Cottage holiday rentals in The Hamptons

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Popular amenities for The Hamptons cottage rentals

Cottage rentals with a hot tub

Cottage in Ocean Beach
5 out of 5 average rating, 18 reviews

Charming and Adorable Beach Cottage

LisaRating, 5 stars22 months ago
Louise's place was perfect. Louise was so easy to communicate with, super responsive, kind, thoughtful and truly appreciated that she had the option of flexible dates (instead of so many sat to sat or sun to sun requirements in summer). The cottage was cozy, cute, spotless & well stocked. My teenage kids loved the hot tub (as it was a bit chilly in the evenings) and I loved the outdoor shower. We loved having the bikes to take rides around the Island and loved the location. Our only regret is that we didn't get to stay there longer! We will definitely try to stay at Old Snuggler again!
Cottage in Cutchogue
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 favourite
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!
Guest favourite
Cottage in Fairfield
4.75 out of 5 average rating, 8 reviews

Lil Nauti Cottage Newly Updated Steps To The Beach

MarilynRating, 5 stars20 months ago
Lil Nauti was perfect for our family. The bedrooms were adequate, with very comfortable beds and plenty of pillows. The wardrobe space and drawers were great as we had a long stay with a lot of baggage! Jason has absolutely everything you could possibly want or need for a stay. The kitchen is really well equipped. Cute cottage and delightful private garden.
Cottage in Sayville
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!
Guest favourite
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 favourite
Cottage in Hampton Bays
4.92 out of 5 average rating, 83 reviews

Hamptons Cottage.

DeniseRating, 5 stars1 week ago
The house was just as pictured. Extremely clean and on a peaceful residential street in a convenient location to explore the surrounding towns. Ana was also very responsive!
Guest favourite
Cottage in Southampton
4.93 out of 5 average rating, 46 reviews

Southampton Village Cottage

CharlieRating, 5 stars6 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 favourite
Cottage in New Suffolk
4.97 out of 5 average rating, 38 reviews

New Suffolk Beach Cottage 1 | North Fork

DouglasRating, 5 stars7 months ago
The beach house was great. Instead of being on a road, it was on a green commons area that gave it a really relaxed neighborly feel. It was a very easy and pleasant 1 minute stroll to the beach, where was a great pastry and shop, and restaurant, and some simply amazing views. Deb's communications were also great and check in went amazingly smoothly. Also the town of New Suffolk itself is quite charming, and is a perfect base for exploring vineyards, beaches, hiking trails and whatnot.
Guest favourite
Cottage in East Hampton
4.98 out of 5 average rating, 41 reviews

Chic cottage on lush, secluded acre by the beach.

CorinaRating, 5 stars2 months ago
We had a wonderful stay at Mischa’s home. The house was truly stunning - beautifully decorated and clean. Mischa has clearly thought about all of the little details that make a stay memorable - the kitchen was well stocked and the place was so cozy.
Top Guest favourite
Cottage in Water Mill
4.97 out of 5 average rating, 69 reviews

Head of Pond House - Waterfront Cottage

JillRating, 5 stars3 months ago
Head of the Pond House was in such a beautiful peaceful setting and was exactly what we needed! Quaint, beautifully decorated, cozy, and thoughtfully stocked for a very relaxing stay. Monika was super proactive and helpful with recommendations and left us lots of local yummies. The birds and the sights on the pond (ice sailing!) were lovely. Highly recommend the cottage to take in all that the Hamptons has to offer in a peaceful and tranquil setting.
Top Guest favourite
Cottage in Montauk
4.92 out of 5 average rating, 159 reviews

Montauk Cottage Escape

JulieRating, 5 stars5 months ago
Wonderful time staying at Milton and Megan's. The location was perfect and the home had everything we needed and more to work remotely for the week. Thank you!
Top Guest favourite
Cottage in Hampton Bays
5 out of 5 average rating, 31 reviews

walk to bay, woods cottage

StephanieRating, 5 stars6 months ago
We had the most wonderful and peaceful fall weekend at Brooke’s cozy cottage to celebrate our anniversary, and it was truly unforgettable! The cottage itself is beautifully decorated and felt like a warm home away from home. Brooke went above and beyond to make our stay special, leaving us complimentary champagne and wine to kick off our celebration. The location was perfect for enjoying the crisp fall air and stunning foliage, providing the peaceful retreat we were hoping for. We can’t recommend this place enough and will definitely be back for another stay!
Superhost
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

Private cottage rentals

Cottage in Laurel
4.75 out of 5 average rating, 313 reviews

North Fork Cottage

MelissaRating, 5 stars1 week ago
This place was perfect for what we needed and the location was great for us. Rich was very helpful and we would stay here again.
Top Guest favourite
Cottage in East Hampton
4.91 out of 5 average rating, 142 reviews

East Hampton Fisherman’s Cottage with Secret Room

AlvaroRating, 5 stars3 weeks ago
Thank you Jordan for the lovely stay, the place looks even better in person. This was hands down one of the prettiest and coziest places I’ve stayed.
Top Guest favourite
Cottage in Miller Place
4.99 out of 5 average rating, 130 reviews

Cozy Country Cottage #2

MelissaRating, 5 stars1 week ago
As always, Robs place was perfect. It is our go to spot to stay when we visit my family on Long Island. I’m sure we’ll be back again soon.
Guest favourite
Cottage in Yaphank
4.85 out of 5 average rating, 61 reviews

Beautiful Waterfront Cottage

JoelRating, 5 stars1 month ago
Felt right at home I’d definitely come again.
Superhost
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.
Superhost
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.
Superhost
Cottage in Kings Park
4.8 out of 5 average rating, 174 reviews

Cozy Riverside Cottage

DonnaRating, 5 stars3 weeks ago
We thoroughly enjoyed staying in this Cozy Cottage located in the quaint town on Long Island of Kings Park.
Top Guest favourite
Cottage in Wading River
4.87 out of 5 average rating, 92 reviews

Cozy Sound-side Cottage steps from beach

ChristopherRating, 5 stars4 months ago
We had a great experience staying at Melissa’s cottage and would happily recommend it to anyone else! We were in town from Florida visiting family in Rocky Point for Christmas and chose Melissa’s property as our place to stay. Melissa was very communicative, check in was super easy and we felt right at home on her property. Would definitely consider staying here again. Thanks Melissa!

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