Vacation rentals in Middlesex County

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Top-rated vacation rentals in Middlesex County

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Guest favorite

The exterior of Lori Warner Studio/Gallery showcases a vibrant red door framed by large glass windows. A deep blue awning offers shade, while decorative planters with greenery are positioned beside the entrance. Outdoor seating is visible in the background, complementing the inviting atmosphere.

Apartment in Chester

4.93 out of 5 average rating, 380 reviews

Chester Village 'Pied-à-terre' above art gallery

ONE night stays are available for last minute bookings, message us! If finding a place in an ideal location w/ thoughtful design matters to you, then you've found it! Sunshine filled livingroom w/high ceilings, quiet, private bedroom in back, and w/large private deck overlooking Pattaconk Brook. A true gem, set up solely for the comfort of our guests. Located in the heart of Chester Village, above our art gallery & boutique, and neighbor to some of the BEST restaurants, art and shopping in CT!!!

Top guest favorite

A well-maintained exterior of a home is framed by lush greenery, showcasing a garden with colorful flowering bushes. A winding gravel path leads through the manicured lawn, inviting exploration of the outdoor space among the trees.

Guest suite in Clinton

5 out of 5 average rating, 14 reviews

Private 2-room suite + bath in beach town

Enjoy 2 rooms + bath. The second floor of my home will be your own private oasis. Large dog (+ cat) on premises (no access to suite). Please be dog-friendly! Spacious bedroom, cozy sitting area, queen bed, TV w/ premium channels. Separate dining/kitchenette with Keurig, microwave & fridge. Brand new private bath with tub/shower. 3 wooded acres by Menunketesuck River. 2-level deck with fire table, patio, propane grill and hot tub. Near premium outlets, beaches, state park, Chamard Vineyard.

Guest favorite

A charming tiny house is featured amidst a lush landscape under a partly cloudy sky. Surrounding greenery enhances the natural setting, while colorful flowers are visible in the foreground, framing the house's entrance and inviting a peaceful atmosphere.

Tiny home in Deep River

4.83 out of 5 average rating, 12 reviews

Her tiny Parisian boat house

SOLO vacation? Reconnect with nature at this unforgettable escape. Perfect work space while lounging by the pool…(in SEASON) this tiny house (on land) has access to SHARED outdoor shower and outdoor soaking tub. Wanna relax? Come Meditate under the giant willow, swing in the hammock or practice yoga. Bathroom (NOT IN THE TINY HOUSE!) is shared and just steps inside the main house with shower and toilet. Great WiFi, front porch to enjoy meals. Bed is a comfytwin with lots of pillows.

Guest favorite

The front exterior of the cottage is shown, featuring a stone pathway leading to the entrance. An orange front door is framed by white railings. Surrounding greenery and seasonal decor complement the inviting atmosphere of the landscaped yard.

Cottage in Chester

4.97 out of 5 average rating, 277 reviews

Updated cottage "Beriozka" on Cedar Lake

Originally from Russia (hence the name “Beriozka” meaning Birch Tree) I live in Stamford CT. About 7-8 years ago I’ve discovered Chester/ Essex area and fell in love. I’ve been coming here during summer to enjoy river rides, during winter just to see snow on the ground of old towns and needless to say during fall – when all the beauty of nature unfolds. Then came an idea to have an own place here and when an opportunity came to buy this small cottage on Cedar Lake I’ve jumped on it.

Top guest favorite

A charming cottage features wood shingle siding and a neatly arranged entrance. The front yard showcases a manicured area with green grass, accompanied by a duck and a chicken. Nearby, expansive fields and a rustic barn complete the serene rural landscape.

Guesthouse in Portland

5 out of 5 average rating, 222 reviews

Guesthouse Farm Stay

Come stay with us on our working farm. Relax and take in our beautiful 12-acre property while sitting on the back deck, overlooking pastures. Or for a more interactive experience, join us on a farm tour during our morning and evening farm chores. Our farm was established in 1739 with a rich history in agriculture and livestock. Our cottage is studio-style with an open bedroom, living room, and dining area. There is a kitchette and bathroom with a shower for your convenience.

Superhost

A spacious guest suite is illuminated by natural light from large windows. A comfortable bed is positioned against a sloped wall, with a seating area featuring a small chair nearby. A simple dining space is equipped with a table and stools, enhancing the room's functionality.

