Cottage vacation rentals in Sag Harbor

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Popular amenities for Sag Harbor cottage rentals

Pet-friendly cottage rentals

Guest favorite
An open living space is presented, featuring a modern kitchen with stainless steel appliances and a white circular dining table surrounded by black chairs. A large television is mounted on a white cabinet, and light enters through a nearby window.
Cottage in Hampton Bays
4.92 out of 5 average rating, 84 reviews

Hamptons Cottage.

SharonRating, 5 stars1 day ago
Honestly probably the BEST AirBnB I have ever stayed in, and we use AirBnb a lot. The place is immaculate, and everything seemed brand new. It is even much nicer than the photos online show, and I feel it's even bigger than the pictures show. I forgot my charger at the unit, and she contacted me right away and saved it for me. She was quick to respond to anything I asked. The location is great, on a quiet dead end street. The neighborhood is very quiet. 10 minute drive to Southampton Village and just a few minutes from Ponquogue Ocean beach. The backyard is huge and pretty. The rooms are sunny and bright. Everything seemed brand new. The beds were comfortable. Sheets and towels were pristine. Kitchen had coffee, and there is a Hampton Coffee 5 minutes away. Design and decor were really top notch. There is a little table and chairs outside. She leaves beach towels! There is even a little electric fireplace. A truly perfect stay and Ana is so nice! Can't wait to come back.
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
Cottage in Shelter Island
4.91 out of 5 average rating, 23 reviews

Waterfront Getaway on Shelter Island

MelissaRating, 5 stars7 months ago
Quiet, peaceful. Pictures do not do this place justice. Perfect place for 2 couples or 2 couples and kids. Set up was great.
Guest favorite
Cottage in North Fork
5 out of 5 average rating, 13 reviews

Lovely North Fork Beach Cottage (2 BR/2 bath)!

ChristinaRating, 5 stars2 weeks ago
Had a great weekend at the cottage! Meredith was so great letting us check in early and was super helpful and responsive. The cottage is gorgeous and has everything you need. Loved it! Thank you!
Superhost
A spacious outdoor deck features a mix of wooden lounge chairs and a dining table, surrounded by greenery. The area is equipped with a gas grill, providing opportunities for outdoor cooking and dining. Sunlight filters through the trees, enhancing the inviting atmosphere.
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.
Superhost
Cottage in Southampton
4.9 out of 5 average rating, 59 reviews

Bay View Cottage- Short Walk to Private Beaches

Stephanie Rating, 5 stars4 months ago
Danielle’s place was adorable and extremely clean! The kitchen was beautiful and the home felt cozy and homey. She was very responsive and a very kind host. I can’t recommend her enough and would absolutely rent from her again!
Superhost
A serene coastal view captures a vibrant sunset, where the sun dips below the horizon, casting warm hues across the sky. Gentle waves lap against dark rocks, creating a tranquil atmosphere along the shore. The scene evokes a sense of calm and natural beauty.
Cottage in North Fork
4.91 out of 5 average rating, 53 reviews

Cottage in Calverton

KaitlynRating, 5 stars8 months ago
Perfect for our weekend getaway. Very clean and relaxing and close walk to a cute little beach. We would stay here again!
Superhost
A charming cottage is framed by vibrant pink azaleas, enhancing the exterior's appeal. Lush green grass surrounds the home, and a clear blue sky provides a bright backdrop. Windows allow natural light to fill the interior, which features a welcoming porch area.
Cottage in Shelter Island
4.95 out of 5 average rating, 39 reviews

Cozy Shelter Island 2 Bedroom 1 Bath Cottage

Brooke BiancaRating, 5 stars7 months ago
Perfect spot for a weekend trip and dog friendly which can be rare. Super responsive host and very clean.

Private cottage rentals

A charming cottage is nestled among lush greenery beside the lake. A wooden dock extends over the water, featuring a pair of white lounge chairs. Lilypad-covered areas float near the shore, creating a serene natural setting.
Cottage in Southampton
4.9 out of 5 average rating, 50 reviews

Swim, kayak, fish - Hamptons Fresh water Getaway!

SeanRating, 5 stars20 months ago
1st initial contact - Our host Richard reminds me of cool eclectic writer I once new. - he provides clear direction as well as a brief history of the lake; if you were to indulge. Mind you no motor powered vehicles on the lake so it’s silent. -Neighbors don’t bother you. -Perfect for a lovers weekend or a small family vacation. Close to everything Hamptons!! My family & I strongly recommend this lakeside gem in South Hampton NY.
A serene coastal view presents a sandy beach stretching along the shoreline. Gentle waves are visible against the sand, with lush greenery lining the top of the dunes. The horizon showcases soft, muted colors of a sunset, reflecting a tranquil atmosphere.
Cottage in North Fork
5 out of 5 average rating, 3 reviews

