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Browse Select Southold Apartments

Hamptons Haven: Sunny 1-bedroom oasis with modern comforts near the bay!

9.6 out of 10, Exceptional, (5)
"Great place great price nice people. This is an apartment in someone’s house, they were welcoming and helpful. Definitely would stay here again."
Hamptons Haven: Sunny 1-bedroom oasis with modern comforts near the bay!

Private & Spacious Five Room Suite..Steps To Bay Beach and walk to Village.

10.0 out of 10, Exceptional, (147)
"Maritza and John were very friendly hosts and we even met their lovely dog Sara! Central location to Greenport. You have access to the top floor of the house where it is both homely and inviting. Would stay here again"
Private & Spacious Five Room Suite..Steps To Bay Beach and walk to Village.

Homeyfeels: Nearshore 1BR with loft + Beach Access

Homeyfeels: Nearshore 1BR with loft + Beach Access

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

Harbor Heights

9.4 out of 10, Exceptional, (3)
"got engaged while we stayed for a quick weekend away, and had a great time with my fiancé. good location and clean."
Harbor Heights

Sag Harbor Suite by the Beach

8.8 out of 10, Excellent, (10)
"Trvis and Alice are great host and the property was a great place to stay close to the beach and downtown Sag Harbor."
Sag Harbor Suite by the Beach

A Touch of Ocean Studio, 1 BTH & Balcony Apt!

10.0 out of 10, Exceptional, (5)
"Being literally on the beach with resident access to chairs towels umbrellas and snacks is really awesome."
A Touch of Ocean Studio, 1 BTH & Balcony Apt!

The Mast at Soundview · Beach+Ocean+Sunrise

2.0 star property
The price is CA $147
CA $326 total
includes taxes & fees
Jan 31 - Feb 1
The Mast at Soundview · Beach+Ocean+Sunrise

Charming Greenport Gem 1, 1 Mile to Ferry!

10.0 out of 10, Exceptional, (15)
"Beautiful property is in a safe walkable area near restaurants and shops. Off street parking was easy to find. Lovely garden path leads you to the front door. Interior flight of curved/circular stairs takes you up one flight to door. Maybe tricky for someone with mobility issues. Bedrooms and one bath were clean, nicely decorated and well stocked with the essentials including soaps, hair dryer and tissues. Kitchen was bright. Please note there is minimal counter space but well stocked...
Charming Greenport Gem 1, 1 Mile to Ferry!

Modern Studio Apt w/ Balcony & Pool View | 1 BTH

Modern Studio Apt w/ Balcony & Pool View | 1 BTH

MATTITUCK, #1 Winery and Beach Town !

10.0 out of 10, Exceptional, (104)
"We meet Manny when we arrived at the property and he showed us around and gave us great tips on things to do and beaches to visit, his wife found out it was my wife's birthday and she made her a special dessert. It was a great time. "
MATTITUCK, #1 Winery and Beach Town !

Industrial Inspired Interior 1BR+Loft & Deck view

10.0 out of 10, Exceptional, (2)
"There for a race and only really slept there, but the place was nice."
Industrial Inspired Interior 1BR+Loft & Deck view

Hamptons apartment getaway

10.0 out of 10, Exceptional, (1)
"The room was a lot more spacious than I anticipated and everything was very clean. There was some music playing upstairs but it was quiet by nighttime. Check in and check out was very straightforward. Turning into the driveway was a bit difficult when the highway was crowded but was otherwise easy to find "
The price is CA $180
CA $328 total
includes taxes & fees
Jan 31 - Feb 1
Hamptons apartment getaway

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
The price is CA $147
CA $326 total
includes taxes & fees
Jan 31 - Feb 1
The Stern at Soundview · Beach+Ocean+Sunrise

Bright Apartment - 1/2 Mi to Greenport Harbor!

10.0 out of 10, Exceptional, (75)
"We loved this quiet and cozy apartment! It was very clean, updated, and easy to access. John was in communication and even provided dining recommendations. We walked into Greenport center every day and it was the perfect location. We hope to be back again!"
Bright Apartment - 1/2 Mi to Greenport Harbor!

Quaint DT Greenport Apt - 2 Mi to Shelter Island!

