House holiday rentals in Middlesex County

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Top-rated house rentals in Middlesex County

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

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Guest favourite

Home in Old Lyme

4.9 out of 5 average rating, 125 reviews

The Beach House

Our Beach House is close to the mouth of the Connecticut River surrounded by the salt marsh and at the end of our street you can see Old Saybrook lighthouses. Quaint local towns, two major shopping outlets and award winning casinos. Close to Gillette Castle, Mystic Seaport and the Coast Guard Academy. Lots of restaurants serving up local fare. Beautiful beaches, theater, music, and a variety of activities (kayaking, hiking, bird watching). Many museums in both directions on I-95 and I-91.

Top guest favourite

Home in Old Saybrook

4.97 out of 5 average rating, 120 reviews

Year Round Beach House in Old Saybrook, CT.- Pets

Our Beautiful Home is Located in Saybrook Manor Association and only a short walk to the beach . We have 4 Bedrooms that can accomadate 8 people,pull out couch,2 bathrooms, a Dining Room,Kitchen, and Spacious Living room.Our Yard is fenced in for your privacy & pets.Our home comes with many ammenities such as movies,games,kayaks, Clamming &Crabbing tools,Bikes,Floats & Beach Chairs.We have a beautiful backyard to enjoy games,barbecue or just to relax & unwind.Enjoy our beautiful & quaint beach

Guest favourite

Home in Clinton

4.93 out of 5 average rating, 134 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 this winter. The well-equipped 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 at almost every turn. Other favorites include Chamard Vineyard, Shopping Outlets, Essex Steam Train, fantastic Restaurants with music, and lots more!

Guest favourite

Home in East Haddam

4.95 out of 5 average rating, 200 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 favourite

Home in East Hampton

4.87 out of 5 average rating, 97 reviews

Beautiful Lake House on Lake Pocotopaug

Enjoy a relaxing vacation in a beautiful, updated lakefront home on Lake Pocotopaug. Summer =grilling out, kayaking & paddle boarding with family & friends. A lakeside marina offers party boat rides & kayak rentals. Winter=relaxation by the cozy fireplace, games and ice skating when the lake freezes over. Projector Screen, Games, Books, AC, Heat, Outdoor Grill and a working fireplace. All year round, we'd love to have you at our home. which we love and use as a getaway from the city.

Guest favourite

Home in Chester

4.98 out of 5 average rating, 209 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.

Superhost

Home in Clinton

4.7 out of 5 average rating, 88 reviews

Year-Round Waterview 4 Bds/2Bths, Sleeps 13 Linens

Welcome to your dream waterview getaway! Our property offers the perfect blend of two private beaches 4 houses away. An 8-minute walk will take you to a public beach with a playground area, basketball court, grill, and pavilion. It's the ideal spot for a fantastic day by the water. Your beds will be made up with fresh linens, and towels ready for your comfort. We've even offer beach towels and provide chairs, making it easy for you to relax and soak up the sun without the hassle of packing.

Guest favourite

Home in Clinton

4.97 out of 5 average rating, 191 reviews

Waterside Beach Retreat

Beautiful New England period home steps from the beach on the Long Island Sound. Recently renovated from top to bottom with new kitchen and bathrooms, hardwood floors throughout. Idyllic location on quaint & quiet street. Hide away and relax or discover the many local attractions - water sports, fishing, winery, antique stores, scenic walks, premium outlet shopping are all on your doorstep. Ideally located off the I-95 halfway between NYC & Boston, both of which are a train ride away.

Guest favourite

Home in Lyme

4.92 out of 5 average rating, 330 reviews

Stunning, peaceful and private home

Stunning recently renovated 3 story cape on 7+ acres and 2000+ square ft. Open kitchen to living room area with a giant island to gather members of your group together to eat, drink, laugh and have a great time. Cook inside with a fully equipped kitchen, pots, and pans, silverware, spices, everything you would want to prep a great meal as well as a propane grill on the deck. Modern amenities throughout the space. Touch lighting, bluetooth music and more.

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!

Superhost

Home in Clinton

4.91 out of 5 average rating, 11 reviews

Clinton Beach House & Cottage w/ Pool, Near Shore

A block and a half from the water and marinas! Beautiful 4BR/2.5 BA beach area home (sleeps 10), close to marina/town beach. Property includes in-ground pool and 1BR/1BA guest house (sleeps 4). A spacious colonial-style main house and carriage house share a bright sunny half-acre. Fully fenced in backyard makes it idea for families. Backyard fire-pit, new plantings, beach stone, window boxes, and an outdoor shower add to the property's appeal.

Top guest favourite

Home in Old Saybrook

4.9 out of 5 average rating, 92 reviews

Best of both worlds!

Great location- 1 mile to the beach, 1/2 mile to shops and restaurants, and less than a 1/4 mile to a park! The house is set back from the road with a good size driveway. The inside is newly renovated and we are working to finish the yard area for the summer! The house has WiFi, large yard, and a great front porch that gets a ton of sun. We’ve made great memories there over the years and are now looking to share it with others!