Waterfront vacation rentals in Middlesex County

Find and book unique waterfront accommodations on Airbnb

Top-rated waterfront accommodations in Middlesex County

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

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Guest favourite

Cottage in Guilford

4.96 out of 5 average rating, 159 reviews

Luxury cottage by the sea with hot tub and pool

We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

Apr. 22 – 29

$536 CAD per night

Guest favourite

Cottage in Deep River

5.0 out of 5 average rating, 9 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.

Dec. 13 – 20

$759 CAD per night

Guest favourite

Home in East Hampton

4.98 out of 5 average rating, 51 reviews

Lake Fun: PingPong, Pool Table, Slide, EV Charger

Fun on Lake Pocotopaug - Fun on the water with swimming, kayaks, rowboat, and paddle boards; fun on land with ping pong, pool table, puzzles, and many games. Gather around the fire pit at night & roast marshmallows. In central CT with easy day trips to Mystic Seaport & Aquarium, Gillette Castle, Mark Twain House and so much more. Close to renowned musical theater at Goodspeed Opera House. Hiking and mountain biking possibilities galore at close by state parks. EV CHARGER FOR YOUR USE IN GARAGE

Jan. 13 – 20

$548 CAD per night

Guest favourite

Apartment in Branford

4.89 out of 5 average rating, 9 reviews

Stony Crk Studio ideal for trvl nurses…

Peaceful shoreline studio/retreat for trvl nurses, grad students etc near New Haven. Single occupancy studio comprises upper east-wing of our home—has its own entrance up the exterior stairway with a dbbl-locked interior door and soundproofing for your privacy. Enjoy the balcony views and sunny chaise lounge chairs in rear-garden. Kick off your shoes and totally RELAX in our sleepy niche called Stony Creek, where the beach and harbor, food and shops & historic Thimble Islands are steps away.

Jan. 8 – 15

$156 CAD per night

Guest favourite

Home in Chester

4.98 out of 5 average rating, 197 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.

Feb. 6 – 13

$577 CAD per night

Guest favourite

Apartment in Chester

4.99 out of 5 average rating, 71 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.

Dec. 19 – 26

$509 CAD per night

Guest favourite

Vacation home in Guilford

4.98 out of 5 average rating, 61 reviews

Spacious Oceanfront Getaway with Spectacular Views

Perfect summer getaway! Awaken to the sun rising over Long Island Sound! Panoramic views from 70 ft of waterfront windows spanning NY to RI. Quiet, private, updated home, NOT a cottage: >2200 sq ft, single level 3B/3B, + bonus lower-level walk-out/office. Master bed double shower/jacuzzi overlooking the water! Multiple oceanfront decks. 100 ft granite shoreline, short stroll to nearby sand beaches. Swim, hike, fish, read a book, or watch sailboats go by! (Not suitable for children/pets.)

Jan. 27 – Feb. 3

$940 CAD per night

Guest favourite

Cottage in Hebron

4.9 out of 5 average rating, 88 reviews

Welcome to The Holly at Amston Lake

Welcome to The Holly at Amston Lake! Great two-bedroom cottage situated in a peaceful lake community. Great place to enjoy time with family and friends. Take a stroll down to the main beach or enjoy the great views of the lake from the deck! Don't forget about the gas fire pit for those chilly evenings. We are located near numerous vineyards, a brewery, the Connecticut Airline Trail, and great local restaurants! Guests have access to the grill, fire pit, kayaks, and two main beaches.

Jan. 27 – Feb. 3

$284 CAD per night

Guest favourite

Apartment in Guilford

4.91 out of 5 average rating, 23 reviews

Cozy Private Lake Q Retreat

Escape to a charming lakeside haven! Our cozy 1-bed, 1-bath retreat is a tranquil getaway. Nestled by the water, it's perfect for a romantic escape or a solo recharge. Enjoy stunning lake views, a comfy bedroom, and a serene bathroom. Unwind on the private deck, take a dip in the crystal-clear waters, or explore nearby nature trails. A lofted office space with l-shaped desk and computer monitor with connection hub invites both creativity and productivity. Your lakeside escape awaits!

May 25 – Jun. 1

$311 CAD per night

Guest favourite

Cottage in Chester

4.98 out of 5 average rating, 229 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.

Feb. 6 – 13

$361 CAD per night

Guest favourite

Vacation home in East Hampton

5.0 out of 5 average rating, 26 reviews

Family Friendly Lake House Lake Pocotopaug Sunsets

Enjoy this newly renovated and decorated, cozy retreat on the lake! With breathtaking views and sunsets, this beautiful lakefront cottage provides a peaceful setting that offers an unforgettable experience for anyone visiting. The 3-bedroom, 2-bathroom cottage is full of charm with cozy indoor and outdoor living spaces for guests to enjoy. With all the amenities of a larger home, this cottage on the lake is the perfect place to make memories that will last a lifetime.

Dec. 1 – 8

$569 CAD per night

Guest favourite

Guest suite in Portland

4.92 out of 5 average rating, 12 reviews

Cozy waterview in-law apartment

Take it easy at this tranquil getaway. This inlaw apartment offers beautiful views overlooking the CT river. Featuring its own separate entrance the house has a two story patio, outdoor seating, and fire pit. Next to a marina for easy access to water sports. Location is conveniently between both downtown Middletown and south Glastonbury (about a five min drive either way) and offers a wide variety of restaurants and entertainment. 25 yo age minimum.

Jun. 12 – 19

$236 CAD per night