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

An aerial view captures the fully remodeled home situated directly on the waterfront, surrounded by lush trees. A large private deck is visible, along with an expanse of green lawn leading to the serene lake, mirroring the trees and sky above.

Home in Harwinton

4.96 out of 5 average rating, 72 reviews

Direct Waterfront with Private Beach - Entire Home

Rare opportunity to enjoy DIRECT WATERFRONT living, great for your next vacation, relaxing weekend, or to work remotely. Fully furnished and completely remodeled home includes all amenities, complete kitchen and accessories, washer/dryer, central air, large deck, fast WiFi, Smart TVs. Featuring beach, swimming, kayaking, canoeing, paddle boarding, biking, skating and fishing. Enjoy spectacular views of the lake from the open concept home We are a SUPERHOST - Nearly 90% booked, so book early

Guest favorite

Adirondack chairs are positioned on a grassy area by the water, surrounded by autumn foliage. Gentle waves lap against the shore, while trees with colorful leaves frame the serene view of the river and distant houses.

Villa in New London

4.87 out of 5 average rating, 30 reviews

Waterfront Holiday Vacation Villa New England

Have fun with the whole family at this stylish VILLA with water (kayak) access to Ocean State Beach Park and a 4 minute drive to the quaint Waterford Beach. This idyllic leisure home has everything you need to enjoy your gateway. SECLUDED setting with 300 ft of waterfront access for kayaking , fishing. Sauna, bicycles, waterfront gazebo with fire pit , basketball hoop and hammocks. All spaces are newly renovated and tastefully decorated. New fully stocked kitchen . Close to Mystic - Foxwoods

Top guest favorite

An outdoor patio features a wooden dining table surrounded by six matching chairs. Sunflowers are displayed in the center. The area is bordered by lush trees and offers scenic views of Hashamomuck Pond, complemented by lounge chairs and a hot tub nearby.

Home in Southold

5 out of 5 average rating, 26 reviews

Beautiful waterfront 3 bedroom home in Southold

Beautiful waterfront home with stunning views of Hashamomuck Pond, making it the perfect escape for a memorable family vacation. Enjoy beaches, wine country, farm stands, and excellent restaurants. Featuring 3 bedrooms and 2 full baths. 1st floor, master bedroom, a guest room, and a bonus room with a pull-out couch. The second floor offers an additional guest room with two queen beds. BBQ, paddle boards, kayaks, fire pit, and plenty of seating to enjoy the beauty that surrounds this home.

Superhost

An aerial view captures the oceanfront condos nestled along the coastline, surrounded by lush greenery and a sandy beach. The serene waters and well-maintained grassy area enhance the natural beauty of the setting.

Condo in Greenport

4.84 out of 5 average rating, 132 reviews

Seaside Summer Escape: 2BR Waterfront Condo w/Pool

Overlooking the Long Island Sound, this oceanfront condo is the ultimate escape. Bask in the sun on a private beach or unwind on the waterfront deck with breathtaking views Minutes from the town center, you’ll find local farms, award-winning wineries, gourmet restaurants & charming shops ⚓️ Explore Greenport: A historic seaport with coastal charm & rich culture 🏖 Premium Amenities – Waterfront deck, private balcony, grills, pool, private beach & parking ⛴ Ferry Access to Shelter Island & CT

Guest favorite

A waterfront home with a unique tower design is reflected in the calm waters of Bantam Lake. The house features multiple outdoor decks, large windows, and is surrounded by trees, providing a serene setting. A private dock extends into the lake, inviting exploration.

Home in Morris

4.86 out of 5 average rating, 151 reviews

Bantam Lake Waterfront Retreat with Private Beach

Waterfront home on Bantam Lake, 3BR/2BA. Relax on the deck, enjoy the sunrise, swim at your private beach. Kayaks available for use (4); bring your boat or jet ski. Minutes away from hiking, snow skiing, vineyards, biking, and so much more. The area offers great restaurants and family friendly activities that are minutes away. BBQ on the gas grill, enjoy the fire pit on the beach. House is great for couples, individuals & families. Please check first if you plan to bring a boat. 7 maximum.

