House vacation rentals in Windsor

4.96 out of 5 average rating, 137 reviews

Home in Waterbury

Amazing views of the Brass City

East Mountain Views at its finest. This clean, 3-bedroom updated ranch is centrally located to highways and shopping centers. Walk out to the back deck and experience some of the best views of Waterbury including Fireworks from the back deck (July). Wi-Fi/cable, central AC/hot air, washer/dryer, and patio furniture/grill (seasonal) are included with the stay. Plenty of entertainment (board games, corn hole, foosball, air hockey) are provided. This house is truly relaxing and will feel like home.

4.96 out of 5 average rating, 117 reviews

The exterior of a newly renovated schoolhouse is depicted, showcasing a welcoming entrance with a red door. Surrounding greenery includes well-maintained lawns and established trees. A carriage house is visible on the left, complementing the charming architecture of the main house.

Home in Collinsville

Nature Lovers Retreat-Wine Vineyards Skiing nearby

Sleeps 6! Newly renovated 1910 schoolhouse. You'll love 2-3 bdr, clean, bright well appointed home. Volume ceilings, and a well stocked kitchen for long stays. Walk to nearby historic downtown Collinsville, where you'll find antique stores, restaurants and beautiful New England scenery. The CT wine trail and Brignole Vinyards nearby, where you will find food trucks and live music. Walk or cycle the Farmington River Trail. You will also find hiking, fishing, skiing, SUP , canoeing kayak rentals

4.99 out of 5 average rating, 236 reviews

A cozy living room features a brown sofa positioned centrally, paired with an ottoman. Striped armchairs flank the space, with two lamps providing soft illumination. Warm wood paneling and large windows contribute to a welcoming ambiance, complemented by a decorative area rug underneath.

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.

4.91 out of 5 average rating, 112 reviews

A private outdoor area features a spacious swimming pool with a connected spa, surrounded by greenery. Two decorative lion statues flank the pool entrance. Lounge chairs and a gazebo provide additional relaxation options under a sunny sky dotted with clouds.

Home in Columbia

Breathtaking home with unforgettable views & pool!

This perfect peaceful and private home on 5 acres is great for unwinding & relaxing whether it is enjoying the day by the incredible pool/spa or star gazing at night. far from the noise and pollution of city life. You can spend a weekend or a week away from work life because you deserve it. Close to Foxwoods casino and Mohegan sun casino, super Walmart and other stores. please let us know before booking more than 4 people whether it is just for the day or night or both. no loud music no parties

4.93 out of 5 average rating, 289 reviews

A tranquil lake scene is captured at sunrise, featuring a wooden dock extending into the water. Soft pink and orange hues reflect on the lake's surface, complementing the surrounding greenery. Two Adirondack chairs sit near a fire pit, inviting relaxation by the scenic view.

Home in East Haddam

Romantic Getaway at The Lake!

Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

Superhost

A globe rests on a polished surface, accompanied by a wooden 'Hello!' sign. Sheer curtains filter soft light, creating a bright and welcoming scene. The composition offers a blend of decorative elements that enhance the living space.

Home in South Windsor

4.88 out of 5 average rating, 172 reviews

Spacious 3 Bedroom Ranch With Office

Forget your worries in this spacious and serene space with room for 8. The entire first floor is yours to enjoy and there aren’t any shared spaces. Relax in the backyard or on the porch. 2 full bathrooms are yours to relax and enjoy. There’s a freshly remodeled bathroom in the master bedroom with walk in shower and a bathtub in the 2nd bathroom. Fully stocked kitchen awaits your inspiration. Much shopping awaits you and all the store are within 10 minutes away from you. BDL is 20 minutes away,

4.94 out of 5 average rating, 229 reviews

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

Paradise On The Hill Luxury Apartment.

Enjoy your own special and separated section of this beautiful, modern colonial home. This spacious home includes central air, an oversize living room with a comfortable Queen Size sectional sleeper sofa, oversize Master Bedroom and very large, newly renovated bathroom with spa like jets. His and hers closets. Beautiful fully stocked kitchenette, 2 large screen Smart TVs, 55 inch in living room, 42 inch in bedroom, Free WiFi, dining for 6, all for the comfort and convenience of our guests.

