House holiday rentals in Middlesex County

Find and book unique houses on Airbnb

Top-rated house rentals in Middlesex County

Guests agree: these houses are highly rated for location, cleanliness and more.

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Top guest favourite
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, 331 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.

Guest favourite
A serene lakeside house is framed by lush greenery, with a wooden dock leading to the water. The porch, adorned with large windows, provides an inviting entrance. The structure features a classic design, complemented by natural surroundings, ideal for enjoying scenic views and outdoor activities.
Home in East Hampton
4.86 out of 5 average rating, 141 reviews

Beautiful lakefront home, 4bed 2.5ba

Fully renovated, on 80ft of lake front. Perfect for summer water activities, stunning fall foliage and often ice skating in the winter! East-facing with stunning sunrises. Very well equipped kitchen, cosy sitting room with wood-burning stove, dining room for 8, and powder room. Large porch faces the lake, with a sitting area, and dining table for 8. Ground floor king-size master & bathroom, with stunning lake views. Upstairs, 3 queen bedrooms, all with lake views and ample closet space.

Superhost
A serene garden space features lush green foliage and vibrant pink flowers, with a rustic wooden chair positioned to overlook a gentle waterfall. The surrounding trees provide a natural canopy, creating a peaceful atmosphere for relaxation.
Home in Chester
4.96 out of 5 average rating, 218 reviews

Stunning Artisan Waterfall Escape, Walk Downtown

Rated one of the top 70 airbnb's near NYC on the online mag "Curbed". Featured on EarthxTV "House of What" series. Over 10 years of craftsmanship went into creating a work of art using more than 80% recycled materials. Known locally as "The Recycle House," this is the perfect place to stay to explore shops and galleries in downtown Chester - just steps away. When you are done shopping, come back and relax in the zen-like garden overlooking a waterfall or curl up inside by the fire place.

Top guest favourite
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
4.99 out of 5 average rating, 164 reviews

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.

Guest favourite
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
4.94 out of 5 average rating, 108 reviews

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)

Top guest favourite
The sunken living room showcases expansive windows offering unobstructed views of the water, allowing natural light to fill the space. A spacious gray couch faces a low black table, while a comfortable reading chair with an ottoman is positioned nearby, creating an inviting gathering area.
Home in Guilford
5 out of 5 average rating, 38 reviews

3BR Waterfront Oasis on Joshua Cove, Private Beach

Kick back & relax in this modern, stylish waterfront home with a private beach. Newly renovated, this house offers beautiful, unobstructed views of the Long Island Sound and a backyard equipped with an outdoor patio & dining area, hammock, firepit, adirondack chairs, chaise lounges, and cushioned outdoor furniture (in season). You can enjoy swimming at the home's private beach in summer, leaf-peeping in fall, and bird watching in spring. The house is located 5 minutes from downtown Guilford.

Guest favourite
A charming stone exterior is visible, featuring a private entrance with a sliding glass door. The path is made of stone, surrounded by a well-maintained lawn. In the background, sitting areas and greenery are discernible, enhancing a serene outdoor experience.
Home in Clinton
4.92 out of 5 average rating, 181 reviews

Amazing 2BR Riverfront Gem

Unwind at this happy getaway on the river. Extremely comfortable house with amazing views in a peaceful neighborhood. The well-equipped kitchen overlooking the river is a pleasure for any cook. You will love to see our fairy-lit lawn, wishing well, chimenea, and charming décor. Only minutes to beaches, groceries, coffee shops, hiking trails and amazing CT scenery at every turn! Other favorites include Chamard Vineyard, Shopping Outlets, fantastic Restaurants, music, and lots more.

Top guest favourite
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
4.99 out of 5 average rating, 155 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!

Top guest favourite
A living area features a comfortable sectional sofa adorned with decorative pillows. Two light blue armchairs are positioned beside a small table with a patterned top, while a television stand and a floor lamp complete the inviting space. Sunlight is visible through a window.
Home in Old Saybrook
4.92 out of 5 average rating, 109 reviews

Best of both worlds!

Great location- 1 mile to the beach, 1/2 mile to shops and restaurants, and less than a 1/4 mile to a park! The house is set back from the road with a good size driveway. The inside is newly renovated and we are working to finish the yard area for the summer! The house has WiFi, large yard, and a great front porch that gets a ton of sun. We’ve made great memories there over the years and are now looking to share it with others!

Top guest favourite
Home in Fairfield
4.96 out of 5 average rating, 214 reviews

Cozy Cottage with Fire Pit, near Beach

Escape to Fairfield Cottage, a stylish 3-bed, 2-bath retreat 90 mins from NYC. Comfortably sleeping 8, this sun-drenched home features a private patio with a fire pit, a fully equipped kitchen, and two fireplaces. Perfect for families and just 3 miles from the beach, it's your ideal getaway for relaxation and connection. Enjoy a dedicated workspace, fast Wi-Fi, and numerous family-friendly amenities.

Top guest favourite
A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.
Home in Cutchogue
4.97 out of 5 average rating, 192 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Private studio suite with separate entrance and full bath in a modern North Fork farmhouse on a peaceful farm property. Enjoy a screened porch, fire pit, and outdoor seating. Includes mini fridge, Keurig, tea, homemade granola, and seasonal eggs/produce. Attached to our home, so some light household noise is possible. Private chef + yoga services available.

Top guest favourite
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
4.99 out of 5 average rating, 134 reviews

Family Stays, CT

Centrally Located Cozy Family Home: Just 1.2 miles from Wesleyan University, this inviting home is a great fit for families, solo travelers, couples, professionals, and business guests alike. Whether you’re exploring Middletown or visiting nearby Connecticut towns, you’ll enjoy the comfort and privacy of having the entire property to yourself.

Popular amenities for house rentals in Middlesex County

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