Vacation rentals in Middlesex County

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Top-rated vacation rentals in Middlesex County

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Guest favorite

A charming cottage is set against a backdrop of lush greenery and a clear blue sky. A white stone chimney rises above the single-story structure. The well-maintained yard features manicured shrubs and towering trees, while a wooden dock lines the water's edge.

Cottage in Deep River

4.92 out of 5 average rating, 26 reviews

Serene Waterfront Cottage

Welcome to Smuggler’s Cove Cottage. Rumor has it that this quaint cottage was once the scene of infamous rum running. Today, it’s our little slice of heaven away from the chaotic city life. It’s the perfect place to curl up and read a book by the fire when it’s chilly out. During the warmer months, take full advantage of the spacious waterfront patio & docks. Whether you’re sunbathing or having a drink watching the local geese and ducks float by, this tranquil cottage has everything you need.

Superhost

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, 239 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 favorite

A riverfront deck is furnished with two lounge chairs and a glass table, surrounded by lush greenery and trees. The view overlooks a calm stretch of the Patchogue River, creating a serene environment for relaxation and enjoyment of nature.

Cottage in Westbrook

4.88 out of 5 average rating, 168 reviews

Peaceful Riverfront Cottage w/Dock, Walk to Beach

This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

Top guest favorite

A cozy outdoor fire pit area features four Adirondack chairs gathered around a warm fire. Soft lighting from string lights above enhances the tranquil setting, with natural greenery surrounding the space. Guests are seen enjoying conversation, adding to the inviting atmosphere.

Apartment in Chester

4.99 out of 5 average rating, 102 reviews

The Millhouse Downtown Chester

An upscale destination with accommodations for foodies & friends in the heart of historic Chester CT. Stay at this beautifully renovated historic Millhouse in charming downtown Chester. Enjoy strolling the streets loaded with shops, award winning restaurants, a microbrewery, art galleries, and more. All within a 1 minute walk. Our prime location is just 20 minutes to the CT shoreline and located in the heart of the CT River Valley. The Millhouse is next door to the Chester Historical Museum.

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, 391 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

Apartment in Chester

4.98 out of 5 average rating, 179 reviews

Charming Chester Retreat - Cottage

Book your Autumn Oasis now ❤️ This 2 bed, 1 bath unit has been redesigned to feature a modern kitchen, soaking tub and wood-burning fireplace. The unit also features a roof deck that overlooks our mature maple trees and a sprawling front porch, complete with rockers. Beach Access 10 min away at Cedar Lake. Great for 1-2 couples, small families or group of friends—Ask about our single roll away bed or pack' n' play(s). Kid friendly! New England getaway / Hidden Gem / Retreat/ Beach Access

Top 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, 286 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, 238 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.

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, 134 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 comfortable living area is presented with a gray sectional sofa and a wooden coffee table resting on a colorful area rug. Natural light enters through large windows, illuminating the hardwood floors and revealing a small antique chest and a decorative lamp.

Apartment in Deep River

4.94 out of 5 average rating, 155 reviews

Lovely Garden-Level Apartment in Heart of Town

This garden-level apartment is centrally located within walking distance to Main Street's retail shops, restaurants, and grocery/pharmacy, and just minutes from The Lace Factory and Deep River Landing, Essex Steam Train & Riverboat, Connecticut River Museum, the CT shoreline and beaches, and so much more. A charming historic home over 200 years old with a classic New England feel, the apartment has two bedrooms, one full bath, and an eat-in kitchen complete with amenities.

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.

Home in Lyme

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.

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, 163 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.