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

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Southampton cottages

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

1. Seabreeze #3 Cozy Cottage steps to the beach

Seabreeze #3 Cozy Cottage steps to the beach
Hampton Bays
8.0 out of 10, Very good, (2 reviews)
"Camila was very communicative and helpful. The cottage clearly has a history of high traffic, and while it holds a certain rustic charm, it's undeniably showing its age. The property feels quite worn and tired, with fixtures and furnishings having seen better days. On the surface, the cottage was tidy upon arrival, but closer inspection revealed that it lacked a deep, thorough cleaning. While the main living areas were presentable, the corners, baseboards, and other area's not immediately...
United States
Anonymous traveller
The price is CA $154
CA $684 total
includes taxes & fees
Sep 3 - Sep 4
Seabreeze #3 Cozy Cottage steps to the beach
A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (52 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is CA $411
CA $469 total
includes taxes & fees
Oct 1 - Oct 2
North Fork Resort
A single-story house with a gabled roof, a front porch, and a well-maintained garden.

3. Seabreeze 4 Charming Cottage footsteps to beach

Seabreeze 4 Charming Cottage footsteps to beach
Hampton Bays
9.0 out of 10, Wonderful, (7 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is CA $154
CA $684 total
includes taxes & fees
Sep 8 - Sep 9
Seabreeze 4 Charming Cottage footsteps to beach
An aerial view of J&S Reeves Cottages, featuring a dock, boats, and a lake.

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

4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Aquebogue
9.8 out of 10, Exceptional, (19 reviews)
"Great cottage on amazing grounds! We loved the screened in porch. Sandy and john are great hosts. We also loved using the kayaks and checking out the bay."
United States
Richard C.
The price is CA $942
CA $1,297 total
includes taxes & fees
Sep 3 - Sep 4
4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
A deck with a gray sofa, a wooden chair, and a metal fire pit.

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

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Greenport
10.0 out of 10, Exceptional, (1 review)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is CA $860
CA $1,485 total
includes taxes & fees
Sep 15 - Sep 16
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
A grassy deck with a view of a lake, boats, and a cottage.

6. 2nd of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

2nd of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Aquebogue
9.6 out of 10, Exceptional, (5 reviews)
"Great rental experience. Owners friendly and available"
United States
Patricia and Michael F.
The price is CA $790
CA $1,120 total
includes taxes & fees
Sep 11 - Sep 12
2nd of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

7. 5th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

5th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Aquebogue
10.0 out of 10, Exceptional, (3 reviews)
"Fantastic experience. Cabin was clean and quiet. Beautiful mornings on the water."
United States
Leah O.
The price is CA $942
CA $1,297 total
includes taxes & fees
Sep 3 - Sep 4
5th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
An aerial view of J&S Reeves Cottages with a dock and boats.

8. 1st of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

1st of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Aquebogue
9.0 out of 10, Wonderful, (7 reviews)
"Nice scenery. Spartan kitchen furnishings and bathroom toiletries. Paid booking (including all ocuppants and pets) and was invoiced by vrbo. Received addtional invoice from the owner adding 250 dolars pet fee (125x2 pets) which was not listed on the property description that only mentions "pet friendly"."
United States
Simon C.
The price is CA $1,131
CA $1,517 total
includes taxes & fees
Sep 2 - Sep 3
1st of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Southampton Hotel Reviews

Hamlet Inn

Hamlet Inn

10/10 Excellent
"I loved staying here! Great location, great rooms, and the woman who runs it (Denise?) is so incredibly helpful in directing guests to the best beaches, restaurants, least traffic routes, activities. Will stay here many times in the future!"
Thomas 3-night trip
Posted 5 hours ago
Hamlet Inn

Find out more about Southampton

Southampton Cottages information

Number of reviews
44
Accommodation
8 Cottages
Lowest Price
CA $469
Highest Price
CA $1,517

Frequently asked questions

How much do cottages in Southampton cost?
Rates for cottages in Southampton range between CA $469 and CA $1,517 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 8 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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