Places to stay in Jamesport

4.94 out of 5 average rating, 137 reviews

An expansive wooden deck offers ample seating with picnic tables, overlooking the sandy beach and ocean. The space is well-lit by natural light, with a clear blue sky visible above, creating an inviting area for outdoor relaxation and dining.

Home in Milford

#2 Milford Beach (across street) Charles Isle 2BR

Welcome to your perfect Milford beachfront escape! This beautifully furnished 2-bedroom, 1-bath 2nd floor unit sits directly across from the beach, with beautiful water views. Just 100 yards from Silver Sands State Park, you’ll have easy access to its beaches, nature trails, and famous boardwalk. This unit offers beach gear, private yard for sunset dining, and proximity to Milford’s lively downtown. Whether here for a romantic getaway or family retreat, this spot offers relaxation or adventure!

5 out of 5 average rating, 9 reviews

A private pool area is shown with a clear blue swimming pool surrounded by four lounge chairs. A charming shed is situated in the background, framed by green trees and landscaped gardens.

Home in North Fork

Stylish Beach Getaway: pool & walking location

Perfectly located within walking distance to shops, beaches, and restaurants, our designer home offers comfort, luxury amenities, and privacy. Interested in a long term rental? Message us! Enjoy a beautifully landscaped backyard with pool, chefs kitchen for hosting, and nearby beach farms & wineries. Bedrooms boast organic linens and bathrooms offer Bathing Culture products. Kitchen is stocked with local organic pantry staples and stainless steel appliances to cook or grill on the patio.

4.89 out of 5 average rating, 484 reviews

A shoreline is depicted with a mixture of smooth, round pebbles covering the sand. Gentle waves are seen rolling onto the beach, and a colorful sunset fills the sky, casting reflections over the water's surface.

Cabin in Rocky Point

Great little place just for a couple

The outdoor courtyard is especially nice and private-,with a fire pit, grill and comfortable chairs. It is a rustic location easy walking distance to North Shore Beach. If you want an ocean beach you can drive straight south for 20 minutes and reach Smiths Point State Park right on the ocean. The North Fork with its vineyards is a short drive and the Hamptons also only 30 minutes to West Hampton. You can fish, golf, walk among the wooded area and relax in peace. A pleasure. linen 100% cotton!

4.93 out of 5 average rating, 464 reviews

A sandy beach scene is depicted with people enjoying the sun and water. Colorful umbrellas provide shade while beach chairs are scattered along the shore. A wooden dock extends into the calm water, surrounded by lush greenery in the background under a clear blue sky.

Home in North Fork

Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)

Ranked #1 AirBNB. Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

4.94 out of 5 average rating, 114 reviews

The interior features a bright, open space with wooden beams and rustic decor. A comfortable couch with a plaid throw faces a wall-mounted TV. A staircase with unique railings leads to the upper level, while a dining area is visible to the side.

Tiny home in Mastic

Cozy craftsman style home close to beaches

Feel refreshed when you stay in this rustic gem. 10 minutes from the fire island beaches this newly renovated home will take your breath away. 20 minutes from local wineries theres no shortage of things to do. This is a single dwelling home. There is a basement apartment with a separate entrance. The tenant does not have access to the house. Everything pictured is yours to use! Kick your feet up and enjoy the details of this handcrafted home. Tree house inside and out!

5 out of 5 average rating, 11 reviews

A view of the Peconic River is depicted from a wooden deck, featuring a small round table and two woven chairs. The water reflects clear blue skies, with boats visible in the distance and trees lining the shore.

Houseboat in North Fork

Peconic River Boatel

Perfectly updated nautical houseboat situated on the scenic Peconic River. Featuring two picturesque bedrooms, a full service eat-in kitchen and a living room with panoramic river view. Enjoy your morning coffee on the outside deck while taking in the sunrise. This historic waterfront town was named to Forbes Advisor’s “Best Places to Travel in 2023” — one of just 11 U.S. destinations on this year’s list. A must see for adventurers and families alike!

4.89 out of 5 average rating, 37 reviews

The front porch features wooden decking and a textured area rug. Two chairs are positioned invitingly, complemented by a potted plant. Lush greenery creates a private atmosphere, enhancing the relaxing outdoor space.

Home in East Hampton

⭐Walk to the Village ❤ of East Hampton

Stay in our Cozy Hamptons Cottage, in one of the most central and convenient locations in East Hampton Village! ✔Self Check-in ✔Private Driveway ✔Ideal for Longer Stays & Flexcations ✔Fast Wifi- Perfect for Working Remotely ✔24/7 Customer Support ✔Walking distance to Shopping/Bars/Restaurants & Grocery Store ✔7 min drive to E Hampton Beach ✔Fully stocked Kitchen ✔Complimentary Netflix ✔King Bed ✔Romantic back Garden w/ BBQ ✔Fully Cleaned & Sanitized

4.89 out of 5 average rating, 94 reviews

A cozy seating area is furnished with a brown sofa and a round marble table surrounded by six black chairs. A flat-screen television is mounted on the wall, and light is softly reflected off the pale wooden floor, enhancing the simplicity of the space.

