Places to stay near Middle Beach

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Top-rated vacation rentals near Middle Beach

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

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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

4.98 out of 5 average rating, 241 reviews

Guesthouse Farm Stay

Come stay with us on our historic working farm! Relax on the back deck and enjoy views of our 12-acre property and peaceful pastures. For a more hands-on experience, join us for a tour to get a closer look at life on the farm. Established in 1739, our farm has a rich history in agriculture and livestock. The cozy studio-style cottage features an open living space with combined bedroom, living, and dining area, along with a kitchenette and bathroom with a shower for your comfort and convenience.

Top guest favorite

The exterior of a two-story building is depicted, featuring natural wood siding and multiple windows. A gravel path leads to a covered entrance surrounded by benches and flower planters. Large trees provide shade, enhancing the serene atmosphere of the setting.

Loft in Essex

4.94 out of 5 average rating, 450 reviews

Unique apartment in former art gallery.

The apartment is private and in a separate wing of a converted factory complex which includes an owner occupied building and artist studio in a quiet residential neighborhood. One bedroom on the ground floor with full bath nearby. The other bedroom is in the loft with queen bed with a daybed in the sitting area for two extra guests. We gladly welcome clean, well behaved pets. ($50 pet fee) Pet sitting and dog walking available for an additional fee. On site babysitting also available.

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, 392 reviews

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

ONE night stays are available for last minute bookings, please message us. Our lovely, well designed place is in an ideal location. A sunshine filled living room w/high ceilings, a private bedroom in back, and 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. We're neighbor to some of the BEST restaurants, art and shopping in CT! We know you'll enjoy your stay!

Top guest favorite

An open-concept living space is illuminated by natural light, featuring a modern kitchen with a large marble island and bar seating. A cozy seating area is positioned nearby, with a view of a decorative sign reading 'Relax.' A spiral staircase leads to the upper loft.

Home in Preston

5 out of 5 average rating, 196 reviews

New Lake Front Home w/ Game Room & Stunning Views

Relax and enjoy the breathtaking views of this new contemporary lake front home. Offering the best of New England, 7 min. from Foxwoods, 15 min. from Mohegan Sun, with multiple choices of hiking, boating, shopping and dining. Stunning 14' cathedral ceilings, fully equipped kitchen w/ granite counter tops, tiled shower w/ full amenities and a full game room. You can not get any closer to the water! This 1 Bdrm, w/ open low ceiling loft, sleeps 6, 1100 square ft. building completed in 2022.

Top guest favorite

Home

4.97 out of 5 average rating, 203 reviews

Waterside Beach Retreat

Beautiful New England period home steps from the beach on the Long Island Sound. Recently renovated from top to bottom with new kitchen and bathrooms, hardwood floors throughout. Idyllic location on quaint & quiet street. Hide away and relax or discover the many local attractions - water sports, fishing, winery, antique stores, scenic walks, premium outlet shopping are all on your doorstep. Ideally located off the I-95 halfway between NYC & Boston, both of which are a train ride away.

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, 287 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 welcoming view of Belle Vue Cottage features a well-kept lawn with a sign indicating its name. The cottage is framed by trees, with a driveway leading to it. A garage is visible in the background, contributing to the serene atmosphere of the neighborhood.

Cottage in Old Saybrook

4.99 out of 5 average rating, 136 reviews

Beautiful View Cottage

Welcome to "Belle Vue Cottage". This charming and inviting cottage is located in a quiet and peaceful neighborhood in the South Cove area of Old Saybrook. Spend your days relaxing at Harvey's Beach, perusing the shops and restaurants along Main Street, taking in a show at The Kate, and unwind at the end of the day in your backyard oasis equipped with an outdoor TV and fire pit. We are less than a mile from Saybrook Point Inn and Spa, and 10 minutes to Water's Edge Resort and Spa.

Guest favorite

The exterior of the barn is showcased, featuring weathered wooden siding and a welcoming entrance. Steps lead to a sturdy front door framed by decorative lights. Planters with vibrant flowers are positioned on either side, enhancing the barn's rustic charm against a backdrop of lush greenery.

Barn in Essex

4.96 out of 5 average rating, 164 reviews

River Barn, Sidewalk Stroll into Essex Village

The Coolest Airbnb in Connecticut (Conde Nast Traveler 2021) The barn is a perfect retreat. Ideal for those looking to take a break from city life or those working remotely. Would also make for a lovely place to call home while you are selling or renovating your own home. Couples, two good friends, singles, or a family with an older child will enjoy the configuration. It will also make for a lovely getaway for a couple with a newborn.

Guest favorite

The exterior of a rustic wooden cottage is surrounded by lush greenery. A spacious deck features seating arrangements and a fire pit area is visible. A stone pathway leads to the entrance, bordered by landscaped stones and grass, enhancing the natural setting.

Tiny home in East Lyme

4.99 out of 5 average rating, 145 reviews

Luxury Tiny Home Near Rocky Neck

Home away from home at our chic hideaway! Create a culinary masterpiece in the fully-appointed kitchen. Pamper yourself with heated floors in the bathroom, outdoor fire pit and heater. An elevated platform perfect for camping or yoga. Nestled just minutes from the picturesque Rocky Neck and McCooks beach, this is the ultimate small family romantic retreat or solo experience!

Guest favorite

A bright living space features vaulted ceilings and modern light fixtures. Two armchairs are positioned beside a wooden table with a decorative plant. A television is mounted on the wall, and natural light filters through sheer curtains, enhancing the inviting ambiance.

Guest suite in Old Saybrook

4.98 out of 5 average rating, 100 reviews

Cozy Loft Getaway

Our private loft is bright and airy with vaulted ceilings and all brand new furniture and appliances. The kitchen and bathroom were thoughtfully designed and sourced from our design showroom right downstairs! Minutes from local beaches and our favorite food spots in town, we hope you enjoy our beautiful and cozy loft as much as we do!

Top guest favorite

The farmhouse, constructed in 1856, is showcased with its classic white exterior and black accents. Large windows allow natural light to fill the space, while lush greenery surrounds the property. A pebble pathway leads to the entrance, enhancing the inviting atmosphere.

Home in Old Lyme

4.97 out of 5 average rating, 194 reviews

Modern Farmhouse with Hot Tub in Old Lyme, CT

Originally built in 1856 this farmhouse has been lovingly restored with stylish and modern amenities for a perfect vacation getaway. Nestled in the heart of downtown, historic Old Lyme the property is convenient to shops, restaurants and local shoreline activities including water sports and hiking.

Superhost

A wooden pathway leads through sandy terrain, flanked by low vegetation. The scene is set against a clear blue sky, creating a serene atmosphere that guides visitors toward the shoreline.

Home in Westbrook

4.85 out of 5 average rating, 221 reviews

Family-Friendly Cottage by The Shore

Whether you’re simply traveling to the area or planning your next vacation, you’ve found the right place. Leave your worries behind and come enjoy our freshly updated home by the shore. With a clean, comfortable and convenient spot to stay you are free to explore & relax.