Vacation rentals in Northwest Hills Planning Region

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Northwest Hills Planning Region

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A cozy living area features a light-colored sofa adorned with red accent pillows. A wooden coffee table sits in the center, accompanied by a vintage armchair and a small desk. Warm lighting is provided by a floor lamp, with simple wall art enhancing the inviting space.
Home in Torrington
4.99 out of 5 average rating, 114 reviews

Country living at it's finest

Cozy country home. Quiet and serene; a great place for a get away in Litchfield County Connecticut. An ideal location ,Torrington is about 2 1/2 hours from Boston and NYC and convenient to the Berkshires. Within driving distance to various outdoor activities and attractions including hiking trails, breweries, distillery, wineries, skiing, golf antique shopping, restaurants and variety of entertainment . The hosts are accessible for directions, assistance, or a fun history lesson of the area.

Top guest favorite
A brick fireplace is centered against a light green wall, featuring a clock above it. A patterned chair is positioned nearby, alongside a small television stand. A woven rug covers the floor, enhancing the cozy atmosphere of the space.
Guest suite in Watertown
4.92 out of 5 average rating, 229 reviews

Lrg Studio Apartment - walk to Taft

Welcome to my downstairs space! This clean open concept space is ready for your long term or overnight stay. This studio space is the lower level of a raised ranch house. I live upstairs with my dog and share laundry with airbnb guests. The space has a private entrance through the garage, private bath, and kitchen area in a quiet neighborhood. Walking distance to Taft and convenient to Rts 8 & 84. Off street pkg. Whether you are interested in two nights or two months, you are welcome here!

Top guest favorite
An elegantly set dining table displays black plates, clear glassware, and cloth napkins. A lit candle adds a soft glow, while a modern kitchen is visible in the background, featuring stainless steel appliances and a cozy living area with seating.
Vacation home in Warren
4.98 out of 5 average rating, 217 reviews

Private new house on 10 acres of pristine nature

Brand new home! Bring friends and family to this private and stylish place. House provides everything you need for a comfortable and peaceful stay. Fully equipped kitchen, inviting living spaces, large front and back yards with many exploring trails and a pond a few steps away from the house. Close to many 5 star restaurants, wineries, galleries and shops. Hiking, swimming, boating, skiing just to mention a few outdoor activities Close by: Kent School Mohawk Ski Area Lake Waramug High Watch

Guest favorite
A rustic cottage is nestled among tall trees, overlooking a flowing brook. A wooden bench sits on a grassy area, with large boulders nearby. The house features a deck and is surrounded by greenery, with a gravel driveway leading up to the front.
Cottage in New Milford
4.95 out of 5 average rating, 241 reviews

The Cottage on Babbling Brook

A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

Top guest favorite
The farmhouse exterior displays a yellow façade with white trim and bright blue front door. Multiple large windows allow natural light to fill the home. A small seating area with two chairs and surrounding greenery adds to the inviting appearance of the property.
Home in Cornwall
4.98 out of 5 average rating, 175 reviews

The Farmhouse

Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!

Top guest favorite
A charming artisan-designed cottage is showcased in a residential setting, featuring a yellow exterior complemented by neatly arranged landscaping. A small tree adds a touch of color to the front yard. The peaceful cul-de-sac is lined with greenery, enhancing the tranquil atmosphere.
Cottage in Canaan
4.97 out of 5 average rating, 114 reviews

The Cottage at Great Falls Luxury Getaway.

Spectacular artisan designed cottage on the banks of the beautiful Housatonic river. Located on a quiet residential cul de sac , no through traffic. Interior features plaster throughout, stone veneer and mosaic flooring and original artwork. Fully equipped kitchen, elegant dining room. Oversized soaking tub in master bath. 2 bedrooms, sleeps 4. Fabulous water and mountain views . Large outdoor deck overlooking the water, second small stone dining deck. wonderful gardens.

