Hotels in Southold

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Check prices for these dates

Tonight
9 Oct - 10 Oct
Tomorrow
10 Oct - 11 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Where to stay in Southold?

Properties are selected based on real traveller reviews and popularity among guests who’ve booked a night in Southold on Hotels.com. These Southold hotels consistently deliver on quality, location and traveller experience. Last updated on 10 October 2026.
A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

1. The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (344 reviews)
Dive into waterside charm at this Southold retreat on the bay. Located near The Old Field Vineyards and Crescent Beach, the hotel offers free WiFi, bicycles, and a cafe/bar lounge. Travellers consistently praise the helpful staff for enhancing their stay experience.
The price is AU$434
includes taxes & fees
1 Nov - 2 Nov
The Shoals Suites and Slips
A two-story house with a balcony, outdoor seating area, and a variety of plants.

2. Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (421 reviews)
Stylish rooms in this boutique hotel offer a peaceful retreat after exploring the harbour. Unwind with a drink at the bar, grab a bite at the coffee shop, or bike to nearby Greenport Harbour Brewing Company and Farmers' Market.
The price is AU$299
includes taxes & fees
26 Oct - 27 Oct
Zey Hotel
A spacious room with wicker furniture, large windows, and a view of the sea.

3. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (749 reviews)
Perched oceanfront in Greenport, this hotel offers a seasonal outdoor pool with poolside bar. Just a short drive from the Railway Museum and The Old Field Vineyards, enjoy American cuisine at The Halyard restaurant and unwind at 2 welcoming bars.
The price is AU$343
includes taxes & fees
3 Nov - 4 Nov
Sound View Greenport
An outdoor patio area with string lights, tables, chairs, and a fire pit.

4. The Chequit

The Chequit
3.0 star property
The Heights
9.2 out of 10, Wonderful, (68 reviews)
Wake to island tranquility at this Shelter Island Heights hotel with premium bedding. Near Shelter Island Country Club and Sunset Beach, this refined retreat offers free WiFi and parking. Convenient to Greenport Station for day trips.
The price is AU$281
includes taxes & fees
9 Nov - 10 Nov
The Chequit
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.

5. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
9.0 out of 10, Wonderful, (664 reviews)
Overlooking Greenport Harbour, this boutique inn combines coastal charm with modern comforts. Just a 3-minute walk from the train station, guests enjoy the seasonal outdoor pool, 24-hour fitness centre, and complimentary breakfast while exploring nearby attractions.
The price is AU$317
includes taxes & fees
3 Nov - 4 Nov
The Harbor Front Inn
A lakeside patio with outdoor seating and a view of the water.

6. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
10.0 out of 10, Exceptional, (174 reviews)
The price is AU$428
includes taxes & fees
1 Nov - 2 Nov
Silver Sands Motel & Beach Bungalows
Terrace/patio

7. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (295 reviews)
The price is AU$437
includes taxes & fees
1 Nov - 2 Nov
Cliffside Resort Condominiums
Front of property – evening/night

8. Shelter Island House

Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very good, (66 reviews)
Tucked away in Shelter Island Heights, this golf-adjacent hotel offers a seasonal outdoor pool and rejuvenating massage services. Enjoy cocktails at the poolside bar, grab bites at the restaurant or deli, then explore nearby Sunset Beach and Shelter Island Country Club.
The price is AU$330
includes taxes & fees
21 Oct - 22 Oct
Shelter Island House
A serene landscape with a calm body of water reflecting trees with autumn foliage.

9. House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (87 reviews)
Overlooking Chase Creek, this inviting guesthouse sits adjacent to a golf course in tranquil Shelter Island Heights. Free WiFi and parking enhance your stay while the garden and terrace offer peaceful spots to unwind near Shelter Island Country Club.
The price is AU$303
includes taxes & fees
2 Nov - 3 Nov
House on Chase Creek
A modern house with a deck, outdoor seating, and a fire pit.

10. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (63 reviews)
The price is AU$437
includes taxes & fees
20 Oct - 21 Oct
North Fork Resort
A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.

11. American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
9.0 out of 10, Wonderful, (208 reviews)
Explore Greenport from this stylish inn with its welcoming bar and restaurant. Grab the complimentary bikes to visit nearby Greenport Harbour Brewing Company. The attentive staff and daily housekeeping ensure a carefree stay, just an 8-minute walk from the train station.
The price is AU$469
includes taxes & fees
20 Oct - 21 Oct
American Beech Hotel
A waterfront property with a large house, multiple boats docked, and lush greenery.

12. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (676 reviews)
Wake up to complimentary breakfast at this waterfront hotel, just moments from Sag Harbour Whaling Museum. The outdoor pool offers refreshing relaxation after exploring nearby attractions. Free WiFi and parking enhance the value, while the attentive staff ensures a memorable stay.
The price is AU$359
includes taxes & fees
2 Nov - 3 Nov
Sag Harbor Inn
A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.

13. The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (596 reviews)
Seasonal outdoor pool and complimentary WiFi create a perfect Southampton retreat. Just a 15-minute drive from pristine beaches, with free parking and clean, comfortable rooms. Water adventures await nearby with kayaking options.
The price is AU$235
includes taxes & fees
26 Oct - 27 Oct
The Bentley Hotel Southampton
A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.

14. Oyster Estate

Oyster Estate
4.0 star property
Greenport
9.2 out of 10, Wonderful, (294 reviews)
Unwind at this North Fork retreat with a refreshing swim or soothing soak after exploring nearby museums. Complimentary bikes let you discover charming Greenport while free WiFi and parking add convenience to your coastal escape.
The price is AU$469
includes taxes & fees
8 Nov - 9 Nov
Oyster Estate
A modern building entrance with a black and white striped awning, a staircase leading inside, and two bicycles parked outside.

