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Next weekend
4 Jul - 6 Jul
In two weeks
11 Jul - 13 Jul
In one month
25 Jul - 27 Jul
In two months
22 Aug - 24 Aug

Featured Apartments in Southold

Ocean Dunes at Amagansett
Lobby

Ocean Dunes at Amagansett

2.5 star property
8.6 out of 10, Excellent, (8)
"Ocean Dunes is a perfect place where the beach meets the village."
Ocean Dunes at Amagansett
Walk to Hawk's Nest Beach: Coastal Old Lyme Apt
Front of property

Walk to Hawk's Nest Beach: Coastal Old Lyme Apt

3.0 star property
Walk to Hawk's Nest Beach: Coastal Old Lyme Apt
Downtown Essex Apartment - Steps to River!
Interior

Downtown Essex Apartment - Steps to River!

3.0 star property
10.0 out of 10, Exceptional, (2)
"A gem situated in downtown Essex."
Downtown Essex Apartment - Steps to River!
Charming Greenport Gem 1, 1 Mile to Ferry!
Front of property

Charming Greenport Gem 1, 1 Mile to Ferry!

3.0 star property
10.0 out of 10, Exceptional, (1)
"extra clean brand new rooms. bathroom door did lock by itself and the small hole on the plate outside did unlock it when depressed otherwise perfect. we had 2 under 3 kids and the way it was set up was safe and fun"
Charming Greenport Gem 1, 1 Mile to Ferry!
Quaint DT Greenport Apt - 2 Mi to Shelter Island!
Interior

Quaint DT Greenport Apt - 2 Mi to Shelter Island!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This was the perfect, in town place to stay for the two of us. Located on a quiet street of well-maintained homes, and with parking right outside, it was a short 1-1/2 block walk to all the shops, restaurants, ferry, docks, etc. The apt is small, but clean and tidy, sun-filled and air-conditioned. We loved staying here and will again in the future."
Quaint DT Greenport Apt - 2 Mi to Shelter Island!
Villa Bridgehampton Village
Outdoor dining

Villa Bridgehampton Village

3.5 star property
Villa Bridgehampton Village
Inviting Beachfront Apartment in Hawk's Nest Beach
Interior

Inviting Beachfront Apartment in Hawk's Nest Beach

3.0 star property
Inviting Beachfront Apartment in Hawk's Nest Beach
Bright Apartment - 1/2 Mi to Greenport Harbor!
Interior

Bright Apartment - 1/2 Mi to Greenport Harbor!

3.0 star property
Bright Apartment - 1/2 Mi to Greenport Harbor!
Sage and Madison House - Hall Suite - 2nd Floor
Exterior

Sage and Madison House - Hall Suite - 2nd Floor

3.0 star property
Sage and Madison House - Hall Suite - 2nd Floor
Best Hamptons Get-Away
Property grounds

Best Hamptons Get-Away

2.5 star property
Best Hamptons Get-Away
Luxurious 8 Bedroom Retreat With Pool East Hampton
Room

Luxurious 8 Bedroom Retreat With Pool East Hampton

2.0 star property
Luxurious 8 Bedroom Retreat With Pool East Hampton
Luxury Villa 7br 7baths With a Private Pool Hamptons
Room

Luxury Villa 7br 7baths With a Private Pool Hamptons

2.0 star property
Luxury Villa 7br 7baths With a Private Pool Hamptons
Shinnecock Bay Waterfront
WiFi

Shinnecock Bay Waterfront

3.5 star property
Shinnecock Bay Waterfront
Plum Guide - Ocean Spray
Outdoor pool

Plum Guide - Ocean Spray

3.5 star property
Plum Guide - Ocean Spray
Sage and Madison House - Madison Suite - 1st Floor
Exterior

Sage and Madison House - Madison Suite - 1st Floor

3.0 star property
Sage and Madison House - Madison Suite - 1st Floor
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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Frequently asked questions

What's it like to stay at an apartment in Southold?
You'll find a lot of options for your stay in Southold with 159 hotels and other accommodation options. Though there aren't many apartments, we can help you locate similar accommodation. When you search on Expedia, you can filter by amenities such as a kitchen--- just one of the conveniences you might find in an apartment. Even filter by similar properties such as holiday homes, condos or guest houses.
Why choose apartments instead of traditional hotels?
Often more spacious than a traditional hotel room, an apartment comes with a kitchen, so you can cook some of your meals. Apartments are ideal for families who want the conveniences of home, and also for couples looking for something with a more local feel.
What can I expect from the weather during my trip to Southold?
Although weather is just one factor, it can really affect your travel plans, especially if you are planning a longer stay in Southold. The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Southold is 1452 mm.
What should I see in Southold?
McCabe's Beach and Horton Lane Beach are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Sparkling Pointe and Croteaux Vineyards.
What's the best way to get to and around Southold?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into East Hampton, NY (HTO), which is located 11.8 mi (18.9 km) from the city centre. Otherwise, you can search for flights to Westhampton, NY (FOK-Francis S. Gabreski), which is 19 mi (30.6 km) away. To venture out into the surrounding area, hop aboard a train at Southold Station.