Top guest favorite
A well-maintained garden is framed by a wooden fence, featuring vibrant sunflowers and lush greenery. The manicured lawn surrounds the garden, creating a serene outdoor space. Towering trees provide a natural backdrop, enhancing the peaceful ambiance of the area.
Guest suite in Litchfield
4.96 out of 5 average rating, 147 reviews

Country Suite

Situated above a charming residential barn this cozy two room suite offers comfort and privacy for those traveling through bucolic Litchfield CT This airy loft boasts Fiberoptic WiFi Smart TV automatic outside lighting A large bedroom overlooks the front of the property in this quiet wooded neighborhood large enough to have a king size bed large bathroom work space and kitchenette Keurig and coffee incl. The front room faces a sweeping lawn on this well kept property

Top guest favorite
A vibrant garden filled with blooming flowers is framed by a well-maintained pathway leading to a red two-story building. Steps ascend through the landscaping, which features a variety of plants and foliage, enhancing the serene outdoor setting.
Apartment in Litchfield
4.99 out of 5 average rating, 217 reviews

Artist's Garden Apartment

Private second floor apartment with entrance. Detached from the host's main house. Overlooks perennial herb and flower gardens located in the backyard. Walking distance to White Memorial Nature Preserve and the historic Litchfield Center. Walk or bike from the backyard to shopping, restaurants, art galleries, bakeries, or to a 3000 acre nature preserve and take in the Flora and Fauna. Quiet residential neighborhood that is close to so many amenities and activities.

Guest favorite
The charming cottage, with its white siding and red door accents, is set amidst lush greenery. A well-maintained yard features grass and flowering plants, while a stone wall frames the scene, adding to the property's rustic appeal.
Cottage in Litchfield
4.87 out of 5 average rating, 403 reviews

Litchfield-Hot Tub-Shops & Eats-Vineyards-Hikes

This vintage style cottage offers guests a comfortable and convenient stay in Litchfield with it’s range of amenities. Essential amenities include air conditioning, cooking basics, a dedicated workspace, dishes and silverware, a dryer, hair dryer, heating, hot tub, kitchen, TV, washer, and Wi-Fi. 5 Min - Litchfield Town center 9 Min - Arethusa Dairy farm- Restaurant 10 Min - White Memorial Conservation Center 8 Min - Bantam Lake 19 Min - Mohawk Mountain Ski Area

Guest favorite
The interior space showcases exposed wooden beams and a bright, open layout. A comfortable seating area is positioned near large windows that provide natural light and views of the surrounding trees. A round dining table is visible, accompanied by a set of stylish chairs.
Home in Cornwall
4.92 out of 5 average rating, 296 reviews

Tucked-away Charming Forest Cabin w/ Private Brook

Renovated cozy cabin (orig 1930s) with modern interior. Two bedrooms, new kitchen & bathroom, overlooking a beautiful private brook and forested hill. Minutes drive to the general store & Kent Falls, 10 minutes from fantastic restaurants, Mohawk Ski Resort & summer activities like swimming & kayaking. Great hiking trails and close to the Appalachian Trail. High speed internet, Netflix, and a deck with outdoor seating. Instagram @GunnBrookCabin

Guest favorite
A cozy living area features two light grey armchairs positioned around a rustic wooden coffee table. Decorative items are arranged on the table, and wood beams add character to the ceiling. A dining area with a black table and chairs is visible in the background.
Cottage in Goshen
4.95 out of 5 average rating, 170 reviews

Stuart Cottage/Minutes to Mohawk Ski Area

The Stuart Cottage is located on the grounds of the Mary Stuart House Bed and Breakfast. Owned by Mary and managed by Elizabeth, the cottage has one bedroom, wifi and plenty of charm...truly the perfect place to relax in a rustic, low-key location in the heart of the Litchfield Hills. Mohawk Mountain and Tyler lake are just a short car ride.

Top guest favorite
The living area features a large leather sectional sofa arranged around a wooden coffee table, with a cozy area rug beneath. Natural light pours in through multiple windows, highlighting the exposed log beams on the ceiling and the warm wooden walls.
Cabin in Harwinton
4.97 out of 5 average rating, 106 reviews

Beautiful Brook-side Log Cabin on 3 Private Acres

Fall asleep to the sound of the rushing brook in this beautifully restored log home. The cabin sits in the middle of three wooded acres overlooking Catlin Brook as it cascades through the gorge below. It seems like wilderness, yet all the amenities of Harwinton are just a few minutes away.

Popular amenities for Northwest Hills Planning Region vacation rentals