A calm lake with a forest in the background during sunset.

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Recommended hotels in Southold

1. The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (312 reviews)
"Great stay"
United States
Connor
The price is CA $446
CA $544 total
includes taxes & fees
Sep 1 - Sep 2
The Shoals Suites and Slips

2. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (681 reviews)
"Great in town getaway"
United States
Yveline
The price is CA $376
CA $549 total
includes taxes & fees
Sep 7 - Sep 8
Sound View Greenport

3. The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (102 reviews)
"Stunning hotel! Will def stay again!"
United States
Anna
The price is CA $812
CA $1,020 total
includes taxes & fees
Sep 7 - Sep 8
The Pridwin Hotel

4. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (281 reviews)
"Great place!"
United States
Christine
The price is CA $427
CA $612 total
includes taxes & fees
Sep 9 - Sep 10
Cliffside Resort Condominiums

5. Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (367 reviews)
"Fantastic location and hugely helpful staff. I would absolutely stay again."
United States
Alex
The price is CA $339
CA $387 total
includes taxes & fees
Aug 25 - Aug 26
Zey Hotel

6. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (634 reviews)
"Very nice property/staff and a great location"
United States
David
The price is CA $362
CA $485 total
includes taxes & fees
Sep 8 - Sep 9
The Harbor Front Inn

7. Shelter Island House

Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very good, (63 reviews)
"This boutique hotel is a true gem. Set among lush trees and beautiful landscaping, and with excellent indoor space, it provides a welcoming and relaxing atmosphere."
United States
Dorothy
The price is CA $441
CA $504 total
includes taxes & fees
Aug 17 - Aug 18
Shelter Island House

8. The Chequit

The Chequit
3.0 star property
The Heights
9.0 out of 10, Wonderful, (45 reviews)
"It’s a beautiful property with a fun bar and delicious restaurant . The rooms were beautiful and the bed was super comfortable"
United States
Kristin
The price is CA $408
CA $466 total
includes taxes & fees
Sep 8 - Sep 9
The Chequit

9. House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (85 reviews)
"We had such an amazing stay! The house was beautiful, comfortable, and very clean. It is an easy walk to grab a great cup of coffee, which we loved. One of our favorite parts was sitting on the two Adirondack chairs on the water. The owner could not have been nicer and had great restaurant recommendations. We really loved it and will absolutely rebook soon!"
United States
Jeanine
The price is CA $342
CA $391 total
includes taxes & fees
Sep 8 - Sep 9
House on Chase Creek

10. West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.2 out of 10, Very good, (43 reviews)
"It was great! The location was perfect, plenty of amenities close by as well. Easy ferry access depending on time of day. Room was very clean. Will be staying again!"
United States
Allie
The price is CA $437
CA $499 total
includes taxes & fees
Aug 17 - Aug 18
West Neck Guesthouse

11. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (44 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is CA $438
CA $500 total
includes taxes & fees
Sep 9 - Sep 10
North Fork Resort

12. Oyster Estate

Oyster Estate
2.0 star property
Greenport
9.2 out of 10, Wonderful, (284 reviews)
"Great location, great hotel, great staff! "
United States
Jenny
The price is CA $459
CA $578 total
includes taxes & fees
Sep 7 - Sep 8
Oyster Estate

13. The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (189 reviews)
"Staff was very accommodating and extremely nice, Great stay!"
United States
Lisa
The price is CA $624
CA $769 total
includes taxes & fees
Aug 16 - Aug 17
The Menhaden

14. American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
9.0 out of 10, Wonderful, (204 reviews)
"The hotel doesn’t reception doesn’t open till 9am. For early risers we had to leave the hotel just to get coffee. 9am is unheard of for a hotel"
United States
kerri
The price is CA $550
CA $684 total
includes taxes & fees
Sep 7 - Sep 8
American Beech Hotel

15. Shorewood Inn

Shorewood Inn
2.5 star property
Riverhead
8.4 out of 10, Very good, (791 reviews)
"The room was beautiful,clean and had a mini stove, fridge, microwave, and walk in closet. The property was very quiet and close to the local beach, restaurants, vineyards and 2 farms. Perfect lovers getaway or girl trip outing."
United States
Denise
The price is CA $227
CA $259 total
includes taxes & fees
Aug 10 - Aug 11
Shorewood Inn

16. Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (328 reviews)
"It was a nice motor lodge with chairs for sitting outside. There’s also a pool out back that was great."
United States
David
The price is CA $123
CA $141 total
includes taxes & fees
Aug 30 - Aug 31
Clinton Motel

17. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (655 reviews)
"Everything about the place was great - great value overlooking the Harbor!"
United States
Christopher
The price is CA $655
CA $748 total
includes taxes & fees
Sep 7 - Sep 8
Sag Harbor Inn

18. The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (557 reviews)
"Great location and hotel"
United States
Yossef
The price is CA $216
CA $282 total
includes taxes & fees
Sep 7 - Sep 8
The Bentley Hotel Southampton

19. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,010 reviews)
"Very friendly staff, easy parking, great breakfast, and clean towels and beds made daily. Great place to stay."
United States
John
The price is CA $141
CA $162 total
includes taxes & fees
Aug 30 - Aug 31
Quality Inn Old Saybrook - Westbrook

20. The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (274 reviews)
"This is a very tastefully decorated B&B in an idyllic location. 6 minute walk to West Beach and near all the famous CT shoreline restaurants and attractions."
United Kingdom
Jessica
The price is CA $318
CA $353 total
includes taxes & fees
Aug 23 - Aug 24
The Captain Stannard
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Top Southold Hotel Reviews

Find out more about Southold

Southold Apartments information

Number of reviews
3,428
Accommodation
128 Apartments
Lowest Price
CA $141
Highest Price
CA $1,020

Frequently asked questions

What's it like to stay at an apartment in Southold?
There are plenty of places to stay in Southold with 139 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?
Below are some of the top apartments in the area: Safari Tent Glamping,S10-CedarPt, East Hampton, NY: Situated in East Hampton, 9.9 mi/16 km from the heart of Southold. Includes private patios. The Nest at Black Hall: Located 16.7 mi/26.8 km away in Old Lyme. Free WiFi and private balconies are included. Access to onsite laundry facilities is available on site. The Mast at Soundview · Beach+Ocean+Sunrise: It's located in Old Lyme, 17.2 mi/27.6 km from Southold. Includes free WiFi and Smart TVs.
How many apartments are there in Southold?
Expedia has 5 apartments to book in Southold.
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?
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 Croteaux Vineyards and Sparkling Pointe.
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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