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
7 Aug - 9 Aug
In two months
18 Sep - 20 Sep
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Colebrook vacation rentals

2 bedrooms, WiFi (free), 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 AED 397
AED 741 total
includes taxes & fees
26 Jul - 27 Jul
Peaceful and cozy 1 bed 1 bath in quaint Winchester
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 AED 560
AED 1,648 total
includes taxes & fees
27 Jul - 28 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, (148 reviews)
"Great location"
United States
Will G.
The price is AED 698
AED 1,293 total
includes taxes & fees
26 Jul - 27 Jul
Big farmhouse in the foothills of the Berkshires
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 AED 478
AED 1,228 total
includes taxes & fees
27 Jul - 28 Jul
Cozy Modern Farmhouse Private Apt - 3 Beds
Property grounds

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.
The price is AED 410
AED 760 total
includes taxes & fees
26 Jul - 27 Jul
Peaceful Meadow Retreat
Interior

Linny's - Lakefront Retreat Private Dock & Firepit

Linny's - Lakefront Retreat Private Dock & Firepit
West Suffield
10.0 out of 10, Exceptional, (41 reviews)
"Everything was spectacular from the check in process to the personal experiences."
United States
leigh
The price is AED 649
AED 1,338 total
includes taxes & fees
5 Aug - 6 Aug
Linny's - Lakefront Retreat Private Dock & Firepit
Smart TV, fireplace

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.
The price is AED 753
AED 1,223 total
includes taxes & fees
17 Aug - 18 Aug
Pristine Cozy Walkable Downtown 2BR Getaway
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 AED 1,146
AED 1,931 total
includes taxes & fees
30 Jul - 31 Jul
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 AED 1,020
AED 2,130 total
includes taxes & fees
4 Aug - 5 Aug
Classy Private Apt - 3 Beds 2nd Flr - Near Downtown
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 AED 390
AED 1,084 total
includes taxes & fees
11 Aug - 12 Aug
Cozy Attic 10 min to Llitchfield
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (12 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.
The price is AED 1,469
AED 2,548 total
includes taxes & fees
5 Aug - 6 Aug
Guesthouse Cabin vacation rentals in Berkshire County
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 AED 606
AED 1,173 total
includes taxes & fees
13 Aug - 14 Aug
River Overlook - What a view from your deck!
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 AED 684
AED 1,564 total
includes taxes & fees
27 Jul - 28 Jul
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Coffee/tea maker, fridge, microwave, oven

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 AED 1,071
AED 1,376 total
includes taxes & fees
26 Jul - 27 Jul
The Jefferson Guest House, Spacious, Special Views
Coffee/tea maker, fridge, microwave, oven

Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.0 out of 10, Very Good, (1 review)
"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.
The price is AED 380
AED 568 total
includes taxes & fees
29 Jul - 30 Jul
Cozy 1-bedroom studio in serene Great Barrington with AC
TV

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.
The price is AED 1,374
AED 2,527 total
includes taxes & fees
27 Jul - 28 Jul
Treetop Hideaway in Tyringham
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 AED 848
AED 1,772 total
includes taxes & fees
19 Aug - 20 Aug
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Interior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
Real Estate: Therapy - Lake, Laundry, Love it
Coffee/tea maker, fridge, microwave, oven

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 AED 992
AED 1,485 total
includes taxes & fees
29 Jul - 30 Jul
Home in Great Barrington
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (19 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 AED 893
AED 1,338 total
includes taxes & fees
30 Jul - 31 Jul
Cozy Riverside Berkshires Retreat
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

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"We have stayed here every time we go to Tanglewood. The service is always friendly, the price is reasonable and central to everything in Great Barrington. Highly recommend."
Arianne 1-night trip
Posted 21 hours ago
Quality Inn Great Barrington

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.