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Name: The Atlantic Hotel
Price range: $172 total

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Cheap Southold Hotels

The Shoals Suites and Slips

61600 Main Rd Southold NY

$185 nightly

$212 total

Dec 16 - Dec 17

Total with taxes and fees

1.41 mi from city center

When you stay at The Shoals Suites and Slips in Southold, you'll be near the bay, within a 5-minute drive of The Old Field Vineyards and Mattebella Vineyards.

Free WiFi

Air conditioning

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT

$244 nightly

$281 total

Dec 16 - Dec 17

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

14.97 mi from city center

With a stay at Water's Edge Resort & Spa in Westbrook (Westbrook Center), you'll be a 4-minute drive from Tanger Outlets and 8 minutes from Clinton Crossing Premium Outlets.

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

$79 nightly

$91 total

Dec 21 - Dec 22

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

15.32 mi from city center

Located in Old Saybrook (Saybrook Manor), Pier Blue Inn Old Saybrook - Essex is within a 5-minute drive of Chalker Beach and Saybrook Country Barn.

Sound View Greenport

58775 County Rd 48 Greenport NY

$202 nightly

$231 total

Dec 18 - Dec 19

Total with taxes and fees

2.63 mi from city center

When you stay at Sound View Greenport in Greenport, you'll be by the ocean, within a 5-minute drive of Kontokosta Winery and 67 Steps Beach.

On private beach

Pool

Saybrook Point Resort & Marina

2 Bridge St Old Saybrook CT

$331 nightly

$380 total

Dec 21 - Dec 22

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

15.58 mi from city center

With a stay at Saybrook Point Resort & Marina in Old Saybrook (Old Saybrook Center), you'll be steps from Fort Saybrook Monument Park and 4 minutes by foot from Connecticut River.

Pool

Hot Tub

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY

$126 nightly

$144 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

11.94 mi from city center

When you stay at The Bentley Hotel Southampton in Southampton, you'll be near the airport, within a 5-minute drive of The Hamptons Beaches and Meschutt Beach.

Pool

Pet friendly

Quality Inn Old Saybrook - Westbrook

100 Essex Rd Old Saybrook CT

$101 nightly

$116 total

Dec 23 - Dec 24

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

17.88 mi from city center

A stay at Quality Inn Old Saybrook - Westbrook places you in the heart of Old Saybrook, a 5-minute drive from Essex Steam Train and 5 minutes from Essex Library.

Hilton Garden Inn Riverhead

2038 Old Country Rd Riverhead NY

$111 nightly

$127 total

Jan 1 - Jan 2, 2026

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

18.01 mi from city center

A stay at Hilton Garden Inn Riverhead places you in the heart of Riverhead, within a 5-minute drive of Splish Splash Water Park and Out East Family Fun.

Pool

Hot Tub

The Harbor Front Inn

209 Front St Greenport NY

$178 nightly

$203 total

Jan 14 - Jan 15, 2026

Total with taxes and fees

4.19 mi from city center

When you a stay at The Harbor Front Inn in Greenport, you'll be near the bay, just steps from Camera Obscura and Greenport Carousel.

The Sagaponack

3720 Montauk Hwy Wainscott NY

$187 nightly

$214 total

Dec 22 - Dec 23

Total with taxes and fees

11.99 mi from city center

With a stay at The Sagaponack in Wainscott, you'll be within a 5-minute drive of Wolffer Estates Vineyard and The Hamptons Beaches.

Spark by Hilton Guilford

300 Boston Post Rd Guilford CT

$101 nightly

$116 total

Jan 3 - Jan 4, 2026

Total with taxes and fees

19.53 mi from city center

A stay at Spark by Hilton Guilford places you in the heart of Guilford, within a 5-minute drive of Hyland House Museum and Guilford Town Green.

The Atlantic Hotel

1655 County Road 39 Southampton NY

$151 nightly

$172 total

Dec 16 - Dec 17

Total with taxes and fees

11.79 mi from city center

Located in Southampton, The Atlantic Hotel is by the ocean, within a 5-minute drive of Shinnecock Hills Golf Course and The Hamptons Beaches.

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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.

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Southold hotels essential information

Accommodation	4,298 hotels
Lowest Price	$91
Highest Price	$380
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, The Sagaponack, Spark by Hilton Guilford, The Atlantic Hotel