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House vacation rentals in Windsor

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Top-rated house rentals in Windsor

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Top guest favorite

The exterior of the farmhouse is captured, showcasing a charming white facade with a screened-in porch. Lush green trees surround the property, with a vibrant red tree providing a pop of color. A spacious grassy area is visible, leading to a wooden deck.

Home in Colebrook

4.99 out of 5 average rating, 227 reviews

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.

A spacious living area is presented, featuring a comfortable gray sectional sofa, a wooden coffee table, and a decorative rug. Two green bar stools are positioned at a small counter, and a ceiling fan is mounted above, enhancing the cozy atmosphere of the penthouse apartment.

Home in West Hartford

4.89 out of 5 average rating, 103 reviews

WeHa Penthouse w/ Private Deck

Welcome to our cozy penthouse-style apartment, where comfort meets tranquility. Enjoy a private deck with exceptional views of West Hartford. Treat yourself with our minibar and indulge without leaving your unit. Centrally located, our apartment provides easy access to the best of West Hartford. Explore Blue Back Square, a vibrant dining hub just 5 minutes away. For a leisurely experience, walk 2 minutes to Park Rd and discover culinary delights like Plan B, Americano Bar, and Zaytoon’s Bistro.

The living room features comfortable seating, including a sofa and two armchairs. A coffee table sits in the center, with a decorative area rug underfoot. Natural light enters through windows, complemented by soft lighting from table lamps. A fireplace adds a cozy touch to the space.

4.92 out of 5 average rating, 260 reviews

FULLY stocked Ranch Home, * Gardens* Gameroom

This is an attached dwelling, with a shared back yard for my 2 dogs. Clean, refreshing three-bedroom , one floor living, centrally located, Mexican, Sushi and Thai, Mediterranean, Italian, Continental, and Vegan ! within 2 min walking to town. 8 minutes to rt 91 and Bradley, minutes to Mass line! Downstairs living space with a game room and or 4 extra sleeping areas for lg parties beyond 3 bedrooms. if needed.I provide everything from razors to coffee , tea and a HUGE snack basket !

A tranquil outdoor scene features a lush green lawn surrounding a calm pond. The reflection of trees and the nearby home can be seen in the water. A picnic table sits on the grass, inviting relaxation amidst the natural surroundings.

Home in Southington

4.95 out of 5 average rating, 121 reviews

Connecticut Chalet: Experience Fall in New England

Escape to a unique & stylish home perfectly tucked away in a picturesque New England town. Indulge in the privacy & serenity of this 5 acre wooded property and peaceful pond while being minutes from an abundance of restaurants, shops & entertainment. Enjoy the natural setting from the comfort of the glass enclosed sunroom with panoramic views of the property. This 3 bed, 2 bath home maintains it’s original 1960’s charm while boasting thoughtful modern touches and intentional functionality.

Top guest favorite

A contemporary lakefront home is surrounded by tall trees, with a spacious deck offering views of Middle Bolton Lake. A fire pit is situated on a stone patio, surrounded by Adirondack chairs. The lush green yard leads to the water's edge, enhancing the natural ambiance.

4.99 out of 5 average rating, 160 reviews

Luxe Bolton Lake

Luxury lake front home! Relax and enjoy the stylish comfort of our 3 bedroom/3 bathroom architecturally-designed lake home. The Luxe lake house features an expansive waterfront, outdoor jacuzzi, gorgeous primary bedroom suite w/ private shower and tub, artistic furniture, cozy fireplace, coffee bar, complimentary snacks, fast WiFi, large deck, fire pit, kayaks, vintage aluminum canoe, board games, and much more. Come stay at the Luxe lake house and make memories that will last a lifetime!

Top guest favorite

The exterior of the house presents a charming two-story design, surrounded by a spacious yard featuring trees and blooming shrubs. A wide driveway leads to a two-car garage, while the house's yellow facade and gray roof create a welcoming appearance.

