Holiday rentals in Colebrook

4.99 out of 5 average rating, 223 reviews

Home in Colebrook

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

Rustic getaway in the beautiful Litchfield Hills of Northwestern Connecticut featuring a 2-acre pond and access to 9 miles of unique hiking trails on 450+ wooded acres. Cozy 1700's farmhouse comfortably sleeps 4 adults in 2 bedrooms, with an additional kids room that has a fold-out double futon and loft with one double air-mattress, perfect for children's sleeping bags. There is a pull out sofa in the living room. Dogs welcome! The house is next to Norbrook Farm Brewery, which you can walk to.

4.94 out of 5 average rating, 416 reviews

Chalet in Otis

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Guest suite in Winchester

4.96 out of 5 average rating, 148 reviews

Private Suite 2 Bedroom Deck Lake Views

Welcome to “The Mermaid” at Highland Lake!!! Modern 2-bedroom private bath suite with kitchenette (see amenities) in the foothills of the Berkshires! Views of Highland Lake from your private sundeck. Moon and star gazing by night. We follow all Airbnb policies & State of CT COVID cleaning guidelines. Please do not trespass on the property of private residences, across the street on the lake side. These are private residences. There are public beaches public access areas for your enjoyment.

4.99 out of 5 average rating, 143 reviews

Flat in Canaan

West Main

1890s home situated on the outskirts of town, entire second floor apartment. The apartment is bright and sunny and super comfortable with 2 bedrooms both with queen beds, 1 bathroom, eat in country kitchen fully equipped.There is a spacious living room with a smart Roku TV, (not cable ) WiFi and access to a private garden space, private entrance and off street parking. Walk to town brewery, pizza and more. Great place to relax after a day of exploring Litchfield county and the Berkshires.

Holiday home in Torrington

4.95 out of 5 average rating, 212 reviews

Modern/Private Five ★ /Hotel quality stay/1 BR Apt

Enjoy the comfort and tranquility of this modern apt. A lovely space to relax after a busy day. This clean and bright apt offers a tranquil residential vibe alongside quick, easy access to the Torrington downtown areas, restaurants, stores and bars. It features an open-concept layout, a neutral color scheme, wood surfaces, tasteful furnishings and decor. Designed comfortably for your stay offering WiFi, Netflix, laundry, queen bed, well equipped kitchen, and clean fresh white bed sheets.

4.98 out of 5 average rating, 166 reviews

Flat in Torrington

Apartment on Main St.

Hidden gem. Large combined living room/bedroom apt with separate kitchen and balcony. Private entrance. This is 1 unit in a 3 family house. 10 to 15 minutes walking distance to downtown shops, restaurants, Warner Theatre and Nutmeg Ballet. Shared huge garden, with Koi pond and pergola. Parking in the driveway for 1 car (possibly more, message for details). WiFi and Smart TV with some local channels (no cable). 45 minutes to Bradley Airport, 2 hours to NYC, 20 minutes to ski slopes.

Guest house in New Marlborough

4.9 out of 5 average rating, 199 reviews

COZY GUESTHOUSE MINUTES AWAY FROM HIKING!

Renovated 1880's one bedroom cozy guesthouse in beautiful Southfield, MA. Full kitchen stocked with all necessities. Comfortable & stylish with a luxury king size bed. Minutes away from Ski Butternut, Berkshire attractions & trails. Walking distance to breakfast and lunch at The Southfield Store or have dinner at nearby The Old Inn On The Green and Cantina 229. 10 minutes from Great Barrington. Enjoy leaf-peeping, hiking, waterfalls, apple picking, skiing, and much more!

Guest suite in East Granby

4.85 out of 5 average rating, 357 reviews

Staying at Ten Hillcrest

What I’ve always thought of as the perfect location! Private enough to see trees and birds and yet close enough to jump on the highway to anywhere. Conveniently located on a dead end street with no through traffic. On your way out take a left and head towards farm and eateries or take a right and head to the city of Hartford or Springfield. Just minutes from Bradley International Airport

4.99 out of 5 average rating, 821 reviews

Guest house in Granby

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!

4.89 out of 5 average rating, 198 reviews

Cottage in Granby

The Little Red Schoolhouse ~ Circa 1877

This wonderful old building is listed on the National Register of Historic Places and operated as the District 9 schoolhouse until 1948. Now, this beautiful piece of history is available for you to enjoy! Located in the picturesque West Granby, Connecticut, this little schoolhouse directly abuts hundreds of acres of open space, Granby Land Trust property, and several organic farms.

