Vacation rentals in Upper Brookville

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Upper Brookville

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

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Guest favorite

Apartment in Greenwood Lake

4.94 out of 5 average rating, 85 reviews

Apartment in Lovely Lake House,Pets welcome!

Love Tree Love Nature Love Lake are welcome! Relax with the whole family and your furbaby at this peaceful place to stay. Just 1 Hour From New York City, Our house in Greenwood lake, NY Surrounded By Natures. Sit at the front porch Enjoys and Relax Lake View, 5 Minutes to Community Lake access, 5 Minutes to Kayak Rental, 10 Minutes Walk to Bus Stop to NYC, Convinent Store Dunkin Donut, Restaurants Near by Boating,Kayaking,Fishing,Skiing, Hiking,Bicycling, Apple and Pumpkin picking and Shopping

Superhost

Home in Woodmont

4.92 out of 5 average rating, 26 reviews

Light-filled Beach House Steps from the Sand

Located in prime Bayview Beach, a one min stroll to the sandiest beach in Milford. Two floors with private patio. Main level: half-bath, Cooks kitchen with a 6 person dining area, living room with flatscreen. Upstairs: master w/king size bed & en-suite bath, kids bedroom w/ bunkbed, another full bath w/ tub. 3rd bedroom with queen bed and trundle twin. If you want a get-a-way from the city, or just an escape then come to this tucked-away home. Enjoy all that this coastline gem has to offer.

Guest favorite

Cottage in Greenwood Lake

4.96 out of 5 average rating, 48 reviews

5 bedroom 7 beds Cottage Sauna, Hike, Winery & Ski

Rental ID# 23-67 4 Season Home for relaxation with cedar sauna, hiking, wineries & skiing! Bring the whole family to this great home with lots of room for fun. This house has it all! The community children’s playground is steps from house. There is a basketball hoop on property & plenty of trees. Passes (6) provided for public beach with lifeguards, lake to swim, BBQ pits with playground & shower facilities on site. We have beach towels, rolling cooler, and beach chairs available for guests.

Superhost

Home in West Haven

4.79 out of 5 average rating, 43 reviews

Beachside Retreat

***Brand new to Airbnb, the Beachside Retreat is perfect for a quick getaway or a longer short term stay. Gorgeously renovated home has 4 spacious bedrooms, living room & dining room large enough to entertain and kitchen perfect for making those home-away-from-home meals. Across the street from the beach, wake up to stunning sunrises with your morning coffee or relax on the wrap around porch and watch the sunset. With walking trails, restaurants and shops close by you never have to go far.

Top guest favorite

Home in Northport

4.94 out of 5 average rating, 114 reviews

Cool pad, Private Rms, Walk to village, Wtr view

Beautiful pad on a tranquil street and walkable neighborhood. 5-10 minute walk to the village and 2-minute walk to the cliffs overlooking the bay and sound. Water view from one bedroom, great outdoor yard - very private. Updated amenities, marble bathroom, cozy indoor living area and very comfortable beds. The rental space is private and is the entire first floor of the home. The home is a two-story duplex with a shared entrance and private locking doors to each space. Wonderful location.

Superhost

Home in Baldwin

4.85 out of 5 average rating, 133 reviews

Clarissa's Paradise

RESERVE NOW: This ideally located five-bedroom totally renovated home is the perfect spot for a family fun vacation. Located within walking distance of the well known playground and spray ground. The home features a spacious patio, central air conditioning, baseboard heating, WiFi, and Cable tv. The open layout provides perfect gathering spaces for your family, and all bedrooms are spacious and comfortably appointed. 4 full bathrooms . Sleeps 10. PLEASE NO PARTIES ARE STRICKLY PROHIBITED

Guest favorite

Home in Greenwood Lake

4.96 out of 5 average rating, 78 reviews

*Waterfront Modern Home w/Hot Tub and Fast Wifi

Waterfront home on Greenwood Lake with a private dock and 6 person hot tub. Situated in a quiet neighborhood and a short walk (1/4 mile) to downtown. Enjoy dinner on the patio, steaks on the grill, and s'mores by the fire pit. A short drive (5 minutes) to the town beach. Professionally cleaned, comfortable, and bright. A perfect place to enjoy Greenwood Lake and the surrounding Hudson Valley area. Nearby hiking, apple picking, and skiing. Fully renovated with top-of-the-line appliances

Guest favorite

Home in Milford

5 out of 5 average rating, 5 reviews

Seaside Paradise

Welcome to our beach house in Milford! This getaway is just a short walk from the beach, making it the perfect vacation spot for families or groups of friends. Whether you're looking to soak up the sun on the sandy shores, explore the charming town of Milford, or simply relax in a comfortable beach house, our rental is the perfect choice. We can't wait to host you and make your beach vacation unforgettable. Book now and start counting down the days until your beachside getaway!

