Vacation rentals with a pool in Middlesex County

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Top-rated rentals with a pool in Middlesex County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

The exterior of a modern wooden house features a sloping roof and a welcoming front porch. Lush green grass surrounds the structure, complemented by small shrubbery thoughtfully arranged near the entrance. Three large windows provide natural light to the interior.

Bungalow in East Hampton

4.93 out of 5 average rating, 107 reviews

East Hampton Ranch with Access to Clearwater Private Beach

Dive into the saltwater pool, set amid professionally landscaped grounds. Later, head for the multiple outside entertaining areas for a meal from the built-in outdoor grill. Round off the day with a soak in the claw foot tub in the marbled bathroom. The pool is available from May to September, and the temperature is regulated at 87 degrees. Check with the host for additional requirements. Walk to the Clearwater Beach Association's private beach, just a few blocks from the house, with a local grocery store also close. East Hamptons village is 12 minutes away, with recommended restaurants including Roudy Hall and Citta Nova.

Top guest favorite

A stone pathway leads to a sparkling pool surrounded by lush greenery. Flowering plants in pots frame the pool area, while lounge chairs and a shaded umbrella provide seating options. Tall trees offer privacy, creating a serene outdoor retreat.

Guesthouse in Southbury

4.93 out of 5 average rating, 319 reviews

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Top guest favorite

A private pool area is shown with a clear blue swimming pool surrounded by four lounge chairs. A charming shed is situated in the background, framed by green trees and landscaped gardens.

Home in Southold

5 out of 5 average rating, 11 reviews

Stylish Beach Getaway: pool & walking location

Perfectly located within walking distance to shops, beaches, and restaurants, our designer home offers comfort, luxury amenities, and privacy. Interested in a long term rental? Message us! Enjoy a beautifully landscaped backyard with pool, chefs kitchen for hosting, and nearby beach farms & wineries. Bedrooms boast organic linens and bathrooms offer Bathing Culture products. Kitchen is stocked with local organic pantry staples and stainless steel appliances to cook or grill on the patio.

Top guest favorite

The expansive patio area features a large pool with a unique shape, surrounded by sun loungers and shaded seating options. A hot tub is positioned nearby, and additional amenities include a fire pit and a shaded cabana. The enclosed space is accentuated by landscaped elements.

Home in East Haddam

4.98 out of 5 average rating, 52 reviews

Spacious 5 bdrm, 6 bth, 30 min to beach & casinos

Spacious 5 bedroom 6 bath sleeps 14 -WHAT YOU’LL LOVE- • Private resort style patio, including STUNNING POOL, HOT TUB, fireplace and firepit, bar and grill, 65" TV, outdoor bathroom and shower. • Open concept floor plan that is great for groups and families. • Authentic New England experience. • Fun game room for adults and kids with wet bar and mini fridge • Quiet street and neighborhood. NY times listed East Haddam in their “52 places to love” in 2021 1 mile to East Haddam Center

Guest favorite

An expansive saltwater pool is surrounded by a spacious patio with lounge chairs. The area is bordered by lush greenery and colorful flowering bushes, enhancing the serene setting. Pebbled landscaping delineates the pool area, creating a calm and inviting atmosphere.

Home in Orient

5 out of 5 average rating, 10 reviews

Luxury Escape - Saltwater Pool

Welcome to our fully renovated sanctuary, on a sprawling 1.5-acre property just one block away from the beach. Indulge in the luxury of our 4-bedroom, 2.5-bathroom home, where tranquility meets elegance. Unwind in the expansive back yard, enveloped in lush greenery, and discover the centerpiece of our oasis—a magnificent, 20x50 saltwater heated pool with an in water tanning ledge. Bask in the sun on one of the two generously-sized decks, perfect for relaxation and taking in the surroundings.

Superhost

An open dining area features a rustic wooden table surrounded by modern chairs. A chandelier hangs above, complementing the natural light from large windows. A cozy living space with a fireplace and plush seating is visible in the background. Warm wood beams add character to the ceiling.

