Colebrook Holiday Rentals from NZ$276: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Colebrook has to offer?

Cozy Riverside Berkshires Retreat : This holiday home rental outside of Colebrook 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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Our top choices for Colebrook holiday rentals

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

Otis

includes taxes & fees

31 Aug - 1 Sept

2. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

winsted

Steve

includes taxes & fees

1 Sept - 2 Sept

3. Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Collinsville

Mike

includes taxes & fees

17 Sept - 18 Sept

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

Winchester

includes taxes & fees

30 Aug - 31 Aug

5. Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

Torrington

Jaimie S.

includes taxes & fees

9 Sept - 10 Sept

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

West Suffield

Wendy C.

includes taxes & fees

13 Sept - 14 Sept

7. Art House 3 Beds Close to Warner Theater

Torrington

Brittany M.

includes taxes & fees

1 Sept - 2 Sept

8. Pristine Cozy Walkable Downtown 2BR Getaway

Torrington

James M.

includes taxes & fees

31 Aug - 1 Sept

9. Cozy Modern Farmhouse Private Apt - 3 Beds

Torrington

Louisa A.

includes taxes & fees

30 Aug - 31 Aug

10. Big farmhouse in the foothills of the Berkshires

Russell

Will G.

includes taxes & fees

31 Aug - 1 Sept

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

Collinsville

Mary S.

includes taxes & fees

9 Sept - 10 Sept

Coffee/tea maker, fridge, microwave, oven

12. The Jefferson Guest House, Spacious, Special Views

Litchfield

"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!"

genevieve

includes taxes & fees

31 Aug - 1 Sept

13. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Sherwood Forest

Frank M.

includes taxes & fees

7 Sept - 8 Sept

14. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

includes taxes & fees

23 Sept - 24 Sept

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

Great Barrington

Rebecca K.

includes taxes & fees

30 Aug - 31 Aug

16. Home in Great Barrington

Great Barrington

HEATHER G.

includes taxes & fees

3 Sept - 4 Sept

17. Peaceful Meadow Retreat

Granby

Todd R.

includes taxes & fees

10 Sept - 11 Sept

18. Treetop Hideaway in Tyringham

Monterey

"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!! "

Samantha G.

includes taxes & fees

23 Sept - 24 Sept

19. Cozy Riverside Berkshires Retreat

Great Barrington

Colin E.

includes taxes & fees

1 Sept - 2 Sept

3 bedrooms, iron/ironing board, WiFi, bed sheets

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

Great Barrington

Mary R.

includes taxes & fees

8 Sept - 9 Sept

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Top Colebrook Hotel Reviews

The Little Lion

8/10 Good

"Clean and comfortable room for reasonable price. Central area/lobby is nice place to sit and read, relax, and/or eat breakfast (coffee provided). Also red Adirondack chairs up on hill behind rooms and small tables/chairs in front of some rooms. Can use the outdoor pool and whirl pool a few miles away at the Red Lion Inn, which is desirable feature on summer days. A few negatives. While the building and rooms are set back from the road, it’s located off a busy road that goes between Stockbridge and Great Barrington. You will hear the cars during the day. It’s also not what I would consider an “Inn” as it’s really a motel. It used to be the Briarcliff Motel before the Red Lion Inn purchased it. Any questions, requests, or comments need to contact them as the Little Lion didn’t have any full time staff and no one at front desk in the lobby when we stayed. We received text with code for room door."

The Abner Hotel

10/10 Excellent

"I think this hotel would be wonderful in any season...beautiful area to walk on the wide, stately streets with beautiful 1800's home in the summer, spring or fall; lots of beautiful autumn leaves in the fall, perfect New England town with center green in winter, summer, spring and fall, to beautiful spring with flowers all over the town too. At Abner Hotel you can enjoy any season with the great rooftop bar, the cozy fireplace in the lounge outside the restaurant in the winter.... A special attraction for attorneys or anyone interested in the law is the unique nature of this property which was a renovated and preserved old courthouse.... Don't forget the fascinating attraction of country's very first Law School, walking distance from the hotel! Lourdes of Litchfield Grotto, lovely with outdoor masses, stations of the cross, gift shop and Cafe, open to all, just down the road."

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent

"It was much better than expected. Subtle lighting in the room was a nice touch. Clean and very comfortable bedding and bathroom. Everything in the fitness room was was clean and operational. The breakfast was superb. A very enjoyable stay."

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent

"Our family loves this hotel! Hot tub and pool are excellent. There’s a fun little game room for kids. The breakfast was plentiful and tasty. Everything is clean and staff is nice. Best part- four working level 2 car chargers!"

Simsbury 1820 House

10/10 Excellent

"The staff at Simsbury 1820 were the highlight of the stay. They were expecially friendly and very helpful. They had some suggestions of things to do that were interesting and area specific. Understandably but a bit disappointing was the inadquacy of the plumbing. It's a very old building but toilets could be updated."

Find out more about Colebrook

Everything you need to know about Colebrook holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Colebrook holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Colebrook holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Colebrook holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Colebrook holiday rentals we have selected for you start as low as NZ$276 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Colebrook rentals

At Expedia, we put the best Colebrook holiday 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 holiday.

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.

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 are some of the best holiday rentals that Colebrook has to offer?

Cozy Riverside Berkshires Retreat: This holiday home rental outside of Colebrook 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 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.

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Check prices for these dates

Our top choices for Colebrook holiday rentals

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

2. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

3. Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

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

5. Classy Private Apt - 3 Beds 2nd Flr - Near Downtown

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

7. Art House 3 Beds Close to Warner Theater

8. Pristine Cozy Walkable Downtown 2BR Getaway

9. Cozy Modern Farmhouse Private Apt - 3 Beds

10. Big farmhouse in the foothills of the Berkshires

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

12. The Jefferson Guest House, Spacious, Special Views

13. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

14. Cheerful 3-bedroom cottage with woodstove

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

16. Home in Great Barrington

17. Peaceful Meadow Retreat

18. Treetop Hideaway in Tyringham

19. Cozy Riverside Berkshires Retreat

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

Find holiday rentals that suit your style

Top Colebrook Hotel Reviews

The Little Lion

The Abner Hotel

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Monument Mountain Motel

Blackberry River Inn

Days Inn by Wyndham Torrington

Simsbury 1820 House

Find out more about Colebrook

Frequently asked questions

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