15. The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (191 reviews)
Escape to this stylish Greenport retreat offering free breakfast and WiFi. Relax at the rooftop terrace or grab a drink from the bar before exploring local attractions on complimentary bikes. Only a 3-minute walk from Greenport Station, near Camera Obscura.
The price is AU$625
includes taxes & fees
8 Nov - 9 Nov
The Menhaden
A round table with a magazine, a plate with a pastry, a cup, and a vase with flowers.

16. Shorewood Inn

Shorewood Inn
2.5 star property
Riverhead
8.4 out of 10, Very good, (830 reviews)
Steps from Riverhead's renowned vineyards, this welcoming motel offers free WiFi and complimentary parking. The 24-hour front desk ensures convenience while clean, comfortable rooms provide a relaxing base to explore nearby Westhampton beaches.
The price is AU$168
includes taxes & fees
11 Oct - 12 Oct
Shorewood Inn
A hotel room with a bed, bedside tables, a desk with chairs, a sofa, a window with curtains, and a door leading outside.

17. The Atlantic Hotel

The Atlantic Hotel
2.5 star property
Southampton
7.2 out of 10, Good, (1,000 reviews)
Overlooking the ocean in Southampton, this hotel offers refreshing swims in an outdoor pool and matches on tennis courts. Guests praise the helpful staff while enjoying free WiFi and parking, with Sebonack Golf Course nearby.
The price is AU$212
includes taxes & fees
28 Oct - 29 Oct
The Atlantic Hotel
A parking lot with a building in the background.

18. Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (339 reviews)
Wake up to seaside charm at this Clinton motel where the ocean beckons nearby. Take a refreshing dip in the seasonal outdoor pool after exploring Clinton Plaza or the historic Adam Stanton House. Free WiFi and parking add value, with Clinton Station just a 19-minute walk away.
The price is AU$129
includes taxes & fees
13 Oct - 14 Oct
Clinton Motel
A pool area with umbrellas, potted plants, and a pathway leading to a building.

19. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (311 reviews)
Immerse in coastal charm at this Sag Harbour retreat where massages await after beach days. The seasonal outdoor pool offers refreshment while the fitness centre keeps routines intact. Friendly staff ensure a memorable stay near historical museums.
The price is AU$683
includes taxes & fees
8 Nov - 9 Nov
Faraway Sag Harbor
An outdoor seating area with Adirondack chairs and a table, surrounded by American flags and flowers, with a view of houses and a body of water in the background.

20. Ocean View Terrace Inn

Ocean View Terrace Inn
2.0 star property
Hampton Bays
8.6 out of 10, Excellent, (137 reviews)
Discover coastal charm at this Hampton Bays motel, just minutes from Cooper's Beach. Unwind with deep-tissue massages after exploring nearby attractions, then cool off in the seasonal outdoor pool. Enjoy complimentary breakfast, WiFi, and parking.
The price is AU$259
includes taxes & fees
12 Oct - 13 Oct
Ocean View Terrace Inn
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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Go beyond your typical stay in Southold

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When is the best time to visit Southold?

Our prices for hotels in Southold are cheapest in November

Price trends for hotels in Southold

Pricing is based on two traveller single night rates
View properties in October
Currently viewing crowd sizes and weather for October.

October

High 17°C / low 14°C. Sunny most days.
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October, no crowd data, average high temperature 17 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
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November, no crowd data, average high temperature 12 degrees Celsius, average low temperature 8 degrees Celsius. Sunny most days.
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December, no crowd data, average high temperature 8 degrees Celsius, average low temperature 4 degrees Celsius. Cloudy most days.
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January, no crowd data, average high temperature 4 degrees Celsius, average low temperature 0 degrees Celsius. Partly sunny.
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February, no crowd data, average high temperature 4 degrees Celsius, average low temperature 0 degrees Celsius. Cloudy most days.
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March, no crowd data, average high temperature 6 degrees Celsius, average low temperature 2 degrees Celsius. Partly sunny.
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April, no crowd data, average high temperature 10 degrees Celsius, average low temperature 7 degrees Celsius. Sunny most days.
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May, no crowd data, average high temperature 15 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
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June, no crowd data, average high temperature 20 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
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July, no crowd data, average high temperature 24 degrees Celsius, average low temperature 21 degrees Celsius. Sunny most days.
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August, no crowd data, average high temperature 25 degrees Celsius, average low temperature 22 degrees Celsius. Sunny most days.
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September, no crowd data, average high temperature 22 degrees Celsius, average low temperature 19 degrees Celsius. Sunny most days.
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Monthly weather averages (˚C)

Top landmarks in Southold

Sparkling Pointe

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

Learn more about Southold

Southold is well known for its attractions such as Sparkling Pointe and Croteaux Vineyards. The city has something for everyone including sights like Sannino's Bella Vita Vineyard and The Old Field Vineyards within a sunny setting.

See all hotels in Southold
A coastal landscape with a white church on a grassy hill, overlooking a sandy beach and the ocean.

Check out reviews of Southold hotels guests love

A waterfront property with a large house, multiple boats docked, and lush greenery.
Sag Harbor Inn

Sag Harbor Inn

Sag Harbor Inn
Sag Harbor

10/10 Exceptional

Great location, room was spacious with great outlook and breakfast was perfect!
Australia
Jennifer
Reviewed May 30, 2026
Sag Harbor Inn

Frequently Asked Questions

How much does a hotel room cost in Southold?

You can choose a great hotel in Southold from AU$128 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 holiday. Our travellers love The Shoals Suites and Slips, a hotel with a restaurant as well as champagne service. Discover more hotels in Southold on Hotels.com for couples by using the "Traveller 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. 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 travellers' favourites 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. Travellers 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 areas for your Southold holiday.

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