Beach cottage bungalow

DavidRating, 5 stars20 months ago
We recently stayed at David's property, enchanted by the ocean view through the lush trees. The clean private balcony presented a captivating panorama. Inside, the accommodation was comfortable with a spotless bathroom and room. Although there was an older wardrobe, the home was well-appointed with super-fast WiFi over 100mbps, Netflix, YouTube, AC, ceiling fans, and a kitchen equipped with essential appliances and utensils. David's place also offered a private entrance, parking, self-check-in with a unique code, and an outdoor dining table, contributing to a secure and convenient stay. The quiet neighborhood, just 30 seconds from beach stairs, created a serene ambiance. The 5 mph property speed limit ensures safety for children. In summary, David's ocean-view property offered a tranquil retreat with modern comforts and an attentive host. Ideal for those seeking peaceful surroundings and convenience, we highly recommend David's place for an unforgettable experience.
A private outdoor seating area features comfortable sectional seating and a single chair situated around a circular fire pit. The space is enclosed by wooden slats for privacy, while light grey decking adds to the neutral aesthetic.
Cottage in North Fork
4.79 out of 5 average rating, 128 reviews

Renovated Cottage, steps to the Beach & Wine Trail

BreeRating, 5 stars7 months ago
Cute little neighborhood tucked away, very clean place with cute outdoor area to hang.
A bright living area features large windows that allow natural light to flood the space. A comfortable white sofa is complemented by a glass coffee table, while a patterned area rug adds warmth. A dining area and kitchen are visible in the background, offering an open and airy feel.
Cottage in East Hampton
5 out of 5 average rating, 7 reviews

Cheerful 3 bedroom cottage with parking

MathieuRating, 5 stars8 months ago
Amanda and Jim’s place is just a dream. Perfectly located in the most peaceful area of East Hampton, walking distance (less than 10 mins) from the beach where most of the time you will be alone. This is just paradise. The house itself is a lovely cottage, fully renovated with the greatest taste and attention to details. It has all the amenities one can expect and you just feel like home. It accommodated perfectly the 4 of us. The garden is also beautiful and we really enjoyed having breakfast and lunch under the trees surrounded by the flowers. Amanda and Jim are the most wonderful hosts answering any question you may have and sharing precious advice always with a smile. Definitely a house we would visit again. Definitely
A row of lush grapevines extends across a vibrant green field, under a clear blue sky. The trellises support the vines, casting soft shadows on the bright grass below.
Cottage in North Fork
4.75 out of 5 average rating, 8 reviews

Baiting Hollow Cozy Cottage w/‘walk-to-beach'

AlexanderRating, 5 stars19 months ago
Kenneth's place is a great little bungalow type home. It is very close to the path down to the beach. For me the spot was very convenient for what I needed. I would definitely stay again.
A serene waterway is captured under a clear blue sky. The green shoreline is visible in the distance, while a small boat navigates the calm waters. The scene conveys a tranquil atmosphere, ideal for observing local wildlife or enjoying a leisurely day on the water.
Cottage in Shelter Island
5 out of 5 average rating, 10 reviews

Cozy, Comfortable Island Cottage

CarisaRating, 5 stars22 months ago
They are great hosts and their place was perfect for our stay. We hope to get back to Shelter Island again. The sailing was great!
The cottage's inviting entrance features a blue front door with a welcome sign. A charming bench with pillows sits beside two lanterns on a stone patio. Windows flank the door, allowing natural light to illuminate the area, surrounded by vibrant greenery.
Cottage in Sag Harbor
5 out of 5 average rating, 36 reviews

the BAT CAVE

TimothyRating, 5 stars34 months ago
This rental is truly a home away from home. It has everything anyone could need or want from a modest summer rental. Clean cozy indoor space and beautifully inviting outdoor space- a Zen oasis.
A serene beach scene presents soft, golden sand meeting gentle ocean waves under a clear blue sky. Small birds can be seen wandering along the shoreline, while puffy clouds drift lazily overhead, creating a tranquil atmosphere.
Cottage in Southampton
4.74 out of 5 average rating, 23 reviews

Summer Cottage

PatriceRating, 5 stars46 months ago
My friend and I had a great stay at Fulvia’s cottage. It was beautifully, tastefully, decorated and so comfortable. The front porch was bright and airy and fun to sit and have a drink in the evening. I was glad for all the amenities Fulvia thought about, like having shower gel, shampoo, conditioner & hairdryer- these things are bulky to bring so I really appreciate them. And, really good bread and eggs as well as espresso, tea was well stocked for breakfast in the morning. We loved the location walking distance to the bay beach and great pizza place. Would love to come back here again!

