Beach house vacation rentals in Middletown

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Popular amenities for Middletown beach house rentals

Beachfront house rentals

Guest favorite
A sunlit deck overlooks the serene lake, featuring a glass-top table and comfortable seating. Flower pots add color, while the gentle waves can be seen against the wooden dock. The expansive waterway and surrounding hills create a peaceful backdrop.
Home in Greenwood Lake
4.97 out of 5 average rating, 186 reviews

The Best Lake House! *Ask About Boat Use Promo*

KevinRating, 5 stars1 month ago
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!
Guest favorite
An aerial view showcases the expansive lakefront home, featuring a large deck with lounge chairs and tables. The entrance is marked by dual staircases leading to the lower level, while two surfboards are propped against the railing. Surrounding trees provide a natural backdrop.
Home in Monticello
4.94 out of 5 average rating, 156 reviews

Magical Lake House-Hot Tub-Deck-Outdoor Kitchen

OpalRating, 5 stars1 month ago
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.
Guest favorite
A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.
Home in Woodstock
4.94 out of 5 average rating, 338 reviews

Woodstock Historic Artist Estate - The Pond House

CodyRating, 5 stars1 month ago
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.
Guest favorite
A serene lakeside view is captured at sunset, with vibrant pink and purple hues reflecting over the calm water. Silhouetted trees frame the scene, and distant hills provide a tranquil backdrop to the picturesque landscape.
Home in Pine Plains
4.98 out of 5 average rating, 123 reviews

Twin Island Lake House • Hot Tub

KaiRating, 5 stars3 weeks ago
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.
Guest favorite
A modern house with a large glass wall is nestled among tall trees beside a serene waterway. A spacious deck extends from the home, offering a view of the surroundings. The landscape features a gently sloping yard leading to the water's edge.
Home in Monticello
4.99 out of 5 average rating, 135 reviews

Secluded lakefront home With an EV charger

AdrianaRating, 5 stars4 days ago
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!
Guest favorite
A private hot tub is situated on a deck surrounded by lush green trees, providing a serene view of the lake in the background. The water appears inviting under the clear sky, reflecting the surrounding nature.
Home in Bushkill
4.93 out of 5 average rating, 142 reviews

25% Off June 18-19 Game Room, Lakefront, Hot Tub

HectorRating, 5 stars2 weeks ago
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.
Guest favorite
The historic waterfront home is shown with a light yellow exterior and an A-frame roof. A welcoming porch with seating faces the river, framed by trees that add touches of color. The serene Hudson River is visible in the background under a clear blue sky.
Home in Nyack
4.86 out of 5 average rating, 142 reviews

Beautiful & Fun Waterfront Duplex on the Hudson

BridgetRating, 5 stars3 weeks ago
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.
Guest favorite
A serene lakeside scene is depicted with a figure leaping from a wooden dock into calm waters, accompanied by a dog. The sun casts a gentle glow on the surface of the lake, while a wooded hillside frames the background.
Home in Putnam Valley
4.87 out of 5 average rating, 293 reviews

The Pudding Pad Lake House

SatvikRating, 5 stars4 days ago
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

Guest favorite
A cozy living room features a dark leather sectional sofa positioned near a brick fireplace. A patterned area rug lays on the floor, while bookshelves display various items and decorations. Natural light enters through a window, illuminating the space.
Private room in Greenwich
4.89 out of 5 average rating, 9 reviews

Our COZY and convenient home

KevinRating, 5 stars3 months ago
this space is super convenien5 to the Cap. That was what I was looking for. terrific!
Top guest favorite
A well-lit room features a spacious bed with a floral-patterned quilt. A television is mounted on the wall, and a small seating area includes a patterned chair. Storage is available with woven baskets and a closet with mirrored doors.
Private room in Stamford
4.98 out of 5 average rating, 43 reviews

