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
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

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, (49 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
$186 nightly
The price is $211
Aug 10 - Aug 11
Total with taxes and fees
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
2 bedrooms, WiFi (free), bed sheets

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
$197 nightly
The price is $223
Aug 5 - Aug 6
Total with taxes and fees
Peaceful and cozy 1 bed 1 bath in quaint Winchester
Property grounds

3. 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.
$183 nightly
The price is $207
Aug 3 - Aug 4
Total with taxes and fees
Peaceful Meadow Retreat
Exterior

4. 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.
$251 nightly
The price is $299
Aug 26 - Aug 27
Total with taxes and fees
Cozy Attic 10 min to Llitchfield
1 bedroom, desk, iron/ironing board, WiFi

5. Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Torrington
$352 nightly
The price is $405
Aug 17 - Aug 18
Total with taxes and fees
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm
Dining

6. 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.
$401 nightly
The price is $464
Aug 26 - Aug 27
Total with taxes and fees
Art House 3 Beds Close to Warner Theater
Interior

7. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
$290 nightly
The price is $324
Aug 26 - Aug 27
Total with taxes and fees
Real Estate: Therapy - Lake, Laundry, Love it
Smart TV, fireplace

8. 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.
$239 nightly
The price is $271
Aug 26 - Aug 27
Total with taxes and fees
Pristine Cozy Walkable Downtown 2BR Getaway
Interior

9. Linny's - Lakefront Retreat Private Dock & Firepit

Linny's - Lakefront Retreat Private Dock & Firepit
West Suffield
10.0 out of 10, Exceptional, (41 reviews)
"Perfect, relaxing and easy!"
United States
Wendy C.
$346 nightly
The price is $365
Aug 5 - Aug 6
Total with taxes and fees
Linny's - Lakefront Retreat Private Dock & Firepit
Property grounds

10. 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
Aug 13 - Aug 14
Total with taxes and fees
River Overlook - What a view from your deck!
Property grounds

11. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (148 reviews)
"Great location"
United States
Will G.
$314 nightly
The price is $332
Aug 4 - Aug 5
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
Interior

12. The Historic Hideaway

The Historic Hideaway
Avon
6.0 out of 10, (4 reviews)
"House exactly as listed. We had a question and the property owner replied instantly - great communication. Close to Talcott Mountain which was an amazing hike with beautiful views. "
United States
Nicole M.
$272 nightly
The price is $291
Aug 18 - Aug 19
Total with taxes and fees
The Historic Hideaway
Outdoor spa tub

13. 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, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
$401 nightly
The price is $447
Aug 12 - Aug 13
Total with taxes and fees
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Outdoor dining

14. 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
$429 nightly
The price is $486
Aug 10 - Aug 11
Total with taxes and fees
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Dining

15. 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.
$436 nightly
The price is $519
Aug 17 - Aug 18
Total with taxes and fees
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
Exterior

16. 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.
$298 nightly
The price is $354
Aug 26 - Aug 27
Total with taxes and fees
Cozy Modern Farmhouse Private Apt - 3 Beds
Exterior

17. 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.
$298 nightly
The price is $321
Aug 11 - Aug 12
Total with taxes and fees
The Old Avon Village
Interior

18. 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.
$403 nightly
The price is $450
Aug 12 - Aug 13
Total with taxes and fees
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Interior

19. Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (13 reviews)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
United States
Tom S.
$626 nightly
The price is $699
Aug 3 - Aug 4
Total with taxes and fees
Guesthouse Cabin vacation rentals in Berkshire County
Coffee/tea maker, fridge, microwave, oven

20. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (35 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
$366 nightly
The price is $409
Aug 12 - Aug 13
Total with taxes and fees
Home in Great Barrington
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

The Litchfield Inn

The Litchfield Inn

10/10 Excellent
"Beautiful place 5 stars"
Sandra 1-night trip
Posted 9 hours ago
The Litchfield Inn

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 $299 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. The Marina at Highland Lake and Infinity Music Hall and Bistro 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.