Beach house vacation rentals in Middletown

Find and book unique beach houses on Airbnb

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Popular amenities for Middletown beach house rentals

Beachfront house rentals

Guest favorite
A private heated pool is set against a backdrop of lush trees, with water reflecting a clear blue sky. Relaxing lounge chairs surround the pool area, offering a serene view of the lake beyond, creating an inviting outdoor space.
Home in Bushkill
4.91 out of 5 average rating, 118 reviews

Sale: June 27-28, Pvt Heated Pool OPEN, Hot Tub

ShevaRating, 5 stars2 weeks ago
Such a beautiful spot on the lake!!! We had the most beautiful weekend, the kids loved he pool and the boats, nothing was missing! We would have stayed another week! Jennifer and Jose answered all our messages within a few minutes and were super accommodating. We will definitely be back!
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, 157 reviews

Magical Lake House-Hot Tub-Deck-Outdoor Kitchen

CurtRating, 5 stars2 weeks ago
Great property, great host. always in communication throughout the stay, helpful with any questions we had. comfortable house, great spaces to relax and take in the scenery. outdoor kitchen/grill is awesome for cooking up burgers and dogs while relaxing on the deck.
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 stars4 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, 136 reviews

Secluded lakefront home With an EV charger

AdrianaRating, 5 stars1 week 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
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 stars1 week 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 stars1 week 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

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 stars22 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.
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 stars9 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!
The iconic New York City skyline is silhouetted against a twilight sky, with the Empire State Building prominent among the skyscrapers. Soft hues of orange and blue blend at the horizon, reflecting the vibrant urban atmosphere as evening approaches.
Home in Weehawken Township
4.82 out of 5 average rating, 157 reviews

NYC area Historic A+ Family friendly 2BR house Apt

LucreziaRating, 5 stars1 week ago
We enjoyed our stay !
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.
Superhost
Home in Oyster Bay

Seabreeze

Nelson D.Rating, 5 stars3 months ago
**Review for Seabreeze** ⭐⭐⭐⭐⭐ **Amazing Weekend Getaway!** Spent a long weekend at **Seabreeze**, and I honestly didn’t want to leave! The house is gorgeous—modern, stylish, and super comfortable. The huge windows made it easy to just sit back and take in the incredible ocean views, especially during sunset. We spent most of our time outside, walking along the private beach, and just soaking up the peaceful vibes around the beautiful natural surroundings. The outdoor deck was the perfect spot for morning coffee and late-night chats under the stars. Inside, everything was top-notch. The kitchen had everything we needed, the living room was cozy and inviting, and the bedrooms were super comfortable. It really felt like a luxury escape while still being relaxing and homey. If you're looking for a place to unwind, enjoy nature, and wake up to ocean views every day, Seabreeze is it. Can’t wait to come back!
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 stars4 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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