Guest suite in Cromwell

4.92 out of 5 average rating, 12 reviews

Private Guest Suite

Private Guest Suite in a New England Cape Cod style home located in a wonderful neighborhood in Cromwell CT. Completely renovated suite. Enjoy private access to a quiet, well lit space with wonderful large illuminating windows and sky light. In-suite washer dryer, double vanity bathroom, bedroom and living room. Internet/TV provided. Bedroom- Full-size bed. Dry kitchen- a toaster oven, microwave, freezer/fridge, Keurig, and water tower. Outdoor pea stone patio, and fire pit.

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.

Home in Haddam

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!

Top guest favorite

A cozy living area is presented with a neutral color palette. A comfortable sofa is draped with a textured throw, and an organic wooden coffee table is centered within the space. Art prints adorn the walls, while natural light gently illuminates the room.

Apartment in Westbrook

4.97 out of 5 average rating, 32 reviews

Meadowview & Pondside Retreat

We welcome you to a serene and peaceful getaway at our recently renovated apartment. Explore 88-acres of woods, New England rock walls, streams, meadow and pond all without leaving our beautiful native landscape. We are conveniently located within a 10 minute ride from I95/Rt.9, the quaint villages of Chester, Deep River & Essex or down to the CT shoreline. We are also a working herb farm and happy to arrange farm tours, medicine making classes, or plant walks/guided hikes.

Guest favorite

The open living area is furnished with a dark sofa and light wooden accents. A round table with a beige tablecloth is paired with four chairs, while framed artwork adorns the walls. A colorful area rug adds a cozy touch, complemented by soft lighting from overhead fixtures.

Condo in Middletown

4.93 out of 5 average rating, 160 reviews

Entire place to yourself Cromwell/Middletown Line

Welcome to Cromwell / Middletown line, open space condo has living room with smart TV, Wi-Fi and sofa bed connected with dining room with four seats, the kitchen is well stocked with all the amenities you need, 24 hours keyless access to the apartment, free parking. Washer / dryer unit on - site paid through a prepaid card. Condo is located near I 91 and Route 9 ramps and just minutes from shopping, restaurants and more, 5 min drive to Wesleyan University, Middlesex Hospital

Top guest favorite

A charming exterior view showcases the entryway to The Village Loft, featuring a decorative sign that identifies the loft. Soft lighting from a hanging lamp creates an inviting atmosphere along the quaint facade above The Village Bistro.

Loft in Chester

4.99 out of 5 average rating, 145 reviews

The Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK

Located in charming downtown Chester, our loft rests above the newly established Village Bistro; with the loft being situated above our restaurant and on Main Street please keep in mind that you may hear some background noise during normal business hours. Additionally, you will be staying in a 200-year-old structure so there is some quirkiness that goes along with an aged building such as ours but rest assured you will feel right at home in this cozy, warm, historic space.

Guest favorite

A compact kitchenette is seen, featuring wooden cabinets and a stainless steel refrigerator. A microwave is mounted above a sink with dark countertops. A light-filled sleeping area is visible in the background, furnished with a blue bedspread and a wooden dresser.

Apartment in Clinton

4.87 out of 5 average rating, 38 reviews

Bright & Cozy Loft Near Beach

Enjoy a peaceful and bright retreat in Clinton! This spacious studio offers plenty of natural light from skylights, creating a cozy atmosphere. Located 10 minutes from Clinton Beach, Hammonasset State Park, and Clinton Premium Outlets. The entrance is up 15 steps to your private, separate space on a shared property. With a private bathroom and all the essentials for a comfortable stay, you’ll enjoy a relaxing experience in a quiet neighborhood, near dining and shops.

Top guest favorite

The exterior of the cottage is characterized by a charming stone chimney and a vibrant green door. The white siding contrasts with lush greenery, while a small seating area features two colorful chairs on the well-maintained lawn. A stone pathway leads toward the entrance.

Cottage in East Haddam

5 out of 5 average rating, 49 reviews

Historic Hearthstone Cottage

Built in 1800 and thoughtfully renovated in 2024, this two-story guest cottage can be the retreat of your dreams. Surrounded by thousands of acres of nature preserve, short walks to scenic vistas, a raging waterfall and countless hiking trails, few places are as peaceful as Hearthstone. Whether you’re looking for a private oasis or romantic getaway, are a parent sharing the beauty of nature, or an artist looking for inspiration, this historic cottage is for you.