Explore top 2025 4 Star Hotels in Southold

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Top Southold 4 Star hotels

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
$291 nightly
The price is $332 total per night from Oct 27 to Oct 28
$332 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 ...
8.4/10 Very Good! (574 reviews)
"Clean and beautiful view"

Reviewed on Sep 16, 2025

Opens in a new windowSound View Greenport
Baron's Cove

Baron's Cove

4 out of 5
31 West Water Street, Sag Harbor, NY
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, ...
8.8/10 Excellent! (289 reviews)
"staff seemed tired and fed up of people staying!"

Reviewed on Sep 25, 2025

Opens in a new windowBaron's Cove
The Pridwin Hotel

The Pridwin Hotel

4 out of 5
81 Shore Road, Shelter Island Heights, NY
$395 nightly
The price is $451 total per night from Oct 9 to Oct 10
$451 total
Oct 9 - Oct 10
Total with 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. ...
9.4/10 Exceptional! (79 reviews)
"The Pridwin is a beautiful property with a stunning view and old New England, Americana historic vibe. It is a quintessential experience if you want to have quiet yet convenience to both the north and south forks. The ferry is quick and the island is beautiful and quiet if you go during off season. ..."

Reviewed on Sep 28, 2025

Opens in a new windowThe Pridwin Hotel
Journey East Hampton

Journey East Hampton

4 out of 5
490 Pantigo Road, East Hampton, NY
$322 nightly
The price is $368 total per night from Oct 9 to Oct 10
$368 total
Oct 9 - Oct 10
Total with 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 ...
9/10 Wonderful! (149 reviews)
"Great staff. Very helpful in recommending beaches, restaurants, etc. Rooms were very clean."

Reviewed on Jul 15, 2025

Opens in a new windowJourney East Hampton
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

4 out of 5
1400 Silvermere Rd, Greenport, NY
$261 nightly
The price is $298 total per night from Oct 7 to Oct 8
$298 total
Oct 7 - Oct 8
Total with taxes and fees
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 ...
9.8/10 Exceptional! (129 reviews)
"Quiet, nice, clean, friendly and helpful staff. It would have been nice if they had more avilable apps for streaming tv."

Reviewed on Sep 26, 2025

Opens in a new windowSilver Sands Motel & Beach Bungalows
Madison Beach Hotel

Madison Beach Hotel

4 out of 5
94 West Wharf Road, Madison, CT
Fully refundableReserve now, pay when you stay
$314 nightly
The price is $361 total per night from Nov 2 to Nov 3
$361 total
Nov 2 - Nov 3
Total with taxes and fees
This 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 ...
9.4/10 Exceptional! (319 reviews)
"the staff was exceptional and our dinner was very good"

Reviewed on Sep 17, 2025

Opens in a new windowMadison Beach Hotel
Canoe Place Inn and Cottages

Canoe Place Inn and Cottages

4 out of 5
239 E Montauk Hwy, Hampton Bays, NY
Fully refundableReserve now, pay when you stay
$450 nightly
The price is $514 total per night from Nov 1 to Nov 2
$514 total
Nov 1 - Nov 2
Total with 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 ...
9.8/10 Exceptional! (58 reviews)
"Amazing property. Really enjoyed our stay."

Reviewed on Sep 16, 2025

Opens in a new windowCanoe Place Inn and Cottages
Topping Rose House

Topping Rose House

4.5 out of 5
One Bridgehampton - Sag Harbor Turnpike, Bridgehampton, NY
$559 nightly
The price is $643 total per night from Oct 8 to Oct 9
$643 total
Oct 8 - Oct 9
Total with 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 ...
9/10 Wonderful! (135 reviews)
"Great rooms, staff and food"

Reviewed on Sep 28, 2025

Opens in a new windowTopping Rose House
Copper Beech Inn

Copper Beech Inn

4 out of 5
46 Main Street, Ivoryton, CT
Fully refundableReserve now, pay when you stay
$279 nightly
The price is $321 total per night from Oct 9 to Oct 10
$321 total
Oct 9 - Oct 10
Total with 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. ...
8.6/10 Excellent! (472 reviews)
"Had a fantastic room 324 in the newer building.. Breakfast was delicious and service terrific.."

Reviewed on May 20, 2025

Opens in a new windowCopper Beech Inn
The Roundtree, Amagansett

The Roundtree, Amagansett

4.5 out of 5
273 Main Street, Amagansett, NY
$624 nightly
The price is $713 total per night from Oct 15 to Oct 16
$713 total
Oct 15 - Oct 16
Total with 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 ...
9.8/10 Exceptional! (88 reviews)
Amazing Staff
"Amazing staff. Great location, very clean. A unique little special place where you are made to feel so welcome. Would definitely recommend a stay here."

Reviewed on Jun 30, 2025

Opens in a new windowThe Roundtree, Amagansett
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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.

Recent Southold hotel reviews by fellow wanderers