Hotels in Southold

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Aug 19 - Aug 20
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Where to stay in Southold?

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Southold on Hotels.com. These Southold hotels consistently deliver on comfort, location and traveler experience. Last updated on .

Exterior
Restaurant
Terrace King | Premium bedding, down comforters, laptop workspace
The Shoals Grand Suite | Private kitchen | Espresso maker, eco-friendly cleaning products, paper towels

1. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
CNY1,961
CNY2,409 total
includes taxes & fees
Sep 1 - Sep 2
The Shoals Suites and Slips
Terrace/patio
Seasonal outdoor pool, pool umbrellas, sun loungers
Private beach, sun loungers, beach umbrellas, beach towels
Premium bedding, iron/ironing board, WiFi (free), individually furnished

2. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
CNY3,603
CNY4,528 total
includes taxes & fees
Sep 13 - Sep 14
The Pridwin Hotel
Condo | Terrace/patio
Private beach
Condo | 2 bedrooms, iron/ironing board, WiFi (free), individually decorated
Flat-screen TV

3. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
CNY2,063
CNY2,957 total
includes taxes & fees
Sep 20 - Sep 21
Cliffside Resort Condominiums
Resort view
Private beach, sun loungers, beach umbrellas, beach towels
Terrace/patio
Yoga

4. Sound View Greenport

Sound View Greenport
Greenport
CNY1,829
CNY2,667 total
includes taxes & fees
Sep 15 - Sep 16
Sound View Greenport
Beach bar
Private beach, sun loungers, beach umbrellas, beach towels
Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
Waterfront Beach Shack Studio | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

5. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
CNY3,164
CNY3,615 total
includes taxes & fees
Sep 20 - Sep 21
Silver Sands Motel & Beach Bungalows
Exterior
Garden Suite, Wheelchair Accessible, Ground Floor, 2 Queen Beds, Non-Smoking | Premium bedding, minibar, soundproofing, iron/ironing board (on request)
Private Suite, 1 King Bed, Non Smoking (Private Suite - Adults Only) | Premium bedding, minibar, soundproofing, iron/ironing board (on request)
Restaurant

6. Zey Hotel

Zey Hotel
Greenport
CNY1,363
CNY1,557 total
includes taxes & fees
Sep 7 - Sep 8
Zey Hotel
Suite, 1 Bedroom, Terrace, Harbor View | Terrace/patio
Studio (Suite, King) | Frette Italian sheets, premium bedding, down comforters, pillowtop beds
Suite, 1 Bedroom, Terrace, Harbor View | Frette Italian sheets, premium bedding, down comforters, pillowtop beds
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, sun loungers

7. The Harbor Front Inn

The Harbor Front Inn
Greenport
CNY1,863
CNY2,475 total
includes taxes & fees
Sep 8 - Sep 9
The Harbor Front Inn
Property entrance
Breakfast served
Lobby
Sundeck

8. The Menhaden

The Menhaden
Greenport
CNY3,496
CNY4,264 total
includes taxes & fees
Aug 25 - Aug 26
The Menhaden
Front of property - evening/night
Property amenity
Property amenity
Terrace/patio

9. Shelter Island House

Shelter Island House
Shelter Island Heights
CNY2,129
CNY2,432 total
includes taxes & fees
Aug 31 - Sep 1
Shelter Island House
Deluxe Room, 1 King Bed | Premium bedding, iron/ironing board, WiFi (free), bed sheets
Beach nearby
Property grounds
Free self parking

10. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
CNY2,110
CNY2,411 total
includes taxes & fees
Aug 23 - Aug 24
West Neck Guesthouse
Lobby
Lobby
Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
Restaurant

11. Oyster Estate

Oyster Estate
Greenport
CNY2,195
CNY2,766 total
includes taxes & fees
Sep 7 - Sep 8
Oyster Estate
Flat-screen TV
Balcony
Cottage, 2 Bedrooms, Patio | Living room | Flat-screen TV
Coffee/tea maker, fridge, microwave

12. North Fork Resort

North Fork Resort
Greenport
CNY2,163
CNY2,471 total
includes taxes & fees
Sep 17 - Sep 18
North Fork Resort
Building design
Free daily continental breakfast
Outdoor pool
Lobby

13. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
CNY2,383
CNY2,723 total
includes taxes & fees
Sep 20 - Sep 21
Sag Harbor Inn
Outdoor dining
View from room
Frette Italian sheets, premium bedding, Tempur-Pedic beds
Frette Italian sheets, premium bedding, Tempur-Pedic beds

14. The Chequit

The Chequit
The Heights
CNY1,969
CNY2,250 total
includes taxes & fees
Sep 17 - Sep 18
The Chequit
Terrace/patio
Bar (on property)
Reception
View from property

15. American Beech Hotel

American Beech Hotel
Greenport
CNY2,658
CNY3,305 total
includes taxes & fees
Sep 20 - Sep 21
American Beech Hotel
Exterior
Breakfast area
Exterior
Exterior

