House vacation rentals in Middletown

4.95 out of 5 average rating, 760 reviews

A serene view of the Poquetanuck Bay is captured at dawn, showcasing a calm water surface reflecting pastel hues of pink and purple. Surrounding trees frame the scene, while homes on the opposite shore are silhouetted against the soft morning light.

Home in Preston

Entire House Magical Waterfront Getaway

4 MINUTES TO MOHEGAN SUN! Yet quiet and secluded! Waterfront home! Come relax in this 3 bedrooms 2 baths well appointed home with breathtaking view of the Poquetanuck Bay! Enjoying the absolutely gorgeous view from the balcony or porch! Or simply relax, sit around, enjoy each other’s company! Smart TV grants you easy access to thousands of streaming apps! 25 minutes to Ocean Beach, Mystic seaport, Mystic aquariums, Submarine and Library Museum in Groton! 15 minutes away from Foxwood casino!

4.94 out of 5 average rating, 310 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.

Large glass doors frame a serene view of the lake, with gentle waves reflecting the sky's colors. A coffee table with a decorative plant occupies the foreground, while outdoor seating is visible beyond the doorways, enhancing the connection between indoor and outdoor spaces.

4.88 out of 5 average rating, 110 reviews

Beautiful Lake House on Lake Pocotopaug

Enjoy a relaxing vacation in a beautiful, updated lakefront home on Lake Pocotopaug. Summer =grilling out, kayaking & paddle boarding with family & friends. A lakeside marina offers party boat rides & kayak rentals. Winter=relaxation by the cozy fireplace, games and ice skating when the lake freezes over. Projector Screen, Games, Books, AC, Heat, Outdoor Grill and a working fireplace. All year round, we'd love to have you at our home. which we love and use as a getaway from the city.

4.99 out of 5 average rating, 158 reviews

The exterior of a lakefront cottage is illuminated by warm lighting at dusk. The structure features a vaulted roof with large windows, surrounded by trees. A deck extends around the cottage, reflecting on the calm water, creating a serene and inviting atmosphere.

Home in Coventry

Cozy cottage 5 minutes from UConn

Wake up to the morning sun over the lake in the loft, or rise after the sun in one of the two back bedrooms. Enjoy a morning coffee or tea while enjoying the lake view from the live edge bar top overlooking the water and watch for the Swans, Bald Eagles, and Blue Herons. After a hike on the trails, kayaking up the lake into conservation land, or fishing off the dock, relax in the hot tub. As the sun sets over the trees cuddle up on the couch with a good book and keep an ear out for the owls.

4.94 out of 5 average rating, 102 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

Welcome to our clean, bright, and private home, just a 15-minute drive from the heart of Hartford! Designed with your comfort and convenience in mind, this cozy retreat is perfect for families, couples, and professionals looking for a peaceful yet central stay! Prime Location, WHOLE HOUSE – Explore New Britain & Beyond! Guest Access: ✔ Private driveway for easy parking ✔ Enclosed garage with keyless entry for secure parking ✔ Keyless pad entry at the front door (host will provide the code)

The exterior of a two-story lakeside home is framed by lush greenery and colorful flower beds. A stone path leads to the water's edge, where a wooden dock and steps offer direct access. The inviting porch features large windows and a deck, perfect for outdoor gatherings.

4.98 out of 5 average rating, 120 reviews

Classic Lakehouse~Fire Pit_Canoes_Kayaks & Sunsets

Private lakefront home on Lake Pocotopaug with a fishing dock, kayaks, fire pit, and spectacular sunset views — perfect for family & friend getaways. Welcome to Lakeside Ferns, where you’ll enjoy direct waterfront access and private dock for swimming, fishing, kayaking, canoeing, and boating. Grill dinner, relax in the hammock by the water, and gather around the outdoor fire pit for s’mores under the stars. End each day with breathtaking sunsets over the lake — beautiful in every season.

4.99 out of 5 average rating, 175 reviews

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.

Home in Vernon

Luxe Bolton Lake

Spring and summer are amazing times for lake vacations! The Luxe lake house features expansive lakefront views, 3 bedrooms/3 full bathrooms and a year-round outdoor jacuzzi. Also included: gorgeous primary bedroom suite, artistic furnishings, cozy fireplace, coffee bar, complimentary snacks, fast WiFi, large deck for relaxing, fire pit, kayaks, board games, and much more. The Luxe is perfectly suited for guests of all ages, so come stay with us and make memories that will last a lifetime!

4.93 out of 5 average rating, 136 reviews

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

Connecticut Chalet: Winter Nights by the Fire

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.

4.99 out of 5 average rating, 152 reviews

An open-concept living space features light-colored wood flooring and a cozy seating area with a white couch and wooden coffee table. A small dining table is positioned nearby, while a stylish staircase leads to an upper level. A television is mounted on the wall, adding to the modern atmosphere.

Home in Haddam

Cozy Comforts!

Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!

4.93 out of 5 average rating, 222 reviews

The exterior of a charming three-bedroom house is displayed, featuring a sloped roof and neatly trimmed bushes. A large tree provides shade in the front yard, while a stone pathway leads to the entrance. Side decorations include a swing and tree remnants.