Sun Room

CourtneyRating, 5 stars1 week ago
Carmen was so friendly and responsive, will definitely stay here again thank you!
Private room in Rye
4.71 out of 5 average rating, 266 reviews

Serene Private Oasis in Rye: Tranquility Suite

CynthiaRating, 5 stars1 month ago
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.
Guest favorite
A wall mural depicting a city skyline at night adds depth to the room. A bed with a light blanket is accented by plush red pillows. A wooden side table holds decorative items, and a dark television screen is mounted on the opposite wall.
Private room in Stamford
4.98 out of 5 average rating, 42 reviews

CJ’s City Room

RussellRating, 5 stars4 days ago
Another overnight stay at JC’s. Extremely comfortable bed and bedding.
Home in Rye
4.63 out of 5 average rating, 8 reviews

Colonial Charm · Walk to Town + Housekeeping

AnthonyRating, 5 stars17 months ago
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

Guest favorite
Three individuals sit on a concrete pier, gazing out over a calm ocean. In the distance, sailboats navigate the water under a clear blue sky, creating a serene coastal scene.
Home in Shippan Point
4.95 out of 5 average rating, 55 reviews

NAUTICAL FAIRYTALE BEACH HOUSE / 45 min to NYC

WendyRating, 5 stars9 months ago
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.
The exterior of the home features a spacious facade with a welcoming front entrance and a large wooden door. Lush landscaping surrounds the property, with a gravel driveway leading to ample parking. Tall trees provide shade and a serene atmosphere.
Home in Darien
5 out of 5 average rating, 12 reviews

Darien Home, sleeps 12 Br/Nursry 50 min train NYC

MelanieRating, 5 stars21 months ago
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.
Superhost
A spacious living room is highlighted by a large window offering views of the water. A modern entertainment unit features a TV displaying streaming options, alongside a comfortable sofa and armchairs. A coffee table is set with decorative plants and floral arrangements.
Home in Stamford
4.87 out of 5 average rating, 86 reviews

Waterview House Walking Distance from Cove Beach

IgorRating, 5 stars6 days ago
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.
Top guest favorite
A charming two-story house with blue siding and white trim is set among greenery. A spacious front porch with railings provides a welcoming entry. Lush landscaping frames the property, while a paved driveway leads to clear pathways, enhancing the inviting character of the exterior.
Home in Old Greenwich
5 out of 5 average rating, 7 reviews

Old Greenwich Gem

CathyRating, 5 stars8 months ago
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!
An open living space is featured, showcasing a cozy seating area with light-colored sofas and patterned chairs. The dining area is visible through a doorway, illuminated by natural light. The kitchen is equipped with modern appliances and offers a seamless transition into the main living area.
Home in Old Greenwich
5 out of 5 average rating, 4 reviews

Old Greenwich - 3000 sq ft, 4BR, 3.5 BA home

ReemRating, 5 stars10 months ago
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.
Top guest favorite
A spacious house stands on a manicured lot, framed by a stone wall and neatly trimmed bushes. The exterior features white siding and multiple large windows, providing natural light. A driveway leads up to the entrance, highlighted by a welcoming front porch.
Home in Greenwich
5 out of 5 average rating, 15 reviews

Stylish 3bed 2.5bath Home in Greenwich

RobinRating, 5 stars3 weeks ago
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.
A well-maintained gray house is situated on a lush green lawn, surrounded by vibrant shrubs and trees. A small porch with steps leads to the front door, and a single-car garage is visible to the left, adding to the property's charm.
Home in Mamaroneck

Stylish Westchester home

HenkRating, 5 stars5 months ago
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!
A bright and inviting living space is presented, featuring light-colored sofas arranged around a central coffee table on a soft area rug. A large television is mounted on a dark wood cabinet. Decorative plants and framed artwork add a touch of warmth to the room.
Home in Bayville
5 out of 5 average rating, 11 reviews

Beautiful Beach House

AndrewRating, 5 stars3 weeks ago
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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