taxes & fees
30 Jul - 31 Jul
Sun Filled Lake House Living
Interior

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,835
HK$3,811 total
includes taxes & fees
22 Jul - 23 Jul
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
The price is HK$3,137
HK$5,510 total
includes taxes & fees
3 Aug - 4 Aug
Guesthouse Cabin vacation rentals in Berkshire County
Interior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is HK$816
HK$2,769 total
includes taxes & fees
16 Jul - 17 Jul
Real Estate: Therapy - Lake, Laundry, Love it
Private kitchen

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
The price is HK$2,047
HK$3,142 total
includes taxes & fees
5 Jul - 6 Jul
Litchfield Retreat, Wineries, Foliage & Skiing
Outdoor dining

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Collinsville
10.0 out of 10, Exceptional, (67 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is HK$2,447
HK$4,123 total
includes taxes & fees
3 Aug - 4 Aug
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Fridge, microwave, oven, stovetop

The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (8 reviews)
"I stayed here for four nights, including one with my son, and it was fantastic.Everything is brand new, clean, and beautifully appointed, with every amenity you could want."
United States
Jennifer A.
The price is HK$2,287
HK$2,954 total
includes taxes & fees
15 Jul - 16 Jul
The Jefferson Guest House, Spacious, Special Views
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 Colebrook Hotel Reviews

Simsbury 1820 House

Simsbury 1820 House

8/10 Good
"A nice place to stay for a night or two. The staff was pleasant and helpful. But not particularly well informed. The decor and interiors could use a dressings. The deteriorating front stairs by which one enters is a sign. There is a restaurant on site but it is not operated by the hotel."
John 1-night trip
Posted 7 hours ago
Simsbury 1820 House

Find out more about Colebrook

Search for holiday rentals in Colebrook on Expedia! You can easily find your home rentals, villas, holiday apartments in Colebrook 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 Colebrook!

Frequently asked questions

Can I find a holiday rental in Colebrook?

Yes, there are holiday rentals close to the most popular sights in Colebrook, 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 Colebrook has to offer?

Cozy Riverside Berkshires Retreat: This holiday home rental outside of Colebrook is located on a river, and has a fireplace, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and kitchenware, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What’s there to see and do in Colebrook?

Explore the area and family-friendly sights such as KidsPlay Museum, or get out into nature at a spot like Highland Lake. Infinity Music Hall and Bistro and Ames Plaza Shopping Center are a couple of places you'll find in the wider area.

What’s a holiday rental in Colebrook like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Colebrook. Holiday rentals offer extras such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.