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Cheap Southold Hotels

The Shoals Suites and Slips
61600 Main Rd Southold NY
$267 nightly
The price is $302 total per night
$302 total
May 25 - May 26
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

Vine & Sand
47100 New York 25 Southold NY
$424 nightly
The price is $485 total per night
$485 total
May 28 - May 29
Total with taxes and fees
1.32 mi from city center
With a stay at Vine & Sand in Southold, you'll be a 2-minute walk from Mattebella Vineyards and 8 minutes by foot from Corey Creek Winery.
Pool
Breakfast included

Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
$98 nightly
The price is $112 total per night
$112 total
Jun 7 - Jun 8
Total with taxes and fees
Free Cancellation
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 Crystal Lake Town Park.
Pet friendly
Parking included

The Bentley Hotel Southampton
161 Hills Station Rd Southampton NY
$191 nightly
The price is $218 total per night
$218 total
May 28 - May 29
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

Sound View Greenport
58775 County Rd 48 Greenport NY
$376 nightly
The price is $429 total per night
$429 total
May 26 - May 27
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

Sag Harbor Inn
45 West Water Street Sag Harbor NY
$315 nightly
The price is $360 total per night
$360 total
May 25 - May 26
Total with taxes and fees
7.85 mi from city center
When you stay at Sag Harbor Inn in Sag Harbor, you'll be near the beach, just steps from The Hamptons Beaches and 9 minutes by foot from Bay Street Theatre.
Pool
Breakfast included

Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
$264 nightly
The price is $304 total per night
$304 total
May 25 - May 26
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.
On private beach
Pool

The Harbor Front Inn
209 Front St Greenport NY
$294 nightly
The price is $336 total per night
$336 total
May 26 - May 27
Total with taxes and fees
4.19 mi from city center
When you stay at The Harbor Front Inn in Greenport, you'll be near the bay, just steps from Camera Obscura and Greenport Carousel.
Pool
Breakfast included

Hyatt Place Long Island East End
451 East Main Street Riverhead NY
$254 nightly
The price is $290 total per night
$290 total
May 27 - May 28
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
15.66 mi from city center
With a stay at Hyatt Place Long Island East End in Riverhead, you'll be on a river, within a 10-minute drive of Splish Splash Water Park and Suffolk Theater.
Pool
Breakfast included

Hilton Garden Inn Riverhead
2038 Old Country Rd Riverhead NY
$188 nightly
The price is $215 total per night
$215 total
May 27 - May 28
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
18.01 mi from city center
With a stay at Hilton Garden Inn Riverhead, you'll be centrally located in Riverhead, within a 5-minute drive of Splish Splash Water Park and Out East Family Fun.
Pool
Hot Tub

The Sagaponack
3720 Montauk Hwy Wainscott NY
$274 nightly
The price is $308 total per night
$308 total
May 25 - May 26
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.
Pool
Pet friendly

Spark by Hilton Guilford
300 Boston Post Rd Guilford CT
$122 nightly
The price is $141 total per night
$141 total
May 31 - Jun 1
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
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.
Breakfast included
Pet friendly
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 | 4,438 hotels |
|---|---|
Lowest Price | $112 |
Highest Price | $485 |
Popular hotels | The Shoals Suites and Slips, Vine & Sand, Pier Blue Inn Old Saybrook - Essex, The Bentley Hotel Southampton, Sound View Greenport, Sag Harbor Inn, Water's Edge Resort & Spa, The Harbor Front Inn, Hyatt Place Long Island East End, Hilton Garden Inn Riverhead, The Sagaponack, Spark by Hilton Guilford |
Most Recent Southold Hotel Reviews

Spark by Hilton Guilford
5 out of 5
Posted 18 hours ago
CheapTickets Verified Review
"From start to finish the experience was stellar. Smooth check in. Super courteous staff and exceptional facilities "
A verified traveler stayed at Spark by Hilton Guilford
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