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Cottage vacation rentals in Litchfield County

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Top-rated cottage rentals in Litchfield County

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Top guest favorite

The living area features multiple seating options, including a spacious sectional and two armchairs, arranged around a low coffee table. Large windows allow natural light to fill the space, providing views of the outdoors, while the ceiling showcases exposed beams for a touch of character.

Cottage in Burlington

4.98 out of 5 average rating, 129 reviews

Cozy Lakefront Cottage w/Swim Spa & Firepit

Discover a charming 1080 sqft lakefront cottage offering modern comfort and tranquility. Wake up to peaceful Lake Garda waterfront views while staying near Farmington Valley’s conveniences. This newly remodeled retreat features a large jetted swim spa, stone patio with fire pit and grill, and direct lake access for kayaking or pedal boating perfect for relaxation. Enjoy a private getaway with nature’s beauty at your doorstep, all while being minutes from dining, shopping, and outdoor adventures.

A modern black cottage is presented, set against a backdrop of tall trees and natural stone landscaping. A gravel driveway leads up to the entrance, where steps ascend to a covered porch. A dog is seen on the grassy area nearby.

Cottage in Cornwall

4.93 out of 5 average rating, 164 reviews

Newly Built Cottage in Housatonic Valley

This newly built modern cottage is located on a historic railroad street nestled in a charming village within the Housatonic River Valley. There are beautiful river views from the front porch, deep woods off the back deck, a white marble kitchen with new appliances, and a dedicated parking spot. Escape the city and surround yourself in this quiet valley and the calm of small village life, located just 2 hours from NYC. This location offers year-round access to nature & outdoor activities.

An outdoor fire pit is surrounded by several adirondack chairs on a grassy area. A stone wall frames the fire pit, with trees and a glimpse of a secondary building in the background. The scene reflects a serene natural setting.

Cottage in Bethlehem

4.98 out of 5 average rating, 116 reviews

Cozy Getaway | Pet Friendly | Litchfield Cty

Escape to the Cottage at the Grove - with a cozy wood burning fireplace and inviting sectional it is the perfect winter sanctuary. Well equipped with all the amenities; from a fully stocked kitchen to bath salts for the deep soaking tub. One bedroom w/ en-suite bath & pull-out full size sofa bed. Just 30 min to Mohawk or Southington Ski Mountains. Just 10 min to downtown Litchfield, close to local farms & vineyards. For security we have two exterior cameras facing the door & driveway.

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, 211 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.

A wood stove sits centrally in a warm wooden interior, surrounded by a stone hearth. Soft lighting is provided by a nearby lamp, highlighting a cozy sitting area with wooden furniture and decorative accents. Reflections of shelving and natural textures can be seen in the backdrop.

Cottage in Falls Village

4.99 out of 5 average rating, 113 reviews

Retreat w 50 acre forest, waterfalls, tennis/bball

Perched above a brook in the woods. See the seasons fold and unfold in 50 acres of private forest, waterfalls, & pond. Fall asleep to sounds of the creek below. Wake to a canopy of beams, dappled sunshine, breakfast on a screened porch. Respite, creativity, and play (hike, sledding, 5 minutes from Mohawk Mtn Skiing). Hand built, inspired by Japanese teahouses, featuring tongue & groove construction, shoji screen doors, & tatami mats. Video: "Cornwall Hollow Teahouse" on YT or IG

The spacious loft features a sloped ceiling with exposed beams, accommodating a king-size bed and a cozy sofa. A work table is positioned beside a large window that allows natural light to fill the room. A flat-screen TV is mounted on the opposite wall.

Cottage in Collinsville

4.97 out of 5 average rating, 144 reviews

The Carriage House

Newly built contemporary light filled spacious 700 ft carriage house/Loft. It is walking distance to the Farmington river and downtown historic Collinsville. Just off the cycling "rails to trails" river trail, you'll find places to also kayak, SUP, fish and swim. CT Wine Trail and Brignole Vineyards nearby where you'll find food trucks and live music along with award winning wine! Skiing nearby. Conveniently close to Farmington, Avon, Simsbury, West Hartford and 84 highway.