4.96 out of 5 average rating, 101 reviews

Home in Becket

HOT TUB! Berkshires: Dog & Family Friendly!

Secluded Berkshires Retreat! -Dog/s, Family Friendly cottage -Patio w/ Hot tub, fire pit, canoe use -Acre wooded/secluded lot -Ski Otis Ridge 15 min or Butternut 30 min -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 30 min! -30 min Monument Mt. & Berkshires Scenic Railway -Naumkeag Lights -Appalachian Trail hiking -Wineries/Breweries -Outlets/Small Shops -Master w/Queen -2nd bed with 1 Twin/Full Bunk -Full size pull out couch -Generator on site

4.88 out of 5 average rating, 152 reviews

The historic home, built in 1880, features a striking red brick exterior with yellow trim accents. Intricate architectural details are visible, including decorative eaves and multi-pane windows. Surrounding trees cast dappled shadows, enhancing the property's charm and inviting atmosphere.

Home in Asylum Hill

Beautiful Historic Home

The apartment is located in a two-family Historic home situated in Asylum Hills in Hartford. This beautiful historic house was constructed in the year 1880 and used to be uninhabitable until about few years ago when it went through an extensive renovation inside and out. This property is close to many of the top attractions in Hartford such as the Mark Twain House & Museum, Wadsworth Atheneum Museum of Arts, Hartford Stage, Connecticut State Capitol, Dunkin’ Park, and more.

4.89 out of 5 average rating, 1,021 reviews

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

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.

4.97 out of 5 average rating, 290 reviews

The exterior of a renovated farmhouse is surrounded by lush greenery and flowering shrubs. A stone pathway leads to the front porch, which features a pair of chairs. A barn is visible in the background, set against a backdrop of trees and hills.

Home in Russell

South Quarter House

Built in the early 1800s, our renovated farm house can accommodate families and friends comfortably. This 1600 square foot home can keep everyone together: three large bedrooms upstairs and an optional fourth downstairs. Large backyard and deck made for outside fun. Two full bathrooms, laundry, large farm table with seating for 10, and a full kitchen. Plenty of options for hiking at or near the house. (Sorry, we are not able to host weddings.)

4.97 out of 5 average rating, 226 reviews

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.

Home in Agawam

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.

Popular amenities for Windsor house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The outdoor area is highlighted by a heated pool surrounded by lounge chairs and a well-maintained garden featuring a mix of hedges and trees. A spa is situated near the pool, with a stone patio providing additional seating under a blue sky dotted with clouds.

4.83 out of 5 average rating, 111 reviews

The Getaway-HOST & Co.

A spacious living area features large windows that provide natural light and views of the surrounding trees. Comfortable leather furniture includes a sofa and an armchair, arranged around a rustic coffee table on a textured area rug. A potted plant adds a touch of greenery.

4.98 out of 5 average rating, 105 reviews

Hilltop House w/POOL/SPA- HOST & Co.

4.9 out of 5 average rating, 218 reviews

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

Hot Tub~Pool~GameRoom~FirePit~BBQ~King Bed~Casinos

A cozy living room features exposed wooden beams and warm wood-paneled walls. A stone fireplace is centrally located, with a basket of wood beside it. A rug with rich colors lays under a wooden table, surrounded by comfortable seating, inviting a relaxed atmosphere.

4.93 out of 5 average rating, 202 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

4.9 out of 5 average rating, 121 reviews

A swim spa with dual zones is shown, featuring illuminated blue and red lights. The adjacent outdoor area includes a large screen displaying a sports event. Steam rises from the hot tub, creating a relaxing ambiance in the evening setting.

Home in Hamden

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

4.96 out of 5 average rating, 182 reviews

A private hot tub is illuminated with soft blue lighting, surrounded by trees and a wooden fence. String lights add a warm glow to the area, creating a serene atmosphere for relaxation under the evening sky.

Home in Montville

Casino Stay & Play House w/Hot Tub, Game Room

4.97 out of 5 average rating, 153 reviews

An expansive aerial view reveals a private pool surrounded by lush green grass and trees. A small pond is visible nearby, with vibrant foliage framing the scene. Open fields stretch into the distance, highlighting the rural setting on the property.

