Beach house vacation rentals in Middletown

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Top-rated beach house rentals in Middletown

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Guest favorite

The spacious living area features large glass walls that provide serene views of the surrounding forest. A modern white sofa complements a wooden ceiling, while a quirky red chair adds a pop of color. Natural light floods the room, enhancing the warm wood tones throughout.

Home in Rye

4.91 out of 5 average rating, 107 reviews

1956 House of the Year Award. Easy commute to NYC.

Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!

Top guest favorite

An aerial view captures a charming blue house surrounded by lush greenery. A heated swimming pool invites relaxation, while a pink umbrella provides shade on the patio. The spacious deck features comfortable seating, ideal for enjoying the serene landscape.

Home in Centerport

5 out of 5 average rating, 10 reviews

Waterfront Home, Heated Pool, 1 Hour from NYC

Escape to your private waterfront oasis! This serene 3-bedroom, 2.5-bath waterfront retreat offers a heated pool (May-Sept), private dock, kayaks, fire pit, pickleball and BBQ lounge. Set 200 feet off the road on a private driveway, it’s perfect for families or quiet getaways. Just 8 minutes west to Huntington’s vibrant shops and restaurants, 6 minutes east to charming Northport Village, and 1 hour by train to NYC. Relax, recharge, and create lasting memories in this peaceful Long Island haven.

Guest favorite

A modern kitchen is highlighted by white cabinetry and a contrasting dark tile floor. Stainless steel appliances are positioned along the wall, while a spacious island offers additional counter space. A window allows natural light to fill the area, complementing the neutral color palette.

Home in Mamaroneck

4.98 out of 5 average rating, 114 reviews

Fully renovated 3 bedroom, 2 bath private home

Come and enjoy our beautifully renovated 3 bedroom, 2 bath home. A fully stocked kitchen with stainless steel appliances await. There is a king size bed (bedroom 1) and two twin beds (bedroom 2) and a twin size bed plus dedicated work space (bedroom 3). Plenty of storage space. Washer, dryer and second bathroom are downstairs. Private driveway. Fenced backyard space w/patio set. We are three blocks away from Metro North, and Mamaroneck Village, which has some the best restaurants around.

Guest favorite

Home in South Norwalk

4.97 out of 5 average rating, 64 reviews

Chic Historic Home w/Water View

Lovingly restored 1890 Regal Farmhouse with water views. Craftsman style kitchen w/coffered ceiling, stainless appliances, gas stove & coffee bar, services the large Dining room w/1/2 bathroom and office space. Spacious and comfy w/AC & Original Wide plank floors. 3 large bedrooms. Master with walk in closet and vanity. Modern Full bathroom with tub. Private Wash/Dry Outdoor space incl front porch, back deck w/grill, picnic table & private driveway. Walk to SONO, Train, Mall, Dinner & more!

Superhost

Sailboats glide across a calm blue sea, with distant shorelines visible under a clear sky. The tranquil waters reflect shades of blue, creating a serene nautical setting that accentuates the beauty of the surrounding landscape.

Home in Shippan Point

4.94 out of 5 average rating, 115 reviews

OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC

Large 4 bdr newer colonial house/w fully-equipped spacious kitchen & huge spa-like bathroom/w Jacuzzi. Just across the road from the beach, 5 min drive to NYC train & downtown Stamford. 10 min drive to Greenwich. 45 min commute to NYC. Popular/w MALS guests. 1bdr and 1 full bthr are on the 1st floor. Everything is new in the house. Spacious bedrooms, private parking. Ocean Coast Beach House is across our other listing - Nautical Fairytale Beach House. Larger groups could book both houses.

Guest favorite

A spacious outdoor deck features a wooden dining table surrounded by six woven chairs, with cushions for added comfort. The serene harbor view is visible in the background, framed by lush greenery and distant houses.

Home in Centerport

5 out of 5 average rating, 13 reviews

Charming waterview house

Major interior renovation 4/2025! 🏆🥳. The beauty of this lovely home is the water view. There is a brand new deck overlooking a quaint harbor and the Long Island sound. Bbq’s and sunset cocktails nightly! There is a quaint ‘modern yet nautical feel with access to a private beach and kayaks. The Waters Edge Catering Hall is down the road and there are many great restaurants in the area. Central air conditioning recently installed so it’s always a “cool” place to stay in summer!

Guest favorite

A dining area features a wooden table set for a meal, surrounded by six turquoise chairs. In the background, a comfortable living room is visible, showcasing a dark sofa and a mounted television. Natural light fills the space through large windows.

