Cottage vacation rentals in Greenport

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Popular amenities for Greenport cottage rentals

Cottage rentals with a hot tub

Superhost
An expansive wooden deck is depicted, surrounded by greenery. Low wooden planters are positioned along the railing, providing a natural element. The clear blue sky and subtle hints of the bay can be seen in the distance, creating a serene outdoor space.
Cottage in Amagansett
4.87 out of 5 average rating, 23 reviews

4 Br Beach House; Short Walk to Beach!

EveRating, 5 stars3 months ago
Beautiful large home, clean linens, plenty of towels, bathtub worked great. John was very responsive and helpful. Slept 9 people comfortably. The living room area was cozy with an indoor fireplace and the kitchen was large with a large oven and dishwasher. Five minute easy walk to a beautiful quiet beach. Highly recommend this place.
An inviting outdoor space surrounds a clear blue pool with several lounge chairs positioned nearby. Tropical foliage adds privacy, and vibrant umbrellas provide shade. The structure features a wooden deck and additional seating areas, creating a relaxing environment for enjoying warmer days.
Cottage in Fire Island Pines
5 out of 5 average rating, 3 reviews

Fire Island Pines Waterfront Oasis - Pool & HotTub

JocelynRating, 5 stars20 months ago
We loved our stay with Audie from the moment we reached out to make the booking. Audie was immediately responsive, kind, flexible and super helpful. Audie’s hosting was fantastic, and the house was even better! We’ve stayed in plenty of houses in the Pines and the Grove and we all agreed it was our favorite and well worth the price. There was plenty of space for the four of us to hang out, and the house had all the amenities we could ask for - a huge pool, cozy hot tub, a beautiful rooftop deck to watch the sunset, grill, perfect kitchen and steps from a great area of the beach. Audie’s instructions to get inside were clear and easy to follow. And again, Audie was extremely responsive whenever we had questions during our stay. We loved our stay here!
Top guest favorite
A large gunite pool is surrounded by a well-maintained grassy yard, featuring comfortable lounge chairs on a sunbathing area. Lush trees provide shade, while a charming cottage stands in the background, contributing to a serene outdoor setting.
Cottage in Bellport
4.93 out of 5 average rating, 27 reviews

Renovated Historic Cottage w/ Pool Bellport Vllage

KellyRating, 5 stars7 months ago
Tabitha's place was perfect for our group stay. Right in the middle of town and perfect for what we needed for the week!
A charming red cottage is framed by lush greenery, set back from a driveway leading to the entrance. A small white bench is visible on the left side of the well-maintained lawn, with flowering plants adding a touch of color in front of the house.
Cottage in North Fork
4.69 out of 5 average rating, 195 reviews

Lovely 2 BR Beach House No. Shore

KateRating, 5 stars6 months ago
Great spot for a long weekend! Wonderful location close to the beach and local wineries. Richard was a great host offering lots of recommendations and clear instructions for check in and using available amenities.
Guest favorite
Cottage in Bellport
5 out of 5 average rating, 9 reviews

Bellport Inn, Charming Cottage in the Village!

JessicaRating, 5 stars9 months ago
Ivana and John are the most wonderful hosts! This was truly like staying at a family cottage and everything was just beautiful. John greeted us upon arrival and even had a bottle of wine for my husbands birthday! We loved staying here from the city because it was only a little over a hour to arrive and less than a hour to South Hampton where we had dinner. Also the little town is so so cute and we were able to walk over so quickly! We can’t wait to stay here again. Thank you again Ivana and John!
The outdoor deck features a hot tub, surrounded by comfortable seating options, including a sectional and individual chairs. A small table sits on the deck, providing a space for drinks or snacks. Light-colored drapes offer a touch of shade.
Cottage in Old Lyme
4.82 out of 5 average rating, 217 reviews

