
Vacation rentals with a pool in Cutchogue
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Top-rated rentals with a pool in Cutchogue
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Cutchogue rentals with a pool
House rentals with a pool

Splendid private cottage
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.

Quaint Chalet w/Salt-heated Pool
Wonderful weekend stay. Charming.

Marvelous 4 Bed East Hampton home w Heated Pool
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

Classic Southampton Village Home w/ Pool
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!

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

Beach House Feel - newly renovated backyard Oasis
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.

Secluded Luxury: New Gunite Pool, Walk to Bay
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 :)

Hamptons Waterview Cottage
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

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

Cliffside Resort Poolside Condo A204
Very clean apartment! Easy check in/check out. Had a nice stay!

Charming Bayfront Condo
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.

Bright and Airy One Bedroom Apartment in the Dunes
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!

Beautiful condo on Long Islands Northfolk
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!

Beautiful Waterview Condo on the North Fork of LI
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!

Waterfront Elevated Bungalow - Spectacular Views
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.

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath
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
East Hampton Ranch with Access to Clearwater Private Beach
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.

Explore the Water & Woods at a Relaxing Retreat
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!
Enchanting Home with Large Decks and Heated Pool
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!!
Perfect Getaway at Sunny Modern Shampton Lake House
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!
Saltbox with Separate Poolhouse in Northwest Woods
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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- Beach
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Napeague Beach
- Cooper's Beach, Southampton
- Robert Moses State Park
- Walnut Public Beach
- Shinnecock Hills Golf Club
- TPC River Highlands
- Dunewood
- Ocean Beach Park
- Woodmont Beach
- Amagansett Beach
- Seaside Beach
- Blue Shutters Beach
- Quotonset Beach
- Calf Pasture Beach
- Jennings Beach
- Heckscher State Park
- Silver Sands Beach
- Sunken Meadow State Park