Home in Coram

Entire independent Apt close to Airport and Ferry

Enjoy the simplicity of this quiet and central accommodation, where you can have close to you the busiest places in Coram New York. You can enjoy a good wine at Harmony Vineyards. You can enjoy the Splish Splash Water Park with your family And if you like everything that has to do with the Marina an ideal place to visit is Danfords Marina. Come and stay with Julio and Karina, we will make your stay a good experience.

5 out of 5 average rating, 24 reviews

Home in Bellport

Monkey Puzzle - Renovated Cottage in Bellport

Monkey Puzzle is affectionately named for a well known tree in the front lawn of this house, it seems that everyone in town is familiar with our Monkey Puzzle tree. We purchased this house last summer and have done a total renovation to get it ready for Summer 20024. Everything in Monkey Puzzle is brand new; including 2 bathrooms, kitchen cabinets and appliances, central air, and an amazing gunite pool.

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What guests are saying

Private Luxe Cottage at Gates of Wine Country

4.98 out of 5 average rating, 46 reviews7 months ago

We had a wonderful stay at Carrie’s listing. When we first arrived, Carrie was still cleaning up so we were invited inside for a cup of wine. The airbnb had almost everything we needed (minus a microwave) and the property had super friendly chickens and every amenity needed for a stay-at-home vacation. Carrie was even kind enough to have us stay a little past check in to finish some work meetings. We appreciated everything and would recommend this to anyone coming to North Fork :)

Guesthouse in North Fork

What guests are saying

East Hampton House

4.89 out of 5 average rating, 193 reviews6 months ago

Clean and comfortable home in a quiet, peaceful neighborhood in Northwest Harbor. Our family of four and pet were able to use the house as home base for the long weekend. This house is close to all the attractions in Amagansett, Montauk, Sag Harbor, and other spots in the Hamptons. Would stay here again!

Home in East Hampton

What guests are saying

Private 1st flr apt w/ patio 3 blocks from beach

4.94 out of 5 average rating, 94 reviews4 days ago

We had a great stay at Melissa’s place. The check in and out was super easy. The house was very clean and cozy. The location was great - a short walk took us to the main street and we were able to get around vineyards by taking Ubers. And it’s only a 10-minute walk to the LIRR train station which is so convenient. We enjoyed our experience and would hope to come back to enjoy more wine tasting in the area!

Apartment in North Fork

What guests are saying

Home Away From Home

5 out of 5 average rating, 8 reviews1 month ago

My sister and I stayed here for a weekend as she was visiting from MA. The place was perfect, with adequate space and clean facilities. The only issue we ran into was the listing describes 2 beds, or at least a futon; however upon staying here we learned there is not one. There is a king bed in the main bedroom, and then narrow couches, one in the bedroom and one downstairs. We had planned on two beds so this was a bit of a surprise. Otherwise, our stay was seamless and we felt very safe and comfortable. The bed was amazing and soft. Hosts were mostly responsive and respectful. A warning for those who use or medicate with cannabis, make sure your car doesn’t smell, as we were parked in front about to go out, one of the hosts insisted we had broken their smoking rules while which definitely was not the case as prior to our stay I had clarified my intent to them to follow all rules and respect their smoking policy. Otherwise, we really enjoyed our weekend and would recommend.

Apartment in Selden

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Popular amenities for Jamesport places to stay

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Jamesport's top sights

Jamesport Vineyards56 locals recommend

RGNY51 locals recommend

Paumanok Vineyards43 locals recommend

Grana38 locals recommend

Magic Fountain34 locals recommend

Main Road Biscuit32 locals recommend

Other great vacation rentals in Jamesport

4.98 out of 5 average rating, 179 reviews

A screened-in patio features a wooden ceiling and overhead fans, providing a comfortable space for relaxation. A navy blue sofa pairs with a coffee table, while tall chairs surround a dining table. Views of a spacious yard and trees are visible through the screens.

Home in North Fork

Greenport Village walking distance to all

4.79 out of 5 average rating, 43 reviews

Two comfortable chairs are positioned on a spacious porch, offering a clear view of the beach and ocean. The horizon is visible in the distance, with calm waters under a blue sky dotted with clouds.

Home in West Haven

Beachside Retreat

4.87 out of 5 average rating, 153 reviews

Large windows allow natural light to fill the open living space, showcasing the stunning view of the Great South Bay. A comfortable sofa with decorative pillows faces the water, complemented by a dining area nearby. Warm wood tones enhance the cozy atmosphere of the room.

Cabin in Shirley

A-Frame cabin with private beach & epic sunsets

4.99 out of 5 average rating, 136 reviews

Cottage in Guilford

"Red House on the Knoll" at Indian Cove

Guesthouse in Shelter Island

A spacious outdoor area is highlighted by a refreshing pool surrounded by lounge chairs. The pool house, featuring a white exterior, sits in the background amidst lush greenery. Flower pots and garden plants frame the scene, enhancing the tranquil environment.

4.96 out of 5 average rating, 27 reviews

Sleek and Chic cottage/Pool House

4.98 out of 5 average rating, 43 reviews

A charming beachside home is showcased, featuring a wrap-around porch with seating. The sandy beachfront extends along the water's edge, and a clear blue sky overhead enhances the coastal atmosphere. Nearby houses are visible, offering a sense of community along the shore.

Home in Woodmont

Beachfront paradise- come, stay, relax!

5 out of 5 average rating, 49 reviews

Home in Old Saybrook

Great Hammcock Getaway, Nearby beaches, Hot tub