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Compare 108 Apartments in Southold with updated reviews, rates, and availability.

Quaint DT Greenport Apt - 2 Mi to Shelter Island!
Greenport Vacation Rental | 1BR | 1BA | 400 Sq Ft | Stairs Required
Quaint DT Greenport Apt - 2 Mi to Shelter Island!
9.8 out of 10, Exceptional, (60)
"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!
Private & Spacious Five Room Suite..Steps To Bay Beach and walk to Village.
Hydrangea Blooming Morning
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.
Hamptons Haven: Sunny 1-bedroom oasis with modern comforts near the bay!
Living area
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!
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
Homeyfeels: Nearshore 1BR with loft + Beach Access
Living area
Homeyfeels: Nearshore 1BR with loft + Beach Access
Homeyfeels: Nearshore 1BR with loft + Beach Access
Sag Harbor Suite by the Beach
Beach
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
MATTITUCK, #1 Winery and Beach Town !
Like having your own private beach
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 !
Unit 1022 - Ocean Colony Beach and Tennis Club
Living area
Unit 1022 - Ocean Colony Beach and Tennis Club
6.0 out of 10, (1)
Unit 1022 - Ocean Colony Beach and Tennis Club
Charming Greenport Gem 1, 1 Mile to Ferry!
Greenport Vacation Rental | 2BR | 1BA | Stairs Required | 900 Sq Ft
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!
TheSweetDwelling 1BR Beachside Home|TennisPoolPKG!
Living area
TheSweetDwelling 1BR Beachside Home|TennisPoolPKG!
2.0 out of 10, (1)
"The accommodation was extremely old like 1970 and hadn’t been renovated since then. Old discusting furniture. They said queen bed only full. The steps and hallway outside was littered with crumbs and crackers. Bags of garbage were outside. The beach was best part from what I could.l see The pool was small and very old. The steps down to the beachwere creepy and many. There are much better motels for less money in the area. Not a place for seniors or anyone with handicaps. "
TheSweetDwelling 1BR Beachside Home|TennisPoolPKG!
A Touch of Ocean Studio, 1 BTH & Balcony Apt!
Interior
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!
Tucked into the quiet woods of Sag Harbor.
Outdoor dining
Tucked into the quiet woods of Sag Harbor.
Tucked into the quiet woods of Sag Harbor.
Modern Studio Apt w/ Balcony & Pool View | 1 BTH
Living area
Modern Studio Apt w/ Balcony & Pool View | 1 BTH
Modern Studio Apt w/ Balcony & Pool View | 1 BTH
Industrial Inspired Interior 1BR+Loft & Deck view
Living area
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
Long Island Sound Studio
View from the front step
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
Bright Apartment - 1/2 Mi to Greenport Harbor!
Greenport Vacation Rental | 1BR | 1BA | 600 Sq Ft | Stairs Required
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!
House in the Great Western 2BR w/PKG | Tennis+WiFi
Living area
House in the Great Western 2BR w/PKG | Tennis+WiFi
8.0 out of 10, Very Good, (2)
"Disappointing for costs."
House in the Great Western 2BR w/PKG | Tennis+WiFi
My Amity 1BR Beachside Home | Tennis+Pool+WiFi+PKG
Living area
My Amity 1BR Beachside Home | Tennis+Pool+WiFi+PKG
8.8 out of 10, Excellent, (3)
"Amazing location. The unit is small but easy and basic. You can’t beat being 2 mins from the beach and the complex has nice amenities. We’ll be back!"
My Amity 1BR Beachside Home | Tennis+Pool+WiFi+PKG
Downtown Essex Apartment - Steps to River!
Essex Vacation Rental | 1BR | 2BA | 900 Sq Ft | Access Only By Stairs
Downtown Essex Apartment - Steps to River!
10.0 out of 10, Exceptional, (18)
"Definitely recommend! We have nothing but great things to say about our trip, starting with this rental apartment. It was absolutely clean, lovely and very interesting. Lots of cool details to this apartment, including the beautiful view of the harbor right outside the bedroom window with comfy reclining chairs to relax and enjoy the view. The grounds are also beautiful and the location was perfect, right in the center of town, with lots of charming shops and good restaurants within a short...
Downtown Essex Apartment - Steps to River!
Hamptons Apartment
Private kitchen
Hamptons Apartment
9.8 out of 10, Exceptional, (7)
"We had a great experience. The location was very convenient and the place was very comfortable and clean. The listing is exactly how it looked when we arrived. We will certainly stay again. "
Hamptons Apartment
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

Windward Shores Ocean Resort
Property grounds
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (262)
"smooth check in, very clean place, via text comunication extremely effective, we also loved the small kitchen in the room, ideal for some coffee making or warming ubp a bite we simply loved the place."
The price is SAR 474
SAR 623 total
includes taxes & fees
3 Dec - 4 Dec
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Room
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (206)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"
Cliffside Resort Condominiums
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
Heated 40ft saline pool and deck in separate secure fenced area with all day sun
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
10.0 out of 10, Exceptional, (166)
"Perfect family home"
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
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 161 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?
Listed below are some of the more popular apartments in the area: Quaint DT Greenport Apt - 2 Mi to Shelter Island!: It’s situated in Greenport, 4.5 mi/7.3 km away. Includes outdoor space. Sag Harbor Suite by the Beach: 9.1 mi/14.7 km away in Sag Harbor. Private & Spacious Five Room Suite..Steps To Bay Beach and walk to Village.: Located in Greenport, 3.8 mi/6.1 km from Southold. Includes free WiFi, private patios, and Smart TVs. 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 Sannino’s Bella Vita Vineyard.
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.