Vacation rentals in Middlesex County

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Top-rated vacation rentals in Middlesex County

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Superhost

A cozy living area features a gray sofa and ottoman, complemented by an artistic wall decoration. A spiral staircase leads to a lofted space above. Natural light streams in from the window, highlighting the exposed beams and the elegant architecture of the room.

Apartment in East Haddam

4.79 out of 5 average rating, 285 reviews

The Federal Suite at the Wisteria Rest

The apartment is beautiful and fully furnished in the historic District of East Haddam close to Rt 9 or 2, the Goodspeed Opera House, River House and CT Shoreline. Gillettes Castle, Fox Hopyard, Devils Hopyard, & more. Just 20 minutes to Middletown and wonderful dining. This apartment is in the 1800 section and has some quirky things to be aware of, floor that have uneven heights, stairs to the bedroom and , a claw foot tub/shower that you have to step into and a full flight of stairs to get in.

Guest favorite

The kitchen area includes a sleek granite countertop with two wire-frame stools positioned underneath. Natural light enters through the adjoining living space, highlighting the warm wooden flooring. Sliding glass doors lead to a bright living room, creating a sense of openness and connection.

Apartment in Chester

4.93 out of 5 average rating, 372 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!!!

Guest favorite

A striking lake scene captures a vibrant sunset, with vivid hues of red and purple reflected on the calm water. The surrounding shoreline is lined with trees silhouetted against the colorful sky, offering a serene and picturesque view.

Home in East Haddam

4.95 out of 5 average rating, 222 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 sandy beach stretches along the water's edge, with individuals walking near the shoreline. A small boat can be seen in the distance, alongside calm waves lapping gently against the sand. Several trees and structures are visible along the waterfront, contributing to a serene coastal atmosphere.

Cottage in Westbrook

4.88 out of 5 average rating, 163 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.

Guest favorite

The interior space features rustic elements, including wooden cabinetry and exposed brick walls. A vintage-style sink is positioned against the wall, surrounded by warm wooden accents. Natural light enters through the window, enhancing the room's warm tones.

Home in Chester

4.98 out of 5 average rating, 210 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.

Guest favorite

A refreshing pool is surrounded by lush green grass and trees, creating a serene outdoor setting. A hammock is visible in the background, inviting relaxation. A single foot rests on a soft cushion at the pool's edge, suggesting a moment of leisure.

Tiny home in Deep River

4.8 out of 5 average rating, 10 reviews

Her tiny Parisian boat house

Solo vacation? Reconnect with nature at this unforgettable escape. Or a Perfect work space while lounging by the pool…(in SEASON) this tiny house (on land) has access to an 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 kitchen features an open layout with vaulted ceilings and large windows that provide ample natural light. Modern appliances, including a gas stove and refrigerator, are complemented by stylish cabinetry and decorative tiles. A farmhouse sink is centrally located on the countertop, enhancing functionality.

Cottage in Chester

4.97 out of 5 average rating, 273 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 young piglet is seen resting on a bed of straw. Its shiny black and white fur contrasts with the golden straw, while its small ears perk up. The background features blurred earthy tones, suggesting a rustic farm environment.

Guesthouse in Portland

5 out of 5 average rating, 203 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

A detailed map indicates three public parking lots and key streets in Downtown Chester. Lot #1 is located on Water Street, Lot #2 at the Cemetery, and Lot #3 on Maple Street. Sidewalks are highlighted for ease of access into the downtown area.

Loft in Chester

4.99 out of 5 average rating, 142 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.

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.

Home in Lyme

4.98 out of 5 average rating, 271 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.

Top guest favorite

The image shows a storage cabinet with two shelves containing a variety of dinnerware. Items visible include plates, bowls, glasses, and mugs. The mugs feature various designs, while the plates are stacked neatly in a row. A clean, neutral backdrop enhances the focus on the organized tableware.

Apartment in East Haddam

4.9 out of 5 average rating, 168 reviews

Penny Corner Airbnb

My place is located up the hill from Good Speed Opera House. The Opera House is on the same side of the river as my place. The folklore is that vacationers used to pay a penny to have their belongings transported by ox and wagon from the port at the river to this corner. A two family home built in 1884. The space is a ground level 1 bedroom apartment with private entrance. There is no TV in the unit, WIFI is available for your devices.

Top guest favorite

A lush garden space is surrounded by vibrant greenery and flowering plants. A brick patio features a red umbrella over a small table and chairs, providing a shaded area for relaxation. Decorative planters enhance the tranquil setting, inviting guests to enjoy the outdoors.

Guest suite in Wallingford

5 out of 5 average rating, 592 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station.

