
Cottage vacation rentals in Sag Harbor
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Top-rated cottage rentals in Sag Harbor
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Vacation rentals for every style
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Popular amenities for Sag Harbor cottage rentals
Pet-friendly cottage rentals

Hamptons Cottage.
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.

Southampton Village Cottage
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!

Waterfront Getaway on Shelter Island
Quiet, peaceful. Pictures do not do this place justice. Perfect place for 2 couples or 2 couples and kids. Set up was great.

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

4 Br Beach House; Short Walk to Beach!
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.

Bay View Cottage- Short Walk to Private Beaches
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!

Cottage in Calverton
Perfect for our weekend getaway. Very clean and relaxing and close walk to a cute little beach. We would stay here again!

Cozy Shelter Island 2 Bedroom 1 Bath Cottage
Perfect spot for a weekend trip and dog friendly which can be rare. Super responsive host and very clean.
Private cottage rentals

Swim, kayak, fish - Hamptons Fresh water Getaway!
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.

Beach cottage bungalow
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.

Renovated Cottage, steps to the Beach & Wine Trail
Cute little neighborhood tucked away, very clean place with cute outdoor area to hang.

Cheerful 3 bedroom cottage with parking
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

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

Cozy, Comfortable Island Cottage
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 BAT CAVE
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.

Summer Cottage
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

Charming Scandinavian Inspired Beach Cottage
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!!!

Beautiful cottage on East End
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

1870's Schoolhouse Converted to Cozy Cottage
Nice house. Well kept. A little crazy trying to get 6 adults dressed and ready for a wedding with only 1 shower.

Scrimshander House
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!

Cozy Seaside Cottage
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!

Beach and Wine Time Country Cottage
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.

Stunning waterfront modern farmhouse with dock.
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.

Luxury Gem At The Heart of Sag Harbor Village
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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- Beach
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Cooper's Beach, Southampton
- Quotonset Beach
- Giants Neck Beach
- Shinnecock Hills Golf Club
- Woodmont Beach
- Clinton Town Beach
- Walnut Public Beach
- Seaside Beach
- TPC River Highlands
- Amagansett Beach
- Blue Shutters Beach
- Shennecossett Beach
- Connetquot River State Park Preserve
- Outer Beach at Smith Point County Park
- Long Island Aquarium
- Groton Long Point Main Beach
- Attawan Beach
- East Beach
- Bayview Beach
- Fort Trumbull Beach