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

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, 182 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

An above-ground pool is shown, featuring clear blue water surrounded by a sturdy gray frame. Lush greenery forms the backdrop, suggesting a private outdoor space. Sunlight creates gentle ripples on the water's surface, inviting relaxation and enjoyment during warmer months.

Home in Montville

4.92 out of 5 average rating, 277 reviews

Casino Wine Down House

Stay at the end of a quiet, cozy, cul-de-sac while minutes from local attractions. Our house is conveniently located near casinos, Mystic, vineyards, Nature's Art Village, Naval Submarine Base, CT College, USCG Academy and several beaches. Enjoy the fire pit on our large deck under the gazebo year round. In the summer cool off in the pool. In the winter relax and enjoy some cozy time under the stars in the heated igloo. Lot of fun and games! Dogs are family and always welcome at no charge.

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, 329 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).

Superhost

A spacious outdoor deck features a large dining table surrounded by several chairs, with an umbrella providing shade. A swimming pool is visible in the background, complemented by well-maintained grass and trees lining the property.

Villa in Morris

4.88 out of 5 average rating, 123 reviews

LuxeCompound-HotTub Pool Sauna Treehouse Gamebarn

Serene, elegantly appointed 19th century compound, fully modernized and set on the edge of a 50 acre land preserve next to boat friendly Bantam Lake. Located in the rolling hills of Litchfield County this expansive home has four buildings and every amenity: pool, hot tub, heated gym, cedar sauna, central AC, 2 chef’s kitchens, game barn, primary suite with wb fireplace and soaking tub, a pool house guest suite with steam shower, & treehouse w/ slides & a swing set built on a 300yr old oak tree.

Guest favorite

A light-filled living area features a cozy neutral sofa, accompanied by a matching armchair. A decorative coffee table sits in the center, and a Smart TV is mounted on the wall. Sliders lead to a private waterfront deck with seating, enhancing the space's openness.

Condo in Greenport

4.85 out of 5 average rating, 138 reviews

Seaside Summer Escape: 2BR Waterfront Condo w/Pool

Overlooking the Long Island Sound, this oceanfront condo is the ultimate escape. Bask in the sun on a private beach or unwind on the waterfront deck with breathtaking views Minutes from the town center, you’ll find local farms, award-winning wineries, gourmet restaurants & charming shops ⚓️ Explore Greenport: A historic seaport with coastal charm & rich culture 🏖 Premium Amenities – Waterfront deck, private balcony, grills, pool, private beach & parking ⛴ Ferry Access to Shelter Island & CT

Guest favorite

A rectangular swimming pool is set within a covered area, featuring clear water illuminated by natural light. Surrounding the pool, several lounge chairs and potted plants are positioned along the deck. A white fence overlooks the pool area, adding a sense of privacy.

Condo in Norwich

4.97 out of 5 average rating, 271 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.

Top guest favorite

A serene garden area is seen, featuring lush green grass and vibrant flowerbeds with orange blooms. A tranquil pond is visible in the background, surrounded by trees and natural landscaping, creating a peaceful outdoor setting.

Apartment in Milford

4.98 out of 5 average rating, 108 reviews

The Pond Mill Retreat w/ 2 Bdrms & Pool

Catch up on a little work or simply unwind. Everything is waiting for you in this cozy, yet functional space surrounded by a beautiful wooded area with pond. Your private entrance accommodations include a finished, walk-out lower-level apartment (~730 sq ft) containing thoughtfully appointed bedrooms, living room, kitchen, and full bathroom. Experience solitude while enjoying the convenience to Rt 15, I-95, & Boston Post Rd destinations. And if you require assistance, we live right upstairs.

Top guest favorite

Condo in Norwich

4.98 out of 5 average rating, 188 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.

Guest favorite

A light and airy living area features a spacious, cream-colored sofa adorned with soft pink and patterned cushions. Natural light filters through sheer curtains on the glass doors, while a potted palm provides a touch of greenery. A textured rug adds warmth and comfort to the space.

Condo in Norwich

4.95 out of 5 average rating, 148 reviews

Near Casino-Heated Pool/Jacuzzi/Sauna- Onsite Spa

- Sleeps 4 (Queen bed & air mattress) -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 - Access to streaming services is provided (no cable TV) -Barware including cocktail shaker set, champagne flutes, margarita/wine/whiskey glasses -Complimentary toiletries & feminine oriented essentials -Indoor fireplace

Top guest favorite

Condo in Norwich

4.94 out of 5 average rating, 174 reviews

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

Guest favorite

An outdoor swimming pool is surrounded by lounge chairs and umbrellas. The pool's clear blue water reflects the evening lights from surrounding windows. Cozy seating areas with striped cabana curtains are visible in the background, creating a welcoming outdoor space.

Apartment in New Haven

4.99 out of 5 average rating, 111 reviews

King 1BR Apt with Cozy Den and Luxury Amenities

This gorgeous apt, located in a brand-new luxury building at the center of New Haven’s historic downtown, offers unparalleled comfort, service, and amenities. You can watch a movie on a 65" HDTV, work in one of 5 co-working spaces, or relax at the pool w/ grills and cabanas. Highlights: • Walkable access to Yale • Deep-clean prior to every guest • Coffee, fresh linens, and bathroom essentials • 24/7 fitness center • Rooftop sun terrace + grills • Entertainment lounge w/ bowling alley

Guest favorite

A spacious living room is highlighted by a unique whale wall art piece and a cozy seating arrangement. A comfortable gray sofa is paired with a nautical-themed chair. Large windows allow natural light to fill the room, creating a welcoming atmosphere.

Home in New London

4.9 out of 5 average rating, 136 reviews

Beauty and the Beach!

Welcome to Beauty and the Beach, where you can come and relax with the whole family or come alone to get away from the busynesses of life! The property is located within an 8 minute walk to Ocean Beach Park and a block away from Alwife cove. With all year recreation. we are located within a short distance to: - Coast Guard Academy -Navy Sub Base -Mohegan Sun -Historic Mystic -Shopping and Great Dining Experiences! -Scenic hiking trails Come and embrace the New England Salty Life!