The exterior of a charming cottage is seen, featuring a front porch with two black chairs and potted plants. Stone steps lead up to the entrance, flanked by shrubs and trees, creating a serene setting within the landscaped grounds.

Cottage in Rhinebeck

4.93 out of 5 average rating, 164 reviews

Intimate Cottage on Private Estate

Bulls Head Cottage is a thoughtfully-designed retreat nestled within a 2.5 acre estate 5 minutes from Omega Institute and 10 minutes from the charming Village of Rhinebeck. The 720 square foot guest cottage is a relaxing place for up to 2 guests, offering cozy indoor and outdoor space including an office overlooking the property's pond. Enjoy quick access to hiking, shopping, fine dining and more. Under 2 hours from New York City by car or train. Pets not typically allowed.

A spacious living area features a large sectional sofa adorned with cushions, offering panoramic lake views through expansive windows. A dining table for two is located nearby, with a small workspace and desk chair positioned to enjoy the serene scenery.

Cottage in Plymouth

4.94 out of 5 average rating, 128 reviews

Lakefront Cozy Oasis 2BR w/ stunning sunset views

It’s the Lakefront Paradise you’ve been searching for: Escape to Cozy Oasis where peaceful waters meet modern comfort! Wake to stunning views, spend the day kayaking around the lake, and unwind with breathtaking sunsets from your private deck. This pet-friendly retreat offers high-speed WiFi for remote work, fully equipped kitchen for home-cooked meals, and cozy entertainment spaces. Perfect for romantic getaways or family adventures - your serene lakeside escape awaits!

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

4.86 out of 5 average rating, 358 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

Top guest favorite

An interior corridor is visible, featuring rustic wooden beams and a warm wood floor. To one side, a glass-paneled room can be seen, likely housing a cozy nook. Light enters from multiple sources, creating an inviting and bright atmosphere.

Cottage in Red Hook

4.98 out of 5 average rating, 680 reviews

bright serene + spacious barn @barn and bike

a bright serene space built by locals on the property we live on. we are in what we think is the most beautiful region of the Hudson River Valley - surrounded by pastoral beauty and dramatic landscapes. quaint yet cultured towns in all directions. please read the entire description & rules before booking • beyond 2 guests, the rate adds 50$/night/per person • please add dogs (2 max. 50$/per dog) when booking • we look forward to having you here!

The living area features a 21’ tall wood-burning fireplace made of stone, complementing the vaulted ceiling and high skylights. A comfortable green sofa is positioned near a rustic coffee table, while a flat-screen TV is mounted on a wooden wall unit. Natural light floods the space.

Cottage in Pawling

4.99 out of 5 average rating, 134 reviews

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

Top guest favorite

A serene landscape is captured with bare trees standing against a colorful autumn sky. Vivid red and orange foliage is visible in the distance, set against fields of green, while a rustic stone wall lines the property. The tranquil scene invites a sense of peace.

Cottage in Sharon

4.93 out of 5 average rating, 182 reviews

Foxfire Hill: A Bit of Luxury in the Countryside

Enjoys luxurious Get away to lovely Sharon, CT, just 2 hours from NYC/3 hours from Boston. Enjoy a chill vibe, garden and mountain views, and fresh organic eggs from our lovely flock of hens. We’ve created a luxurious and spacious modern feel, in a bucolic farmland setting. All newly refurbished with a luxurious modern bath with rain shower and fabulous marble stone work. Coyuchi bedding, soft organic cotton linens, and gourmet kitchen!

Vacation rentals for every style

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Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Litchfield County cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

A wooden dock extends into the calm water of Lake Zoar, framed by lush green hills in the background. Sunlight reflects gently on the surface, while a fire pit made of metal is positioned nearby on the wooden deck, creating a cozy atmosphere for relaxation.

