Search Cottages in Southold

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sep - 27 Sep

Our top choices for Southold cottages

Exterior

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (43 reviews)
"The place was super cozy and the host was wonderful! "
United States
Philip L.
The price is AED 460
AED 862 total
includes taxes & fees
7 Jun - 8 Jun
1-bedroom cottage with Grove Beach 🏖️ access.
Balcony

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (20 reviews)
"Great stay & great staff!"
United States
James
The price is AED 1,015
AED 1,159 total
includes taxes & fees
17 Jun - 18 Jun
North Fork Resort
Exterior

Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (11 reviews)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
The price is AED 1,466
AED 2,601 total
includes taxes & fees
23 Jun - 24 Jun
Beach Cottage, private beach and pass
Exterior

Seabreeze #3 Cozy Cottage steps to the beach

Seabreeze #3 Cozy Cottage steps to the beach
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
The price is AED 511
AED 1,951 total
includes taxes & fees
8 Jun - 9 Jun
Seabreeze #3 Cozy Cottage steps to the beach
Pool

Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!

Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!
Calverton
9.4 out of 10, Exceptional, (42 reviews)
"The description and photos are accurate. The beach is close."
United States
L A.
Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!
Exterior

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Old Saybrook Center
9.4 out of 10, Exceptional, (46 reviews)
"Lovely cottage! Enjoyed our stay! "
United States
Joyce S.
The price is AED 1,234
AED 2,299 total
includes taxes & fees
8 Jun - 9 Jun
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Terrace/patio

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 AED 2,086
AED 3,684 total
includes taxes & fees
7 Jun - 8 Jun
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Exterior

Town walking distance-Bridgehampton Cottage

Town walking distance-Bridgehampton Cottage
Bridgehampton
9.4 out of 10, Exceptional, (10 reviews)
"Walking distance to Bridgehampton and a short drive to sag harbor. Great for 2 couples."
United States
Jim M.
The price is AED 4,683
AED 6,832 total
includes taxes & fees
19 Jun - 20 Jun
Town walking distance-Bridgehampton Cottage
Exterior

Seabreeze 4 Charming Cottage walk to US Open

Seabreeze 4 Charming Cottage walk to US Open
Hampton Bays
8.8 out of 10, Excellent, (3 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is AED 408
AED 1,808 total
includes taxes & fees
7 Jun - 8 Jun
Seabreeze 4 Charming Cottage walk to US Open
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southold Hotel Reviews

The Atlantic Hotel

The Atlantic Hotel

6/10 Okay
"Hotel is fine if you are just there for a night, maybe two, but the room, especially the carpet, need some major updates."
Michelle 1-night trip
Posted 1 hour ago
The Atlantic Hotel

Frequently asked questions

Why book your cottage in Southold with Expedia?
Reserving a cottage in Southold is as easy as working out your travel dates and selecting your ideal place for a getaway in nature. From high-end retreats to low-cost properties and cottages that feature perks like a hot tub, Expedia has something for all traveler styles. As for unbeatable deals? We have them too!
How can I find cheap cottages in Southold?
A good way to spot cheap cottages in Southold is with Expedia's convenient filter tool. Refine your search by budget, star rating and amenities to secure unbeatable prices in just a few keystrokes.