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

Colebrook Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Colebrook vacation rentals

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 ￥15,854
￥45,956 total
includes taxes & fees
Jul 27 - Jul 28
Cozy Attic 10 min to Llitchfield
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 ￥22,734
￥69,873 total
includes taxes & fees
Jul 13 - Jul 14
Art House 3 Beds Close to Warner Theater
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 ￥18,043
￥33,441 total
includes taxes & fees
Jul 22 - Jul 23
Peaceful Meadow Retreat
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 ￥11,803
￥43,264 total
includes taxes & fees
Jul 13 - Jul 14
The Historic Hideaway
Interior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is ￥14,875
￥54,542 total
includes taxes & fees
Jul 16 - Jul 17
Real Estate: Therapy - Lake, Laundry, Love it
2 bedrooms, free WiFi, bed sheets

Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is ￥17,461
￥32,772 total
includes taxes & fees
Jul 22 - Jul 23
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Exterior

Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds
Torrington
10.0 out of 10, Exceptional, (4 reviews)
"My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. "
United Kingdom
Louisa A.
The price is ￥20,881
￥53,860 total
includes taxes & fees
Jul 15 - Jul 16
Cozy Modern Farmhouse Private Apt - 3 Beds
Interior

Linny's - Lakefront Retreat Private Dock & Firepit

Linny's - Lakefront Retreat Private Dock & Firepit
West Suffield
10.0 out of 10, Exceptional, (40 reviews)
"Everything was spectacular from the check in process to the personal experiences."
United States
leigh
The price is ￥31,225
￥62,057 total
includes taxes & fees
Aug 5 - Aug 6
Linny's - Lakefront Retreat Private Dock & Firepit
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 ￥30,719
￥57,592 total
includes taxes & fees
Jul 15 - Jul 16
Big farmhouse in the foothills of the Berkshires
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 ￥30,558
￥69,710 total
includes taxes & fees
Jul 13 - Jul 14
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
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 ￥33,468
￥73,322 total
includes taxes & fees
Jul 13 - Jul 14
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 ￥34,777
￥53,656 total
includes taxes & fees
Jul 14 - Jul 15
Cozy Riverside Berkshires Retreat
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, (26 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.
The price is ￥31,528
￥56,427 total
includes taxes & fees
Aug 8 - Aug 9
River Overlook - What a view from your deck!
Smart TV, fireplace, table tennis, offices

Owl`s Nest - Cozy Westfield Home w/ Fire Pit

Owl`s Nest - Cozy Westfield Home w/ Fire Pit
Westfield
9.8 out of 10, Exceptional, (11 reviews)
"Excellent communication from host and clean. "
United States
Julie W.
The price is ￥33,492
￥93,270 total
includes taxes & fees
Jul 12 - Jul 13
Owl`s Nest - Cozy Westfield Home w/ Fire Pit
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 ￥16,491
￥49,438 total
includes taxes & fees
Jul 30 - Jul 31
Sun Filled Lake House Living
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (34 reviews)
"Adorable guest home in Great Barrington! Light and bright. Perfect space for our family of 4. Well equipped kitchen and easy walk to downtown and groceries at the co-op. Would definitely stay here again!"
United States
Julie J.
The price is ￥42,053
￥63,770 total
includes taxes & fees
Jul 19 - Jul 20
Home in Great Barrington
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (12 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 ￥64,672
￥111,068 total
includes taxes & fees
Jul 13 - Jul 14
Guesthouse Cabin vacation rentals in Berkshire County
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 ￥47,146
￥60,889 total
includes taxes & fees
Jul 14 - Jul 15
The Jefferson Guest House, Spacious, Special Views
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, (68 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is ￥50,444
￥84,987 total
includes taxes & fees
Jul 30 - Jul 31
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Dining

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Torrington
10.0 out of 10, Exceptional, (1 review)
"Good communication. Clean place in good location. Would stay again. "
United States
Jaimie S.
The price is ￥37,833
￥83,910 total
includes taxes & fees
Jul 27 - Jul 28
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Colebrook Hotel Reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"Always love going to Oak n Spruce. The 2 bedroom delux with 2 king beds and near the small pool is the best. It's quiet and so relaxing. Love going to the gym and game room. So convenient to Lee Premium Outlets on rainy days."
Jennifer 5-night trip
Posted 16 hours ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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:

  • View our selection of featured holiday rentals in Colebrook
  • Use the map to find apartments and other holiday homes in the Colebrook neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Colebrook while they last

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

Frequently asked questions

Can I find a vacation rental in Colebrook?

Yes, we give you a choice of vacation rentals close to the most popular sights in Colebrook, or you can go with a more secluded option if you're looking for a relaxing stay.

What's the top vacation rental in Colebrook?

Cozy Riverside Berkshires Retreat: Visitors like this Colebrook vacation home rental. It 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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. The Marina at Highland Lake and Northwestern Connecticut Community College are a couple of places you'll find in the larger area.

What’s a vacation rental in Colebrook like?

A vacation rental is a private property you can stay in for a couple of days or more in Colebrook. Vacation rentals feature extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for a family trip or a small group gathering.