Explore the best 2025 4 Star Hotels Hotels in Southold
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Top Southold 4 Star hotels
Baron's Cove
31 West Water Street, Sag Harbor, NY
$344 nightly
The price is $393 total per night
$393 total
Jun 9 - Jun 10
Total includes taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Enjoy the seasonal outdoor pool and perks like free valet parking and free WiFi. Free self parking, a business center, and a coffee shop are also offered.
Pool
Spa
Silver Sands Motel & Beach Bungalows
1400 Silvermere Rd, Greenport, NY
This smoke-free hotel features a private beach and 2 restaurants. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.
On private beach
Parking included
Sound View Greenport
58775 County Rd 48, Greenport, NY
$295 nightly
The price is $337 total per night
$337 total
Jun 2 - Jun 3
Total includes 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
Madison Beach Hotel
94 West Wharf Road, Madison, CT
$349 nightly
The price is $401 total per night
$401 total
May 29 - May 30
Total includes taxes and fees
This smoke-free hotel features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Enjoy the gym and perks like free WiFi.
On private beach
Spa
Journey East Hampton
490 Pantigo Road, East Hampton, NY
$545 nightly
The price is $622 total per night
$622 total
May 28 - May 29
Total includes taxes and fees
A seasonal outdoor pool is featured at this hotel, along with a coffee shop and a garden. Enjoy the free on-the-go breakfast each morning. A picnic area, dry cleaning, and luggage storage are also on offer.
Pool
Breakfast included
The Maidstone
207 Main Street, East Hampton, NY
$545 nightly
The price is $623 total per night
$623 total
May 28 - May 29
Total includes taxes and fees
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, a lobby fireplace, and a library are also on offer.
Pet friendly
Parking included
Canoe Place Inn and Cottages
239 E Montauk Hwy, Hampton Bays, NY
Free Cancellation
Reserve now, pay when you stay
$578 nightly
The price is $660 total per night
$660 total
May 29 - May 30
Total includes taxes and fees
This smoke-free hotel features a full-service spa, a marina, and a restaurant. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like valet parking and a beach shuttle. There's a 24-hour gym on site, and a 24-hour front desk and a coffee shop are also provided.
Pool
Spa
Topping Rose House
One Bridgehampton - Sag Harbor Turnpike, Bridgehampton, NY
$667 nightly
The price is $766 total per night
$766 total
Jun 9 - Jun 10
Total includes taxes and fees
A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and free valet parking. Enjoy the gym and perks like free self parking and a free area shuttle.
Pool
Spa
The 1770 House Restaurant & Inn
143 Main Street, East Hampton, NY
$604 nightly
The price is $786 total per night
$786 total
Jun 2 - Jun 3
Total includes taxes and fees
This inn features 2 restaurants and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, a lobby fireplace, and a library are also on offer.
Parking included
Free WiFi
The Pridwin Hotel
81 Shore Road, Shelter Island Heights, NY
$351 nightly
The price is $401 total per night
$401 total
May 28 - May 29
Total includes taxes and fees
This smoke-free hotel features a private beach, a full-service spa, and a restaurant. Enjoy the gym and free perks like continental breakfast and free self parking. Enjoy the seasonal outdoor pool and unwind at the bar/lounge and poolside bar.
On private beach
Pool
The Roundtree, Amagansett
273 Main Street, Amagansett, NY
$1,045 nightly
The price is $1,194 total per night
$1,194 total
May 28 - May 29
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the picnic area. Business travelers can take advantage of the business center.
Breakfast included
Spa
Copper Beech Inn
46 Main Street, Ivoryton, CT
$279 nightly
The price is $321 total per night
$321 total
May 28 - May 29
Total includes taxes and fees
A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A business center, a terrace, and a garden are also on offer.
Breakfast included
Spa
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.
4 Star Hotels Southold
Looking to live it up on your vacation with a bit of luxury? Or maybe you’ve decided that your boss can afford to put you up at a place of your choice on your next business trip?
Come on, you deserve it!
The best part about staying in Southold 4 star hotels is that you’ll often be close to all the local sights and attractions. Whether you’re visiting the area for the first time or you’re back in town for more fun, a 4 star hotel is going to put you right in the heart of all the action.
Plus, you can rest easy knowing that you’re being well taken care of during your visit. Instead of worrying about where to eat or what to see, your friendly hotel staff will be happy to help you get whatever you need.
The best four star hotels in Southold will also frequently include access to high-quality fitness centers and pools, so you’ll feel like you’re staying in an exclusive resort rather than a hotel. You won’t have any excuse for not keeping up with your workout routine!
If you’re looking for 4 star hotels in Southold, you’ll find the most bang for your buck by booking your stay with Travelocity. Go explore a new city, and know you’re getting the best deal on a great hotel with the Travelocity Price Guarantee.
Southold hotels essential information
Accommodation | 4,377 hotels |
|---|---|
Lowest Price | $321 |
Highest Price | $1,194 |
Popular hotels | Baron's Cove, Silver Sands Motel & Beach Bungalows, Sound View Greenport, Madison Beach Hotel, Journey East Hampton, The Maidstone, Canoe Place Inn and Cottages, Topping Rose House, The 1770 House Restaurant & Inn, The Pridwin Hotel, The Roundtree, Amagansett, Copper Beech Inn |
Recent Southold hotel reviews by fellow wanderers
Greenview Inn Riverhead
5 out of 5
Posted 7 hours ago
Travelocity Verified Review
"Allround great place to stay"
A verified traveler stayed at Greenview Inn Riverhead
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