Private Beach Cottage

BillRating, 5 stars5 days ago
This well-appointed space is perfect for two people. Old Lyme is justly famous for its Florence Griswold Museum, as well as one of the better historic main street walking tours. (Currently, there's an exhibit at the museum about Old Lyme's slave-owning past.) And, then, of course, there's the ocean. Remember to ask your hosts about their beach parking pass. P.S. You may also need to bring your own coffee for the drip system.
Guest favorite
A serene backyard is showcased, featuring a stone patio, a vibrant flower garden in colorful pots, and a tranquil pond with a water feature. A hammock is suspended between two trees, offering a relaxing spot surrounded by greenery.
Private room in Hampton Bays
4.8 out of 5 average rating, 97 reviews

Private Room in the House that Art Built

BohdannaRating, 5 stars7 months ago
The place was charming, quaint, and exactly as described. It had a cozy vibe that made it feel like a home away from home. The location was perfect, with easy access to everything I needed. The host was incredibly responsive and helpful throughout my stay. Highly recommend this spot for anyone looking for an enjoyable experience!

Pet-friendly cottage rentals

Guest favorite
A charming country cottage is framed by lush green trees, showcasing a well-maintained exterior with dark wood siding. The driveway leads to a garage, and flower beds enhance the entrance. The surrounding yard offers ample greenery, contributing to a peaceful atmosphere.
Cottage in Southampton
4.93 out of 5 average rating, 46 reviews

Southampton Village Cottage

CharlieRating, 5 stars7 months ago
We absolutely loved Michael's cottage. It is a ~15 minute walk from the village and is on a quiet street. The cottage feels like a beach house but is very well appointed and homey. We loved our stay and would absolutely stay here again!
Top guest favorite
A cozy living area features a brown leather sofa, accompanied by a striped armchair and a small coffee table with flowers. Light enters through large windows, illuminating the room's warm wooden floors. Decor includes a world globe and framed artwork on the walls.
Cottage in Groton
4.96 out of 5 average rating, 314 reviews

Charming Historic Schoolhouse on Mystic River

ThomasRating, 5 stars1 week ago
This was our second stay here and it was just as nice as the first. Really responsive host and we love sitting outside at night with a drink enjoying the beautiful view. Nice spot where you don't even need to drive anywhere if you want to experience Mystic and even the seaport if you are up for a 20 minute walk. A+ again, thanks so much!
Top guest favorite
Cottage in Patchogue
4.94 out of 5 average rating, 233 reviews

Quaint Cottage on Long Island's South Shore.

TylerRating, 5 stars2 weeks ago
Leah was an incredible host, but a bit nervous at first. Our stay was absolutely amazing, and our dogs felt right at home in their cozy cottage. It was such a cute and comfortable place, and we’re so glad we chose Leah as our host. She went above and beyond for us during our stay.
Guest favorite
The sunroom features a light pink wall and a high ceiling with exposed beams. A comfortable wicker sofa with decorative throw pillows accompanies two matching chairs. A patterned area rug covers the floor, while a small table sits in the center. Soft light filters through sheer curtains.
Cottage in Guilford
4.93 out of 5 average rating, 267 reviews

Charm + location. Walk to beach, town, & harbor.

AllisonRating, 5 stars1 month ago
This was my fifth stay in Jeanne's wonderful cottage! The cottage gets better and better each time I visit: a newly renovated bathroom, redecoration in lighter/brighter colors, etc. The home is extremely well stocked - every kitchen item you might need (including loads of glasses/plates/silverware, pots/pans, etc.), thick towels, extra blankets and throws, and lots of cleaning and paper products. There are plenty of cozy places to sit and relax, both indoors and out. The best thing of all is Jeanne herself, who is without a doubt the most generous host I've encountered on AirBnB. She is friendly, communicates proactively, and is quick to respond to any issues/questions. She truly opens her home to her guests, encouraging visitors to use the space fully and to make themselves at home. The cottage is an easy walk to the beach ane/or to town and is lovely, homey, and peaceful. I'll definitely return!
Guest favorite
A welcoming living area features a comfortable couch and a textured ottoman, complemented by natural wood accents on the ceiling. Light fills the space from multiple windows, highlighting the hardwood floors and decorative stone wall that adds character to the room.
Cottage in Milford
4.95 out of 5 average rating, 315 reviews

