Southold Hotels

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Top 10 trending Southold hotels

The Shoals Suites and Slips

3.5 star property
9.4 out of 10, Exceptional, (155)
"Great stay! Would come back again. "
The price is €219
includes taxes & fees
13 Apr - 14 Apr
The Shoals Suites and Slips

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (282)
"Condo was great, family of 5 , clean, no hassle"
The price is €169
includes taxes & fees
13 Apr - 14 Apr
Windward Shores Ocean Resort

The Roundtree, Amagansett

4.5 star property
9.8 out of 10, Exceptional, (85)
"My wife and I stayed a couple nights in October. We felt very pampered. Felix served us up late night snacks with homemade cookies and ice cream! Beautiful and charming hotel with attentive staff."
The price is €760
includes taxes & fees
29 Apr - 30 Apr
The Roundtree, Amagansett

The Reform Club

2.0 star property
10.0 out of 10, Exceptional, (1)
"We went to the area for a last minute concert. We loved all the staff and the property was exquisite. We would like to recommend that if you are sensitive to noise you should stay in the upstairs suites. High quality and we will be back if ever in this area in the future."
The price is €1,131
includes taxes & fees
20 Apr - 21 Apr
The Reform Club

Journey East Hampton

4.0 star property
9.0 out of 10, Wonderful, (126)
"Clean and up to date "
The price is €335
includes taxes & fees
13 Apr - 14 Apr
Journey East Hampton

East Hampton House Resort

3.0 star property
9.0 out of 10, Wonderful, (248)
"Perfect location and super clean"
The price is €190
includes taxes & fees
24 Apr - 25 Apr
East Hampton House Resort

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (68)
"What a lovely space and wonderful thoughtful staff! Absolutely loved everything about it, and the breakfast was beyond excellence! Hats off to the chef you can tell she cooked with ❤️ love. Highly Recommend you experience it for yourself. "
The price is €373
includes taxes & fees
13 Apr - 14 Apr
Mill House Inn

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (61)
"What a beautiful, quiet, peaceful place to stay, even in the dead of winter. The home itself is modern, welcoming, bright, everything you could dream of. The hosts are very active and successful artists who all but gave us a private master class in how their work is imagined and created. I don’t know when we’ve had a more delightful weekend. The walks to the beach were lovely, too. "
The price is €440
includes taxes & fees
14 Apr - 15 Apr
East Hampton Art House Bed & Breakfast

The Huntting Inn

3.5 star property
8.6 out of 10, Excellent, (87)
"One of the very few options in East Hampton that offered a one night stay, most have a 2-night minimum. An old, charming inn that was very welcoming and clean. Our king bed room was spacious enough and decorated nicely. The bathroom was very clean and modernized. We did have to walk up a flight of stairs with our luggage which wasn’t difficult for us but may be for some."
The price is €433
includes taxes & fees
4 May - 5 May
The Huntting Inn

The 1770 House Restaurant & Inn

4.0 star property
9.8 out of 10, Exceptional, (149)
"Loved the property. Well kept and very quaint. Room was comfortable and immaculate. We ate at the restaurant for dinner. Food and service were amazing. Can’t say enough good things about this place. Highly recommend. Does not disappoint. "
The price is €309
includes taxes & fees
14 Apr - 15 Apr
The 1770 House Restaurant & Inn

The Maidstone

4.0 star property
7.8 out of 10, Good, (121)
"Excellent stay!"
The price is €271
includes taxes & fees
27 Apr - 28 Apr
The Maidstone

EHP Resort & Marina

3.5 star property
7.8 out of 10, Good, (8)
"Beautiful property and the cottages were clean, gorgeous, and comfortable. It was just hard to get in touch with anyone for service related issues. The restaurant on site, Si Si was amazing and the staff there went above and beyond!"
The price is €376
includes taxes & fees
17 Apr - 18 Apr
EHP Resort & Marina

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (146)
"It’s okay for a night or two not a first or second choice however. The cosmetic upgrade for this property is okay in comparison to the cost of the stay. The doors only have a button lock on some cottages and seems like the original handle, it was loose and the key was sticking. Though I was accommodated with a different cottage that had a padlock as well, there was a visible mold and moisture issue causing the laminate floors to bubble. Some groundskeeping opportunities with pathways and the...
The price is €238
includes taxes & fees
20 Apr - 21 Apr
The Sagaponack

A Room At The Beach

3.0 star property
9.0 out of 10, Wonderful, (83)
"Beautiful property and amazing staff, I will definitely be back soon!"
The price is €459
includes taxes & fees
13 Apr - 14 Apr
A Room At The Beach

