Vacation rentals with a pool in Cutchogue

Find and book unique homes with a pool on Airbnb

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Popular amenities for Cutchogue rentals with a pool

House rentals with a pool

Guest favorite
A well-appointed bedroom features a spacious bed with a quilted white comforter. Soft light fills the room from a nearby window, and a wooden dresser displays decorative items and lamps. Framed artwork adorns the walls, providing a touch of elegance.
Home in The Hamptons
4.93 out of 5 average rating, 59 reviews

Splendid private cottage

AndrewRating, 5 stars5 days ago
The house was perfect for a weekend in Hampton Bays! Michael was very responsive and accommodating and the house had everything we needed. Beautiful little house tucked away in a quiet neighborhood.
Guest favorite
A heated saltwater pool is surrounded by a stone patio, featuring lounge chairs and sun umbrellas. Lush greenery and landscaping enhance the serene atmosphere. Pool floats are visible in the water, inviting relaxation and leisure.
Home in North Fork
4.89 out of 5 average rating, 9 reviews

Quaint Chalet w/Salt-heated Pool

VaughnRating, 5 stars8 months ago
Wonderful weekend stay. Charming.
Superhost
A spacious outdoor area features a heated pool surrounded by a stone patio. Lounge chairs are placed under umbrellas for shade, and the well-maintained lawn is bordered by lush hedges and flowering plants. The modern home is visible in the background.
Home in The Hamptons
4.95 out of 5 average rating, 97 reviews

Marvelous 4 Bed East Hampton home w Heated Pool

JuanRating, 5 stars2 weeks ago
We had a wonderful stay at this well-appointed and comfortable home. Everything was exactly as described and met all our expectations. The space was clean, thoughtfully furnished, and had everything we needed for a relaxing visit. It truly felt like a home away from home. We would stay here again and highly recommend it to anyone looking for a hassle-free and enjoyable stay
Guest favorite
Home in The Hamptons
4.92 out of 5 average rating, 106 reviews

Classic Southampton Village Home w/ Pool

MichaelRating, 5 stars2 weeks ago
The house has an incredible location, walkable to town but quiet, with a large private backyard with a pool. The house is nicely decorated and the beds are very comfortable. It was cold and rainy during our stay in late May, but the heating system worked very well. The kitchen is well stocked if you want to cook dinner, but it would be helpful to have a colander to rinse vegetables and berries. Overall, a wonderful place to stay!
Superhost
A well-maintained outdoor space features a heated pool surrounded by lush greenery. A wooden pool house stands alongside, offering shade from the sun. An umbrella is positioned near the pool, and a bright pink float can be seen on the water's surface, inviting relaxation.
Home in The Hamptons
4.88 out of 5 average rating, 93 reviews

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)

SujataRating, 5 stars3 weeks ago
Neha is surprisingly super prompt and helpful with her responses. Her place has beautiful views, is calm and easy to locate. The furnishings are great too
Top guest favorite
A spacious outdoor pool is surrounded by a stone patio, featuring a pink flamingo floatie. Aqua-colored lounge chairs are positioned nearby on a gravel surface, with greenery and trees framing the area for privacy.
Home in The Hamptons
4.98 out of 5 average rating, 127 reviews

Beach House Feel - newly renovated backyard Oasis

StephanieRating, 5 stars3 weeks ago
Absolutely wonderful stay! Christine was extremely helpful and responsive. She was so clear with instructions and everything was exactly as described. The house was very clean and exactly as described. The yard was also very big. Perfect for a weekend getaway as it was close to everything. Highly recommend if you are looking for somewhere to stay near Hampton Bays. Would absolutely return.
Guest favorite
A pool area is surrounded by greenery, featuring a gunite pool reflecting the blue sky. Lounge chairs are positioned by the water, and a patio dining set is visible, accompanied by an umbrella providing shade. The house has large glass doors, inviting natural light.
Home in The Hamptons
5 out of 5 average rating, 21 reviews

Secluded Luxury: New Gunite Pool, Walk to Bay

MeganRating, 5 stars1 month ago
Beautiful home, really well stocked and super comfortable. Warm, clean and lots of amenities. Comfortable beds, good showers, big lovely kitchen. Lots of space. We had a great stay. Thanks :)
Superhost
A charming cottage-style home is set amid lush greenery, featuring a covered porch with white railings. A gravel pathway leads to the entrance, surrounded by manicured shrubs and a well-kept lawn. The exterior is finished with natural wood siding and a sloped gray roof.
Home in The Hamptons
5 out of 5 average rating, 3 reviews

Hamptons Waterview Cottage

LisaRating, 5 stars9 months ago
This place is a gem! When we arrived the home was spotless and exactly as pictured. It seemed brand new and in excellent condition. The hosts were very kind and helpful and even gave us a bottle of wine and left bottled water in the fridge. The beds were so comfortable and the home was stocked with everything we needed. Our young kids loved swimming in the beautiful pool and we enjoyed exploring the rest of the picturesque property—so cool to see the wild turkeys walking around. We had a wonderful vacation and hope to return one day!