Home in Bloomfield

4.96 out of 5 average rating, 134 reviews

Spacious Charming New England Cape

Beautiful, relaxing area across from woods. Enjoy sitting on the covered veranda with your coffee or tea in the morning listening to nature and watch the golfers in the distance. In winter bring your x-country skis or snow shoes - just walk across the street and enjoy the golf course trails! Well trained dogs are welcome on the trails in winter too! Close to Skiing, MGM Casino, tons of golf courses, beaches. Need a few more rooms? Ask about our 3br house next door which may be available.

Top guest favorite

A cozy living area features a comfortable gray sofa and an armchair positioned around a circular wooden coffee table. A flat-screen television is mounted above a brick fireplace. Natural light enters through multiple windows, highlighting the inviting space.

4.99 out of 5 average rating, 118 reviews

Welcome to The Avery!

Welcome to The Avery at Amston Lake! Great three-bedroom lake cottage situated in a peaceful lake community. Great place to slow down and relax. Lay out in the sun on the beach, enjoy a fire in the backyard, and even spend some time playing games in the cozy sun room! We are located near numerous vineyards, a brewery, the Connecticut Airline Trail, and great local restaurants! Guests have access to the grill, fire pit area, two kayaks located at the kayak launch, and two main beaches.

Top guest favorite

A spacious kitchen is complemented by large windows that allow natural light to fill the area. An island with a countertop of mixed materials serves as a central gathering spot. A colorful rug lies on the concrete floor, while various kitchenware is neatly arranged on shelves.

4.99 out of 5 average rating, 288 reviews

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relax by the firepit- we hope you enjoy your stay and will visit us again.

A welcoming entrance features a maroon front door with glass panes, flanked by a wooden railing. A slight wooden ramp leads up to the door, surrounded by a manicured area of small plants and gravel, creating an inviting first impression.

Home in Feeding Hills

4.89 out of 5 average rating, 995 reviews

Farm Fresh Feeding Hills

Private in-law suite attached like a garage. Best view in the house overlooking the pond, ducks, goats, horses, & mtn. 1 Bedroom, small shower stall bath, combo kit/lvg room and a screened porch. Approx. 600 sq ft. ttl. The space is perfect for 2 people, ok for 4 and a squeeze for 6 people. Only a few miles to The Big E, 6 Flags, MGM Casino, BB Hall of Fame & Dr. Suess. 20 ish min to Hartford Int. Airport, 30 ish to Htfd & 40 ish north to 5 college area.

A charming house is visible along the riverbank, surrounded by lush greenery and blooming trees. The landscape features the calm waters of the river, reflecting the clear blue sky dotted with soft clouds, providing a scenic backdrop to the quaint property.

Home in Collinsville

4.99 out of 5 average rating, 120 reviews

Best River View, on Rail Trail in Collinsville!

This quaint and spotless home is perched on a knoll across the road from the Farmington River & Rails to Trails you can walk to restaurants, gift shops & antique shops; Canoe/Kayak/Paddleboard; go fishing; enjoy the Farmington River Rail Trail; hiking trails, and Ski Sundown close by; or just relax & enjoy the view! Enjoy the best view in Collinsville - one of "America's 10 Coolest Small Towns" by Arthur Frommer's Budget Travel Magazine. Beautiful year round!

A serene riverside deck features two striped lounge chairs, positioned for optimal views of the Connecticut River. Lush greenery frames the scene, and flower pots add a touch of elegance. The wooden deck offers a natural and inviting space to relax by the water.

4.97 out of 5 average rating, 197 reviews

Sunrise on the Water's Edge - Riverside Bungalow

Cozy riverside bungalow celebrates panorama views of the peaceful Connecticut River. Multiple levels of outdoor living space, open-air and screened-in. Just minutes from all major points of interest in the Pioneer Valley - including Six Flags New England, MGM Casino Complex, Big E Fairgrounds, Basketball Hall of Fame, and the Greater Springfield Metro area. Only 20 minutes from Bradley International Airport (BDL) in Windsor Locks.

