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

Colebrook Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Colebrook vacation rentals

A wooden cabin interior with a bench, a rug, and a hanging plant.

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

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
10.0 out of 10, Exceptional, (4 reviews)
"Great place and wonderful host."
United States
Thomas C.
$186 nightly
The price is $211
Nov 1 - Nov 2
Total with taxes and fees
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A balcony with a view of a lake, white railings, and outdoor furniture.

2. River Overlook - What a view from your deck!

River Overlook - What a view from your deck!
Collinsville
10.0 out of 10, Exceptional, (27 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.
$297 nightly
The price is $336
Oct 25 - Oct 26
Total with taxes and fees
River Overlook - What a view from your deck!
A square fire pit with flames, surrounded by a grassy field and a green chair.

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.
$164 nightly
The price is $185
Oct 26 - Oct 27
Total with taxes and fees
Peaceful Meadow Retreat
A two-story house with a front porch, a small balcony, and a white picket fence.

4. Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.6 out of 10, Exceptional, (7 reviews)
"The check-in process was easy and all instructions were clear. Jonathan, the owner, was very responsive and easy to get a hold of if I had any questions. The place was cute, clean, and perfect for what I needed (a place to stay during my medical school rotation). As the review says, it is not ideal for taller guests as the roof slopes down in certain areas, but I found the place cozy."
United States
Nicole N.
$312 nightly
The price is $357
Nov 3 - Nov 4
Total with taxes and fees
Cozy Attic 10 min to Llitchfield
A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

5. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake
Otis
9.8 out of 10, Exceptional, (55 reviews)
"Quiet and peaceful"
United States
Michael S.
$515 nightly
The price is $575
Oct 23 - Oct 24
Total with taxes and fees
Cozy Cottage-Sunset On The Lake
A two-story house with a front porch, a small balcony, and a white picket fence.

6. 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.
$368 nightly
The price is $424
Oct 19 - Oct 20
Total with taxes and fees
Cozy Modern Farmhouse Private Apt - 3 Beds
A modern kitchen with a wooden dining table, blue chairs, and a colorful bowl centerpiece.

7. 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.
$376 nightly
The price is $434
Nov 2 - Nov 3
Total with taxes and fees
Art House 3 Beds Close to Warner Theater
A recreational vehicle with a beige sofa, pillows, a small table, and potted plants.

8. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
10.0 out of 10, Exceptional, (1 review)
"This was a completely hidden gem. I stayed here for one night because I was visiting a friend but I wished I had booked it longer. My friend and I ended up staying here the whole time. I woke up to the sounds of crickets and chickens, and had fresh eggs for breakfast. Then I went for a hike in the pristine woods. Matt and Grace offered to let me use the paddle boards to enjoy the lake! It was a total vacation… no need to go anywhere else. The camper itself was extremely clean and adorably...
United States
hannah w.
$179 nightly
The price is $200
Nov 9 - Nov 10
Total with taxes and fees
Cozy Camper tucked into the woods
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

9. 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, (9 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
$148 nightly
The price is $165
Oct 25 - Oct 26
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
A living room with a sofa, coffee table, and chairs, a kitchen area with a bar, and a door.

10. Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (22 reviews)
"It was great!"
United States
Amanda T.
$271 nightly
The price is $307
Nov 9 - Nov 10
Total with taxes and fees
Pristine Cozy Walkable Downtown 2BR Getaway
A hot tub with a string of lights above it, set against a dark night sky.

11. 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, (18 reviews)
"Great place and welcoming stay!"
United States
Frank M.
$352 nightly
The price is $393
Oct 28 - Oct 29
Total with taxes and fees
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A modern kitchen with blue cabinets, a dining area with a glass table, and a living room with a brown leather sofa.

12. Collinsville River Escape / Fall Foliage, Deck & Yard

Collinsville River Escape / Fall Foliage, Deck & Yard
Collinsville
10.0 out of 10, Exceptional, (1 review)
"We loved the place, which feels like your own house in the woods. The setting is gorgeous especially with the leaves changing colors. We specifically chose the location so we could bike the Farmington Trail loop which starts at the bottom of the hill. The house is so well stocked with everything you could think of, especially coffee and there is plenty of space to relax inside and out. The host was very attentive to our needs. It couldn’t have been better for us."
United States
Margaret A.
$196 nightly
The price is $223
Nov 2 - Nov 3
Total with taxes and fees
Collinsville River Escape / Fall Foliage, Deck & Yard
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

13. 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, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$336 nightly
The price is $375
Oct 27 - Oct 28
Total with taxes and fees
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A house with a porch, a garden with pink flowers, and a stone wall along the road.

14. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (153 reviews)
"Great place and stunning location. Absolutely loved the quiet and perfect mix of old times with modern convenience. Had a short stay this trip but intend on returning in the future."
United States
Dale B.
$340 nightly
The price is $359
Oct 22 - Oct 23
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.4 out of 10, Exceptional, (3 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
$285 nightly
The price is $318
Nov 3 - Nov 4
Total with taxes and fees
Real Estate: Therapy - Lake, Laundry, Love it
A red door with a wicker basket hanging on it, leading to a laundry area with a brick wall and two large speakers.

16. 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.
$252 nightly
The price is $268
Oct 20 - Oct 21
Total with taxes and fees
The Historic Hideaway
A historic building with red brick architecture, snow-covered roofs, and a prominent chimney.

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.
$257 nightly
The price is $273
Oct 20 - Oct 21
Total with taxes and fees
The Old Avon Village
A modern kitchen with a wooden dining table, blue chairs, and a decorative bowl centerpiece.

18. 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.
$509 nightly
The price is $591
Oct 19 - Oct 20
Total with taxes and fees
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

19. Sun Filled Lake House Living

Sun Filled Lake House Living
Avon
6.6 out of 10, (4 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.
$246 nightly
The price is $261
Oct 26 - Oct 27
Total with taxes and fees
Sun Filled Lake House Living
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

20. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
$320 nightly
The price is $358
Oct 26 - Oct 27
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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Perfect place for our two night stay. Good location for exploring the local area. The room was clean and spacious. Good restaurants nearby and there was plenty of parking. Staff were friendly and helpful."
Sarah 2-night trip
Posted 11 hours ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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.

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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?

Riverside Retreat in the Berkshires: Visitors like this Colebrook vacation home rental. It is located on a river and has a fireplace, a selection of games, 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.

What’s there to see and do in Colebrook?

Explore the area and family-friendly sights such as Flamig Farm, or get out into nature at a spot like Highland Lake. Infinity Music Hall and Bistro and Haystack Mountain 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.