Spring Sale|CozyCottage|Walk to Beach|Pet-friendly

AnnRating, 5 stars1 week ago
We had nice weekend at the cozy cottage. We loved that it was pet friendly and a short walk to the beach. Cameron was very friendly and responsive. She offered great suggestions for food and activities.
Guest favorite
A charming outdoor space features a wooden pathway leading to a cozy fire pit surrounded by blue chairs. A vibrant turquoise umbrella provides shade over a nearby table, while a hammock hangs invitingly in the background amidst lush greenery.
Cottage in East Lyme
4.97 out of 5 average rating, 274 reviews

Your Nest Near The Beach

ShanieceRating, 5 stars2 months ago
This has hands down been the best winter Airbnb I’ve ever had. Even though it has a beach theme, this could easily double as a winter wonderland cabin. I came here with my boyfriend to celebrate his birthday and before we left we were already planning our next trip back! This is hands down the cleanest feeling airbnb we’ve ever stayed at. They really put effort into making this place feel like a loved home. Everywhere you look theres a nod to the theme in home! The heating/cooling in the house is seriously impressive. The customizable fireplace upstairs (be careful on the stairs!) was a dream. Stargazing at night was incredible. I missed the sunset sleeping in on the incredible bed but the sunrise was AMAZING. Direct view on the front porch! Seeing the moon through the skylight while still being comfy on the couch and watching tv was absolutely terrific. From the endless amenities to the delicious food in the area, I can’t stop praising this place. Thank you guys for the great stay!
Superhost
The kitchen features modern gray cabinetry and stainless steel appliances. A wooden dining table is accompanied by three black stools. Natural light fills the space through the window, and a small plant is placed on the countertop, adding a touch of greenery.
Cottage in East Quogue
4.78 out of 5 average rating, 23 reviews

Cheerful and beautifully remodeled Beach cottage

HectorRating, 5 stars2 months ago
Definitely is the best place that we have been , nice location ,super clean, kitchen is beautiful, the cottage is extremely private, bathroom super clean, in summer would be great to come back ,in other words absolutely fantastic!!! 100% recommended
Superhost
The image captures a serene beach scene at sunset, with soft colors reflecting on the calm water. Silhouetted figures are seen on the shore, engaged in various activities as the sun sets on the horizon, creating a peaceful atmosphere.
Cottage in Rocky Point
4.93 out of 5 average rating, 160 reviews

Adorable cottage

JoAnnRating, 5 stars5 months ago
Angela was a great host and very accommodating after an unfortunate personal event we encountered just after arriving. The cottage was very comfortable and immaculately clean. Love the keyless entry. Neighborhood is quiet and we felt extremely safe. Deer pass through the yard throughout the day and what's more beautiful than that!!! We absolutely recommend Angela as a host and would not hesitate to book again in the future.

Private cottage rentals

Guest favorite
A wooden dock extends over calm bay waters, leading towards a small boat anchored in the distance. Lush greenery lines the shoreline, and a clear blue sky complements the serene landscape. Birds are seen casually swimming near the water’s edge.
Cottage in Shelter Island
4.78 out of 5 average rating, 55 reviews

Large Waterfront Cottage on Historic Estate

JainéRating, 5 stars6 months ago
We had a lovely time spending the long weekend on Shelter Island. This private bungalow is on a property w other homes, but you still have privacy and feel secluded. The beds were so comfortable and the house was stocked with everything you need for your stay. The host was gracious and very responsive which I really appreciate. We would love to stay here again. It looked just like the photos and was so clean! I also loved the color theme for each room. Thank you again!
Top guest favorite
An aerial view showcases a spacious estate with a large, heated swimming pool surrounded by patio furniture. Lush green lawns frame the property, which includes a charming cottage and a main house. The bay is visible in the background, enhancing the tranquil setting.
Cottage in Remsenburg-Speonk
5 out of 5 average rating, 20 reviews