Guest favorite

A charming cottage exterior showcases a soft yellow façade and a slate-shingled roof. Flower boxes adorned with vibrant blooms are positioned beneath the windows, while a wooden bench provides a welcoming touch. A quiet street and greenery are visible in the background.

Cottage in Stonington

5 out of 5 average rating, 22 reviews

Sea Spray…Waterfront cottage in Stonington Borough

Waterfront getaway located in Stonington Borough features views of Long Island Sound and the open ocean beyond. This seaside gem is a perfect summer retreat with an enclosed waterfront for maximum privacy and dock for swimming and kayaking. Enjoy sea breezes and water activities . Swim off the dock or kayak over to the sandy beaches of a nearby island for a picnic. Visit quaint shops, coffee shops waterfront restaurants and galleries. A charming little beach is only a few blocks away!

Guest favorite

A serene view of Pattagansett Lake is presented, with gentle ripples reflecting the sky. Surrounding hills are adorned with trees displaying autumn colors, while fluffy clouds drift above. The calm waters enhance the tranquil atmosphere of the natural setting.

Apartment in East Lyme

4.97 out of 5 average rating, 229 reviews

Brand New Direct Lakefront - Panoramic Sunsets

Completely remodeled lakefront apartment offering sweeping views of Pattagansett Lake. Open floor plan, fully equipped kitchen and massive deck make for an ideal gathering place to catch up with family or friends. All three spacious bedrooms offer comfy queen memory foam mattresses, fresh linens and UHD smart TVs. Two full bathrooms, high speed internet and in-unit laundry. Picturesque natural setting yet close to town amenities, restaurants, beaches, casino and area attractions.

Superhost

The exterior of the cottage features two levels of decks, surrounded by trees and greenery. The upper deck offers ample space for outdoor seating, while the lower deck is furnished for dining. A stone pathway leads to a landscaped area beside the house.

Home in Stonington

4.87 out of 5 average rating, 113 reviews

Waterfront Cottage with Dock

Arts and Crafts cottage on an ocean cove in Stonington with dock and close to the beaches. On same cove as Saltwater Farm Vineyard and nearby to Mystic Aquarium and Seaport, great restaurants, and Foxwoods and Mohegan Sun resorts. You’ll love the backyard and dock. I offer complimentary canoe, kayak and paddle board use so you can enjoy the water. Bring your own boat or rent one for 50% off at Stonington Marina. My place is good for couples, families with kids, and pets.

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, 266 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

A charming cottage is nestled alongside a lush green lawn, leading towards the water. Directly visible are several white adirondack chairs placed near the water's edge, creating a serene outdoor space. The quaint cottage features a red brick chimney and a tasteful shingle exterior.

Cottage in Old Saybrook

5 out of 5 average rating, 99 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.

Guest favorite

An aerial view captures the Reed House situated near the shoreline, with the Long Island Sound visible in the background. Surrounding homes and a sandy beach area are present, while lush green lawns and a winding waterway enhance the natural setting.

Home in Waterford

4.95 out of 5 average rating, 116 reviews

Coastal New England Waterfront Home-The Reed House

The Reed House – Waterfront Getaway in Waterford, CT Enjoy the best of both relaxation and adventure at The Reed House, located in the peaceful Pleasure Beach neighborhood of Waterford. This charming home offers breathtaking views of Jordan Cove and is just steps away from the beach, making it the ideal retreat for families, friends, or anyone looking to unwind by the water..

Top guest favorite

The image captures a serene view of a calm lake surrounded by trees displaying autumn foliage. A small dock extends into the water, featuring a wooden platform and a seating area. The reflection of the sky and trees creates a tranquil atmosphere.

Cottage in Colchester

4.97 out of 5 average rating, 172 reviews

Lakefront peaceful getaway cottage

Newly renovated house. New kitchen with skylights. New bathrooms with standing showers. New bedroom en-suite with small balcony overlooking the lake. Quiet area. AC units in bedroom only. Sorry no pets because of owner allergies. Queen bed in master and full-size+ twin second bedroom.