Search Southold Cottages

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

Next weekend
Nov 14 - Nov 16
In two weeks
Nov 21 - Nov 23
In one month
Dec 5 - Dec 7
In two months
Jan 2 - Jan 4

Cottages in Southold

Free WiFi, bed sheets
North Fork Cottages & RV Resort

North Fork Cottages & RV Resort

3.0 star property
Greenport
10.0 out of 10, Exceptional, (1)
"Great stay! Very clean and new. Comfy beds, great location "
United States
Lisa
$195 nightly
The price is $223
Nov 9 - Nov 10
Total with taxes and fees
North Fork Cottages & RV Resort
Smart TV
Hidden gem! Southampton beach cottage

Hidden gem! Southampton beach cottage

Hampton Bays
10.0 out of 10, Exceptional, (1)
$400 nightly
The price is $457
Nov 16 - Nov 17
Total with taxes and fees
Hidden gem! Southampton beach cottage
Exterior
1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.

Clinton
9.2 out of 10, Wonderful, (36)
"Host was very friendly and accommodating"
United States
Monika M.
$192 nightly
The price is $218
Nov 11 - Nov 12
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Exterior
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Old Saybrook Center
9.6 out of 10, Exceptional, (38)
"Nicely decorated and clean. "
United States
Lauren
$450 nightly
The price is $509
Nov 9 - Nov 10
Total with taxes and fees
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)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
$484 nightly
The price is $553
Nov 18 - Nov 19
Total with taxes and fees
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Terrace/patio
Orient Village — Historic Bayfront Cottage — 2025 Season

Orient Village — Historic Bayfront Cottage — 2025 Season

Orient
10.0 out of 10, Exceptional, (23)
"Step away from your busy schedule, step back in time, and step down to the beach. Bayside Cottage is an idyllic, charming, and rare place -- one increasingly harder to find as grandiose properties populate many parts of the Island. Thankfully the North Fork has retained much of its character since we began visiting some 20 years ago, and Orient is beautifully preserved with a lot of tender loving care, especially towards nature. It was turtle season in June! At Bayside, circa 1887, one doesn't...
United States
Jennifer G.
$621 nightly
The price is $710
Nov 30 - Dec 1
Total with taxes and fees
Orient Village — Historic Bayfront Cottage — 2025 Season
Exterior
Southampton cozy cottage by the beach

Southampton cozy cottage by the beach

Hampton Bays
8.8 out of 10, Excellent, (3)
"Great stay. Would stay again. "
United States
Weston B.
$400 nightly
The price is $457
Nov 16 - Nov 17
Total with taxes and fees
Southampton cozy cottage by the beach
Exterior
East End Escape

East End Escape

Flanders
$463 nightly
The price is $529
Nov 9 - Nov 10
Total with taxes and fees
East End Escape
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

Hotel Indigo East End by IHG

Hotel Indigo East End by IHG

10/10 Excellent
"The accommodations were compact and comfortable. The restaurant offers exceptional cuisine; I highly recommend it and anticipate a return visit."
JUDINE 2-night trip
Posted 2 days ago
Hotel Indigo East End by IHG

Find out more about Southold

Southold Cottages information

Number of reviews
99
Accommodation
198 Cottages
Lowest Price
$218
Highest Price
$710

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.

Explore a world of travel with Expedia