Overlooking Greenport Harbor, this boutique inn combines coastal charm with modern comforts. Just a 3-minute walk from the train station, guests enjoy the seasonal outdoor pool, 24-hour fitness center, and complimentary breakfast while exploring nearby attractions.
Stylish rooms in this boutique hotel offer a peaceful retreat after exploring the harbor. Unwind with a drink at the bar, grab a bite at the coffee shop, or bike to nearby Greenport Harbor Brewing Company and Farmers' Market.
Perched oceanfront in Greenport, this hotel offers a seasonal outdoor pool with poolside bar. Just a short drive from the Railroad Museum and The Old Field Vineyards, enjoy American cuisine at The Halyard restaurant and unwind at 2 welcoming bars.
Explore Greenport from this stylish inn with its welcoming bar and restaurant. Grab the complimentary bikes to visit nearby Greenport Harbor Brewing Company. The attentive staff and daily housekeeping ensure a carefree stay, just an 8-minute walk from the train station.
Unwind at this North Fork retreat with a refreshing swim or soothing soak after exploring nearby museums. Complimentary bikes let you discover charming Greenport while free WiFi and parking add convenience to your coastal escape.
Escape to this stylish Greenport retreat offering free breakfast and WiFi. Relax at the rooftop terrace or grab a drink from the bar before exploring local attractions on complimentary bikes. Only a 3-minute walk from Greenport Station, near Camera Obscura.
Wake to island tranquility at this Shelter Island Heights hotel with premium bedding. Near Shelter Island Country Club and Sunset Beach, this refined retreat offers free WiFi and parking. Convenient to Greenport Station for day trips.
Overlooking Chase Creek, this inviting guesthouse sits adjacent to a golf course in tranquil Shelter Island Heights. Free WiFi and parking enhance your stay while the garden and terrace offer peaceful spots to unwind near Shelter Island Country Club.
Dive into waterside charm at this Southold retreat on the bay. Located near The Old Field Vineyards and Crescent Beach, the hotel offers free WiFi, bicycles, and a cafe/bar lounge. Travelers consistently praise the helpful staff for enhancing their stay experience.
Tucked away in Shelter Island Heights, this golf-adjacent hotel offers a seasonal outdoor pool and rejuvenating massage services. Enjoy cocktails at the poolside bar, grab bites at the restaurant or deli, then explore nearby Sunset Beach and Shelter Island Country Club.
Wake up to complimentary breakfast at this waterfront hotel, just moments from Sag Harbor Whaling Museum. The outdoor pool offers refreshing relaxation after exploring nearby attractions. Free WiFi and parking enhance the value, while the attentive staff ensures a memorable stay.
Wake up to seaside charm at this Clinton motel where the ocean beckons nearby. Take a refreshing dip in the seasonal outdoor pool after exploring Clinton Plaza or the historic Adam Stanton House. Free WiFi and parking add value, with Clinton Station just a 19-minute walk away.
Steps from Riverhead's renowned vineyards, this welcoming motel offers free WiFi and complimentary parking. The 24-hour front desk ensures convenience while clean, comfortable rooms provide a relaxing base to explore nearby Westhampton beaches.
Immerse in coastal charm at this Sag Harbor retreat where massages await after beach days. The seasonal outdoor pool offers refreshment while the fitness center keeps routines intact. Friendly staff ensure a memorable stay near historical museums.
Relax at this coastal Westbrook resort with a private beach, 3 restaurants including Italian cuisine at Dattilo's Fine Dining, and rejuvenating spa services. Near Tanger Outlets and just 9 minutes from Old Saybrook Station.
Tucked beside Old Saybrook Station, this peaceful inn offers comfortable beds and free parking. Explore nearby Chalker Beach or hike local trails before relaxing in clean rooms. Himalaya Café and The Teakettle Cafe are just steps away for tasty meals.
Escape to this charming Wainscott B&B offering a refreshing seasonal outdoor pool and complimentary WiFi and parking. Just a 5-minute drive from stunning Hamptons Beaches and Wolffer Estates Vineyard, with attentive staff praised by past guests.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
If you can't wait to get to the beach, you might enjoy a trip to 67 Steps Beach located 1.3 mi (2.1 km) from central Greenport. Enjoy the sunset by the shore at Sunset Beach, Crescent Beach, and Norman E. Klipp Marine Park.
Travelers might want a tour of Kontokosta Winery, just one of the places to visit, and located 1.9 mi (3.1 km) from central Greenport West.
Why not take a stroll along the beaches and watch the sunset while you're here?
If you're planning a bit of sightseeing during your trip, head to Greenport Carousel— just one of the monuments in central Greenport. If you have fun at Greenport Carousel, you'll love East End Seaport Maritime Museum and Railroad Museum of Long Island, both a short walk away.
