Waterfront vacation rentals in Middlesex County

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Middlesex County

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

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Guest favorite

Guesthouse in Essex

4.82 out of 5 average rating, 28 reviews

Privateers Boathouse (Village Waterfront)

Right in the middle of all Essex Village offers: shopping, dining, boating. Short drive to beaches, farmstands, golf, hikes, theatre, colleges & more. Very special little waterfront cottage with unrivaled views, private deck & access to town. Park your car once and enjoy all the wonders of Essex Village by foot during your visit. 🌟 Secluded, yet utterly central Village location. 🛶 Access to swimming pool WITH ARRANGEMENT (2 towels provided) 🚣‍♀️ No proper launch for kayak/SUP- but several close

Guest favorite

A large window with a slanted frame provides a view of the coastal landscape. Lush green trees are visible, with an expansive sky overhead, showcasing soft clouds. In the distance, the shimmering water can be seen, creating a serene and natural setting.

Cottage in Guilford

4.95 out of 5 average rating, 177 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)

Guest favorite

A serene view of a calm lake reflects the sky and surrounding trees, with autumn colors visible in the foliage. A small dock extends into the water, accompanied by two chairs and a table on a balcony overlooking the scenic landscape.

Home in East Haddam

4.95 out of 5 average rating, 205 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

4.89 out of 5 average rating, 151 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 charming family home is nestled along the water, featuring a private dock with a small boat. Lush greenery surrounds the property, while the sun casts warm light on the exterior, highlighting the inviting porch and scenic views of the tidal Hammock River.

Home in Clinton

5 out of 5 average rating, 11 reviews

Waterside retreat! 4BR/3BA with private dock/views

**7/5-12, 7/23-26, 9/1-4, 9/7-10 STILL AVAILABLE FOR SUMMER 2025! NOW ALSO AVAILABLE SEPT. - MAY, BOOK LONG WEEKENDS NOW!!** Welcome to Waterside! Just steps from Clinton Town Beach, our beautiful family home has been welcoming guests since 1793. Swim off the private dock, explore beaches, kayaking, birding, fishing, antiquing, golf, & more - then come home to your personal oasis. Grill on the patio, get lost in a good book, or relax and watch the sunset from the porch overlooking the harbor.

Guest favorite

A stone fireplace serves as a focal point in the living area, featuring a mounted television above. A cozy armchair with a cushion is paired with a small side table, while light from the windows enhances the warm wood flooring.

Cottage in Hebron

4.89 out of 5 average rating, 134 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.

Guest favorite

A sunny pathway leads alongside a vibrant yellow wall of the house, bordered by stone. White outdoor chairs and tables are positioned neatly on a patio overlooking a serene river, with trees gently framing the scene in the background.

Home in Clinton

4.93 out of 5 average rating, 135 reviews

Amazing 2BR Riverfront Gem

Unwind at this happy getaway on the river. Comfy cozy with amazing views. Come experience the charm of New England in any season! The well-equipped, intimate kitchen overlooking the river is a pleasure for any cook. You will love our fairy-lit lawn, wishing well, and warm charming décor. Only minutes to groceries, coffee shops, beaches and amazing CT scenery. Other favorites include Chamard Vineyard, Shopping Outlets, Essex Steam Train, fantastic Restaurants with music, and lots more!

Guest favorite

The cottage features a spacious deck with a fire pit surrounded by Adirondack chairs. A dining area is placed under a yellow umbrella, and a cushioned seating area is visible on the porch. Lush trees provide a natural backdrop for a serene outdoor space.

Cottage in Chester

4.97 out of 5 average rating, 266 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

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, 261 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.

Superhost

Home in Lebanon

4.84 out of 5 average rating, 25 reviews

Breathtaking Lake Williams Lakefront

Relax lakefront with the whole family at this peaceful, private seasonal retreat. Expansive double lot lakefront with 125’ of direct waterfront and steps into lake. Fishing, kayaking and paddle boarding. Daydream in the large custom outdoor shower overlooking the lake with private changing area. Then, barbecue and have a wiffle ball game while overlooking the lakefront at sunset. There's even a boat house with couch and TV looking out to the water!

Guest favorite

The exterior of a charming cottage is visible, featuring a wraparound porch and American flag. A set of wooden steps leads to the entrance. An umbrella-covered table and chairs are positioned on a sandy area, with a grill in view. A quiet atmosphere surrounds the home.

Cottage in Guilford

4.95 out of 5 average rating, 80 reviews

Direct Shoreline Long Island Sound Waterfront

A quintessential New England cottage with views of the water from all rooms. Spectacular sunrises and sunsets, enchanting panorama views. A stone's throw from the beautiful Grass Island state park and boat launch, a waterfront natural preserve, perfect for hiking or communing with nature. The interior underwent a full renovation in 2020 with new appliances and bath fixtures. Original structure preserved. A tranquil, quiet place.

Top guest favorite

The cottage's exterior is shown, featuring natural shingles and a welcoming entrance. Lush green grass and flower beds with blooming plants enhance the yard, while the serene waterfront and dock are visible in the background, framed by a clear blue sky.

Cottage in Old Saybrook

5 out of 5 average rating, 98 reviews

Cozy Waterfront Retreat

Serene waterfront retreat! Direct waterfront property on Oyster River perfect for kayaking, fishing, paddle boarding or just soaking up the sun. This cozy cottage with views of stunning sunsets allows guests to relax and unwind. Minutes to local restaurants and shopping, walking/bicycling distance to the towns best beaches; close to outlets and casinos. Quaint, charming cottage with beach decor throughout.