Luxury cottage rentals

Top guest favorite
A bright and airy living space features a comfortable white sofa adorned with purple accents. Natural light pours in through large windows, illuminating the open-plan kitchen with modern appliances. A cozy wood stove complements the warm wood flooring, inviting relaxation in the room.
Cottage in Sag Harbor
4.98 out of 5 average rating, 65 reviews

Charming Scandinavian Inspired Beach Cottage

JeffRating, 5 stars3 weeks ago
Had a lovely time at Daniels adorable rental! The space was bright, airy and cozy. Loved the kitchen setup and open living area. The place was thoughtfully designed, the location was less than 10 minutes from downtown Sag Harbor. Only wish the weather was better, the beach is a 2 minute walk from the house! We'll most certainly be heading back!!!
Superhost
An open-plan interior showcases a staircase leading to a loft area, with wooden railings highlighting the space. The kitchen features white cabinetry and modern appliances. Natural light floods in from the windows, enhancing the inviting atmosphere of the living area and dining space.
Cottage in North Fork
4.92 out of 5 average rating, 52 reviews

Beautiful cottage on East End

AshleyRating, 5 stars4 months ago
Vincent’s place was great for my husband, myself, our baby and my parents to stay when visiting Jamesport for a wedding. Beautiful cottage, close to everything, and Vincent was very easy to communicate with. Would stay here again
Superhost
The exterior of a charming blue home features a vibrant yellow front door and a symmetrical design. Lush greenery surrounds the property, with well-maintained gardens framing the entrance. A pathway leads toward the door, and ample lawn space enhances the inviting approach.
Cottage in North Fork
4.95 out of 5 average rating, 62 reviews

1870's Schoolhouse Converted to Cozy Cottage

PeterRating, 5 stars7 months ago
Nice house. Well kept. A little crazy trying to get 6 adults dressed and ready for a wedding with only 1 shower.
Guest favorite
An inviting outdoor seating area is framed by neatly arranged greenery. Comfortable sofas are paired with a low coffee table, which holds refreshments. Natural wood decking surrounds the space, enhancing the bright, outdoor atmosphere while providing a cozy gathering spot.
Cottage in North Fork
5 out of 5 average rating, 72 reviews

Scrimshander House

ChristinaRating, 5 stars6 months ago
Stephen was extremely communicative and accommodating. We booked this last minute and the home was in mint condition. Beautiful northfolk style home that is walking distance to town, local beach/park, and the ferry. Highly recommend Stephen’s home if you are looking for a place local to town with a great backyard. We spent most of our time enjoying the yard!
Guest favorite
An aerial view of a historic home surrounded by lush greenery and trees. The exterior features a large porch and multiple windows, showcasing the architectural details. Nearby streets and other residences are visible, along with a glimpse of the water in the background.
Cottage in North Fork
4.97 out of 5 average rating, 92 reviews

Cozy Seaside Cottage

SophieRating, 5 stars4 months ago
I stayed here with my mom and siblings over Thanksgiving weekend and it was absolutely perfect. The entrance was a little hard to find at night, but Allison's directions made it easier. The house was notably spotless. We joked that we must have been the first guests based on how clean it was. All of the beds were comfortable, the house was nice and quiet, and we genuinely had no complaints! So happy we found this place. Allison is a great host. She was very responsive and friendly. I would recommend this stay to anyone and hope to stay here again!
Guest favorite
Cottage in North Fork
4.9 out of 5 average rating, 60 reviews

Beach and Wine Time Country Cottage

PaulaRating, 5 stars7 months ago
Deb’s place was very peaceful, comfortable, and well appointed. We immediately felt at home and enjoyed the interesting decor and personal style. It felt like staying in your own bed and breakfast. There were so many places to relax, and the front and back porches were so welcoming. The location can’t be beat if you want to check out the local wineries, farmstands, and great restaurants. An easy walk across the street to Peconic Bay, you can see from the upstairs bedroom. Kitchen was well appointed with everything you would need for cooking. Short ride to markets, farmstands, and Love Lane for shops and restaurants, about 20 minutes to Greenport.
Guest favorite
A peaceful waterfront view is captured, showcasing a wooden deck with light blue lounge chairs centered around a small table. A private boat dock extends into the calm water, bordered by lush greenery and trees along the shoreline.
Cottage in North Fork
4.98 out of 5 average rating, 44 reviews

Stunning waterfront modern farmhouse with dock.

PatriciaRating, 5 stars4 weeks ago
Returning guest, we had a wonderful weekend at Michelle's idyllic home. Plenty of space for our two families and 3 kids. The kids love having their own space in the "she shed" while the adults enjoy the lakeside views from both the yard and inside the spacious living area. The house is always immaculately clean. Beds and other furnishings are comfortable, and the house is an easy drive to everything the North Fork has to offer. We look forward to returning (again!) soon.
Top guest favorite
The exterior of the cottage features a charming gray facade with large windows. A brick patio is surrounded by landscaped areas, including greenery and a water feature. Outdoor seating is provided at a rectangular table and chairs, creating an inviting space for relaxation.
Cottage in Sag Harbor
5 out of 5 average rating, 49 reviews

Luxury Gem At The Heart of Sag Harbor Village

MaryRating, 5 stars3 weeks ago
Lovely, charming and comfortable little house. Perfect location and very walkable. We had a little trouble with the lockbox (user error!) but Marie was immediately responsive and helpful. We loved our stay and hope to return next time we are in the area.

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