Beach house vacation rentals in Middletown

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Top-rated beach house rentals in Middletown

Guests agree: these beach houses are highly rated for location, cleanliness, and more.

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Guest favourite

Home in Rye

4.9 out of 5 average rating, 113 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!

Guest favourite

Home in Greenwich

4.91 out of 5 average rating, 56 reviews

Super SAFE 2.5 bds Greenwich Healing Sanctuary

Beautifully decorated 2+ bedroom Healing Sanctuary in a 2 family home, which is felt the moment you walk in, among amethysts and crystals. Separate entrance, free parking, large backyard beautifully landscaped. Healthy living: Filtered water in the sinks, shower and toilet, hypoallergenic sheets, extra cleaning and disinfecting... Peaceful surroundings, safe neighborhood and only 45 min from NYC! 1 Mile from Greenwich Train station - Easy access to 95 and everything NY & CT have to offer!

Guest favourite

Home in Mamaroneck

4.95 out of 5 average rating, 124 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.

Superhost

Home in Mamaroneck

4.9 out of 5 average rating, 89 reviews

Entire 2nd floor House: yard, parking, train NYC.

Entire 2nd floor of our house with private entrance. Enjoy this cozy and very newly renovated 2 + bedroom, couch'TV, WIFI, free street or back yard parking. The train is literally 2 blocks away ,Metro North, quick way to NYC to avoid parking. A few blocks from downtown Mamaroneck with dozen of restaurants and the harbor/beach under a 10 minute walk. With a washer & Dryer, Full kitchen, table and chairs, folding couch and love seat. You'll have a great time at this comfortable place to stay.

Superhost

Home in Shippan Point

4.94 out of 5 average rating, 116 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 favourite

Home in Greenwich

4.94 out of 5 average rating, 17 reviews

Best hotel alternative for big group, near train

Location, location, location. Nestled in downtown Greenwich, this charming kid-friendly 4-BR house/2.5 bath offers prime location w/ 2 free parking spots. Enjoy a full kitchen, washer/dryer, private entrance, garden & patio. Steps away from Greenwich train station, Greenwich Ave, & key landmarks. Drive minutes to other parks & Greenwich Hospital. Easy access to NYC via train (45-55 mins to Grand Central) & via 95. Experience the best of downtown Greenwich with the convenience of home.

Guest favourite

Home in Shippan Point

4.96 out of 5 average rating, 51 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 favourite

Home in Downtown Stamford

4.99 out of 5 average rating, 136 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

Home in Stamford

4.84 out of 5 average rating, 161 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

Home in Stamford

4.88 out of 5 average rating, 33 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 favourite

Home in Stamford

4.93 out of 5 average rating, 105 reviews

Stylish Beach Home near Downtown/Cove Beach

This spacious 5 bedroom home with water views and a lot of natural light tucked away in a quiet and serene residential neighborhood. The house is perfect for a large family or a corporate retreat. If this property is booked for the dates you selected, click on the profile to see our other amazing properties in Stamford.

Guest favourite

Home in New Rochelle

4.89 out of 5 average rating, 45 reviews

Modern | 2Bed | Near NYC + Parking

This 2BR/1BA is completely renovated. It has a spacious kitchen with new appliances. The master bedroom has a king sized bed with two closets filled with hangers and a 6 drawer dresser. the second br has a full sized bed and one closet. The tv console is filled with a bunch of board games and books for entertainment.