Southampton, NY Cottage Rentals from $257

A beach with a wooden fence, a lifeguard tower, and a house with a balcony overlooking the ocean.

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Our top choices for Southampton cottages

A residential area with houses, a driveway, and a body of water in the background.

1. Steps to the beach | Seabreeze Cottage #3

Hampton Bays

"The property needs a major cleaning and repairs. The floors were sticky, and the carpet was dirty. Furniture was dirty and soiled. There was dried food on the utensils. The pipes groaned at all hours, several times an hour. The bed creaked with every movement. Bedroom blinds were broken and wouldn’t close all the way. The bedside lamp on the wall was falling off. The last straw was the huge spider that jumped down from the closet onto me. We ended up leaving after less than 24 hours and...

Lydia

$406 nightly

Oct 5 - Oct 6

Total with taxes and fees

A single-story house with a gabled roof, a front porch, and a well-maintained garden.

2. Walk to Beach | Seabreeze Cottage #4

Hampton Bays

Weston B.

$434 nightly

Oct 12 - Oct 13

Total with taxes and fees

A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

3. North Fork Resort

Greenport

Harold

$225 nightly

Oct 4 - Oct 5

Total with taxes and fees

A sign for J&S Reeves Cottages with a view of a house and trees.

4. 6th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

Riverhead

Donna M.

$794 nightly

Oct 3 - Oct 4

Total with taxes and fees

5. 5th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

Aquebogue

Leah O.

$836 nightly

Oct 3 - Oct 4

Total with taxes and fees

A lakeside cottage with a covered porch, a sign for J&S Reeves Cottages, and a grassy lawn with lounge chairs.

6. 1st of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

Aquebogue

Simon C.

$928 nightly

Oct 5 - Oct 6

Total with taxes and fees

A deck with a gray sofa, a wooden chair, and a metal fire pit.

7. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Greenport

Jeannette M.

$857 nightly

Nov 2 - Nov 3

Total with taxes and fees

8. 3rd of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

Aquebogue

Wendy B.

$928 nightly

Oct 3 - Oct 4

Total with taxes and fees

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Top Southampton Hotel Reviews

The Bentley Hotel Southampton

10/10 Excellent

"Kind of expected to be disappointed. However, really delighted. Room was lovely, clean and thoughtful appointments. Location was OK, but doable."

Hamlet Inn

10/10 Excellent

"The hotel location is ideal. About a 2 mile radius from the town center, shopping, attractions and beaches. The room is very comfortable where all necessary amenity items are available. We had a nice closet in the room, a refrigerator and microwave. It would have been nice to have a couple of drawers if we had stayed more than 2 nights. The shower was particularly nice! Coffe, tea, soft drinks along with a wide variety of snacks, cakes and candy bars are available the entire day."

Stunning Private Sunny Modern Southampton home-5 beds Last minute discounts

10/10 Excellent

"Loved this home- it was a perfect place for our group of 7 adults! Plenty of comfortable space to sit and talk, both inside and out. Rooms were spacious and comfortable! Check in and check out had limited instructions, which was a bit unusual based on prior experiences, but everything was simple enough. Host was responsive to questions through the app. Overall would recommend and would stay again!"

Newly Renovated, Serene Property with Heated Pool, Tennis, and Resort-Like Spa

10/10 Excellent

"We had a great stay at this house. This was our 3rd year doing this and by far the favorite house of my family. (3 adult kids plus sig others.) The deck and pool space were really comfortable and we used them a lot. The gym and sauna were huge bonuses that were also a big hit. I've actually rented in this area before and I really like the neighborhood. We would definitely consider renting this house next year, depending on our availability around this time of summer. Thanks to the owners for providing fun way to end the summer."

Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

10/10 Excellent

"We did a large family trip to the Hamptons for Labor Day weekend 2026. It was a bucket list trip and the house well exceeded our expectations! It was plenty big and fit our group nicely. We also really enjoyed the location, the large yard and pool. It's a short walk to the water and a quick drive to get into Sag Harbor. The host was great and responded to all of our questions. The check-in, check-out process was also super easy. Highly recommend. We hope to book again in the coming years!"

Find out more about Southampton

Southampton Cottages information

Number of reviews	65
Accommodation	7 Cottages
Lowest Price	$257
Highest Price	$979

Frequently asked questions

How much do cottages in Southampton cost?

Rates for cottages in Southampton range between $257 and $979 per night. Whatever your budget, you're sure to find the perfect place to touch base with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

How many cottages are there in Southampton?

Stay in touch with nature in one of the 7 cottages located in Southampton. To help you choose an ideal property, use our filters to search for must-have amenities or perks.

Are there any family-friendly cottages in Southampton?

Throw your bags down at Villa Gavin and make your family trip to Southampton the best one yet. This family-friendly cottage has a 3.5-star rating and conveniences including laundry facilities and a fireplace. After checking in and chilling out together in your new digs, it's time to head out and start sightseeing. The Hamptons Beaches and Ponquogue Beach are among the family-friendly attractions in Southampton.

Why book your cottage in Southampton with Expedia?

We think that a vacation should be a walk in the park, so if you're in search of cottages in Southampton at an affordable rate, Expedia has got you covered. Save those pennies and select a wallet-friendly option far from the downtown buzz, or book a luxury cottage to treat your loved ones.

How can I find cheap cottages in Southampton?

Expedia can help you look for cheap cottages in Southampton. To discover your special stay in just a few keystrokes, simply use the filter tool to tailor your search results by star rating, budget and amenities.

What is there to do in Southampton near my cottage?

The ideal travel accessory is a well-planned to-do list. Shinnecock Hills Golf Course is an excellent place to start your adventures in Southampton.

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Things to do in Southampton

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Our top choices for Southampton cottages