Condo rentals with a pool

Condo in North Fork
5 out of 5 average rating, 6 reviews

Water front, sunsets, sail boats, Wi-fi, birds

CharlesRating, 5 stars9 months ago
John and Cathy are amazing hosts. This was our second consecutive summer stay in their condo and it does not disappoint. The place and the amenities they provide are amazing and they are a wonderful couple who respects your privacy but are there for anything you need. I recommend anyone to stay here and know they would want to return. Thank you John and Cathy for making our second summer with you a fantastic vacation!
A heated swimming pool is surrounded by lounge chairs and umbrellas, with multiple access steps leading into the inviting, clear blue water. In the background, a two-story building features private balconies overlooking the pool area.
Condo in North Fork
4.94 out of 5 average rating, 17 reviews

Cliffside Resort Poolside Condo A204

MichelleRating, 5 stars1 month ago
Very clean apartment! Easy check in/check out. Had a nice stay!
A bright living area is furnished with a light-colored sofa, floral-patterned chairs, and a coffee table with decorative items. A large television is positioned on a dark wooden console. Natural light filters in through windows, illuminating the space with a cozy ambiance.
Condo in The Hamptons

Charming Bayfront Condo

SaraRating, 5 stars9 months ago
Stop whatever you’re doing in the area and take 10 minutes to walk across the street to enjoy the sunset. I guarantee it’s addictive. Spent a post-Labor Day weekend with some friends and had an amazing time. The condo is centrally located between downtown Southampton, Bridgehampton and Sag Harbor and all that those areas have to offer. Several beaches, both bay-side and ocean-side, are also close by, but we mostly ended up lounging by the pool. The condo itself is spacious which is only further amplified by the amount of natural light reflecting off the bright interiors that let you know you’re near the beach. There are plenty of towels—both bath and beach—and there is ample beach equipment that you can use. The kitchen is fully stocked for cooking/dining at home, and there’s an outdoor patio equipped with a grill and dining furniture. Hostess could not have been nicer or more responsive, so I will definitely want to stay here again.
A bright bedroom features a spacious bed with a light-colored plaid duvet cover. Two bedside tables with lamps are positioned on either side. A wall art piece of a tree adds a touch of nature, while natural light streams through a door leading to another room.
Condo in The Hamptons

Bright and Airy One Bedroom Apartment in the Dunes

TimRating, 5 stars21 months ago
A fantastic place to stay in the Hamptons, a special gem of a place located in the Dunes of Amagansett, will be back every year!
Guest favorite
A well-maintained heated pool is surrounded by lounge chairs and shaded tables. Umbrellas provide shelter over the seating areas. A club house is visible in the background, complementing the inviting outdoor space designed for relaxation.
Condo in North Fork
4.84 out of 5 average rating, 106 reviews

Beautiful condo on Long Islands Northfolk

LauraRating, 5 stars1 month ago
We very much enjoyed our stay at the Cliffside for our wedding weekend! Alice was very flexible with us, which we appreciated because getting married is chaotic enough LOL. Would highly recommend staying here. The unit was spotless and had a wonderful view. We could not have asked for a better stay!
A well-maintained heated pool is surrounded by lounge chairs arranged on a paved deck. The pool reflects the evening sky, while nearby tables and grilling areas invite relaxation. The condominium buildings, featuring multiple balconies, are positioned in the background.
Condo in North Fork
4.89 out of 5 average rating, 152 reviews

Beautiful Waterview Condo on the North Fork of LI

SarahRating, 5 stars1 month ago
Mia’s place is excellent. Exactly what the listing describes and more — Mia is a great host and super attentive despite us being a last minute booking, she even helped us through a tough time late in the day when I thought my daughter’s stuffie had been picked up by the maid service. Above and beyond!
Superhost
A bright and airy living space is highlighted by skylights and white wooden beams. A spacious kitchenette is situated behind a dining table surrounded by light chairs. Large windows invite natural light, and a television sits on a white console between soothing tones of gray and cream.
Condo in The Hamptons
4.78 out of 5 average rating, 23 reviews

Waterfront Elevated Bungalow - Spectacular Views

SteveRating, 5 stars56 months ago
If we don't give a good review, can we keep this to ourselves?! Patti was a perfect host; the views were fantastic, whether from the outdoor porch or inside through the French doors looking out on the water. Access to the small beach and pool were excellent and we were close to several good restaurants (many of which Patti suggested, including some on the water) for take-out during the pandemic. Wifi was great and everything was very clean and as advertised. We generally fly for vacations and long weekends but had to stay closer to home this year and this was a perfect choice.
Superhost
A spacious outdoor pool area is framed by lush greenery and vibrant flowers. The rectangular pool is surrounded by a paved deck, with several lounge chairs positioned around it. A corner of the property includes a poolside storage shed, providing functional space.
Condo in The Hamptons
4.88 out of 5 average rating, 17 reviews

