Vacation rentals with a pool in Middlesex County

Find and book unique homes with a pool on Airbnb

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

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 spacious pool area is framed by well-maintained greenery and flowering plants. Two large umbrellas provide shade over lounge chairs beside a sparkling pool, with expansive coastal views and a serene landscape of grasses and trees beyond.

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 vibrant flower arrangement in the foreground draws attention to a serene swimming pool surrounded by lush greenery. A hammock is visible on the lawn, along with small seating areas for relaxation. The scene conveys a peaceful outdoor retreat.

Barn in Deep River

4.91 out of 5 average rating, 32 reviews

Zen retreat

You won’t forget your time in this romantic, memorable place. Perfect for a couple that want to retreat to renew and reset. Bathroom has an accujet shower in a steam capsule. Outdoor shower and bath tub in our healing garden. Swimming pool (in season) with a sun deck. Meditation garden and weeping willow will relax and rejuvenate your spirit. Wintertime a sauna is available after we close the pool. Windows and some of the furnishings were last in Katherine Hepburns home. Imagine the stories.

Top guest favorite

A well-maintained pool occupies the center of a spacious wooden deck, surrounded by greenery and tall grass. A patio dining set is visible in the background, providing an inviting space for outdoor meals. Sunlight reflects off the clear blue water, enhancing the tranquil setting.

Home in Old Saybrook

5 out of 5 average rating, 45 reviews

3BR Updated Cottage w/ Pool in Old Saybrook

Welcome to Osprey Lookout! 3 bedroom, 1 full bath updated cottage located in the quintessential New England beach town of Old Saybrook, CT. With distant views of Long Island Sound from the pool deck, this single-family cottage in a private setting has everything you need to enjoy a relaxing family vacation, including an outdoor shower to rinse off after a day at the beach! Nearby: - Harvey's Beach - Connecticut Wine Trail - Essex Steam Train - Mohegan Sun & Foxwoods - Historic Mystic Seaport

Top guest favorite

An aerial view of a spacious in-law apartment is presented, framed by vibrant autumn foliage. A circular above-ground pool is visible in the yard, surrounded by a well-maintained lawn. The property features multiple outdoor seating areas and a separate entrance, complemented by a peaceful neighborhood setting.

Guest suite in Portland

4.95 out of 5 average rating, 22 reviews

Cozy water view in-law private apartment 2bd/1ba

Take it easy at this tranquil getaway. This in-law apartment offers beautiful views overlooking the CT river. Featuring its own separate entrance to the house, 2bd/1ba, kitchen, and living and dining spaces. Also outdoor seating and 2 parking spaces for guests. 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) and offers a wide variety of restaurants and entertainment. 25 yo age minimum.

Top guest favorite

Villa in Guilford

5 out of 5 average rating, 27 reviews

TREETOPS! An upscale, unique 5 bdrm home with POOL

TREETOPS is a 4850 square ft 5 bedroom Mid century Modern perched on an outcropping of granite cliffs, surrounded by 2 acres of beautiful forest. *Property not suitable for children under 8 years old* Stroll along the loop trail in our woods, sit in the garden, have a fire in the fire pit, or relax and get some sun by the marine-blue, stone-decked pool! Birdwatching, breakfast, and evening cocktails are best on the spacious wrap-around deck. Hiking is just steps away at "Westwoods Trailhead".

Guest favorite

An open living space showcases a wooden table with candles, surrounded by wooden chairs. A white sofa with decorative cushions is positioned next to a reddish armchair. A coffee table sits central, with a small plant atop a patterned rug. Light illuminates the cozy atmosphere.

Apartment in Glastonbury

4.9 out of 5 average rating, 432 reviews

Quiet 2 bed room apt w/ private entrance.

NOTE WELL: This light, spacious basement apartment is located in a residential neighborhood in South Glastonbury near the Connecticut River and many good hiking areas, shops, and restaurants. We are working professionals who rise and retire early. We have a large exuberant dog who is fenced (electric) away from the apartment and house entrances and driveway. The space is not appropriate for parties. Do not inquire or book if your life situation is not amenable to this description.

Guest favorite

A serene pool area is surrounded by lush greenery and blooming hydrangeas. Comfortable lounge chairs are positioned near the water, with a shaded gazebo in the background. The pool is clear, inviting with blue water under a bright sky.

Apartment in Westbrook

4.95 out of 5 average rating, 20 reviews

Meadowview & Pondside Retreat

We welcome you to a serene and peaceful getaway at our recently renovated apartment. Explore 88-acres of woods, New England rock walls, streams, meadow and pond all without leaving our beautiful native landscape. We are conveniently located within a 10 minute ride from I95/Rt.9, the quaint villages of Chester, Deep River & Essex or down to the CT shoreline. We are also a working herb farm and happy to arrange farm tours, medicine making classes, or plant walks/guided hikes.

Guest favorite

Aerial view of the property showcases a spacious multi-level home surrounded by greenery. An above-ground pool is situated in the backyard, with a deck featuring seating areas. The neighborhood features several nearby houses set back among trees, providing a sense of privacy.

