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

Private completely fenced in property. Near beach.
This is a beautifully furnished large home with lots of extras, including very well outfitted gym, hot tub and pool (although the pool was not open yet during our visit). The backyard is huge and our dogs loved it. All of the bedroom are spacious and well appointed. It is a great entertaining house or a family with kids. We loved and in fact have already re-booked it for another visit!

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.

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.

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!

The Hideaway
Dorina’s home was the calm, peaceful reprieve from the city we were looking for. Her home was so comfortable and she went above and beyond to make sure we had everything we needed. The backyard was a little oasis with a large pool (with floats!), several (6 I think) lounger chairs, two 6 top tables in different areas and a functioning grill. We spent most of our time here! Dorina was fast to respond, helpful with recommendations and overall what you hope to have in a host. We would definitely come back to Dorina’s home!

Long Island home w/ large pool
This house was fantastic! We cooked a full Thanksgiving dinner here! The house was well stocked with everything we needed, from kitchen essentials to paper products. The layout of the house was great. Jane was very accommodating and made things easy for us! The house was immaculate and met all of our needs. I hope it’s available next Thanksgiving! Perfect location! Close to town, yet quiet and private! It was my granddaughter’s first Thanksgiving and I’m so glad we had this house to celebrate in!

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!

New Southampton mega home with heated gunite pool!
Great place to stay and great host !
Condo rentals with a pool

Oceanfront Condo – Incredible Spring Rates!
Lovely stay in greenport! Short drive from major north fork activities. Can imagine its even better during the busy season!

Cozy French style Villa-3 Bed-Casino-Pools-Jacuzzi
I would highly recommend Natalie’s place for anyone looking to spend time in the Norwich area. Our group of 6 adults had a great overnight, and being 4 minutes from Mohegan was incredibly convenient. Natalie was incredibly responsive, and it’s clear she puts a lot of thought into curating a space that makes her guests feel at home!

Peaceful Oasis steps from Mohegan Sun
This was by far one of the best Airbnbs I have ever stayed at and I have stayed at quite a few! Christina provided clear instructions in advance of how to access the property so no time was wasted trying to figure out how to access anything. I also had mentioned it was an anniversary surprise and Christina went out of her way to decorate and provide wine which my fiancé absolutely loved! There were also many board games provided along with smart tvs in the living room and bedroom which was perfect for any staycation. Also no need to stress if you forget a toiletry because most were also provided which was extremely convenient! Not only was the place extremely accommodating but it was also unbelievably clean and the decor was so fun and welcoming! If you are also planning on going to the casino or the spa at Norwich Inn the location is beyond perfect! I absolutely will be staying here again for future staycations and will recommend it to absolutely anyone!

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!!!

"Breathtaking Waterfront Water's Edge view"
Overall relaxing stay and trip to Greenport. Sherri is very communicative and her instructions and listing is clear and accurate. The condo is well decorated and clean and has everything you need for a nice weekend. One thing to note- we were aware check in is between 3 and 5 pm based on the listing (wound up being around 4) but it would be nice for it to be earlier. Still 5 stars though!

A Unique Piece of Paradise, Water Front pool
We really enjoyed our stay. The unit was just enough space for my husband and I and our two daughters. Having a kitchen to prepare quick breakfasts in the morning before heading out for the day and having the pool and beach in the late afternoons gave us everything we needed to start and end busy days at the Hamptons Classic or visiting family. We are hopeful to visit again!

Beachside Waterview 2Br Condo w/ Pool in Greenport
Irinas place was exactly as she described. She answered all inquiries in a timely manner. We will definitely be back.

The N-V ...The Spa at the Norwich Inn.
very clean and close to attractions. clear communication with host throughout stay. would def recommend.
Home rentals with a private pool

Walk to Water. Stunning Home with Gorgeous Pool & Grounds.
House is well represented. Spacious, very clean, and great location. Good for families or groups of friends.

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.
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.
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- Beach
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Quotonset Beach
- Giants Neck Beach
- Clinton Town Beach
- Shennecossett Beach
- Six Flags New England
- Cooper's Beach, Southampton
- Woodmont Beach
- Horton Lane Beach
- Mystic Seaport Museum
- South Pine Creek Beach
- Wildemere Beach
- Morningside Beach
- Anchor Beach
- Sasco Hill Beach
- Fenway Beach
- East Beach
- Sasco Beach
- Lordship Beach
- Short Beach
- Milford Point Unit