
Beach house vacation rentals in Middletown
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Top-rated beach house rentals in Middletown
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Vacation rentals for every style
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Popular amenities for Middletown beach house rentals
Beachfront house rentals

The Best Lake House! *Ask About Boat Use Promo*
This beautiful lake house is a lovely retreat from the chaos of the city. We spent the day lounging by the dock, and relaxing in the sun. It was awesome to have a full private bar with your own pool table right in the house!

Magical Lake House-Hot Tub-Deck-Outdoor Kitchen
Dave's place is absolutely phenomenal. The house is immaculate and fully stocked. Dave was very responsive and friendly. It was a great experience and I will definitely recommend this place to friends when they're in the vicinity.
Woodstock Historic Artist Estate - The Pond House
No notes, incredible escape even in the pouring rain. The ambience, even down to the little things like walking through the door to classical music, was truly top notch.

Twin Island Lake House • Hot Tub
We had a wonderful stay at this location during my daughter’s graduation from Bard College. The location has beautiful views of the lake and the layout of the property was perfect for the family to gather and celebrate, while also giving everyone the space for their own quiet time or rest. I would definitely recommend this location and hope to have the opportunity to stay again.

Secluded lakefront home With an EV charger
We stayed up here for a weekend and it was very quiet and there is stream nearby which is lovely to listen to the water falling over rocks--so incredibly peaceful. The neighbors are very close and its right off the road but you're tucked away into a little cove so it feels more nature. Great natural light and lots of windows!

25% Off June 18-19 Game Room, Lakefront, Hot Tub
It was great, enjoyed the days we stay my familiy had an amazing time. Enjoyed the lake and activities they have great service and easy to get in touch with the owners.

Beautiful & Fun Waterfront Duplex on the Hudson
We traveled to Nyack for a family wedding and this place was absolutely perfect for what we needed! Plenty of space, beautiful outdoor area overlooking the river, and located close to everything we needed. The rest of my family decided we had the best AirBnB for the wedding weekend! Mia was very responsive when we needed anything. Furthermore, my son left his kindle in the bedroom he slept in and Mia shipped it to us immediately after it was found. We will absolutely be booking here again.

The Pudding Pad Lake House
One of the best and coziest weekend getaways I’ve ever had. The location is perfect, only a 1.5 hour drive from the city and suddenly you feel like you’re in a whole other world. The house is absolutely stunning inside-out, the vintage 70s aesthetics through the living room and kitchen/dining is stunning and the vinyl collection made for some very enjoyable background music to our wine filled evenings. The large backyard that opens out into the private dock on the gorgeous and extremely clean lake just makes it all better too. We took the canoe out on the water, swam till dusk, and had the greatest times. Thank you to our host, extremely responsive, super supportive and accommodating of our requests, and just overall very kind in ensuring we had the bestest experience!!! We will be back for sure!
Beach house rentals with a pool

Our COZY and convenient home
this space is super convenien5 to the Cap. That was what I was looking for. terrific!

Sun Room
Carmen was so friendly and responsive, will definitely stay here again thank you!

Serene Private Oasis in Rye: Tranquility Suite
We loved this cozy place within a beautiful very old home. The scale is small but everything is there that you need for a getaway. Located perfectly between Larchmont and Rye, only a few miles from all the best things. One of very few places to stay that close to the waterfront. Beautiful safe neighborhood.

CJ’s City Room
Another overnight stay at JC’s. Extremely comfortable bed and bedding.

Colonial Charm · Walk to Town + Housekeeping
Thank you to Daniel and Lexie for a wonderful stay. Their home is beautifully presented and we felt right at home straight away. The street is charming and Rye has lots to offer families and couples. Daniel was super responsive and helpful with local recommendations and advice. 5 STARS!
Private beach house rentals

NAUTICAL FAIRYTALE BEACH HOUSE / 45 min to NYC
Victoria is the most helpful, accommodating, responsive host I have come across renting a home. The house is really lovely and set up nicely with everything you need. It is a 3 bedroom home with 3 queens and one of the queen rooms also has a nice bunkbed. There is a bit of traffic on the road but that seems to be normal for most places around the area. I brought a couple of West Point Cadets there since they got an unexpected Labor Day Weekend pass. We ended up hanging at the house one night and just having frozen pizzas and watching TV and it was really comfortable and relaxing.

Darien Home, sleeps 12 Br/Nursry 50 min train NYC
I booked Jeffrey's house to lodge some crew working on a film of mine nearby and they all loved it. It is large with lots of beds and places to sit, perfect for a large group like ours. The place was accurately described and Jeffrey was responsive as well as extremely kind and accommodating. They actually let us park our production truck on the property for a day while we needed it to be off our set nearby. We are so grateful for such a great stay. I would absolutely book again.

Waterview House Walking Distance from Cove Beach
Wonderful place steps from cove beach with a magical view. The amenities are wonderful for entertaining with a great backyard and playroom for kiddos and kayaks available to enjoy the water.

Old Greenwich Gem
We had a wonderful stay in Joseph’s Old Greenwich home! The location was great- a very nice quiet neighborhood within walking distance to small restaurants and shops. The house was very comfortable, clean and well provisioned. The back porch was a bonus. Joseph was very responsive and hospitable. We hope to return!

Old Greenwich - 3000 sq ft, 4BR, 3.5 BA home
My stay was fantastic ! the place was spotless, cozy, as descripted. the host was incredibly responsive and thoughtful, making sure i had everything needed. The location was perfect. Easy commute to New York City and to New jersey as well. and i truly felt at home. i would definitely recommend it.

Stylish 3bed 2.5bath Home in Greenwich
The house is great and immaculate! Laurie is a great host and got beach passes for us as well. Would highly recommend this beautiful home.

Stylish Westchester home
We a family of 6 had a great time for a holiday trip to New York. The house is very close to shops and restaurants and only 30 minutes drive from Manhattan. The house is spacious and in a beautiful neighbourhood. Everything you need is in the house. The host is very responsive and everything was as agreed upon. We loved our time!

Beautiful Beach House
Fantastic find. Owner is incredibly gracious and the area is gorgeous. A must-stay for anybody in the area looking for serenity and access to nature while also providing the option to eat at great restaurants! The host is very organized and responsive. Seriously, I never leave reviews but this Airbnb deserved a shout out for being stellar.
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- MetLife Stadium
- Yankee Stadium
- Mountain Creek Resort
- Bethel Woods Center for the Arts
- Bushkill Falls
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- The Kartrite Resort & Indoor Waterpark
- Delaware Water Gap National Recreation Area
- Ringwood State Park
- Promised Land State Park
- Resorts World Catskills
- Rockland Lake State Park
- Walkway Over the Hudson State Historic Park
- Riverside Park
- Van Cortlandt Park Golf Course
- Hudson Highlands State Park
- Brotherhood, America's Oldest Winery
- St. Nicholas Park
- Inwood Hill Park
- Great Falls Park
- Wawayanda State Park
- Sterling Forest State Park