Search for Cheap Deals on
Hotels in Southold

Check Last Minute Southold Hotel Deals

Tonight Jun 5 - Jun 6This weekend Jun 5 - Jun 7

Choose from 4471 Southold Hotel Deals

The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
  • 8 min drive from Croteaux Vineyards
Stay at this hotel in Southold. Enjoy free WiFi, free bicycles on site, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (278 reviews)
"We had such a wonderful time, and the staff was incredibly helpful and attentive. We definitely recommend staying at the Sholas—it's a fantastic place!"

Reviewed on Jun 3, 2026

The Shoals Suites and Slips
Vine & Sand

Vine & Sand

3 out of 5
47100 New York 25 Southold NY
  • 7 min walk from Croteaux Vineyards
Book a stay at this business-friendly B&B in Southold. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mattebella Vineyards and Croteaux ...
9.8/10 Exceptional! (16 reviews)
"Location was perfect for visiting the wineries… breakfast was to die for!"

Reviewed on Mar 22, 2026

Vine & Sand
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
  • 41 min drive from Croteaux Vineyards
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (1,002 reviews)
"Friendly staff, clean room, nice location"

Reviewed on Jun 3, 2026

Pier Blue Inn Old Saybrook - Essex
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
  • 25 min drive from Croteaux Vineyards
Stay at this hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
7.2/10 Good! (1,005 reviews)
"Hotel is fine if you are just there for a night, maybe two, but the room, especially the carpet, need some major updates."

Reviewed on Jun 4, 2026

The Atlantic Hotel
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
  • 39 min drive from Croteaux Vineyards
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,000 reviews)
"The location and the amenities provided by the hotel was first classed"

Reviewed on May 27, 2026

Water's Edge Resort & Spa
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
  • 26 min drive from Croteaux Vineyards
Book a stay at this business-friendly hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
9.6/10 Exceptional! (514 reviews)
"I loved My stay"

Reviewed on Jun 5, 2026

The Bentley Hotel Southampton
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
  • 16 min drive from Croteaux Vineyards
Book a stay at this boutique hotel in Greenport. Enjoy free parking, free bicycles on site, and daily housekeeping. Popular attractions Greenport Harbor Brewing ...
9.2/10 Wonderful! (314 reviews)
"They advertised sound proof rooms. Not happening They advertised well stocked mini bar not happening There are pictures indicating a dining room Not happening They make no indication you can get coffee in the ad we brought coffee and find out there is coffee in the lobby In the room was a long bench ..."

Reviewed on Jun 3, 2026

Zey Hotel
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
  • 11 min drive from Croteaux Vineyards
Book a stay at this beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (653 reviews)
"Great"

Reviewed on Jun 1, 2026

Sound View Greenport
Sag Harbor Inn

Sag Harbor Inn

3.5 out of 5
45 West Water Street Sag Harbor NY
  • 24 min drive from Croteaux Vineyards
Book a stay at this business-friendly hotel in Sag Harbor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (622 reviews)
"Wonderful accommodations within walking distance of all things Sag. The staff were responsive and courteous!"

Reviewed on Jun 3, 2026

Sag Harbor Inn
Hyatt Place Long Island East End

Hyatt Place Long Island East End

3 out of 5
451 East Main Street Riverhead NY
  • 42 min drive from Croteaux Vineyards
Book a stay at this business-friendly hotel in Riverhead. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,003 reviews)
"The staff were very friendly."

Reviewed on Jun 4, 2026

Hyatt Place Long Island East End
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd Old Saybrook CT
  • 47 min drive from Croteaux Vineyards
Book a stay at this business-friendly hotel in Old Saybrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.8/10 Good! (1,002 reviews)
"Everyone was friendly, the rooms were clean and breakfast was great!"

Reviewed on May 30, 2026

Quality Inn Old Saybrook - Westbrook
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
  • 16 min drive from Croteaux Vineyards
Book a stay at this business-friendly hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (607 reviews)
"Wonderful, relaxing stay. Convenient to both train and ferry. Warm and inviting reception team."

Reviewed on May 28, 2026

The Harbor Front 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.

Find cheap hotels in Southold

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Southold hotel with Hotwire to complete your one-of-a-kind travel checklist.

For you, intrepid voyager, Hotwire has a large selection of the best hotels in Southold.

Choosing the right hotel in New York has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Southold’s 4,471 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $123. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Southold hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Southold. No matter your reason for visiting Southold, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Southold hotels

Where can I find the best last-minute travel deals?

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Southold for as low as $123.

How many hotels are there in Southold?

With over 4,471 hotels in Southold, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $123.

How to find cheap car rentals in Southold?

Finding a cheap car rental deal in Southold is as easy as scoring cheap hotels in Southold. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.