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Popular amenities for Middlesex County vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Middlesex County

Top guest favorite

A covered patio area features comfortable outdoor seating framed by lush greenery. A small table is positioned near the seating, creating a cozy space for relaxation. The well-maintained yard extends in the background, offering a serene setting for outdoor enjoyment.

Apartment in Chester

5 out of 5 average rating, 26 reviews

New, modern studio steps from downtown Chester CT

CraigRating, 5 stars1 week ago

Great place! We stayed here on our wedding night and it exceeded our expectations. Quaint, well maintained and beautifully decorated. It was modern, clean with thoughtful attention to detail. Located near the center of Chester, a true hidden gem on the CT river. Friendly hosts.

Guest favorite

Barn in Deep River

5 out of 5 average rating, 9 reviews

Salt House

AlisonRating, 5 stars1 week ago

Beautiful and peaceful space with generous and friendly hosts who are nearby to help out. The house is fun, with multiple sources of joy. Definitely the first place where I’ve been supplied with the makings for s’mores. The stairs up to the bedrooms may be tough for a less ambulatory person, so keep that in mind. Also note the earlier than usual checkout time. Neither were an issue for me and I’m likely to stay again if I am in the neighborhood.

Top guest favorite

A two-level deck is positioned at the back of the property, featuring a seating area with comfortable cushions and a coffee table. Potted plants frame the deck, while an umbrella provides shade. Nearby, outdoor grilling equipment is visible, along with bicycles in the background.

Guest suite in Clinton

5 out of 5 average rating, 6 reviews

Private 2-room suite + bath in beach town

TraciRating, 5 stars2 weeks ago

Loved it! What stood out for me was peepers at night and the birds in the morning! The bed is so comfortable, and what a bonus.... snacks! Loved the little touches! Looking forward to staying again!

An open interior space features a circular design with wooden beams converging at a skylight. Comfortable seating areas include two sofas and multiple chairs, complemented by a dining table. The warm wooden flooring enhances the inviting atmosphere, with natural light filtering through the windows.

Yurt in Guilford

4.86 out of 5 average rating, 125 reviews

Hartwoods Yurt

AlexRating, 5 stars3 weeks ago

We stay here often, and always find something new to appreciate. It's been a chilly spring, but thankfully, the wood stove kept us all cozy. Being up in the trees, we could hear so many unique birds! We usually cook, but found the local restaurants in Guilford to be quite good. I say it every time, but it's always the getaway my family needs with the right amount of nature to escape, without sacrificing too many creature comforts. It's our happy place!

Guest favorite

A modern kitchen is presented, featuring white cabinetry and gray countertops. Stainless steel appliances, including a microwave and gas stove, are visible. An inviting layout connects to the living area, with natural light filtering through the doorway in the background.

Apartment in Middletown

5 out of 5 average rating, 45 reviews

Renovated 2-bedroom Near Wesleyan-Middletown

MichaelaRating, 5 stars6 days ago

This airbnb is very well stocked and has everything you will need. Very clean and updated. Would stay again if we were back in the area!

Superhost

A bright kitchen features white cabinetry and light yellow walls. Equipped with modern appliances including a stove and refrigerator, the space includes a sink and ample counter space. A dining table for three is present, positioned to allow views of the window and living area.

Apartment in Middletown

4.81 out of 5 average rating, 53 reviews

Cozy Apartment Near Wesleyan and Town Center

KristiRating, 5 stars1 week ago

The apartment was perfect for what I needed. It was on the same street as some of the family I was visiting so very convenient. Quick easy drive to stores or restaurants. The bed was super comfortable. There was a very nice fenced in backyard.

Top guest favorite

A large two-story house features a dark exterior with stone accents and multiple gabled roofs. Large windows allow ample natural light to enter, while a wooden front door adds a welcoming touch. Lush greenery surrounds the property, enhancing its natural setting.

Apartment in Branford

5 out of 5 average rating, 30 reviews

Stedley Creek

LorettaRating, 5 stars1 month ago

Selestria was super kind & supportive! She made us feel welcomed and made herself available for calls if needed. The home was clean and nice looking :)

Guest favorite

A welcoming living area showcases exposed wooden beams and a spacious layout. A round dining table sits center stage, surrounded by natural light from windows. A comfortable seating arrangement is present, along with a stone fireplace that adds character to the space.

Home in Haddam

4.97 out of 5 average rating, 29 reviews

The Farmhouse Stay

MarisaRating, 5 stars3 weeks ago

Chelsea was communicative and helpful about her beautiful house. It had all we needed, was well appointed, beautifully decorated and in a gorgeous natural setting. We spent time lounging in the living room as a family and it was so comfortable. Top notch! Grab this place now!

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Vacation rentals in Middlesex County

Top-rated vacation rentals in Middlesex County

Vacation rentals for every style

Popular amenities for Middlesex County vacation rentals

Other great vacation rentals in Middlesex County

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