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

Colebrook Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Colebrook vacation rentals

Terrace/patio

1. 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
9.4 out of 10, Exceptional, (51 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
$212 nightly
The price is $240
Sep 1 - Sep 2
Total with taxes and fees
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Room

2. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
$198 nightly
The price is $224
Sep 1 - Sep 2
Total with taxes and fees
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Property grounds

3. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (149 reviews)
"Great location"
United States
Will G.
$316 nightly
The price is $334
Sep 3 - Sep 4
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
Dining

4. 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.
$438 nightly
The price is $520
Sep 1 - Sep 2
Total with taxes and fees
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Living area

5. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (19 reviews)
"Wow what an enjoyable stay! Clean, fresh, relaxing, and wonderful to meet owners Corin and Jen… gracious and hospitable hosts. Very comfortable, great location, well appointed… everything we were looking for!"
United States
James M.
$237 nightly
The price is $268
Sep 16 - Sep 17
Total with taxes and fees
Pristine Cozy Walkable Downtown 2BR Getaway
Interior

6. Linny's - Private Dock - Lake Access - Firepit

Linny's - Private Dock - Lake Access - Firepit
West Suffield
10.0 out of 10, Exceptional, (43 reviews)
"Perfect, relaxing and easy!"
United States
Wendy C.
$361 nightly
The price is $381
Sep 13 - Sep 14
Total with taxes and fees
Linny's - Private Dock - Lake Access - Firepit
Exterior

7. 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.
$358 nightly
The price is $412
Sep 1 - Sep 2
Total with taxes and fees
Cozy Modern Farmhouse Private Apt - 3 Beds
Outdoor dining

8. 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, (71 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
$434 nightly
The price is $491
Sep 16 - Sep 17
Total with taxes and fees
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Living area

9. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
$1,187 nightly
The price is $1,326
Sep 1 - Sep 2
Total with taxes and fees
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Interior

10. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 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.
$269 nightly
The price is $301
Sep 8 - Sep 9
Total with taxes and fees
Cozy Riverside Berkshires Retreat
Property grounds

11. Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (24 reviews)
"Great location, quite country yet close to MA and airport."
United States
Todd R.
Peaceful Meadow Retreat
Property grounds

12. 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.
$264 nightly
The price is $299
Sep 8 - Sep 9
Total with taxes and fees
River Overlook - What a view from your deck!
Private kitchen

13. The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (9 reviews)
"Everything about Jefferson House was perfect. It was located in a beautiful part of Connecticut adjoining a state park. The house was beautifully decorated. The kitchen was fully equipped and had a large island for dining. The bed, pillows and living room furnishings were very comfortable. The house was well up-to-date with two TVs, a charging device with multiple cords, a double oven (!), and countless thoughtful touches. I cannot recommend it highly enough!"
United States
genevieve
$398 nightly
The price is $398
Sep 1 - Sep 2
Total with taxes and fees
The Jefferson Guest House, Spacious, Special Views
Private kitchen

14. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.0 out of 10, Wonderful, (2 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
$148 nightly
The price is $165
Sep 7 - Sep 8
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
Living area

15. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Otis
$309 nightly
The price is $345
Sep 7 - Sep 8
Total with taxes and fees
Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Private kitchen

16. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
$364 nightly
The price is $407
Sep 3 - Sep 4
Total with taxes and fees
Home in Great Barrington
Property grounds

17. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
$465 nightly
The price is $519
Sep 22 - Sep 23
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
Room

18. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
$500 nightly
The price is $558
Sep 8 - Sep 9
Total with taxes and fees
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Dining

19. 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.
$377 nightly
The price is $434
Sep 1 - Sep 2
Total with taxes and fees
Art House 3 Beds Close to Warner Theater
Living area

20. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
$551 nightly
The price is $582
Sep 21 - Sep 22
Total with taxes and fees
Treetop Hideaway in Tyringham
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

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent
"Great for families"
DANIEL 3-night trip
Posted 4 hours ago
Holiday Inn Club Vacations Oak 'n Spruce Resort

Find out more about Colebrook

Everything you need to know about Colebrook vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Colebrook vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Colebrook vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Colebrook vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Colebrook. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Colebrook in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $165 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Colebrook rentals

At Expedia, we put the best Colebrook vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Colebrook rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Colebrook vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Colebrook. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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. Infinity Music Hall and Bistro and Campbell Falls State Park 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.