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House vacation rentals in Middletown

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Top-rated house rentals in Middletown

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Top guest favorite

The kitchen showcases a spacious layout with white cabinetry and modern stainless steel appliances. A large island with seating for several guests is highlighted. Warm lighting from pendant fixtures complements the hardwood floors, while a cozy fireplace is visible in the adjacent living area.

Home in North Haven

5 out of 5 average rating, 152 reviews

Luxury Stay in Expansive Historical Home

The Bassett House, originally built in 1802, this large historic farmhouse was elegantly remolded in 2018. North Haven, CT is centrally located and just minutes from Yale, Quinnipiac, UNH, and SCSU as well as shopping, the best restaurants, hiking trails state parks and beaches, and many local attractions including various vineyards. If you’re planning a business trip or a gathering for family or friends, then our home can provide you with an exceptional level of comfort during your time in CT!

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

4.92 out of 5 average rating, 238 reviews

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.

Home in Lake Pocotopaug

4.88 out of 5 average rating, 104 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.

An aerial view showcases a coastal neighborhood with homes situated along a sandy beach. Vibrant blue waters and marshlands surround the area, emphasizing its seaside location. The arrow points to the property's location within the community, illustrating proximity to the beach.

Home in Milford

4.96 out of 5 average rating, 236 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

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 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.

An inviting living room features a green sofa paired with an armchair, set on a wooden floor. A white brick fireplace is flanked by a dark shelving unit filled with books. Natural light streams in through the windows, enhancing the room's cozy ambiance.

Home in Cromwell

4.83 out of 5 average rating, 106 reviews

Cozy Mid Century home in prime location!

Enjoy an updated, mid century modern inspired, home minutes away from Wesleyan University & TPC River highlands! This eclectic space offers you a cozy retreat that is centrally located. The bedrooms have 1 King, 1 Queen, & 1 Full with luxury mattresses! High speed Wi-Fi, chefs kitchen, dedicated work desk, and garage space! A few mins from RT 9 & 91! Easy to get everywhere in CT!!! Only 5 mins to TPC, 10 mins to Wesleyan, 20 mins to Hartford! Scald protector on shower upstairs!

Top guest favorite

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.

5 out of 5 average rating, 133 reviews

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!

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

4.93 out of 5 average rating, 192 reviews

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.

Top guest favorite

A serene riverfront retreat is displayed with a spacious outdoor deck and patio area. The home features large windows allowing natural light, greenery surrounding the property, and a floating dock accessible from the water, creating a peaceful and inviting outdoor atmosphere.

4.98 out of 5 average rating, 285 reviews

“The Answer” Your Unique, Tidal, Riverfront Escape

“The Answer” is listed in “Only In Your State” 2024 - titled “This Riverfront Retreat Will Be Your New Favorite Destination” and Travellers Worldwide 2022 and 2023 Kayaks included This unique glass-front, tidal river retreat, is privately nestled on historic Hamburg Cove. It offers gorgeous year-round, tranquil tidal water and valley views. Extraordinarily and serene. The interior is open/spacious and bathed in light. Wake up to the many sounds of nature.

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.

Top guest favorite

A charming two-story home is surrounded by lush greenery and colorful trees. A well-maintained lawn features flowerbeds, while a two-car garage is visible on the right. The brick chimney adds a classic touch to the home's exterior, under a clear blue sky adorned with scattered clouds.

Home in Middletown

4.99 out of 5 average rating, 104 reviews

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.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Hotels

Stylish accommodations with great services and amenities

Popular amenities for Middletown house rentals

Free parking on premises

Air conditioning

House rentals with a pool

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

4.96 out of 5 average rating, 74 reviews

Country getaway - pool, huge yard,

Top guest favorite

A private fenced pool area is showcased, featuring a rectangular pool filled with clear water reflecting sunlight. Concrete surrounds the pool, and there are steps leading into it. A blue inflatable float rests on the side, bordered by a white picket fence and greenery in the background.

Home in Wolcott

5 out of 5 average rating, 20 reviews

Amazing Oasis Private Pool, BBQ, Pool Table.

Top guest favorite

A heated pool is surrounded by a spacious, patio area featuring lounge chairs and a shaded table set, providing a relaxing outdoor space. Lush greenery and fencing enhance privacy, while a comfortable seating area can be seen beyond the pool.

4.98 out of 5 average rating, 93 reviews

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

Four orange lounge chairs with side tables are positioned on a wooden deck beside a sparkling blue swimming pool. Flower pots with blooming plants are placed around the chairs. Lush greenery is visible in the background beneath a clear blue sky.

