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

Cottage in Guilford

4.96 out of 5 average rating, 159 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)

25 Oct – 1 Nov

₹28,863 per night

Guest favourite

Home in Montville

4.96 out of 5 average rating, 106 reviews

Casino Stay & Play House

Come have an unforgettable, fun packed vacation at our newly remodeled home! The house is packed full of games and conveniently located close to Mohegan Sun, Foxwoods, Mystic, Vineyards, Navel Submarine Base, Ct College and several beaches. Enjoy our game room where you can sing karaoke, play over 3,000 classic games and write on our giant chalk board wall. Outside enjoy swimming in your own private pool, take dip in the hot tub, play a game of corn hole and watch tv by the fire pit on the deck

27 May – 3 Jun

₹36,735 per night

Guest favourite

Apartment in Norwich

4.9 out of 5 average rating, 147 reviews

Renovated Condo rental at Norwich inn villa & Spa

Hi welcome to our home here at the Norwich inn and villacondos We aim for you to find peace and relaxation. Minutes away from Mohegan sun as well as fox woods casino. This location has a state of the art Spa and dinning as well as a 18 hole golf course. The landscape here at Norwich is amazing in the summer and spring and you have your own personal view of the water fall that was just put in. Great walking trails Nature friendly and salt water pools and jacuzzi.Come stay here @villa you love it

13–20 Dec

₹12,550 per night

Guest favourite

Home in Shelter Island

4.97 out of 5 average rating, 198 reviews

Huge Island Getaway Pool HotTub Walk To Beach

Relaxation begins on the 6 minute ferry ride to this magical island. Summerfield is a spectacular, grand compound that has it all. Huge main house great for groups, 4700ft w/ privacy for all overlooking serene nature reserve. Star gaze in the bubbling hot tub, grill outside after a swim, play in the rec room with movie theater, pool table or ping pong,or watch TV by the fire! Open plan layout, gourmet kitchen, heated gunite pool, separate guest house. Prime location close to beach + restaurants.

28 Feb – 7 Mar

₹82,044 per night

Superhost

Apartment in Norwich

4.88 out of 5 average rating, 211 reviews

The N-V ...The Spa at the Norwich Inn.

Welcome to The Spa @ the Norwich Inn Villas.. Updated with lightness and comfort in mind. You open to an updated kitchen with all the amenities you’ll need for your stay ..and of course your Keurig stocked up for u. You’ll be walking on engineered flooring with suppressed corking for comfort and sound reduction. The dining is a well designed top with stools that tuck away..just in case you need the Queen sized Murphy bed.. Master bedroom has a queen bed, private bathroom, 32” tv and full WiFi.

4–11 Sep

₹12,398 per night

Guest favourite

Flat in Norwich

4.9 out of 5 average rating, 233 reviews

Cozy Stay w Pool 4 mi to Mohegan, 7 mi to Foxwoods

THE POOL IS OPEN AS OF MAY 1st! Welcome to our charming 2-bedroom apartment. This centrally located spot is the perfect getaway to escape the hustle and bustle of the big city and enjoy a more relaxed pace of life. The unit comes in at a spacious 950 sq ft - ideally suited for couples, solo travelers, families and can comfortably accommodate up to 4 people. Feel free to use the grill of course, but you may have to fill the propane tank. You can do so at the Walmart which is 12 minutes away!

14–21 Oct

₹8,493 per night

Guest favourite

Apartment in Norwich

4.99 out of 5 average rating, 167 reviews

Modern & Cozy Villa with low cleaning charge!

Located on the Norwich Inn and Spa property, this Villa is a true one bedroom unit with access to two clubhouses (9am-10pm) which include a sauna, gym, hot tub, and saltwater pool access (seasonal). It is also located a few miles away from both Mohegan Sun Casino and Foxwoods Resort and Casino with many amazing restaurants to chose from in the area. If you are a fan of golf, we are located right on the back 9 of the Norwich Golf course! Lake of Isles golf course is also about 15 minutes away.

7–14 Sep

₹18,375 per night

Guest favourite

Apartment in Norwich

4.99 out of 5 average rating, 114 reviews

Peaceful Oasis steps from Mohegan Sun

Feel at home at our contemporary yet cozy villa. A private and quiet space in the heart of the area's local attractions (walkable to Mohegan Sun/short drive to Foxwoods). Perfect for a fun-filled weekend or a simple and quiet getaway. Enjoy the scenic views of the surrounding golf course or indulge at the on-site renowned spa. Other noteworthy amenities include a year round opened clubhouse, sauna, and hot tub as well as two beautiful seasonally opened pools. This unit comfortably sleeps 4.

9–16 Nov

₹13,940 per night

Guest favourite

Apartment in Norwich

4.99 out of 5 average rating, 101 reviews

Jacuzzi/Sauna/Pool, On-site Spa, 3-mins to Mohegan

“Attention to detail, beautiful decor, thoughtful touches, cleanliness- cutest and cleanest villa” -Heated towel/robe warmer, plush robes, microfiber hair wrap, makeup mirror -Coffee bar w/ french press, espresso machine, fresh coffee beans, flavored syrups, tea -Fully stocked kitchen w/ airfryer, baking essentials, toaster -Barware including cocktail shaker set, champagne flutes, margarita/wine/whiskey glasses -Complimentary toiletries & feminine oriented essentials -Indoor fireplace

18–25 Jan

₹20,526 per night

Guest favourite

Flat in Glastonbury

4.9 out of 5 average rating, 410 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.

17–24 Mar

₹9,514 per night

Guest favourite

Barn in Bloomfield

4.97 out of 5 average rating, 111 reviews

Mountaintop Horse Farm with Pool

Come sleep above the horses at Bloombury Hill Farm. With stunning mountaintop views, this immaculate 2 BR apartment is spacious and boasts over 2000 square feet. Basque in the sunshine at the pool (open Memorial Day through Labor Day from 11a-5pm.) Close to thriving West Hartford Center with loads of restaurants and shopping. Hiking trails, local breweries and wineries, and farm stands are all located close by. All the ingredients for a magical weekend getaway.

26 Nov – 3 Dec

₹25,341 per night

Guest favourite

Flat in Enfield

4.99 out of 5 average rating, 146 reviews

FROG Suite Apartment

Welcome to the FROG Suite apartment, the prefect place in a comfy private space. Be it for work, pleasure, travel or leisure, this alluring updated space is located upstairs over the garage in a quiet residential neighborhood and includes a private keyless entry door lock. Apartment is located upstairs over the garage and is attached to the house.

5–12 Dec

₹8,426 per night