Newly built cottage near the bay and hamptons

PatriciaRating, 5 stars2 days ago
Lovely peaceful cottage in beautiful location. Beautifully decorated. We enjoyed our month very much and hope to return.
Guest favorite
An open-concept kitchen and living area feature a modern design. The kitchen includes white subway tile, stainless steel appliances, and wooden stools at the counter. A dining area with a rectangular table and a light fixture above is visible, enhancing the room's spacious feel.
Cottage in Yaphank
4.85 out of 5 average rating, 62 reviews

Beautiful Waterfront Cottage

Kasha MarieRating, 5 stars1 week ago
I loved staying at Walter’s place! It was safe for my kids, a nice big back yard! The house was clean, the instructions were clear. Overall it made my stay nice, safe and comfortable! Thank you!
Superhost
A serene beach landscape showcases smooth sandy stretches under a clear blue sky. Gentle waves lap at the shore, with grassy dunes in the foreground providing a natural border. The horizon features a distant landmass, creating a tranquil atmosphere.
Cottage in Milford
4.78 out of 5 average rating, 32 reviews

Cheerful 2 bedroom cottage on beach

MatthewRating, 5 stars9 months ago
This house is absolutely perfect. It's clean, charming, has everything you need. The beautiful back yard has plenty of space and good stuff for kids to play with. Also, it's about a 30 second walk to the beach... neighbors are out on their patch of beach but yours is yours to yourself. It's perfect. We cannot wait to come back.
Top guest favorite
A charming cottage is set against a backdrop of lush greenery, with a spacious yard framed by trees. A gravel driveway leads to a white garage, while the cottage features a welcoming facade with well-maintained shrubs and a clear blue sky above.
Cottage in Madison
4.94 out of 5 average rating, 32 reviews

Adorable cottage close to beaches and downtown

AmandaRating, 5 stars4 days ago
This is by far one of the best and cutest airbnbs I’ve stayed in up until now! My friends and I stayed here for my bachelorette weekend and absolutely loved it. We’d definitely recommend it and stay here again if we could! The hosts were so sweet and friendly. They left us wine and rose and gave us an extended checkout. Their place was so cozy and clean too!
Superhost
Three sailboats are anchored in a calm body of water, their sails catching the gentle breeze. A large, well-appointed house with a brick façade and white railings is visible in the background, surrounded by green trees and manicured lawns.
Cottage in Stonington
4.87 out of 5 average rating, 89 reviews

Mystic Magical Sunsets awaits your arrival

HillaryRating, 5 stars9 months ago
Fran’s rental is just as lovely as she is. Her place was perfect for three adults and when the Keurig went on siesta she brought a brand new one within a couple of hours. She thoughtfully chose the furnishings and provides top quality bedding and towels. The kitchen is very well equipped. This is a case of an owner who truly cares and is trying her hardest to provide an excellent guest experience and it shows.
Guest favorite
A wooden deck leads to a mid-century cottage, framed by trees. Two white chairs are positioned on the deck, allowing for a serene space that captures sunlight. The structure features large glass doors that reflect the natural light of the sunny day.
Cottage in Fire Island Pines
5 out of 5 average rating, 22 reviews

Classic Fire Island Pines Cottage

CraigRating, 5 stars7 months ago
The cottage is steps from the beach. You can hear the waves crashing in the house. The natural light inside is stellar and the wraparound deck always has both shady and sunny spots to relax, read, etc. There is a very useful laundry setup in a small basement utility shed and an outdoor shower with hot water. You are under 10 minutes walking to/from the ferry and harbor area. There are two water filters available for drinking water and the WiFi was strong and reliable throughout our stay.
Guest favorite
An outdoor pool area is surrounded by well-maintained greenery and a spacious stone deck. Lounge chairs are positioned around the pool, inviting relaxation. A pergola is visible in the background, providing a shaded space near the cottage.
Cottage in East Patchogue
4.89 out of 5 average rating, 57 reviews

Bellport Beach Estates Private Cottage with Pool

NicoleRating, 5 stars10 months ago
The house was so peaceful and quiet. The deer were just walking around and calming to watch! The backyard is better than the pictures and would stay there again! My only issue was with the lack of privacy in the house. The doors are similar to shutters to allow airflow, but you could here everyone in all the rooms. Not a huge deal unless you have loud kids!

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