4.88 out of 5 average rating, 104 reviews

Flat in Winsted

Haven at Highland lake

Kick back and relax in this calm, stylish space. This studio apartment offers fast internet, TV , a comfortable couch , a stylish new bathroom, a lovely kitchenette, as well as black out curtains in the bedroom. And a cozy warm fireplace. This apartment comfortably sleeps 1 adult or a couple. The couch folds out into a bed and there is bedding in a tote stored Under the bed.

4.91 out of 5 average rating, 380 reviews

Flat in Winchester

Gateway to the Berkshires

Remodeled apartment on 2nd floor of a 1910 Victorian house near the center of Winsted, CT. The apartment is unique and cozy, with large windows, some stained glass, tin ceilings, hand painted kitchen cabinets, and plants. Close proximity to all Litchfield County and the Berkshires have to offer, in all seasons. It's an easy drive from NYC or Boston. Great weekend get-away.

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Other great holiday rentals in Colebrook

4.8 out of 5 average rating, 20 reviews

Cabin in Otis

Simple, rustic, cozy get away

ChrisRating, 5 stars9 months ago

It was a perfect price. With the ABNB it was double+. I would rather pay John more for the one night personally, than what I did. And have done twice. I have always left the place the same or better than I found it. I understand the cleaning fee, but kills single fathers like me for a 1 night trip. That being said. Walker cabin is great! Kayaks, all safety gear, fully outfitted down to toothpicks, brushes, floss, ect. You think you forgot it. It’s there. Baby monitors!

Cottage in Colebrook

5 out of 5 average rating, 64 reviews

Blueberry Cottage

JoanRating, 5 stars8 months ago

Blueberry Cottage is truly a gem! John and Catherine were lovely to deal with and very responsive. Their home is in an idyllic setting on a quiet country road surrounded by beautiful grounds. The cottage itself is laid out nicely, furnished tastefully with lots of comfortable places to relax and is spotless. The kitchen is large, very well equipped and easy to cook in. The bathrooms are also very nice. The 2 fireplaces work extremely well, and the bed is very comfy. Having good, seasoned firewood and kindling is a bonus if you plan to make fires while you’re there. We have only positive things to say about this place and recommend it without reservation. In fact, we’re already discussing when we can go back!

Cabin in Monterey

4.87 out of 5 average rating, 235 reviews

Secluded cabin with babbling brook

CoriRating, 5 stars3 weeks ago

Truly a magical spot. We’ve stayed at many unique Airbnbs, and this one is up there as a favorite. It’s so peaceful and beautiful; the walk down makes it feel like you are truly remote and alone. The screened porch is perfect for listing to the stream at all points of the day. The cabin itself is furnished in a quirky and cozy way, and the beds are very comfortable. The full kitchen had everything needed. The host was super friendly and responsive. We would absolutely would recommend to others!

5 out of 5 average rating, 35 reviews

Cabin in Saugerties

Luxury A-Frame Cabin w/ Hot Tub

ChrisRating, 5 stars3 days ago

Fil & Ellie’s place was the perfect stay for our getaway. Their home is amazing. We were very impressed by the amenities, the cleanliness and attention to detail. This place has everything you’ll need for a great stay. The hosts were also very helpful in answering our questions and assisting us with check-in. I would highly recommend staying here if you have the chance.

5 out of 5 average rating, 5 reviews

Cabin in Becket

WALK to lake! Dog friendly, A-Frame in Berkshires!

AustinRating, 5 stars1 week ago

What more could you want? This quaint cabin situated in the woods offers privacy, unique architecture, comfort, and peace. It’s equipped with everything you could possibly need, and the hosts were truly some of the most responsive and kind people I have ever interacted with. They truly went above and beyond for us. We stayed with a toddler and two dogs, and they all loved the property and the cabin. We will most definitely be back!

Cabin in Litchfield County

4.8 out of 5 average rating, 10 reviews

Blackberry Cottage

GretchenRating, 5 stars6 days ago

Heather's place is LOVELY. It's got a homey, charming vibe in a bright green setting. It was clean and bright and comfortable. Even the pull-out couch was comfy, thanks to the thoughtful addition of a mattress pad. We're all vegan, and Heather made sure we had oat milk (Oatly!) and vegan butter. And the dog-friendly piece is fantastic!! Can't wait to go back with the pups.