Vacation home in Westbrook

4.88 out of 5 average rating, 33 reviews

Modern Coastal Home with Pool

Welcome to Salty Marsh! This stylish 3-level home is perfect for just about anyone looking for beautiful sunsets, coastal vibes, and a comfortable and unique vacation. Every inch of this space has been thoughtfully designed and decorated to make you feel at home while on vacation. A perfect location for a family gathering, a few couples get away, girls weekend or any excuse to escape. This unique property offers 3-levels of living with two equipped kitchens.

Superhost

An in-ground pool featuring clear blue water is surrounded by a concrete patio. Several lounge chairs are arranged nearby, and a fenced backyard provides privacy. Lush greenery is visible in the background, enhancing the outdoor space.

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.

Guest favorite

A serene pool area is surrounded by lush greenery, featuring lounge chairs positioned beside the inviting water. Soft lighting is suspended overhead, enhancing the tranquil atmosphere. A shaded gazebo is visible in the background, complemented by stone walls and vibrant plants.

Cottage in Haddam

4.98 out of 5 average rating, 53 reviews

Private Cottage Retreat with Heated Pool

A beautifully serene guest cottage at the historic Stephen Smith House. Located in the gorgeous Connecticut River Valley, in the town of Haddam, the cottage is a private relaxing getaway just 2 hours from NYC and Boston. The special home and bucolic property is situated above a lovely brook, surrounded by mountain views, waterfalls, stone walls, gunite pool, magical gardens and 175 acres of private hiking trails.

Guest favorite

Home in East Hampton

4.95 out of 5 average rating, 60 reviews

Country getaway - huge yard, pool

Private rental unit on 2nd and 3rd floors of historic 2-family home (owners live in rest of house) amid forests, lakes, rivers and ponds. Private deck, outdoor shower, & full access to the 4 acre property. Just minutes from swimming, hiking, cycling, boating and more! Enjoy the area’s many tourist destinations, family attractions, restaurants, vineyards & breweries, antique shops, golf courses and entertainment!

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What guests are saying

15 acres! * Pine Pond at Devils Hopyard State Park

5 out of 5 average rating, 23 reviews4 months ago

The house was immaculate and exceeded our expectations. We enjoyed the well -equipped kitchen and even included flour, spices and sauces. Top quality everywhere. We hiked in the adjacent state park and enjoyed that immensely. The game room was fun with billiards and pinball as well as other games. Alexa activated all the lights on voice command. Hosts met us when we arrived and walked us through the house. We hope to return each year.

Home in East Haddam

What guests are saying

Spacious historic cottage w/pool - walk to beach

4.7 out of 5 average rating, 20 reviews8 months ago

We really enjoyed our stay in Westbrook and are so happy we were there for 1 month. Alicia’s home is totally charming. It is older and not without its quirks, but it is decorated beautifully, functionally and comfortably. The pool was such a needed relief from the heat of July, and the hosts had everything we needed for a day at the beach and even pickleball. The hosts were very responsive, friendly and helpful, as well as the pool cleaners and house cleaners. We would definitely stay there again. Thank you, Alicia!

Cottage in Westbrook

What guests are saying

Secluded Family escape w/ pool & jacuzzi

4.73 out of 5 average rating, 133 reviews2 months ago

Everything was great and as advertised, we had an issue with the hot tub however mark was so helpful and took care of it right away to help enjoy during our stay. I would recommend this place again it was so quiet and peaceful and I’m sure being there on the summer to enjoy the pool would be fun.

Home in Westbrook

What guests are saying

Beautiful 1820 Colonial, Madison, CT

4.79 out of 5 average rating, 38 reviews10 months ago

My husband and I stayed with our 19-month-old son for three nights and it was a perfect choice! Susan had a toys and books that he loved, as well as a sandbox and pool outside - and the home was stocked with everything we needed for our stay. We used the location as a jumping off point for other activities and then had quiet afternoons at the house while my husband rode his bike (we saw lots of other cyclists!). If you are vegan or vegetarian, check out the Shoreline Diner in Guilford - it was delicious.

Home in Madison

What guests are saying

59 Old Maids Lane pool house

4.77 out of 5 average rating, 96 reviews4 months ago

We enjoyed the coziness of the pool house during our Thanksgiving stay. The location was close to our family and friends. It was private and quiet. Alice responded promptly to our questions. We would like to return when the weather is warmer to take advantage of the pool and the outside surroundings. The Goulds

Guesthouse in Glastonbury

What guests are saying

Country escape w/pool, waterfall - 2h NYC/Boston

4.83 out of 5 average rating, 6 reviews33 months ago

We had such a wonderful time in this home. We loved the pool and used it everyday. We also loved the outdoor space. Perhaps the outdoor space is understated in the advertisement for the house, it is truly magnificent. The air conditioners worked very well and kept things cool inside even on the especially hot days. Thank you for a wonderful experience!

Home in East Hampton

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