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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, 148 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

4.93 out of 5 average rating, 232 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.

An open-concept living area showcases a modern kitchen with stainless steel appliances and a granite island with stool seating. A spacious dining table is set nearby, complemented by a comfortable seating area with a sectional couch. Natural light filters through the large windows.

4.92 out of 5 average rating, 126 reviews

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

Stay with us for a relaxing, family lake vacation! Bring your family to our peaceful, private and BRAND NEW 3 bedroom - 2-bathroom home. We are located one block from the Gardner Lake public boat launch, easy access to the public beach. Just a short drive to Mystic, Stonington, Vineyards, Mohegan Sun & Foxwoods. Close to CT College, Mitchell, and USCGA. Cook your favorite meal in our fully equipped kitchen, you will think you never left home! Contact Peter or Adam to discuss your situation.

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 East Hampton

4.87 out of 5 average rating, 103 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.

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, 120 reviews

Connecticut Chalet - Private Pond, Firepit, Views!

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

An open-concept kitchen and living space features modern appliances and a wood-topped island with seating for three. Light cabinets and blue walls create a bright environment, while a hallway visible in the background leads to the entrance of the cottage.

Home in Branford

4.98 out of 5 average rating, 167 reviews

“The Lighthouse” A Beach Cottage by the Sea!

Relax at this unique and tranquil getaway. Long Island Sound to the left, hiking trails to the right. Come kick your feet up at this quiet dead-end road. Enjoy all the modern amenities in this gem of a cottage community. Restaurants and nightlife are just a quick stroll away. Avoid roadside hotels and take a vacation for a night, week, or longer! Check in anytime and at your convenience!No keys to lose or to return! This property provides secure, keyless entry with an August Smart Lock!

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, 111 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

4.82 out of 5 average rating, 102 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, 129 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, 187 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

The cottage is depicted from across the tranquil river, showcasing its large glass windows reflecting the warm glow of the interior lights. The surrounding greenery and outdoor dining area create a serene atmosphere, enhancing the peaceful riverside setting.

4.98 out of 5 average rating, 277 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 modern kitchen features sleek black cabinetry and stainless steel appliances. A large island with bar seating is centered, adorned with a vase of fresh flowers. Natural light floods in through the windows, and a sliding glass door leads to the outdoor deck.

4.92 out of 5 average rating, 334 reviews

Stunning, peaceful and private home

Stunning recently renovated 3 story cape on 7+ acres and 2000+ square ft. Open kitchen to living room area with a giant island to gather members of your group together to eat, drink, laugh and have a great time. Cook inside with a fully equipped kitchen, pots, and pans, silverware, spices, everything you would want to prep a great meal as well as a propane grill on the deck. Modern amenities throughout the space. Touch lighting, bluetooth music and more.

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 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, 72 reviews

Country getaway - pool, huge yard,

An above-ground pool is shown, featuring clear blue water surrounded by a sturdy gray frame. Lush greenery forms the backdrop, suggesting a private outdoor space. Sunlight creates gentle ripples on the water's surface, inviting relaxation and enjoyment during warmer months.

Home in Montville

4.92 out of 5 average rating, 283 reviews

Casino Wine Down House

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

4.93 out of 5 average rating, 44 reviews

Hot Tub and pool Home away from home

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

4.93 out of 5 average rating, 171 reviews

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

A serene backyard features a glistening pool surrounded by lush green grass and shaded areas. The house showcases large windows leading to a wooden deck with outdoor seating. Nearby, sun umbrellas provide shelter, enhancing the inviting outdoor space under the trees.

Home in North Fork

4.96 out of 5 average rating, 112 reviews

Quiet, Upscale Retreat by the Beach with NEW Pool

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, 114 reviews

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

Home in Litchfield

4.93 out of 5 average rating, 191 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

Home in New London

4.9 out of 5 average rating, 137 reviews

Beauty and the Beach!

Weekly house rentals

A bright bedroom features a spacious bed adorned with a blue plaid blanket. Two windows allow natural light to illuminate the room, complemented by matching bedside lamps on either side. A round mirror hangs on the wall, enhancing the room's open feel.

Home in Middletown

4.96 out of 5 average rating, 27 reviews

Middletown Loft

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, 51 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, 48 reviews

Waterfront Lake House on Pickerel Lake

Top guest favorite

Home in Madison

5 out of 5 average rating, 32 reviews

Stylish Modern Home, 4-Bedroom, Madison CT

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, 46 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 East Hampton

4.94 out of 5 average rating, 18 reviews

Lake House, Pet-Friendly

Top guest favorite

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

5 out of 5 average rating, 29 reviews

Pet-Friendly Getaway in Historic East Haddam Home

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

4.96 out of 5 average rating, 55 reviews

Clean, Bright & Private WHOLE HOUSE 4 YOU. 6 Beds

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

4.97 out of 5 average rating, 35 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

4.95 out of 5 average rating, 44 reviews

Adorable Beach House on LI Sound

The living area features large windows adorned with striped curtains, allowing natural light to filter in. A black and white patterned rug anchors the space, with a glass coffee table and an accent table nearby. A minimalist art piece hangs on the wall above a sleek black bench.

Home in Meriden

4.67 out of 5 average rating, 12 reviews

Luxury Modern Hideaway

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 East Hampton

4.9 out of 5 average rating, 30 reviews

Lakeside Paradise with Breathtaking Sunsets

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.

Home in East Hampton

5 out of 5 average rating, 9 reviews

East Hampton Lake Lodge

Top guest favorite

A spacious living area features a comfortable sectional sofa adorned with decorative pillows. A sleek glass coffee table sits in front, and a modern fireplace is framed by a light-colored mantel. A large flat-screen TV is mounted above the fireplace, with natural light flowing in from the adjoining windows.

Home in New Britain

4.96 out of 5 average rating, 45 reviews

Home in New Britain

A cozy living area is furnished with a gray sofa adorned with decorative pillows. A soft area rug anchors the space, complemented by a square coffee table. Floor-to-ceiling drapes frame the windows, and a framed artwork adds a modern touch to the wall.

Home in Bloomfield

5 out of 5 average rating, 11 reviews

Entire home in Bloomfield, CT

This charming home is set against a backdrop of lush greenery, featuring a well-maintained lawn. The exterior showcases a welcoming entrance with steps and a spacious driveway leading to a two-car garage, framed by neatly placed shrubs and trees.

Home in East Hartford

4.91 out of 5 average rating, 53 reviews

Heart of Connecticut - New England (1800 sq ft)

Quick stats about house rentals in Middletown

Total rentals
50 properties
Nightly prices starting at
R717 ZAR 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