16. Shorewood Inn

Shorewood Inn
Riverhead
CNY1,098
CNY1,254 total
includes taxes & fees
Aug 23 - Aug 24
Shorewood Inn
Living area
Business center
Exterior
Interior entrance

17. The Captain Stannard

The Captain Stannard
Westbrook Center
CNY1,575
CNY1,748 total
includes taxes & fees
Sep 20 - Sep 21
The Captain Stannard
View from property
Property grounds
A house with a porch, a sign reading "House on Chase Creek," and a tree with red leaves.
Restaurant

18. House on Chase Creek

House on Chase Creek
The Heights
CNY1,654
CNY1,890 total
includes taxes & fees
Sep 8 - Sep 9
House on Chase Creek
Lobby
Desk, laptop workspace, blackout drapes, iron/ironing board
Free daily buffet breakfast
Indoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers

19. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
CNY681
CNY783 total
includes taxes & fees
Sep 20 - Sep 21
Quality Inn Old Saybrook - Westbrook
BBQ/picnic area
Restaurant
Exterior
Bar (on property)

20. Hyatt Place Long Island East End

Hyatt Place Long Island East End
Riverhead
CNY1,322
CNY1,510 total
includes taxes & fees
Sep 9 - Sep 10
Hyatt Place Long Island East End
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Our prices for hotels in Southold are cheapest in January
Price trends for hotels in Southold
Pricing is based on two traveler single night rates
View properties in August
Typical weather for Southold
August
High 25°C / low 22°C. Sunny most days.
View properties in August
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Top landmarks in Southold

Sparkling Pointe

8.8/10 (11 reviews)
Travelers might want a tour of Sparkling Pointe, just one of the places to visit, and located 1 mi (1.6 km) from central Southold.
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Croteaux Vineyards

10.0/10 (12 reviews)
Travelers might want a tour of Croteaux Vineyards, just one of the places to visit, and located 1.5 mi (2.4 km) from central Southold. Why not take a stroll along the beaches and watch the sunset while you're here? If you enjoy your tour, head to Mattebella Vineyards or Corey Creek Winery, both within a short walk.
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Sannino's Bella Vita Vineyard

9.6/10 (4 reviews)
Travelers might want a tour of Sannino's Bella Vita Vineyard, just one of the places to visit, and located 2.2 mi (3.5 km) from central Southold. If you enjoy your tour, head to Osprey's Dominion, just a short walk away.
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McCabe's Beach

When the beach is calling your name, you might want to head down to McCabe's Beach, located 1.6 mi (2.5 km) from central Southold. If you want to continue walking by the waves, head to Horton Lane Beach located nearby.
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Horton Lane Beach

9.0/10 (4 reviews)
If you can't wait to get to the beach, you might enjoy a trip to Horton Lane Beach located 1.6 mi (2.6 km) from central Southold. If you want to continue walking by the waves, head to McCabe's Beach located nearby.
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Horton Point Park

9.4/10 (3 reviews)
Horton Point Park is 1.7 mi (2.8 km) from central Southold, why not stop by during your stay. Want to stretch your legs some more? Head to Goldsmith's Inlet Park, located nearby.
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Osprey's Dominion

9.6/10 (5 reviews)
Travelers might want a tour of Osprey's Dominion, just one of the places to visit, and located 1.9 mi (3 km) from central Southold. Why not take a stroll along the beaches and watch the sunset while you're here? If you enjoy your tour, head to Mattebella Vineyards or Corey Creek Winery, both within a short walk.
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Custer Institute and Observatory

Custer Institute and Observatory is 1 mi (1.6 km) from central Southold, why not stop by during your stay. If you have fun at Custer Institute and Observatory, you'll love Railroad Museum of Long Island and 8 Hands Farm, both located nearby.
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Learn more about Southold

Southold is well-known for its attractions such as Sparkling Pointe and Mattebella Vineyards. The city has something for everyone including sights like Croteaux Vineyards and McCabe's Beach within a sunny setting.

See all hotels in Southold
A pebbled beach at sunset with the sun reflecting on the water.
Photo by Benny Goh

Check out reviews of Southold hotels guests love

North Fork Resort

North Fork Resort

10/10 Excellent
"THERE WAS ONLY ONE THING. THE LAST MORNING THERE WAS NO HOT H2O HOWEVER THE PROBLEM WAS FIXED."
KATHLEEN 2-night trip
Posted 2 hours ago
North Fork Resort
Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"This hotel chain is MY NEW FAVORITE! We had never stayed at a Hyatt Hotel before, but I am so impressed! From the super-friendly staff, cleanliness, modern look, breakfast varieties galore, eating with actual cutlery, not plastic, real cups and plates, not paper, what a treat! I truly felt pampered! The A/C in the room was perfect, and the hot water in the shower was 'so relaxing and soothing!' Great job Hyatt Place Long Island-Riverhead! See you again!"
Maryellen 2-night trip
Posted 3 hours ago
Hyatt Place Long Island East End
Sound View Greenport

