Vacation rentals with a pool in Middlesex County

Joe's place was perfect for a girl's trip with two 1 year olds. The house was beautiful and had so much personality and warmth. The area was super private and quiet surrounded by nature. Joe was very informative about check in process and recommendations were plentiful.

I stayed at Ashton's place by myself on a visit to see my parents, who also live in Springs. It was everything I could have hoped for. So peaceful, and such a beautiful space. Amazing high ceilings and natural light. The yard is gorgeous, so I can only imagine how lovely it is when the weather is warm. Ashton himself is very responsive and accommodating. I was sad to leave!

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.

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!

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!

Home was very cozy and comfortable! The basement was a nice place to hangout!

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!

I had an amazing experience staying at this Airbnb! Luz, the main host, was absolutely wonderful—so kind, welcoming, and incredibly helpful throughout my stay. She went above and beyond to make sure I had everything I needed and even took the time to recommend some great local spots to visit. Her hospitality truly made this stay special. David was also fantastic so professional and accommodating. He made everything so easy, from check-in to answering any questions I had during my stay. It’s clear he takes pride in ensuring guests have a great experience. The space was spotless, beautifully decorated, and just as described in the listing. It felt so cozy and inviting, and the little details, like the complimentary snacks and toiletries, made all the difference. The location was also perfect. I couldn’t have asked for a better stay. Luz and David are a fantastic team. I highly recommend this Airbnb to anyone looking for a comfortable, welcoming, and enjoyable experience.

Erin's Villa is perfect for a spa getaway or a trip to the casino. The Villa is beautiful with everything you could need for the stay.

Lovely stay in greenport! Short drive from major north fork activities. Can imagine its even better during the busy season!

My stay at Villa Maisonet was delightful! Warm hospitality greeted me at this charming French-style villa, exuding coziness and elegance. The decor and amenities' attention to detail was impressive. A selection of water, snacks, coffee, and tea welcomed me, making me instantly feel at home. The beautifully decorated villa blended modern comforts with classic French style. Plush furnishings, soft lighting, and picturesque views added to the cozy atmosphere. The super host, Natalie, was friendly and accommodating, ensuring a comfortable and memorable stay with personalized touches. Villa Maisonet is a peaceful retreat in a beautiful setting. Thank you, Natalie, for the wonderful experience! I will return in the future!

We stayed at this location because of a cheer competition at Foxwoods, and it was perfect for our needs. The place was exactly as described—cozy and thoughtfully equipped with all the little touches you’d typically find in a hotel. Christine was also very responsive throughout our stay. I would love to experience this place in the summer. We’ll definitely be back next year!

My husband and I stayed at Krista's Villa last weekend as my husband had to attend the Boat Show at Mohegan Sun. After looking at Mohegan Sun and the surrounding hotels we found ourselves looking on airb&b. Krista's place was affordable, clean, perfect for my husband and daughter, had everything you needed and more. She was quick to respond to me, offered early check in and late check out and really made us feel welcomed and comfortable from a distance. We hope to go back for sure.

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!

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!

We enjoyed our stay in the villa at the Norwich Inn. The surroundings were so peaceful and the loft was very comfortable. The hot tub and suana were perfect for relaxing on a fall day, we loved staying here!

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.

Lovely place, great for having friends and family for a home cooked meal

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!!

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.

House is well represented. Spacious, very clean, and great location. Good for families or groups of friends.

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!

My family and I had the most perfect time. My daughter was over the moon with the kids play area in the basement and the toys! The entire house was gorgeous. Everything we were looking for. Everett was extremely responsive and allowed us to check out an hour later and check in an hour earlier. The pool was just perfect for us too! We definitely would stay here again!!

My family had a great stay. Mary Ann was sweet and helpful. Very comfortable home with tons of amenities that we enjoyed. The kids really liked helping to feed the chickens and all the natural wild life at the property. Highly recommend for family or groups.