Home in Windham

mid century ranch style house on farmland

4.87 out of 5 average rating, 159 reviews

A spacious living room is highlighted by a unique whale wall art piece and a cozy seating arrangement. A comfortable gray sofa is paired with a nautical-themed chair. Large windows allow natural light to fill the room, creating a welcoming atmosphere.

Home in New London

Beauty and the Beach!

Weekly house rentals

Superhost

A cozy living room features a brown sectional sofa with plush cushions and a decorative mirror on the wall. A console piano is positioned next to a large television on a wooden stand. Natural light enters from large windows adorned with sheer curtains, highlighting the warm wood flooring.

Home in Asylum Hill

4.77 out of 5 average rating, 94 reviews

The Silhouette in Hartford

4.97 out of 5 average rating, 63 reviews

The exterior of a two-story waterfront home is shown, featuring a modern design with blue siding. A spacious deck is visible above a landscaped area with carefully arranged plants and gravel, while a driveway leads to the front of the house, surrounded by greenery.

Home in Rocky Hill

Cozy Waterfront Home w/ Hot Tub Connecticut River

4.91 out of 5 average rating, 82 reviews

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

Charming Cape Home, Close to All

4.97 out of 5 average rating, 64 reviews

A spacious kitchen features wooden cabinetry with glass accents, contrasting with granite countertops. Stainless steel appliances, including a refrigerator and oven, are showcased. Natural light fills the room through a large window above the sink, enhancing the warm colours of the cabinetry and countertop.

Home in Windsor

By The River

5 out of 5 average rating, 7 reviews

Home in Granby

Lake House Retreat Granby CT

5 out of 5 average rating, 11 reviews

A spacious cabin is surrounded by lush greenery and features a wooden deck with outdoor seating. A hot tub is located on the deck, overlooking the yard. A stone fire pit is centered on the lawn, with a gravel driveway leading to a detached garage.

Home in Tolland

Cabin with Hot Tub and Lake Access

4.94 out of 5 average rating, 97 reviews

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

Bright & Private WHOLE HOUSE 4 YOU Near Everything

4.83 out of 5 average rating, 65 reviews

A living area features a navy sofa paired with wooden chairs around a circular table. A stone fireplace creates a focal point, with a clock affixed above. The kitchen is visible in the background, showcasing stainless steel appliances and wooden cabinetry.

Home in Agawam

Home near Six Flags/ hot tub

Private house rentals

4.83 out of 5 average rating, 36 reviews

An aerial view captures the serene landscape surrounding Congamond Lake, highlighting lush greenery and residential areas along the water's edge. Several boats are visible on the lake, and the peaceful ambiance of the community is evident in the well-maintained homes and natural surroundings.

Home in Southwick

My Lake House w/dock and kayaks

Superhost

A spacious living area features a large, L-shaped sectional sofa adorned with decorative pillows. A light-colored area rug complements the space, while natural light filters through the window. A dining area with wooden chairs is visible in the background, framed by an archway.

Home in East Hartford

4.92 out of 5 average rating, 13 reviews

Renovated Single Family Home

4.97 out of 5 average rating, 34 reviews

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

Nest&Rest Escape

5 out of 5 average rating, 18 reviews

Home in Mansfield

Boondocks Oasis On The River

5 out of 5 average rating, 17 reviews

The kitchen features modern appliances, including an oven and refrigerator, set against stylish gray cabinetry. A patterned area rug lies on the floor, and a window provides natural light. The countertops offer ample workspace, complemented by a decorative backsplash of hexagonal tiles.

Home in West Hartford

Modern Cozy Home for Families & Pets

4.98 out of 5 average rating, 86 reviews

Home in Haddam

Winter at the Haddam House

5 out of 5 average rating, 43 reviews

A comfortable living area features a gray sofa positioned around a low coffee table. A television rests on a media console against the wall, with natural light streaming through two windows that overlook greenery outside.

Home in Haddam

The Doll House

A welcoming living area is highlighted by a large flat-screen television, a dark wooden coffee table, and a comfortable leather sofa. Natural light filters through a window, illuminating a decorative cabinet and various indoor plants, while a chandelier hangs from the ceiling, adding an elegant touch.