Home in Litchfield

4.9 out of 5 average rating, 50 reviews

Woodland Country Retreat-Pool+FirePit-nearWineries

20% off JULY/AUG MONTHLY- Leave your worries at the front door of this New England gateway. An open, airy interior may make you feel like staying at home reading all day long, but there's so much to explore nearby. Head out to Black Rock State Park for a scenic hike through lush forests, followed by a leisurely afternoon sampling wines at local vineyards. Gather at this stylish home by the firepit w/loved ones. Pool deck area in rear of house is closed, under maintenance work until 5/26/25

Guest favorite

A spacious pool area features a crystal-clear swimming pool surrounded by a wooden deck. Colorful sun loungers are arranged neatly, accompanied by large umbrellas offering shade. Lush greenery is visible in the background, enhancing the tranquil outdoor setting.

Home in East Hampton

4.93 out of 5 average rating, 149 reviews

Large heated pool, games room, near private beach

Contemporary 4-bed + 4 1/2 bath home sitting on a park-like acre of gardens. Swim in the large pool (opens 04/25 and closes mid-October (there's an additional charge for heating - see below), relax in a hammock or bbq on the deck. Play ping-pong, darts, pool or take a 15 min walk to private bay beach to swim and paddle board. Or drive 15mins to the Atlantic beaches and visit picturesque Sag Harbor, Montauk. Reduced cleaning fee for small groups. RentReg RR-25-399 Local taxes included

Guest favorite

The studio features a queen-sized bed adorned with a floral-patterned blanket. A comfortable sofa and armchair are positioned nearby, along with a small table. Natural light filters through a nearby door, illuminating the warm wood flooring.

Condo in Montauk

4.83 out of 5 average rating, 176 reviews

Coastline View Studio

This sun drenched studio apartment is perfect for families, couples or friends looking to get away and discover Montauk! Located in Montauk's harbor district. This unit is perfectly located to experience all that Montauk has to offer... Sit back on the balcony and enjoy a glass of wine as the sun sets perfectly over Culloden Point. A short walk to the Harbor, the Dock, Gosmans, TTs, Salivars, Sunday Funday, La Fin, Viking Fleet (fishing, Whale watching & Ferry).

Guest favorite

A clear view of a gunite pool reveals crystal blue water, surrounded by a spacious lawn. Four lounge chairs are positioned nearby, and the house is seen in the background, framed by lush hedges and trees, with a deck that offers steps leading up to the entrance.

Home in Cutchogue

4.92 out of 5 average rating, 25 reviews

North Fork Farmhouse with Saltwater Pool

Enjoy spectacular sunsets from the great room and deck overviewing your secluded hedged yard and saltwater pool. Located in the heart of the North Fork this 1820s farmhouse with modern amenities is nestled amongst vineyards and farmland with dramatic views in every direction. Quaint villages, premier restaurants, wineries, farms and beaches surround you. A truly magical, peaceful paradise for you and your group. Note pool is open May through mid October.

Top guest favorite

A spacious living area features large windows dressed with natural shades, allowing ample light to filter in. Comfortable seating includes a plush sofa with blue accents, woven chairs, and a wooden coffee table. A modern kitchen area with a wine fridge is visible in the background.

Home in East Hampton

5 out of 5 average rating, 37 reviews

Stunning Central E. Hampton Home w/ gunite pool.

EH Registry #24-65. This 2800 sq foot home boasts 10' ceilings & has been re-vamped from top to bottom. Beautiful landscaping, 44' x20' deck & a 6' privacy fence Outdoor lounge furniture & dining set. The indoor dining room seats 10. Upstairs: 4 bedrooms: All mattresses are new! Baths fully stocked. Pool closes in mid Oct. and opens mid May. Pool heat is a separate fee! NO PETS. Significant pet fee required for your non shedding well behaved dog.

Guest favorite

Home in Cutchogue

4.97 out of 5 average rating, 203 reviews

Private Oasis W/Stunning Vinyard and Pool Views

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

Guest favorite

A heated pool is surrounded by a spacious, patio area featuring lounge chairs and a shaded table set, providing a relaxing outdoor space. Lush greenery and fencing enhance privacy, while a comfortable seating area can be seen beyond the pool.

Home in Litchfield

4.99 out of 5 average rating, 84 reviews

Hilltop House w/POOL/SPA- HOST & Co.

Nestled just outside the center of Bantam, this immaculate 3 bedroom 2.5 bath home with a pool is the ultimate retreat. The home is perfectly located for enjoying the area's top attractions, like lake activities, skiing at Mohawk, hiking the trails of White Memorial, Litchfield's Village Green where you can enjoy fine dinning, shopping and visit historic sites. Pool is open and heated May 15th to Sept 15th.