East End Seaport Maritime Museum is just one of the attractions in Pipes Cove, Greenport so you might want to stop by during your trip. If you want to experience more of the culture Greenport has to offer, head to Greenport Carousel, Eastern Long Island Hospital, and Stony Brook Eastern Long Island Hospital.
Railroad Museum of Long Island is just one of the attractions in Pipes Cove, Greenport so you might want to stop by during your trip. If you want to experience more of the culture Greenport has to offer, head to East End Seaport Maritime Museum, Greenport Carousel, and Eastern Long Island Hospital.
Imagine strolling along Safe Harbor Stirling for some great waterfront pics. It's located 0.6 mi (0.9 km) from central Greenport.
If you carry on walking you'll get to 67 Steps Beach and Norman E. Klipp Marine Park for some more water views.
Fishing boats bob gently in the harbor where this former whaling village now welcomes visitors with maritime charm. The vintage carousel at Mitchell Park spins with childlike delight before revealing spectacular water views. Sample North Fork wines at Kontokosta Winery or taste fresh-shucked oysters at waterfront restaurants that showcase the day's catch. The East End Seaport Maritime Museum chronicles seafaring history while the Railroad Museum of Long Island celebrates transportation heritage. Take a short walk to 67 Steps Beach for quiet contemplation away from summer crowds. The compact downtown offers independent shops in historic buildings, and Greenport Harbor Brewing Company pours craft beers perfect after a day of North Fork exploration.
The Captain Stannard house is a true gem in Westbrook. There are many restaurants, shops, parks, and beaches close by. The property has a private yard and a large rear porch for relaxation. My room was impeccably clean and spacious for being the smallest one in the house. Dianne was incredibly sweet and went out of her way to help all the guests.
This property deserves it's designation as one of the best small luxury hotels.
Great,attentive staff,many included amenities and perks ample parking and great location including proximity to the beach.
A few of the furnishings are showing some wear, but this is really the only negative point.
Quick anniversary night get away! Location was great, rooftop was amazing, and staff was super helpful! Made our stay special and memorable! Cant wait to go back for 2 nights!! Or more!
It was my wife's Birthday Lorna, she loves the East Hampton but we din't want to stay more than 3 days. We found the Hedges Inn and we love it. We will go back soon.
friendly staff and welcome on arrival, tastefully decorated. comfortable and relaxed. Breakfast could be improved, A place of this caliber, I would expect fresh bread and toast, sweet butter, eggs to order, rather than the packaged food service microwave prepared hash browns, sausage slice and packaged mini quiche tarts. The caned tangerine accented with mint was refreshing. good coffee.
Beautiful property close to everything in East Hampton. Randye and her entire staff ensured we wanted for nothing our entire trip!
The breakfast was awesome every day of the weekend and the Dinner, wow.........Chilled Pea soup, amazing! Travel is our passion, we will be back again someday soon.............
Gorgeous gorgeous hotel!! And the absolute nicest staff I have ever encountered! The restaurant breakfast wasn’t that great but everything else was 11/10!!
I enjoyed my stay from the moment I met the valet attendant! Check in was easy and efficient. Bar staff and room service were extraordinary!
I highly recommend the Madison Beach Motel to everyone!
Beautiful view and excellent location. A short walk to the ferry to Greenport and a short drive to preserves. Owner more than accommodating. I will visit again.
It’s a nice hotel, it has a funky vibe to it and it’s very clean and the rooms are excellent. I definitely recommend it’s the perfect couple gate away hotel. Definitely coming back!!
My stay was perfect. This family run hotel is outstanding, and great value for the money. Room (facing pool) was large, quiet and in perfect condition. Small private terrace with lounge chairs a big plus. Bathroom is large and modern with 5 star amenities (I appreciate that). Entire hotel feels like it was recently renovated. Will definitely stay here again!
Receptionist walked us to our room. What a great start to a wonderful stay.
Oyster estate is almost complete from a total redo.
Our room was fresh & right on point
The grounds are 80% with the parking lot and onsite lounge unfinished
What remains to be completed is overshadowed by the staff.
Smiles abound, attentive and helpful suggestions.
If you want the flexibility to change your plans to Greenport, most properties offer refundable* bookable rates. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.
Where can I stay in Greenport if I want a cheap accommodation?
Greenporter Hotel is an accommodation you might want to consider that'll save you money.
Where can I stay in Greenport if I want a vacation home instead of a traditional hotel?
If you want to find a good alternative to a hotel, browse our selection of 97 vacation homes. In addition, there are 11 apartments and 6 condos.
What will the weather in Greenport be like during my visit?
August and July are typically the warmest months in Greenport when the average temp is 70°F. January and February are the coldest months when the average temperature is 38°F. October and December are the months with the most rain.
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