A comfortable sleeping area features a dark tufted headboard and a soft, neatly arranged bedding with multiple pillows. A lamp is positioned on a bedside table, while a floor lamp provides additional light. A floral wall art piece adds a subtle touch above the bed.

Home in Manchester

4.94 out of 5 average rating, 217 reviews

Paradise On The Hill Luxury Apartment.

Enjoy your own special and separated section of this beautiful, modern colonial home. This beautiful home includes an oversize living room with a comfortable Queen Size sectional sleeper sofa, oversize Master Bedroom and very large bathroom with spa like jets. His and hers closets. Beautiful kitchenette. 50 inch T.V., Free WiFi. , comfortable dining and more, all for the comfort and convenience of our guests.

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Popular amenities for Windsor house rentals

Free parking on premises

Air conditioning

House rentals with a pool

The exterior of a single-story home is presented, featuring a manicured lawn and a symmetrical facade. Solar panels are installed on the roof. Large windows are visible, providing natural light to the interior. A path leads to the front door, flanked by neatly trimmed shrubs.

Home in Montville

4.92 out of 5 average rating, 179 reviews

Hot Tub~Pool~Game Room~Fire Pit~BBQ~Casinos

Top guest favorite

A serene outdoor view showcases a lush, landscaped yard bordered by trees. An inground heated pool, currently closed for the season, is visible alongside the greenery. A modern home with expansive windows reflects the natural surroundings, creating a peaceful retreat.

Home in Roxbury

5 out of 5 average rating, 23 reviews

Bright Mid-Century Modern Retreat-90 min from NYC

An outdoor area shows a large swim spa beside a brick chimney, with a seating arrangement featuring dark furniture. The spa is equipped with a television, surrounded by trees in a serene setting.

4.91 out of 5 average rating, 117 reviews

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton

A circular above-ground pool is surrounded by a grassy yard, decorated with string lights that create a soft glow. The two-story house is visible in the background, featuring a deck area and large windows. Trees frame the space, adding to the serene setting.

Home in Montville

4.96 out of 5 average rating, 164 reviews

Casino Stay & Play House

Home in Litchfield

4.93 out of 5 average rating, 192 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

A graceful three-story mansion is framed by lush greenery, featuring classic white siding and black shutters. The front porch is supported by elegant columns, and a large arched window is prominently displayed above the entrance, adding to the home's traditional charm.

Home in Norwich

4.81 out of 5 average rating, 216 reviews

Grand 9 BR Near Casinos

Home in New London

4.88 out of 5 average rating, 141 reviews

Beauty and the Beach!

Home in New London

4.9 out of 5 average rating, 178 reviews

Sunset Oasis 2 @ Ocean Beach: Ranch w/ 6 Queen

Weekly house rentals

A comfortable living area is equipped with a large, beige sectional sofa adorned with patterned cushions. A coffee table is centered in front of the sofa. A wall-mounted television displays a colorful screen, while natural light enters through large windows.

Home in Windsor

4.78 out of 5 average rating, 41 reviews

NEW: Spacious Quaint & Convenient Hideaway!

A living area features a gray sofa paired with an accent chair and a coffee table. A dining table with four chairs is situated nearby. Light-colored walls are enhanced by a piece of wall art, and natural light enters through multiple windows.

Home in West Hartford

4.87 out of 5 average rating, 93 reviews

Charming home in West Hartford

A cozy bedroom features a queen-size bed, dressed in soft white linens and a teal accent throw. A piece of wall art adds character above the bed. Natural light filters in through a window, complemented by light curtains. A wooden dresser provides storage space.

Home in Enfield

4.93 out of 5 average rating, 15 reviews

Nest&Rest Escape

A dining area features a round wooden table surrounded by six gray chairs. A white vase filled with fresh flowers is placed center stage. A staircase with a black railing leads to an upper level, while an open kitchen is visible in the background.