Home in Bristol

Cozy Family Home - Kid & Pet Friendly

3 bedroom house on a quiet street. 5mins down the road from ESPN and Lake Compounce. Kid friendly. Pet friendly. Workspace available. 1 bedroom w/ king bed. 1 bedroom w/ queen bed. 1 bedroom w/ 2 twin beds. Fully finished basement with 60inch TV, kids toys and fitness equipment/stationary bike. Deck and below deck hang out space. Though we aren’t living here full time, it’s still the place we call home, and we will use it when it’s not booked. Long stays welcome.

4.97 out of 5 average rating, 231 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.

4.99 out of 5 average rating, 128 reviews

The living room features a large Smart TV above a fireplace, complemented by a cozy area rug. Various seating options include a white leather sofa and two reclining chairs. Sunlight filters through sheer curtains, enhancing the inviting ambiance of the space.

Home in Middletown

Family Stays, CT

Centrally Located Cozy Family Vacation Home: Just 1.2 miles from Wesleyan University, our welcoming home is an ideal choice for families, solo travelers, couples, professionals, business travelers, and almost anyone. Whether you're here to explore Middletown or the surrounding Connecticut towns, you'll have the entire property to yourself for a comfortable and enjoyable stay.

Popular amenities for Middletown house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Superhost

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

4.9 out of 5 average rating, 113 reviews

Breathtaking home with unforgettable views & pool!

4.83 out of 5 average rating, 111 reviews

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.

Home in Litchfield

The Getaway-HOST & Co.

4.98 out of 5 average rating, 107 reviews

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.

Home in Bantam

Hilltop House/HOST &Co.

4.93 out of 5 average rating, 205 reviews

A serene view of the pool is presented, framed by lush greenery and vibrant plant life. The clear water reflects the sky, while distant hills and a pond are visible at the horizon, creating a peaceful outdoor retreat.

Home in Litchfield

Stunning Views, Bucolic Bliss in 1790s Farmhouse

4.96 out of 5 average rating, 192 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

4.9 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

4.97 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

4.88 out of 5 average rating, 164 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

5 out of 5 average rating, 35 reviews

Home in East Haddam

15 acres! * Pine Pond at Devils Hopyard State Park

4.96 out of 5 average rating, 76 reviews

The historic two-family home is bordered by lush greenery and blooming flowers. A white picket fence frames the vibrant garden, while the house features dark shutters and a welcoming front porch. A winding pathway leads to the entrance, inviting guests into the serene surroundings.

Home in East Hampton

Country getaway - pool, huge yard,

4.97 out of 5 average rating, 70 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

5 out of 5 average rating, 82 reviews

The spacious living area features a large sectional sofa with plush cushions, arranged around a minimalist coffee table. A flat-screen TV is mounted on the wall above a stylish console. Natural light streams in through multiple windows, which are framed with light-colored treatments.

Home in Newington

Urban Luxury in Central CT w/ free RV parking

Four black Adirondack chairs are arranged around a fire pit on the grassy lakeside. A serene view of the lake and trees is visible in the background, reflecting a clear sky and gentle sunlight. The peaceful setting invites relaxation and outdoor gatherings.

5 out of 5 average rating, 9 reviews

Lovely, peaceful lakefront home.

4.93 out of 5 average rating, 15 reviews

Home in Southington

1,500 sq feet one level ranch completely remodeled

A serene lakeside view captures a vibrant sunset reflected on the calm water. The sky is filled with shades of orange and purple, framed by distant hills. A stone wall borders the foreground, leading into a pebbled area near the water's edge.

4.91 out of 5 average rating, 47 reviews

Lakeside Paradise with Breathtaking Sunsets

5 out of 5 average rating, 45 reviews

Home in Tolland

Backyard Tiny House in the Woods

Private house rentals

4.9 out of 5 average rating, 89 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

Superhost

4.7 out of 5 average rating, 60 reviews

Grammy's Lake House on Lake Pocotopaug

4.82 out of 5 average rating, 44 reviews

A contemporary home with textured wooden siding is depicted. A small front porch with white railings is accessible via a brick pathway surrounded by shrubbery and flower pots. Natural light illuminates the windows, creating a welcoming entryway.

Home in East Hampton

Charming River Home

A view of Lake Pocotopaug, framed by lush greenery. A spacious deck extends towards the water, furnished with outdoor seating. A yellow inflatable sits on the dock, which is accessible for guests. The tranquil lake is surrounded by gentle hills in the background.

4.99 out of 5 average rating, 82 reviews

Fun on the Lake: Games, Dock, Slide, EV Charger

The exterior of a modern ranch home is shown, highlighted by a vibrant yellow front door. A well-maintained front yard features a mix of grass and landscaping, including a small stone border and flower bed. The house is surrounded by mature trees and has multiple windows for natural light.

5 out of 5 average rating, 18 reviews

East Hampton Lake Lodge

4.89 out of 5 average rating, 45 reviews

Two chickens can be seen pecking at colorful corn cobs placed on the grass. The home’s staircase and porch railings in the background provide a glimpse of the inviting entryway. Seasonal corn stalks and a potted mum add charm to the serene outdoor setting.

Home in East Haddam

East Haddam Village | Walkable, Pet Friendly

4.95 out of 5 average rating, 19 reviews

Home in Wolcott

Cozy Ski-Lakefront Retreat