Home in Middletown

4.94 out of 5 average rating, 49 reviews

Hot Tub and pool Home away from home

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

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

Home in Litchfield

4.93 out of 5 average rating, 192 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

Top guest favorite

An exterior view of a quaint cottage is shown, featuring a green facade surrounded by manicured grass and hedges. Distant views of a landscape are visible beyond the property, with trees framing the scene and a pathway leading through the yard.

Home in Saybrook Manor

5 out of 5 average rating, 62 reviews

3BR Updated Cottage w/ Pool in Old Saybrook

Weekly house rentals

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

5 out of 5 average rating, 5 reviews

Renovated Single Family Home

A modern kitchen features a central island with three stools, surrounded by sleek countertops and essential appliances. Large windows and glass doors provide abundant natural light and a view of the outdoor area, seamlessly connecting the interior and exterior spaces.

Home in Clinton

4.88 out of 5 average rating, 25 reviews

Boulder Lake House Retreat

Top guest favorite

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

5 out of 5 average rating, 55 reviews

Urban Luxury in Central CT w/ free RV parking

Top guest favorite

A fire pit area is surrounded by multiple red Adirondack chairs, providing a cozy gathering space. The grassy area leads to the lakefront, where a dock is visible. Lush greenery lines the opposite shore under a clear blue sky.

Home in Colchester

4.98 out of 5 average rating, 53 reviews

Waterfront Lake House on Pickerel Lake

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.

Home in Lake Pocotopaug

4.91 out of 5 average rating, 32 reviews

Lakeside Paradise with Breathtaking Sunsets

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

The cottage exterior is framed by lush greenery, featuring a welcoming entrance with a white door accented by a wreath. Blue hydrangeas bloom in pots beside the steps, leading to a stone pathway that invites guests to explore the property.

Home in Lake Pocotopaug

4.96 out of 5 average rating, 23 reviews

Lake House, Pet-Friendly

The modern villa is depicted from an aerial view, showcasing its unique architectural design. The exterior features soft curves and a light-colored façade, harmoniously blending with the surrounding greenery. A wooden walkway leads to the entrance, emphasizing its connection to the natural landscape.

Home in Deep River

4.86 out of 5 average rating, 81 reviews

Starship River Views: Dates Just Newly Released

Private house rentals

Top guest favorite

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

4.98 out of 5 average rating, 41 reviews

Cozy Waterfront Home w/ Hot Tub Connecticut River

A spacious beachfront property is showcased, featuring a well-maintained lawn and a patio area with outdoor seating. The ocean is visible in the background, providing serene water views. The home is characterized by its coastal architecture and nearby neighboring structures.

Home in Branford

4.96 out of 5 average rating, 52 reviews

Adorable Beach House on LI Sound

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

Top guest favorite

A two-story waterfront home is positioned on a spacious lawn, featuring a mix of beige and red siding. A stone chimney adds character, while the large front porch invites relaxation. Views of the lake are visible in the background, framed by leafless trees.

Home in Andover

4.98 out of 5 average rating, 56 reviews

Spacious Classic Lakefront Home with jet tub

Top guest favorite

A stone exterior corner of the home presents a covered porch with white railings. The adjacent grassy area leads to a serene river view, where trees surround the water's edge, reflecting the soft light of the sky.

Home in Windsor

4.97 out of 5 average rating, 60 reviews

Relax By The Water

Top guest favorite

A spacious living room features a large sectional couch adorned with colorful pillows, next to a smaller armchair. Natural light floods through wide windows framed by vibrant curtains. A wooden coffee table sits in the center, with art pieces displayed on the walls and a guitar nearby.

Home in Westville

5 out of 5 average rating, 86 reviews

Westville Schoolhouse by Stephanie and Damian

Top guest favorite

A spacious bedroom features a comfortable bed with white linens and accent pillows. Natural light filters through two windows, adorned with light curtains. A ceiling fan provides ventilation. A vintage mirror and dark wooden nightstands add character, while a woven chair offers additional seating.

Home in Wallingford

5 out of 5 average rating, 65 reviews

New England Charmer

The two-story home features a charming exterior with red shutters and a prominent chimney. Soft lighting illuminates the deck area, where a grill and seating are visible. Surrounding greenery and blooming flowers contribute to the tranquil atmosphere of the property.

Home in Colchester

5 out of 5 average rating, 11 reviews

Lake Hayward, Central CT / Vacation Paradise

Quick stats about house rentals in Middletown

Total rentals
50 properties
Nightly prices starting at
ﺩ.ﺇ147 before taxes and fees
Total number of reviews
1.7K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace

Destinations to explore