Home in Bloomfield

4.88 out of 5 average rating, 16 reviews

The Majestic View

Top guest favorite

An outdoor deck features a large table surrounded by several comfortable chairs. A gas fire pit is centrally located on the table, and a grill is positioned nearby. Lush greenery can be seen in the background, enhancing the outdoor space.

Home in West Hartford

5 out of 5 average rating, 82 reviews

Prime West Hartford Center Location: Historic Gem

Top guest favorite

A serene outdoor space is framed by tall trees and lush greenery. A white chair is positioned on the grass, complemented by a stone birdbath nearby. Sunlight filters through the leaves, creating a tranquil atmosphere that invites relaxation.

Home in Glastonbury

4.96 out of 5 average rating, 47 reviews

Serene Apartment in Glastonbury

A welcoming living room features a comfortable couch and two textured armchairs, arranged around a central round coffee table. Natural light filters through large windows, highlighting a cozy atmosphere. A small side table displays a plant and a soft throw blanket.

Home in New Britain

4.95 out of 5 average rating, 66 reviews

Bright & Private WHOLE HOUSE 4 YOU Near Everything

The historic red brick farmhouse is nestled among a field of vibrant yellow dandelions. A grassy area surrounds the house, which features multiple windows and a central door. Trees stand in the background, complementing the serene rural setting.

Home in Broad Brook

4.97 out of 5 average rating, 65 reviews

Farmhouse Broad Brook: Comfort & Charm.

Private house rentals

An outdoor firepit area is surrounded by natural scenery, featuring light-colored chairs and a wooden swing suspended from a pergola. The ground is covered in white gravel, with scattered leaves from nearby trees, creating a peaceful spot for gatherings.

Home in Barkhamsted

4.91 out of 5 average rating, 22 reviews

Woodland Sanctuary-hot tub|fireplace|hikes|fishing

The dining area features a wooden table surrounded by sleek chairs, illuminated by a modern chandelier. A decorative circular placemat sits at the center of the table. Nearby windows allow natural light to fill the space, highlighting the neutral wall colors and fireplace.

Home in West End

4.91 out of 5 average rating, 82 reviews

Renovated & Modern Victorian in Historic West End

A spacious living area features a red sectional sofa and a small round coffee table with a plant centerpiece. The open layout connects to a well-lit kitchen in the background, visible through a doorway, blending comfort and functionality.

Home in Manchester

4.88 out of 5 average rating, 59 reviews

Charming Cape Home, Close to All

Top guest favorite

A canoe glides smoothly on the lake's calm surface, with three individuals seated inside. Lush greenery and a charming wooden dock are visible in the background, enhancing the serene lakeside setting.

Home in Belchertown

4.98 out of 5 average rating, 84 reviews

Moonstone Lake House – romantic, serene, fun!

A multi-story wooden house is set against a backdrop of lush green trees. Colorful flowering bushes, primarily in shades of pink, enhance the natural landscape, while a glass solarium extends from one side of the house, showcasing outdoor living space.

Home in New Hartford

4.96 out of 5 average rating, 81 reviews

Private Woodland Sanctuary—3 mins to a lake beach!

A comfortable living area is arranged with a sectional sofa featuring a mix of decorative pillows. A coffee table is centered in the space, accompanied by a soft rug. Light streams in through the windows, enhancing the neutral color palette of the room.

Home in Enfield

4.94 out of 5 average rating, 67 reviews

Cozy First Floor Living Nestled in the Woods

5 out of 5 average rating, 7 reviews

Lake House Retreat Granby CT

A single-story home is framed by vibrant autumn foliage, with a well-maintained front yard covered in fallen leaves. The house features a welcoming entrance with a set of stairs, and large windows that allow natural light to fill the interior.

Home in Ellington

4.81 out of 5 average rating, 74 reviews

Cheerful 3 bedroom home with large back yard

Quick stats about house rentals in Windsor

Total rentals
40 properties
Total number of reviews
1.2K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi

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