Holiday 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 favourite

Guest house 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 favourite

Cottage in Guilford

4.95 out of 5 average rating, 175 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 favourite

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.

Guest favourite

Place to stay in Middletown

4.96 out of 5 average rating, 52 reviews

A Luxury Estate Elegant & Private~White Lion Manor

Escape the frenzy of the world in this family friendly rental, every detail is taken care of, From the garden, saltwater pool, and courtyard views. With over 7,500 sq ft of opulent living space, White Lion Manor is more than a stay it’s a unique experience tailored for those seeking the extraordinary.The 6 person hot tub, sauna, massage chair, and endless amenities will help you Indulge in the opulence of our meticulously curated mansion and immerse yourself in the lavish lifestyle you deserve.

Guest favourite

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

Guest favourite

Guest suite in Portland

4.95 out of 5 average rating, 21 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.

Guest favourite

Villa in Guilford

5 out of 5 average rating, 26 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 favourite

Flat in Glastonbury

4.89 out of 5 average rating, 426 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 favourite

Flat in Westbrook

4.92 out of 5 average rating, 12 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 favourite

Holiday 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

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 favourite

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 live music!