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath

StaceyRating, 5 stars9 months ago
Had a wonderful stay with my family. Clean, comfortable, great location. Good communication. Had a little trouble with the front door first day but someone was available quickly to help. A+

Home rentals with a private pool

Guest favorite
The exterior of a modern wooden house features a sloping roof and a welcoming front porch. Lush green grass surrounds the structure, complemented by small shrubbery thoughtfully arranged near the entrance. Three large windows provide natural light to the interior.
Bungalow in The Hamptons
4.93 out of 5 average rating, 108 reviews

East Hampton Ranch with Access to Clearwater Private Beach

KateRating, 5 stars8 months ago
We had a wonderful stay at Peter's home. It was beautifully decorated, very comfortable and a quick drive to Springs. Access to the private clearwater beach was a plus! Thank you for sharing your beautiful home with us.
Top guest favorite
Four lounge chairs are arranged under large umbrellas, providing shade beside a serene pool area. The colorful cushions on the chairs complement the lush green landscaping, which features diverse foliage and natural textures, enhancing the outdoor relaxation space.
Home in The Hamptons
4.98 out of 5 average rating, 130 reviews

Explore the Water & Woods at a Relaxing Retreat

LaelRating, 5 stars1 month ago
Absolutely beautiful home and wonderful experience!! The host was quick to respond and the amenities were excellent. There was zero lack! Would definitely return for another stay!
Guest favorite
An inviting heated pool is surrounded by lush greenery and flowering landscaping. Comfortable loungers are positioned along the wooden deck, accompanied by a shaded umbrella. Steps lead from the poolside to a charming surrounding garden, offering a serene environment for relaxation.
Home in The Hamptons
4.82 out of 5 average rating, 45 reviews

Enchanting Home with Large Decks and Heated Pool

LynnRating, 5 stars8 months ago
Beautiful home worked perfect for our wedding visit. Loved sitting on the deck! Beautiful landscaping and very private! We were very confortable and able to relax between events and visit. Donna wad very flexible and allowed us to enter early so a dew of our family members could do s little remote eork. I hope to rent here again in the future! As a special surprise we saw the northern lights from the deck one night!!
Guest favorite
A spacious backyard is highlighted by a bright blue swimming pool, featuring a whimsical white swan float. Surrounding the pool are several lounge chairs and umbrellas, set against lush green hedges and trees that provide privacy.
Home in The Hamptons
4.95 out of 5 average rating, 20 reviews

Perfect Getaway at Sunny Modern Shampton Lake House

ScottRating, 5 stars8 months ago
One could not ask for a better hosts than Christina and Phil - they are extremely communitive, proactive and helpful. Their house is beautiful - gourmet kitchen, in-ceiling speakers throughout the house, nice deck, pool and a picturesque location. The master bedroom has access to the back deck and a great shower. We had all three bedrooms full and everyone enjoyed their stay. We did not take advantage of the kitchen, but if we come back to the Hamptons we would stay here for longer and cook some meals. We are art collectors, so definitely appreciated the works Christina & Phil have amassed. The one thing I would bring to the attention of future renters is that you definitely know you are in somebody else's home - this is the first time we have unpacked only to find that every drawer was full, so we had to place stuff on top of the dresser or on the few open shelves in the closet. That said - totally worth it and would definitely recommend this Airbnb. Hope to be back soon!
A spacious deck is shown surrounding a large pool, with wooden flooring and colorful umbrellas providing shade. Comfortable outdoor couches with striped throws are positioned to face the pool, creating an inviting space for relaxation amid lush greenery.
Home in The Hamptons
5 out of 5 average rating, 13 reviews

Saltbox with Separate Poolhouse in Northwest Woods

KatieRating, 5 stars35 months ago
Mike’s place made for the perfect Hamptons vacation. The location was the perfect starting point for day trips to Montauk and the harbors and we enjoyed the short walk to the beach daily… but there really is no need to leave this amazing property. Our family cannot stop raving about the amazing outdoor setup that we took full advantage of every day. Mike was very responsive and provided a detailed guide for the house and excellent recommendations for the area. We would 100% book again when we’re in the area and would recommend this place to anyone looking for an amazing Hamptons experience.

Quick stats about vacation rentals with a pool in Cutchogue

  • Total rentals

    40 properties

  • Nightly prices starting at

    ﺩ.ﺇ735 before taxes and fees

  • Total number of reviews

    1.1K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

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