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

Villa in Norwich

4.91 out of 5 average rating, 120 reviews

Private Villa 1mi from Casino! New King Bed

Relax at this villa condo that is at the Norwich Inn and Spa. Only 1 mile from Mohegan Sun, this condo a great secret escape after a night of fun at casino. Or as a quaint and quiet spa retreat! This studio condo has an open floor plan. A NEW King-size bed and a pull out couch. Living room suite area. Fireplace and desk area. Full-size kitchen and refrigerator. Private deck, shded by trees. The Club house has shared spa amenities; including fitness, dry sauna, whirlpool, and seasonal pools.

Guest favorite

Cottage in Guilford

4.95 out of 5 average rating, 173 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

Home in Shelter Island

4.95 out of 5 average rating, 224 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.

Guest favorite

Home in Cutchogue

4.98 out of 5 average rating, 131 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Beautiful, quiet, studio apartment-style unit (private entrance w/full bath) tucked away in a modern farmhouse on a gorgeous, secluded North Fork farm. Guests have exclusive use of screen porch, fire pit, bbq and outdoor seating area. Jess is a private chef and yoga instructor, so be sure to inquire for services! Private hiking trails, fresh eggs, produce from garden, beach gear, Keurig, mini fridge, homemade granola, tea. Fresh eggs, seasonal veg from the garden, and meals available (inquire!)

Guest favorite

Home in Hamden

4.92 out of 5 average rating, 103 reviews

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton

Looking for privacy, seclusion, and direct access to Sleeping Giant State Park right from your back yard? Then look no further! Entire Mid Century home centrally located to many great attractions and colleges. Featuring an open floor plan characterized by large glass windows and open space featuring simplicity and an integration with nature. Access to I-91 or Rt15 are both about 1 mile away, with Yale University and Downtown New Haven about a 20 minute drive. Farmington Canal bike trail-.5 miles

Guest favorite

Home in Montville

4.95 out of 5 average rating, 128 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

Guest favorite

Home in Montville

4.97 out of 5 average rating, 115 reviews

Hot Tub~Pool~Game Room~Fire Pit~BBQ~Casinos

Welcome to the Lucky Lounge! Minutes away from Mohegan Sun, Foxwoods, Mystic, Naval Submarine Base, USGC College, CT College, and numerous beaches. We have all you need to enjoy your time inside and outside during your stay! - Hot tub - Private pool - Fire pit - Pool table - NFL Blitz 4 player arcade game - Air hockey - Foosball - Giant connect four - Darts - Corn hole - Smart TV - Karaoke - Board games - Ultra comfy beds - BBQ - Kid friendly - Super fast WiFi - Stocked kitchen

Guest favorite

Condo in Norwich

4.98 out of 5 average rating, 220 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.

Guest favorite

Condo in Norwich

4.95 out of 5 average rating, 130 reviews

KINGbed-Casino-HotTub-Pool-Sauna-Massagechair-golf

Guest favorite

Rental unit in Glastonbury

4.9 out of 5 average rating, 423 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

Rental unit in Old Saybrook

4.96 out of 5 average rating, 120 reviews

Convenient and Cute in Downtown Old Saybrook

Welcome to Old Saybrook! Our apartment sits over our garage and is attached to our primary residence. It is conveniently located within walking distance to Main Street, the beach, local parks, and other town attractions. We have recently made many upgrades to the property and we're ready for guests! We look forward to sharing our home with you! **PETS: DOGS ALLOWED BY PRE-APPROVAL ONLY and ADDITIONAL $25 PET CLEANING FEE. Please see House Rules for more info.

Guest favorite

Rental unit in Norwich

4.88 out of 5 average rating, 286 reviews

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

THE POOL OPENS MEMORIAL DAY! Welcome! This is a 2-family home. So there are a total of two units who have access to the pool. 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 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!