Deals on vacations and trips to Southold

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Top Southold hotels deals

The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
$254 nightly
The price is $286 total per night
$286 total
Oct 1 - Oct 2
Total with taxes and fees
A restaurant and a bar/lounge are featured at this hotel. A business center, a communal living room, and a picnic area are also on offer.
Free WiFi
Restaurant
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
$91 nightly
The price is $104 total per night
$104 total
Oct 5 - Oct 6
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A picnic area is also provided.
Pet friendly
Parking included
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
$218 nightly
The price is $251 total per night
$251 total
Oct 7 - Oct 8
Total with taxes and fees
This smoke-free resort features a private beach, a full-service spa, and 3 restaurants. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Enjoy the 2 outdoor tennis courts and perks like free valet parking and free WiFi.
On private beach
Pool
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$250 nightly
The price is $286 total per night
$286 total
Oct 27 - Oct 28
Total with taxes and fees
A private beach and a restaurant are featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like continental breakfast and WiFi in public areas.
On private beach
Pool
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39 Southampton NY
$119 nightly
The price is $136 total per night
$136 total
Oct 25 - Oct 26
Total with taxes and fees
This hotel's 2 outdoor tennis courts and outdoor pool are among the featured amenities. Guests will appreciate free perks like free self parking and WiFi in public areas. Free parking, free newspapers, and barbecue grills are also on offer.
Pool
Pet friendly
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
$169 nightly
The price is $193 total per night
$193 total
Oct 12 - Oct 13
Total with taxes and fees
A bar/lounge and a coffee shop are featured at this hotel, along with free self parking. WiFi in public areas is free. A terrace, a garden, and a picnic area are also on offer.
Pet friendly
Parking included
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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.

Stay near popular Southold attractions

Sparkling Pointe

8.8/10 (11 reviews)
You can enjoy a tasting or tour at Sparkling Pointe during your travels to Southold. Discover the sunsets and wineries in this family-friendly area.
See properties

Frequently asked questions

How much are vacation packages to Southold?
With a Travelocity vacation package, you could paint the town red in Southold for only . Activities, flights and hotels — we've got you. You'll save loads just by bundling together your bookings. And with all of that taken care of before you even set off, you don't have to worry about a thing.
Where can I get the best vacation package deals for Southold?
No matter what you enjoy doing, Travelocity can help you score the perfect Southold package deal. All you have to do is mix and match from our 400 air carriers and 1,000,000 properties around the world.
Why should I purchase my Southold vacation bundle with Travelocity?
Because life is one incredible journey, and we offer everything you could hope for to help you along the way. With our top-quality service and Price Match Guarantee, you can book with confidence. Plus, you can sleep easy while you're on the road knowing you can reach us with our 24/7 support.
Can I save on my Southold car rental if I book it with a hotel or flight?
You can with our Southold vacation packages. With one of these, there are tons of ways to stretch your travel budget further. Combine any two or more car, hotel, flight and tour bookings and watch your savings start to grow. With your own set of wheels, all the popular attractions around Southold are an unforgettable road trip away.

Photos of local treasures

Browse Southold vacation photos for more inspiration

A calm lake with a forest in the background during sunset.
A calm lake with tall grasses in the foreground and a forested shoreline under a pink sky.
A river with red vegetation and a forest in the background.
A lifeguard tower, a boat, and a sandy beach with the ocean in the background.
A river with boats, a marina, and residential areas.