Home in Shippan Point

4.95 out of 5 average rating, 38 reviews

Seashell Bungalow | 3 Bed 1 Bath | Beach House

Seashell Bungalow - located in Stamford, just a stone's throw from NYC. Less than a 2-minute walk from the beach. Perfect for those looking to enjoy the tranquility of the beach with the city life nearby. Outdoor dining area - perfect for summer evening relaxation. Fully equipped for fun and adventure - paddle boards and various games available. Ideal for family vacations or a friends’ getaway. Book your stay today and enjoy an unforgettable beachside adventure!

Top guest favorite

Decorative pillows with intricate patterns are placed on a spacious bed. A soft, textured pillow complements the patterned ones. A warm bedside lamp provides gentle illumination, creating a cozy ambiance. Subtle floral accents are visible in the background.

Home in Downtown Stamford

4.99 out of 5 average rating, 127 reviews

45 Minutes from NYC | Urban Hideaway in Stamford

Welcome to our charming home! Escape the city and unwind in this fully equipped house, just 5 minutes from downtown Stamford, CT. We’re conveniently located 5 minutes from I-95, as well as Cove Island and Shippan Beach, top restaurants, parks, grocery shops, and pharmacies. Our house is only 45 minutes from New York City. It’s the perfect spot for a fun and relaxing stay! With thoughtfully curated decor and all the comforts you need, you’ll truly feel right at home.

Superhost

A charming outdoor area is presented, featuring a comfortable circular chair and several bright green seating options arranged on a patio. Lush greenery surrounds the space, with flowering plants adding a touch of color and string lights overhead, creating a cozy atmosphere.

Home in Stamford

4.83 out of 5 average rating, 155 reviews

Gem by the water+ firepit and all fenced backyard

Take it easy at this unique and tranquil getaway. One block away from the water and three blocks away from Dolphin Cove. Enjoy walkings and site-seeings. Perfect for going kayaking, paddle boarding or just stay relaxing in the backyard. It is located at 5 minutes walking distance from the train station and 7 minutes away from downtown. Bus stop in front of the house. The house has a lower level that mostly is occupied by the host and sometimes with guests.

Superhost

A modern living area showcases a large window with a stunning city skyline view, featuring prominent buildings like the Empire State Building. The space is furnished with a plush blue couch and a matching armchair, complemented by a minimalist coffee table.

Home in Stamford

4.88 out of 5 average rating, 32 reviews

Spacious 7BR by Stamford Beaches, I-95 & Workspace

Welcome to Our Luxurious 7-Bedroom Retreat in Stamford! 🌟🏡 Discover the perfect home base for your group’s needs in our spacious and stylish vacation rental. Conveniently located near the city center, you can enjoy family picnics in nearby parks or relax on 3 beautiful beaches just a short distance away. With top-rated restaurants, exciting local events, and a vibrant community to explore, you’ll find plenty to keep everyone entertained.

Guest favorite

The exterior of the cedar home features a gently sloped roof and large windows allowing natural light in. Steps lead up to a double door entrance, bordered by lush greenery and pathways lined with stones.

Home in Centerport

4.75 out of 5 average rating, 8 reviews

Harbor Hill: Beach Retreat 1 hour from NYC

Harbor Hill is a stylish cedar home nestled in Centerport’s historic waterfront bluffs. Enjoy the water view outside through the trees as you walk up the steps. The house is walking distance to Fleets Cove beach! This area offers many wonderful sites to enjoy including Vanderbilt Mansion & Planetarium, Del Vino Vineyards, Paramount Theater, and downtown Northport, Cold Spring Harbor, & Huntington. Permit #P263644

Guest favorite

A sandy pathway leads from the house to the private beach, framed by low greenery. A shaded seating area with a green umbrella and white chairs is visible on the beach, set against the backdrop of tranquil waters.

Home in Westport

4.82 out of 5 average rating, 49 reviews

Charming & open Beach house w/*OWN PRIVATE BEACH*

Idyllic setting with YOUR OWN PRIVATE BEACH to enjoy! 1 story/ranch style house flooded with light. Casual beach living for up to 6 people. Note: This home has 3 bedrooms, 1 master suite and 2 bedrooms that adjoin with a pass-through. Enjoy your morning coffee & memorable dinners with exceptional views, as beautiful in SPRING & FALL as SUMMER. Tranquility in an idyllic location awaits you.