Top guest favorite

Home in Milford

5 out of 5 average rating, 101 reviews

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

🌴Steps from Walnut Beach & Silver Sands State Park, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Explore the scenic coastline, build sandcastles, or enjoy a day of kite flying. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC & 15 from New Haven, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

Guest favorite

Home in Mastic

4.88 out of 5 average rating, 102 reviews

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

Top guest favorite

Cottage in Sea Bright

4.95 out of 5 average rating, 131 reviews

Sea Bright NJ Cottage 1 block from BEACH sleeps 6!

RARE Off Street Parking for 4 compact cars or 3 SUVs This 3 bedroom beach cottage is a perfect, cost effective alternative to a hotel stay. Wifi, N64, HBO, Cable & board games for those rainy days. Fully furnished bedrooms, one bedroom has home office desk set up, living area, and kitchen, to our comfortable lounge area, BBQ, and outdoor shower. Perfect way to relax after a fun day at a beach, event, or exploring the beautiful town of SeaBright!

Guest favorite

Home in Milford

4.91 out of 5 average rating, 57 reviews

Modern Beach Getaway

This 4 bedroom, 3 bathroom vacation rental in Milford, CT, boasts beautiful hardwood floors, high ceilings, and an open-concept living area perfect for entertaining guests. Each bedroom is tastefully decorated, and the fenced-in private yard features a deck and firepit area. The rental is located across the street from a private beach and is a short drive from local shops and restaurants, making it the ideal spot for a summer getaway.

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What guests are saying

Cozy Jersey Shore Cottage near Sandy Hook Beach

4.9 out of 5 average rating, 31 reviews3 weeks ago

You are immersed in a neighborhood here, with a friendly and professional host living next door. Lots of local eateries rather than chains, and good proximity to Atlantic Highlands, Sandy Hook and Sea Bright. Reminds me of my childhood summers at the Jersey Shore. The place is small but clean and well thought-out from the guest point of view.

Cottage in Highlands

What guests are saying

Salty Kisses Beach Cottage Milford CT

4.92 out of 5 average rating, 51 reviews8 months ago

We had a wonderful stay at Salty Kisses. The home is very comfortable and extremely well appointed. We enjoyed the proximity to the ocean as well as the ability to relax in the yard on the hammock or by the fire pit. Denise was very responsive to all communications and gave us lots of information about the area. Thank you for being such a great hostess!

Cottage in Milford

What guests are saying

Cozy Milford Beach House

4.92 out of 5 average rating, 26 reviews2 weeks ago

Thank you for a wonderful stay! Your property was perfectly located, making it easy to explore the area and access all the amenities we needed. We highly appreciate the cleanliness - everything was spotless and well-maintained throughout our visit. Communication was smooth and efficient with promptly responses. The check-in process was straightforward, and appreciated the clear instructions. The accommodation itself was comfortable and had everything necessary for a pleasant stay. I would happily recommend your place to other travelers looking for a clean, well-situated rental with a responsive host.

Home in Woodmont

What guests are saying

La Sirena Beach Cottage

4.96 out of 5 average rating, 24 reviews4 days ago

House was just as it looked in the pictures - beautifully decorated. Has everything needed for a vacation. Comfortable, bright and cheerful. Back yard was private. House was fully stocked with what was needed along with beach supplies in the outdoor shed. Quick walk to the beach. Would easily rent again!

Home in Woodmont

What guests are saying

Seaside Cottage: water views, walk to beaches!

4.99 out of 5 average rating, 72 reviews1 week ago

Ken is hands down the best host I’ve ever had. He not only genuinely cares about the property but also the people who stay there. We booked on very short notice due to a family emergency and he wasted no time getting that place together for us. We stayed for almost a full 2 weeks and every day Ken just does a good morning text making sure everything is good! Very consistent and considerate host! The location is nice, it’s sits across the road from the LI sound but you’re able to still see the water from the front porch. My morning runs were filled with dog walkers, other runners and some very impressive homes and beautiful ocean side runs. The back yard is perfect for a family BBQ after a beach day. He has so many different toiletries and amenities at the house where you can almost come with nothing but clothes and be perfectly fine. I rate the host and the property 5stars because that’s the experience I guarantee you’ll have as well.

Home in Woodmont

What guests are saying

Newly built twin beach house within steps to beach

5 out of 5 average rating, 8 reviews8 months ago

We stayed here for a wedding at The Burr Mansion, which was extremely close to the house! The house was clean and updated. A few spots to walk to including a local bar. Just a walk to the beach. Bedrooms are all spacious and were very clean. Would definitely stay again.

Home in Fairfield

What guests are saying

2BR Apartment with Terrace

4.8 out of 5 average rating, 5 reviews8 months ago

Mathew was very accommodating and very responsive. His location on the board walk was very centrally located. Walking distance to everything. He allowed late check out which was nice. It was my first time on the island so was not aware of many rules and regulations. I suggest researching before booking.

Apartment in Ocean Beach

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