Topping Rose House

4.5 star property
9.2 out of 10, Wonderful, (131)
"Had an excellent stay at Topping Rose House! Can’t wait to be back soon!"
The price is €415
includes taxes & fees
13 Apr - 14 Apr
Topping Rose House

The Niantic Inn

2.0 star property
9.2 out of 10, Wonderful, (89)
"Loved this hotel! Friendly staff and extremely clean. I plan on coming back. The only place I will stay."
The price is €165
includes taxes & fees
15 Apr - 16 Apr
The Niantic Inn

Bridgehampton Inn

3.5 star property
9.4 out of 10, Exceptional, (213)
"Lovely inn, with very accommodating staff. "
The price is €312
includes taxes & fees
17 Apr - 18 Apr
Bridgehampton Inn

Baron's Cove

4.0 star property
9.0 out of 10, Wonderful, (226)
"Wonderful weekend- wonderful hotel!"
The price is €286
includes taxes & fees
15 Apr - 16 Apr
Baron's Cove

Sag Harbor Inn

3.5 star property
9.4 out of 10, Exceptional, (507)
"Great cozy stay. Very nice staff, amazing location."
The price is €224
includes taxes & fees
13 Apr - 14 Apr
Sag Harbor Inn

The 1708 House

3.0 star property
10.0 out of 10, Exceptional, (2)
"We absolutely loved our stay here. The house is stunning, the service is fabulous. The best bed ever to sleep in! Great location and a fabulous breakfast. Thank you. "
The price is €317
includes taxes & fees
26 Apr - 27 Apr
The 1708 House
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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Learn more about Southold

Come to Southold and enjoy its wineries, island views and beaches.

Frequently asked questions

Where is the best place to stay in Southold?

The Shoals Suites and Slips is one of the top choices for your stay based on our traveller data. This hotel offers a restaurant and private balconies. Other good choices for your stay in the area are Water's Edge Resort & Spa and Pier Blue Inn Old Saybrook - Essex. See all available top hotels, or vacation rentals in Southold.

What are some of the best holiday rentals that Southold has to offer?

Stunning Hampton Holiday Family Fantasy for your Team : This holiday home rental outside Southold is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday. See all vacation rentals in Southold.

If I need to cancel my hotel reservation in Southold, will I receive a refund?

Yes, most hotel bookings are fully refundable if you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If you have a non-refundable reservation, you may still be able to cancel and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Southold.

What's the best accommodation for a couple visiting Southold?

The Shoals Suites and Slips is a favourite hotel for couples, and features wedding services and free breakfast. See all romantic hotels in Southold.

What's the best dog-friendly accommodation option in Southold?

White Blossom House Inn is a top hotel for people travelling with their pets, and offers free use of bicycles and in-room kitchens for its human guests. Cozy Long Island Escape is another good option if you're bringing your pet along. See more pet-friendly hotel accommodations in Southold.

What's the best accommodation option to stay near the beach in Southold?

Shorecrest Bed and Breakfast is a top beach B&B with free breakfast and free WiFi, and it's located close to Crescent Beach . See more stays near the beach in Southold.

What's the best high-end place to stay in Southold?

Vine & Sand is a luxury B&B with a private beach and a seasonal outdoor pool, and it's a popular choice for Expedia travellers looking for an elegant place to stay. Find more luxury hotels in Southold.

What are some accommodation options with pools in Southold?

Water's Edge Resort & Spa: Features a seasonal outdoor pool, an indoor pool and a private beach. Hyatt Place Long Island East End and Baron's Cove are a couple of other choices that offer an on-site pool. View all hotels with pools in Southold.

What is the best spa hotel in Southold?

Shorecrest Bed and Breakfast is a top spa hotel with 5 rooms, free WiFi and a fireplace in reception. Enjoy a massage at the on-site spa. See all spa hotels in Southold.

What's it like to stay in Southold?

Visitors can enjoy all that Southold has to offer, including the wineries, beaches and gardens. Tourists can also enjoy the city's football games and monuments. In Southold, there are 159 hotels and other accommodation options to choose from. Find out more about Southold.

What should I do while I'm visiting Southold?

Favourite places to visit include Sparkling Pointe, Croteaux Vineyards and Osprey's Dominion. A couple of additional sights to add to your itinerary are Sannino's Bella Vita Vineyard and The Old Field Vineyards. Take a look at what more there is to see and do in Expedia's Southold guide.

What's the best way to get around Southold?

To see more of the larger area, hop aboard a train at Southold Station. If you want to venture out around the area, you may want a rental car in Southold for your journey.

What's the weather like in Southold?

The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Southold is 1452 mm.