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Colebrook Holiday Rentals

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Holiday Rentals in Colebrook

Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (7)
"My wife and young daughters live in central CT, and the drive to Becket was both scenic and relatively short at around an hour and a half. The property offers great privacy in a remote wooded setting in the heart of the always beautiful Berkshires. We brought our dog along, and we all were able to relax by the fire, read our favorite books, as well as peruse interesting titles on the impressive bookshelf built into the living room wall—a book lover’s delight. We admired the openness and light...
Pristine Home In Becket Woods
Waterview Home in the Berkshires: Near Hiking
9.2 out of 10, Wonderful, (14)
"Lovely house and kind owner. We had a great time. The view is amazing."
Waterview Home in the Berkshires: Near Hiking
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The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (195)
"We’ve stayed at the cabin with our dog four times and always enjoy our peaceful stay. It’s cozy, clean and private. Also, the Sherwood Shoppe - just down the road - is a wonderful place for breakfast, homemade chili and much more."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Peace and quiet on the lake
9.6 out of 10, Exceptional, (184)
"My husband and I had a very peaceful and relaxing long weekend at this lake house! It was very clean and has everything you need. We spent the majority of our time on the wonderful screened-in porch. The location was great and there was a little store/restaurant only a couple minutes walk up the street that was convenient and the food was really good! Overall, a great place to stay!"
Peace and quiet on the lake
Private Island - Largest Fresh Water Reservoir in Mass....
10.0 out of 10, Exceptional, (3)
"So grateful to Bill for such a wonderful stay! The cottage was so lovely and had everything you could need for a weekend on the lake. Will definitely be returning in the future 😊"
Private Island - Largest Fresh Water Reservoir in Mass....
Perfect Vacation Get Away - Historical New Marlborough
9.6 out of 10, Exceptional, (49)
"This was our first stop on a long journey from VA to ME, traveling with 2 dogs. It was perfect, the dogs were safe with lots of freedom to roam. What a beautiful, peaceful village and sweet little cottage."
The price is NZ$440
per night
24 Jun - 25 Jun
Perfect Vacation Get Away - Historical New Marlborough
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, (6)
"My wife and I were looking for a nice little getaway within reasonable driving distance and came across this great property. As soon as we saw the big windows in the living room we were sold. Definitely getting added to our short list of places to go back to."
Berkshires Cabin 2 Mi to Appalachian Trail!
Tranquil 3-BR Waterfront Retreat
10.0 out of 10, Exceptional, (7)
"The house is immaculate! One of the cleanest properties we've stayed in. The house was the perfect size for my family of 4 (2 adults, 2 teens) with room for more. The beds are comfortable, and there were plenty of linens and towels. The linens and towels are high quality, very soft. The kids had fun fishing in the pond and made good use of the kayak (they caught some bass, pickerel and sun fish). The neighborhood is nice and quiet, dirt roads, no traffic...great for taking walks. We used the...
Tranquil 3-BR Waterfront Retreat
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
6.0 out of 10, (2)
"Be aware they will not proactively provide you with a local host name or contact info. It was very difficult to get Vacasa support to help me get this info to resolve wifi issue - like hours long to get them to just give me the property managers info and even then, they wouldn't give it to me, just had them contact me. Otherwise, amazing pool and great location. Outdated indoors but clean to the extent that it could be. Utensils were dirty and tons of flies in the house upon arrival - like 50...
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, (4)
"Perfect place to relax and have dogs as part of a mini vacation. Very clean, organized, and provided helpful local information. Will definitely stay there again."
Serene Acreage - Pond - Hiking Trails Nearby
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, (20)
"Relaxing get away. Great hot tub, table shuffleboard. 3 floors of comfort."
The Meadows House @ Otis Ridge w/ 7-person hot tub
The Blue Elm - A Historic Berkshire Cottage
10.0 out of 10, Exceptional, (2)
"If I could have given it more than 5 stars I would have. Beautiful, quiet area and the place is stunning. The gas fireplace in the dining area was great, has pretty much everything you could need and incredibly stylish (the retro fridge and microwave were very cool). Can’t speak to the pullout but the king in the master might have been the most comfortable bed I’ve ever slept in and the double shower is awesome. The hosts were friendly and responsive. Went to hike and the number of trails within...
The price is NZ$668
per night
16 Jun - 17 Jun
The Blue Elm - A Historic Berkshire Cottage
Quintessential 6-BR Berkshires Lodge
10.0 out of 10, Exceptional, (4)
"We had a great time. Place is amazing. Highly recommend. We had four different families and we never felt cramped. Lovely open main room allowed us to stay connected. Bedrooms were nice and spacious, good bed options. Nice decor."
Quintessential 6-BR Berkshires Lodge
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
9.8 out of 10, Exceptional, (6)
"This house was awesome! Plenty of room and amenities for all! Great location to the downtown, local restaurants and bars. Communicating with the host was also so easy to do. Would definitely recommend for a weekend getaway!"
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Private Cabin On Over 12 Acres Of Woods!
10.0 out of 10, Exceptional, (3)
"The cabin is cozy and absolutely beautiful. We had everything we needed for a a relaxing stay in The Berkshires. Thanks for the comfort and welcoming hospitality."
The price is NZ$2,596
per night
6 Jul - 7 Jul
Private Cabin On Over 12 Acres Of Woods!
Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (122)
"Loved the entire experience."
The price is NZ$587
per night
24 Jun - 25 Jun
Big farmhouse in the foothills of the Berkshires
Little Longbow Lakefront Chalet
10.0 out of 10, Exceptional, (4)
"House is well kept and very clean. Pretty view. Quiet and calm area to relax in, wish we had more days here. Very good WIFI and flat screens also."
Little Longbow Lakefront Chalet
Peaceful, Post and Beam Loft, Sleeps 9
10.0 out of 10, Exceptional, (8)
"beautifully stay for couples."
Peaceful, Post and Beam Loft, Sleeps 9
Don't see what you're looking for?
See all available properties in Colebrook
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.

Other types of properties in Colebrook you may be interested in

Quality Inn
2.5 star property
8.2 out of 10, Very good, (1009)
"Really clean and great staff"
The price is NZ$187
per night
11 Jun - 12 Jun
Quality Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
3.5 star property
9.0 out of 10, Wonderful, (477)
"This resort is an excellent place for families to relax and spend time together without having to worry about anything, just focus on having fun. The staff were great!"
The price is NZ$287
per night
19 Jun - 20 Jun
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Residence Inn by Marriott Hartford Avon
3.0 star property
8.8 out of 10, Excellent, (320)
"Fabulous staff, loved our suite & the area is lovely!"
The price is NZ$314
per night
16 Jun - 17 Jun
Residence Inn by Marriott Hartford Avon
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Colebrook holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Colebrook. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Colebrook. Seeing all the best attractions is bound to make you fall in love with Colebrook. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Colebrook short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Colebrook?

Yes, there are holiday rentals close to the most popular sights in Colebrook, or you can select a more secluded option if you're looking for a relaxing stay.

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 Otis Reservoir are a couple of places you'll find in the wider area.

What’s a holiday rental in Colebrook like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Colebrook. Holiday rentals offer extras such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.

Recent reviews of Colebrook properties
Expedia verified reviews