Cottage in Newtown

Magical Lakeside – Lake Zoar Views & Private

A two-story cottage is visible in the background, with a cozy gazebo covering a private hot tub on a red deck in the foreground. A warm sunset casts a golden hue over the scene, illuminating the surrounding trees and the inviting exterior of the cottage.

Cottage in Plymouth

4.97 out of 5 average rating, 33 reviews

Peaceful Fall Getaway | Hot Tub + Lake Views

A spacious living area features light wood beams and large windows allowing natural light to fill the room. A cozy seating arrangement includes a green sofa, a rattan chair, and a plush rug. Bookshelves line one wall, filled with an array of books.

Cottage in New Marlborough

Light-filled cottage

A two-story house with light green siding and contrasting dark shutters stands amidst a natural landscape. The front entrance features a covered porch and bright red door. A two-car garage with red doors complements the exterior, bordered by landscaped bushes and flowering plants.

Cottage in Kent

4.82 out of 5 average rating, 244 reviews

NEW - Hot Tub - Mohawk Mtn - Appalachian Trl

A hot tub with bubbling water is showcased under a covered patio, offering a view of the serene lake and surrounding trees. Soft lighting enhances the tranquil setting, while glimpses of the lake's shoreline and distant boats are visible in the background.

Cottage in Southwick

4.98 out of 5 average rating, 123 reviews

Lake View, Hot Tub, 4 Kayaks, Central AC, Fire Pit

A hot tub is illuminated by bright lights during nighttime, surrounded by a snowy landscape. Nearby, outdoor seating and a heating lamp are visible, creating a cozy atmosphere. The main house stands in the background, framed by trees.

Cottage in Monterey

4.68 out of 5 average rating, 19 reviews

mountain refuge

A charming guest room features a spacious bed with a white coverlet framed by two wooden posts. Comfortable green chairs are positioned beside a small table, which is adorned with a vase of roses, grapes, and glasses of wine.

Cottage in Norfolk

4.94 out of 5 average rating, 16 reviews

The Cottage at Blackberry River Inn

A welcoming living area features two striped armchairs complemented by turquoise cushions, arranged around a round wooden coffee table. A marble fireplace adds a focal point, topped with a framed artwork. Natural light brightens the space through multiple windows, overlooking a green backdrop.

Cottage in Great Barrington

4.85 out of 5 average rating, 40 reviews

THE GREAT ESCAPE BERKSHIRE SKI COTTAGE w/HOT TUB!

Pet-friendly cottage rentals

A wooden deck is surrounded by lush greenery, featuring two lounge chairs positioned for relaxation. A charming cabin stands in the background, accentuated by a mix of trees and plants that create a secluded atmosphere.

Cottage in Carmel Hamlet

4.84 out of 5 average rating, 176 reviews

Lake Cabin Escape–Fenced Yard+Firepit.Dogs welcome

A charming two-story country cottage is shown, featuring natural wood siding and a welcoming entrance. A stone pathway leads to the front door, bordered by a manicured lawn and mature trees, embodying a peaceful rural setting.

Cottage in Craryville

4.92 out of 5 average rating, 551 reviews

Columbia County Getaway - Raspberry Ridge Cottage

A two-story home is nestled among trees, featuring light-colored siding and a gray roof. A red patio umbrella provides shade over a seating area in the yard, while a gravel pathway leads to the front door, enhancing the natural surroundings.

Cottage in Newtown

4.93 out of 5 average rating, 275 reviews

Private and Serene home close to I-84 and shopping

A quaint blue cottage is nestled among vibrant trees, reflecting a peaceful aesthetic. The pond in the foreground features natural greenery and a water fountain, creating a serene environment surrounded by nature.

Cottage in Redding

4.93 out of 5 average rating, 272 reviews

Cozy Cottage by the pond

Top guest favorite

A cozy living area features a light-colored couch with patterned cushions, illuminated by natural light. A television sits against a textured wall adorned with decorative plates. A dining table with modern chairs is visible, alongside an opening leading to a well-lit kitchen.

