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Compare 85 Apartments in Southold with updated reviews, rates, and availability.

Charming 2 Bedroom Guest Apartment in Essex, CT
10.0 out of 10, Exceptional, (20)
"The host had so many special touches to make this place a wonderful spot to stay. She had little snacks in the kitchen, with coffee and tea in the cupboard. There was half-and-half and the refrigerator, which we really appreciated. The towels in the bathroom were folded like you were in a special hotel. There was also lovely soap, shampoo and conditioner. Due to the cold temperature in the teens, she actually purchased some space heaters to make sure we were warm. Although there was a second...
Charming 2 Bedroom Guest Apartment in Essex, CT
Beautiful 2bedroom w Pool close to the beach and Southampton Village
9.6 out of 10, Exceptional, (4)
"We had a wonderful stay at this property. The apartment was spacious and very clean. The outdoor area was perfect, the kids enjoyed the pool and swing/slide set. Would definitely recommend!"
Beautiful 2bedroom w Pool close to the beach and Southampton Village
MATTITUCK ! The North Forks #1 Winery & Beach Town !
10.0 out of 10, Exceptional, (98)
"Manny is a great guide for your visit. A very quiet and private place with a beautiful patio garden."
MATTITUCK ! The North Forks #1 Winery & Beach Town !
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Charming Greenport Gem 1, 1 Mile to Ferry!
10.0 out of 10, Exceptional, (8)
"My family and I visited for 3 nights in late April, and this was the perfect place for us! Conveniently located in walking distance to downtown Greenport, with ample street parking, and the unit was modern, clean and spacious. The home itself is beautiful and with a lovely, well-cared-for garden. Definitely recommend!"
Charming Greenport Gem 1, 1 Mile to Ferry!
A Touch of Ocean Studio, 1 BTH & Balcony Apt!
A Touch of Ocean Studio, 1 BTH & Balcony Apt!
Downtown Essex Apartment - Steps to River!
10.0 out of 10, Exceptional, (14)
"We loved our stay! Apartment was perfect. Upstairs views to the harbor were lovely to wake up to. Easy, quick walk to town and restaurant. We will be sure to go back and stay there again."
Downtown Essex Apartment - Steps to River!
Convenient and cute in Downtown Old Saybrook
9.6 out of 10, Exceptional, (42)
"I had some business in CT and decided to take a few days of rest and relaxation. I packed my sewing machine and a few books and headed north! This property was perfect. I felt safe and comfortable. I had everything I needed for a quiet weekend."
Convenient and cute in Downtown Old Saybrook
Homeyfeels: Nearshore 1BR with loft + Beach Access
Homeyfeels: Nearshore 1BR with loft + Beach Access
Newly Renovated Luxe 1BR+Bunkbed & Private Deck
Newly Renovated Luxe 1BR+Bunkbed & Private Deck
Sag Harbor Suite by the Beach
9.0 out of 10, Wonderful, (8)
"We were in town to celebrate thanksgiving. Nice cozy 1 bedroom apartment. 5 minute drive to town."
Sag Harbor Suite by the Beach
3 bedroom apartment near Beaches and Outlets Mall
10.0 out of 10, Exceptional, (1)
"They did a great job for one of their 1st times around! Very helpful and communicative."
3 bedroom apartment near Beaches and Outlets Mall
TheSweetDwelling 1BR Beachside Home|TennisPoolPKG!
TheSweetDwelling 1BR Beachside Home|TennisPoolPKG!
Quaint DT Greenport Apt - 2 Mi to Shelter Island!
9.8 out of 10, Exceptional, (56)
"We had a good time. Great location."
Quaint DT Greenport Apt - 2 Mi to Shelter Island!
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
Modern Studio Apt w/ Balcony & Pool View | 1 BTH
Industrial Inspired Interior 1BR+Loft & Deck view
10.0 out of 10, Exceptional, (1)
"We had a wonderful stay at this property! Very clean, just steps to the beach and close to everything we love in the Hamptons!"
Industrial Inspired Interior 1BR+Loft & Deck view
Long Island Sound Studio
10.0 out of 10, Exceptional, (5)
"The place is absolutely magical, both the surrounding area and the studio itself. Studio was very clean and had everything we needed for our stay. We will be back!"
Long Island Sound Studio
Bright Apartment - 1/2 Mi to Greenport Harbor!
10.0 out of 10, Exceptional, (68)
"This is absolutely our favorite home in Greenport - spotlessly clean, lovely renovation, and such an easy walk right into town, just a block or two from everything! Terrific host makes everything easy. Will continue to stay here - a gem!"
Bright Apartment - 1/2 Mi to Greenport Harbor!
House in the Great Western 2BR w/PKG | Tennis+WiFi
House in the Great Western 2BR w/PKG | Tennis+WiFi
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See all available properties in Southold
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.

Other property types in Southold

Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (237)
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is AED 887
AED 1,092 total
includes taxes & fees
2 Jun - 3 Jun
Windward Shores Ocean Resort
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (183)
"Wonderful stay and super clean! Can’t wait to come back. "
The price is AED 1,002
AED 1,303 total
includes taxes & fees
23 Jun - 24 Jun
Cliffside Resort Condominiums
North Fork Escape Near Wineries, Beaches And Hamptons
9.4 out of 10, Exceptional, (18)
"Lovely quaint home. Very clean and spacious. Perfect for a family getaway . Highly recommend."
North Fork Escape Near Wineries, Beaches And Hamptons
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 160 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 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 Croteaux 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.

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