Sound View Greenport

8/10 Good
"Stayed here for 2 nights mid-August. Pool was nice (could have been a little cleaner). Restaurant, excellent. Valet staff, excellent. Front desk staff, good. Bar, nice. Breakfast included, very nice. Room, a bit dated but nicely renovated. Through the years I always wanted to stay here - glad I did. The view (and sunset) of the Long Island Sound from the shared balcony cannot be beat. Breathtaking."
Barbara 2-night trip
Posted 4 hours ago
Sound View Greenport
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

8/10 Good
"Clean and comfortable room. Very dated furniture."
Leon 1-night trip
Posted 7 hours ago
Pier Blue Inn Old Saybrook - Essex
Water's Edge Resort & Spa

Water's Edge Resort & Spa

8/10 Good
"I booked through Expedia because I believed the price I was quoted would be the final cost other than incidentals. Additional resort fees and tax were added to the final bill. Over 130.00 in unexpected cost. Be aware when booking."
Debra 1-night trip
Posted 9 hours ago
Water's Edge Resort & Spa
The Chequit

The Chequit

10/10 Excellent
"Everything was great ! Wish we had been there when restaurant was open."
Kathleen 1-night trip
Posted 23 hours ago
The Chequit
Hampton's Vacation Inn

Hampton's Vacation Inn

10/10 Excellent
"Great place to stay. The closing of the pool at 7pm is a bit early."
Theresa 4-night trip
Posted 1 day ago
Hampton's Vacation Inn
Zey Hotel

Zey Hotel

10/10 Excellent
"James was amazing"
ROBIN 3-night trip
Posted 2 days ago
Zey Hotel
The Hampton Maid

The Hampton Maid

10/10 Excellent
"Wonderful place, room is clean, modern and spacious. Such a nice garden right in front of the rooms, very relaxing atmosphere. Very professional and helpful staff. Great location, close to restaurants. Highly recommend it."
Mehmet B 2-night trip
Posted 2 days ago
The Hampton Maid

Frequently asked questions

How much does a hotel room cost in Southold?
You can choose a great hotel in Southold from CNY613 with properties to suit all budgets and needs. If you're after an affordable hotel in Southold that meets all of your requirements, set your filters and then sort the results by "Price: low to high".
How can I find deals and earn rewards at Southold hotels?
Discover great deals on Southold hotel stays with Hotels.com. It's also a good idea to look at hotel prices mid-week or during the low season as you're likely to find off-peak deals. If it's a spontaneous trip, check out our last-minute deals on Southold hotels.
Can I book Southold hotels with free cancellation?
To book a refundable Southold hotel on Hotels.com, just filter hotels by "Property cancellation options" and select "Fully refundable property". The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.
What are some of the best hotels in Southold for couples?
Stay at a top-rated Southold romantic hotel and make the most of your couple's vacation. Our travelers love The Shoals Suites and Slips, a hotel with a restaurant as well as in-room champagne service. Discover more hotels in Southold on Hotels.com for couples by using the "Traveler experience" filter in your search and selecting "Adults only" or "Romantic".
What are the top Southold hotels with a pool?
For some added luxury, discover the best Southold hotels with a pool. Vine & Sand is a great bed & breakfast with a seasonal outdoor pool and a guest rating of 9.8 out of 10. Plus, you can make the most of its free buffet breakfast and free bicycle rentals. You can select "Pool" in the "Amenities" filter of your search on Hotels.com to find even more places to stay in Southold with a pool.
What are some of the best Southold hotels with free parking?
If you're driving, a great Southold hotel with free parking is a bonus. Our travelers' favorites include:
What are some popular hotels in central Southold?
For hotels in central Southold, check out The Harbor Front Inn and Silver Sands Motel & Beach Bungalows. Travelers love The Harbor Front Inn for its location, as well as the seasonal outdoor pool, free continental breakfast and 24-hour gym this hotel offers. Silver Sands Motel & Beach Bungalows is another popular central hotel with a private beach, a free beach club and a full-service spa. Pipes Cove and The Heights are some of the most central neighborhoods for your Southold vacation.
What accommodations do travelers recommend in Southold?
Guests like The Shoals Suites and Slips, Vine & Sand and Sound View Greenport.
Can I book refundable accommodations in Southold?
If you want the flexibility to change your travel plans to Southold, most properties offer refundable* rates you can book. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Southold if I want a vacation home instead of a traditional hotel?
If you want to find a good alternative to a hotel, browse our selection of 118 vacation homes. You can also consider one of the 12 cottages for your trip.
What will the weather in Southold be like during my vacation?
The warmest months in Southold are usually August and July with an average temp of 70°F. January and February are the chilliest months when the average temp is 38°F. The rainiest months are October and December.
Why should I book my Southold accommodation with Hotels.com?
There are plenty of reasons to book your Southold travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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