Holiday rentals with a pool in Wallingford

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Top-rated rentals with a pool in Wallingford

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
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, 189 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
A serene view of the Long Island Sound is captured at sunset, featuring soft pastel hues in the sky. A few clouds are present, and the gentle water surface reflects the vibrant colors. A flagpole with an American flag stands prominently in the foreground.
Home in Milford
4.83 out of 5 average rating, 109 reviews

Spacious 4 bedroom, oasis with ocean views galore

Scio by the sound is a home that is steps from the water, overlooking the Long Island Sound. Whether you want to lounge by the in ground pool or walk to the beach, you will find your happy place here. The home sleeps up to eleven guests in beautiful Milford, CT with a great location to local beaches and downtown Milford. It is also the perfect place with a large private backyard great for families for vacations or a friends get together or for a local wedding. The possibilities are endless!

Superhost
A swim spa with dual zones is shown, featuring illuminated blue and red lights. The adjacent outdoor area includes a large screen displaying a sports event. Steam rises from the hot tub, creating a relaxing ambiance in the evening setting.
Home in Hamden
4.9 out of 5 average rating, 119 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

Top Guest favourite
A white Dutch door is framed by rustic wooden walls, showcasing a combination of horizontal and vertical planks. A small lantern hangs nearby, and a woven basket adorns the wall beside the door. A simple bench with a patterned cushion sits on the side.
Guesthouse in Southbury
4.93 out of 5 average rating, 362 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).

Top Guest favourite
Apartment in Milford
4.98 out of 5 average rating, 133 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.

Superhost
A clean and inviting bedroom features a spacious bed with neutral bedding, accent pillows, and soft bedside lighting. Built-in shelves are displayed with decorative items, and a window allows natural light to brighten the area, complemented by light curtains.
Condo in Farmington
4.82 out of 5 average rating, 57 reviews

Farmington -NEWLY UPDATED NEAR UCONN HC and WEHA

NEWLY UPDATED - Bright Spacious One bedroom condo in Farmington!! Convenient to airport (BDL)/bus/train transportation, Hartford (18mins), Miss Porters School (6mins), Avon Old Farms (7mins), UCONN HC (9mins), ESPN (20mins), the Hartford Mormon Temple (2mins). We are just a few miles off of route 84. Includes kitchenware & granite counter-tops, WiFi, and a HDTV. Restaurant (2mins) walking distance and many other amenities close by. Located in a quiet residential neighborhood with parking.

Guest favourite
The image captures a serene view of a clear pool reflecting the colorful sunset, framed by a meticulously paved patio. Two cabana beds are positioned next to the pool, with surrounding greenery and a decorative fence enhancing the outdoor space.
Apartment in Burlington
4.84 out of 5 average rating, 120 reviews

Charming apartment with breathtaking view!

The guest apartment ( FULLY RENOVATED FINISHED BASEMENT) is an addition to our luxurious home. A 2 bedroom apartment with one king sized bed, Queen sized bed and a plush leather pull out sofa. Pool ltable. Large in ground pool, 4 lounge chairs, fire pit and dining table. Pool and gated backyard is exclusive to guests. We include netflix, hulu and hbo max. HEATED POOL IS OPENED IN MAY AND CLOSED LATE SEPTEMBER. The pool is cleaned daily in the morning. The pool is exclusive to guest.

Guest favourite
A charming tiny house is featured amidst a lush landscape under a partly cloudy sky. Surrounding greenery enhances the natural setting, while colorful flowers are visible in the foreground, framing the house's entrance and inviting a peaceful atmosphere.
Tiny home in Deep River
4.88 out of 5 average rating, 25 reviews

Her tiny Parisian boat house

SOLO vacation? Reconnect with nature at this unforgettable escape. Perfect work space while lounging by the pool…(in SEASON) this tiny house (on land) has access to SHARED outdoor shower and outdoor soaking tub. Wanna relax? Come Meditate under the giant willow, swing in the hammock or practice yoga. Bathroom (NOT IN THE TINY HOUSE!) is shared and just steps inside the main house with shower and toilet. Great WiFi, front porch to enjoy meals. Bed is a comfytwin with lots of pillows.

Superhost
The living area features a light-colored sofa and accent chair positioned around a glass coffee table. Large windows allow natural light to enter, while sheer curtains frame the view of the outdoor space. A television and elegant decor add comfort to the setting.
Apartment in New Haven
4.98 out of 5 average rating, 119 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

Superhost
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
4.89 out of 5 average rating, 448 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.

Top Guest favourite
The kitchen features modern cabinetry and a sleek countertop with a bar area furnished with four metal stools. Stainless steel appliances, including an oven and microwave, are integrated into the cabinetry. Natural light illuminates the space, creating a bright and functional cooking area.
Home in Wallingford
4.94 out of 5 average rating, 68 reviews

Family Oasis 4bd/2ba Private Yard & POOL!

Just minutes from Quinnipiac University, Choate Rosemary Hall, & Oakdale Theater. This 4- Bedroom, 2-Full Baths home includes 1-master suite, 3-bedrooms, full kitchen, & lots of room for the whole family to spread out. Located on the edge of the wood line, find yourself immersed in the peaceful surroundings with a book on the patio, or go on an adventure in minutes to local attractions. This property has an inground swimming pool (open during season Mid May/June- mid/late Sept)

Top Guest favourite
A cozy living area is presented with a neutral color palette. A comfortable sofa is draped with a textured throw, and an organic wooden coffee table is centered within the space. Art prints adorn the walls, while natural light gently illuminates the room.
Apartment in Westbrook
4.95 out of 5 average rating, 40 reviews

Meadowview & Pondside Retreat

We welcome you to a serene and peaceful getaway at our recently renovated guesthouse. 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.

Popular amenities for Wallingford rentals with a pool

Quick stats about holiday rentals with a pool in Wallingford

  • Nightly prices starting at

    Wallingford holiday rentals start at $257 AUD per night before taxes and fees

  • Verified guest reviews

    Over 200 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Wallingford rentals

  • 4.9 Average rating

    Wallingford stays are highly rated by guests—averaging 4.9 out of 5!