Cottage in Pine Plains

4.99 out of 5 average rating, 138 reviews

Pine Plains Cottage

A screened-in porch is visible, featuring a wooden rocking chair positioned to overlook a lush garden. A dog sits on the floor nearby. Natural light filters through the screens, illuminating the wooden flooring and surrounding greenery.

Cottage in Great Barrington

4.91 out of 5 average rating, 254 reviews

Cottage on Scenic Road

A spacious kitchen is equipped with white cabinetry and a large wooden island, featuring bar seating. Natural light floods the room through multiple windows. A dining table for six complements the space, with a fruit bowl as a centerpiece.

Cottage in Sheffield

4.94 out of 5 average rating, 156 reviews

Cheerful 3-bedroom cottage with woodstove.

A charming country cottage is set on a lush green lawn, surrounded by trees and fields. A gravel road runs alongside the property, and a car is parked nearby. The front porch features seating, creating an inviting space for relaxation.

Cottage in North East

4.87 out of 5 average rating, 164 reviews

Sunset Cottage: Unplug - Relax - Recharge

Private cottage rentals

Top guest favorite

A spacious living area showcases wooden beams overhead and a cozy seating arrangement. A striped armchair and floral sofa complement a central coffee table on a textured rug. An inviting stone fireplace adds warmth, with a view into the well-lit kitchen area featuring yellow chairs.

Cottage in Clinton Corners

5 out of 5 average rating, 39 reviews

Sun Bear Cottage: 3-Bdrm with Sauna

A cozy living area features a light-colored sofa alongside a woven chair and a circular patterned ottoman. Large windows provide natural light, while a decorative fish hangs from the ceiling. A small plant and a lamp add subtle touches to the inviting space.

Cottage in Winsted

4.92 out of 5 average rating, 48 reviews

Cottage Ease.

Top guest favorite

A vibrant sunset reflects off the water, casting golden hues across the sky. The landscape features rolling hills in the background and a serene lake bordered by trees and homes along the water's edge.

Cottage in Brookfield

4.93 out of 5 average rating, 40 reviews

Longview Lakehouse - 5 min walk to private beach

A bright living room features large windows displaying a colorful sunset. A plush sectional sofa, dressed with several cushions, surrounds a round coffee table. A textured area rug adds warmth to the space, enhancing the inviting and comfortable atmosphere.

Cottage in New Fairfield

4.95 out of 5 average rating, 43 reviews

Sunset Cabin Modern Home Kayak FirePit Lake Access

Top guest favorite

The modern kitchen features stainless steel appliances, including a compact refrigerator and a gas range beneath a sleek vent hood. Light gray cabinetry complements the hexagonal tile flooring, and ample natural light fills the space through the nearby window.

Cottage in Cornwall

5 out of 5 average rating, 44 reviews

Cornwall Cottage

Top guest favorite

The screened porch is illuminated at dusk, showcasing wooden walls and ceiling. Several seating options are visible, including wicker chairs and a dining table. A warm, inviting atmosphere is created by the soft lighting, enhancing the sense of outdoor comfort in the serene setting.

Cottage in Sheffield

5 out of 5 average rating, 74 reviews

The Blue Elm - A Historic Country Cottage

Top guest favorite

The seasonal cottage is set amidst lush greenery with a large American flag displayed on the front porch. A smooth pathway leads to the house, which features a stone wall in the foreground. Two outdoor chairs are positioned on the verdant lawn.

Cottage in Otis

5 out of 5 average rating, 20 reviews

Lake Escape: Lakefront Cottage in the Berkshires

Top guest favorite

A modern cottage is set against a backdrop of lush greenery. The exterior features dark siding, white-framed windows, and a prominent brick chimney. A potted plant adds a touch of color near the entrance, while the surrounding yard includes well-maintained grass and flowering shrubs.

Cottage in Monterey

4.97 out of 5 average rating, 29 reviews

New! Fully renovated private cottage

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