Book Cheap Hotels in Southold

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Check prices in Southold for tonight, Dec 18 - Dec 19
Dec 18 - Dec 19
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Check prices in Southold for this weekend, Dec 19 - Dec 21
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Check prices in Southold for next weekend, Dec 26 - Dec 28
Dec 26 - Dec 28

Most frequently booked Southold hotels

The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
2.28 km from city centre
The price is CA $217 per night
CA $217
CA $248 total
Jan 18 - Jan 19, 2026
includes taxes & fees
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 The Old Field Vineyards and Crescent Beach are located nearby.
Free WiFi
Air conditioning
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Free cancellation
Reserve now, pay when you stay
24.1 km from city centre
The price is CA $247 per night
CA $247
CA $308 total
Dec 21 - Dec 22
includes taxes & fees
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 attractions Tanger Outlets and Westbrook Town Beach are located nearby.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Free cancellation
Reserve now, pay when you stay
24.68 km from city centre
Get rates
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. Popular attractions Chalker Beach and Crystal Lake Town Park are located nearby.
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
4.24 km from city centre
The price is CA $219 per night
CA $219
CA $318 total
Dec 22 - Dec 23
includes taxes & fees
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 attractions Railroad Museum of Long Island and The Old Field Vineyards are located nearby.
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St Old Saybrook CT
Free cancellation
Reserve now, pay when you stay
25.08 km from city centre
The price is CA $396 per night
CA $396
CA $490 total
Jan 18 - Jan 19, 2026
includes taxes & fees
Book a stay at this spa hotel in Old Saybrook. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Fort Saybrook Monument Park and General William Hart House are located nearby.
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
Free cancellation
Reserve now, pay when you stay
19.23 km from city centre
The price is CA $172 per night
CA $172
CA $198 total
Jan 4 - Jan 5, 2026
includes taxes & fees
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 rooms in our reviews. Popular attractions Sebonack Golf Course and Shinnecock Hills Golf Course are located nearby.
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd Old Saybrook CT
Free cancellation
Reserve now, pay when you stay
28.79 km from city centre
The price is CA $139 per night
CA $139
CA $160 total
Dec 23 - Dec 24
includes taxes & fees
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 staff in our reviews. Popular attractions Ferry Landing State Park and Essex Saybrook Antique Village Shopping Center are located nearby.
Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

3 out of 5
2038 Old Country Rd Riverhead NY
Free cancellation
Reserve now, pay when you stay
29 km from city centre
The price is CA $157 per night
CA $157
CA $179 total
Jan 1 - Jan 2, 2026
includes taxes & fees
Stay at this hotel in Riverhead. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Splish Splash Water Park and Tanger Outlet Center are located nearby.
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
6.74 km from city centre
The price is CA $184 per night
CA $184
CA $278 total
Dec 22 - Dec 23
includes taxes & fees
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 rooms in our reviews. Popular attractions Greenport Carousel and Camera Obscura are located nearby.
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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.

Top hotels in Southold for Extended Stay

The modern farmhouse view

The modern farmhouse view

East Quogue NY
10/10 Exceptional! (9 reviews)
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.

Southold hotels essential information

Accommodation
4,295 hotels
Lowest Price
CA $160
Highest Price
CA $490
Popular hotels
The Shoals Suites and Slips, Water's Edge Resort & Spa, Pier Blue Inn Old Saybrook - Essex, Sound View Greenport, Saybrook Point Resort & Marina, The Bentley Hotel Southampton, Quality Inn Old Saybrook - Westbrook, Hilton Garden Inn Riverhead, The Harbor Front Inn

Frequently asked questions

What are the top kid-friendly hotels in Southold?
Family getaways are where the best memories are made, but it's no secret that traveling with youngsters can be tricky. These kid-friendly Southold hotels come with perks designed to keep adventurers of all ages relaxed and happy: The Stucco House will help make your next trip the most memorable one yet. It features an assortment of conveniences geared toward families, such as a king bed and a fireplace. Otherwise, spend your nights in Southold at Idyllic waterfront home with dock, kayaks, bikes, firepit, & fireplace - dogs OK. Make the most of cycling, a king bed and more here.
Where can I find cheap hotels in Southold?
At Travelocity you'll find really nice hotels in Southold at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Southold rather than in Southold. We may find you even better rates, too.
How do I find the best Southold hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Southold then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Southold?
The cheapest hotel in Southold is CA $160 This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Southold?
There are 4,295 hotels in Southold on Travelocity.
What are the best hotels in Southold?
Southold has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Southold for you!
When is the best time to visit Southold?
If you want the joy of a fun-filled trip in peak season, visit Southold during May, June and July. If you'd prefer the peace of off-season, book a stay during quieter months, such as January, October and December.
When is the cheapest time to stay in Southold?
Based on historic data is usually the cheapest month to visit Southold. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Southold?
There are multiple hotels in Southold that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Southold. We have plenty of kid-friendly hotels in Southold to choose from on Travelocity!
Why book a hotel in Southold through Travelocity?
Because we have the top hotels in Southold! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Southold on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Southold hotel reviews by fellow wanderers

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

5 out of 5
Posted 3 days ago
Travelocity Verified Review
"Nice, pet friendly facility with an amazing Indian restaurant next door!"
A verified traveller stayed at Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex

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