
Vacation rentals with a pool in Middlesex County
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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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Popular amenities for Middlesex County rentals with a pool
House rentals with a pool

4 BD w/ Heated Pool in E Hampton, Fully Furnished
We had a wonderful time in this beautiful home that is in an idyllic Hampton's setting. Ashton was a great host and for sure we will be back.

Modern East Hampton Home w/ Heated Saltwater Pool
The house is beautiful, looks like photos. Stephen is a great host! Overall great stay, could not recommend more!

Pool House
This was our second time back to the pool house and it was amazing, again. We thinks of everything to make you feel welcome. Milk and eggs in the fridge. Muffins and croissants waiting for you. Pristine home. Fully stocked kitchen. I was even able to host a few family members for Christmas dinner and had everything I needed to make a lovely dinner. We also travel with two dogs and Sue is so accommodating, making our pups feel right at home. Thank you, Sue, for making our holidays away from home so peaceful and enjoyable.

Southampton Escape, Heated Pool, hot tub, 3 bed,
The house was great! Our two infants loved the large deck and pool. So close to town and the beach. It was a perfect getaway!

Stunning Central E. Hampton Home w/ gunite pool.
Our family enjoyed a wonderful post- Christmas getaway at Jennifer’s beautiful home. The house is fabulous - well- located, pristine , beautifully decorated and well-stocked. It was relaxing and perfect. We did not have much need to reach out (everything was effortless) but when we did, Jennifer was very responsive and helpful. Highly recommend!

Long Island home w/ large pool
My stay here was phenomenal! From the host’s response time, down to the amenities that were placed throughout the house. As soon as you walk in, it felt like home. The house is spacious and highly functional. The design of the house offers a perfect blend of modern mixed with nostalgic elements. The best stay by far. Would love to book again!

POOL in APRIL! Waterview, Free For Dogs! Kayaks
Right off of 27 so it is super easy to get to. House is on a nice private street with beach access. We walked to the beach several times a day to let the kids play and the dogs run wild. It was beautiful. House is exactly as described and Roger and Amy were great at responding. Quiet neighborhood. Only about 5 minutes outside of Southampton town.

Private East Hampton Estate
Marks home was beautiful, peaceful and near to so many great areas. The pool and backyard were wonderful and relaxing. We loved it! Highly recommend!
Condo rentals with a pool

Villa Flora @ Norwich Inn & Spa
There is nothing more frustrating than not being able to have a decent shower while you are on vacation. That was absolutely not the case here. The hot water and water pressure in both bathrooms was exceptional. This is a great place in a great area. We will definitely try to get back here.

CASiNO, Spa, Hot Tub, Pool, Private Villa, Kingbed
Wonderful stay, lots of small added touches that made a big difference. My 13-year-old son loved it. Convenient and quiet.

Oceanfront Condo – Incredible Spring Rates!
We had an amazing stay! We stayed off peak season, although alot was closed we felt right at home and were more than happy to spend family time at this condo! The views were stunning, and the condo was immaculate. We were close to everything and was still within very reasonable driving distance to the surrounding towns. Julie was a pleasure to work with and was always very responsive and accomadating throughout the process. Hoping to stay again next year!

Cozy French style Villa-3 Bed-Casino-Pools-Jacuzzi
Loved our stay, Natalie was an excellent host. Already figuring out when we can return.

Peaceful Oasis steps from Mohegan Sun
This place has everything you need and a lot more. All of furniture is new and comfortable especially the huge king bed. Bathroom and shower was super clean and comfortable. Linens and towels are top notch. The TV in the bedroom and living room is a plus. The private outdoor patio is comfortable and relaxing. 5 min to Mohegan Sun. I could go on and on about this place it is amazing and a great value. You won't be disappointed!

The Vacay Villa
Had a wonderful stay! It was so cute and cozy and just what we needed for a wonderful weekend getaway. My daughter and I had a great mix of fun at local wineries, concert and dancing at Mohegan Sun just minutes away and a wonderful relaxing time at the spa just a short walk away. We also took a trip to Mystic for some shopping and a great dinner and still managed to have some nice wind down time in front of the fire watching a comedy on Netflix. The condo had everything we needed as well as great touches of snacks and coffee plus all sorts of creamers. Would definitely come back again!!!

Beachside Waterview 2Br Condo w/ Pool in Greenport
The place was perfect nice and clean what I like the best is the it was close to the beach to go for a walk.

The N-V ...The Spa at the Norwich Inn.
We stayed in town for an event at Mohegan Sun. The flexible check in was helpful as we got in late at night. The place was clean and welcoming.
Home rentals with a private pool
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!!

Explore the Water & Woods at a Relaxing Retreat
We had an amazing time staying at this house! It was in a great location, well-stocked with everything we needed, and the host was incredibly responsive. The check-in process was seamless, making our stay even more enjoyable. My family and I had a wonderful experience, and we would definitely book again!
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.

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!
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- Beach
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Quotonset Beach
- Giants Neck Beach
- Cooper's Beach, Southampton
- Clinton Town Beach
- Woodmont Beach
- Shennecossett Beach
- Six Flags New England
- Shinnecock Hills Golf Club
- Seaside Beach
- Walnut Public Beach
- Shoreham Beach
- Horton Lane Beach
- Burlingame State Park
- Mystic Seaport Museum
- South Pine Creek Beach
- La Ronde Beach Club Inc
- Rogers Beach
- Road F Beach
- Jennings Beach
- The Connecticut Golf Club