9.8 out of 10, Exceptional, (61)
"Very nice spot for a couple to stay. Fully equipped and thoughtfully laid out. Comfortable bed. Updated in all ways. Exceptionally clean and well stocked. Very convenient to downtown and extremely walkable."
Quaint DT Greenport Apt - 2 Mi to Shelter Island!

Villa Bridgehampton Village

3.5 star property
The price is CA $6,000
CA $8,648 total
includes taxes & fees
Feb 1 - Feb 2
Villa Bridgehampton Village

Unit 823 - Ocean Colony Beach and Tennis Club

Unit 823 - Ocean Colony Beach and Tennis Club

Ocean Dwelling w/PKG+Balcony+WiFi+HeatedPool

2.5 star property
9.0 out of 10, Wonderful, (2)
"The property was in a great location. Walk to the beach. The unit we stayed in was also very well organized, and mostly clean aside from the floors needing a good mopping, they were at least debris free which at least kept the ants at bay. The huge shower was a plus! A couple of suggestions, blackout curtains or blinds would be helpful for people who are hoping to get a restful sleep during their vacation. The blinds were completely transparent (light filtering blinds) and let in a lot of...
Ocean Dwelling w/PKG+Balcony+WiFi+HeatedPool

Long Island Sound Studio

10.0 out of 10, Exceptional, (9)
"The studio cottage was charming, quiet and a stone’s throw to the calm waters of the Sound showcasing remarkable views, including the Old Saybrook Light and Finwick Light too. "
Long Island Sound Studio
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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Other property types in Southold

North Fork Dream Getaway, Walk to Private Beach & New In-Ground Pool!

2.0 star property
10.0 out of 10, Exceptional, (1)
"We loved walking down to the beach in the mornings. The house was spacious and clean! Really enjoyed our time! Thank you!"
North Fork Dream Getaway, Walk to Private Beach & New In-Ground Pool!

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (268)
"Was a winter wonderland. Quiet and clean. Staff were very helpful and kind!"
The price is CA $190
CA $248 total
includes taxes & fees
Feb 2 - Feb 3
Windward Shores Ocean Resort

Holiday Specials!!!/Out Door Theater Fire Pit/ Bocce court- WATCH VIDEO!!!

10.0 out of 10, Exceptional, (34)
"This home is quintessentially charming! I arrived late at night, alone. It has a charming curved drive in and there sat the wood home with a large front porch and Forrest behind it. It seemed like little house on a prairie with the porch and dormer windows. The motion lights went on immediately, which I was grateful for. There is a narrow stairwell up to 3 bedrooms, as is customary in older style homes. High ceilings and windows everywhere enhance this property. When I woke there was a family of...
Holiday Specials!!!/Out Door Theater Fire Pit/ Bocce court- WATCH VIDEO!!!
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.

Frequently asked questions

What's it like to stay at an apartment in Southold?
There are plenty of places to stay in Southold with 158 hotels and other accommodations. Though there aren’t many apartments, we can help you locate accommodations that are similar. When you search on Expedia, you can filter by amenities you might find in an apartment such as a kitchen. You can also search for similar properties such as condos, vacation homes, or cottages.
Why would you choose an apartment over a traditional hotel room?
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 who want to stay away from the tourist areas.
What's a favorite apartment I should consider for a stay in Southold?
Here are some of the favorite apartments in the area: Hamptons Haven: Sunny 1-bedroom oasis with modern comforts near the bay!: Situated in Hampton Bays, 12.6 mi/20.2 km from the heart of Southold. Includes free WiFi and Smart TVs. Private & Spacious Five Room Suite..Steps To Bay Beach and walk to Village.: Located 3.8 mi/6.1 km away in Greenport. Free WiFi, private patios, and Smart TVs are included. Access to a spa tub is available on site.
What can I expect from the weather in Southold?
Though 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 temp of 70°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Southold is 57 inches.
What should I see in Southold?
Horton Lane Beach and Horton Point Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Sparkling Pointe and The Old Field Vineyards.
What's the best way to get to and around Southold?
Knowing a bit about the transportation options can save you time when you get to your destination. Fly into East Hampton, NY (HTO), which is located 11.8 mi (18.9 km) away from the city center. Otherwise, you can search for flights to Westhampton, NY (FOK-Francis S. Gabreski), which is 19 mi (30.6 km) away. If you want to explore the larger area, ride aboard one of the trains from Southold Station.