Explore top 2026 4 Star Hotels in Southold

Start date: Check-in selected.
To Date
End date: Check-out

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Check prices for these dates

This weekend
Next weekend

Top Southold 4 Star hotels

Madison Beach Hotel

Madison Beach Hotel

4 out of 5
94 West Wharf Road Madison CT
$339 nightly
The price is $390 total per night from Jan 3 to Jan 4
$390 total
Jan 3 - Jan 4
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! (341 reviews)
beautiful room and views

Reviewed on Dec 13, 2025

Opens in a new windowMadison Beach Hotel
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$169 nightly
The price is $193 total per night from Jan 8 to Jan 9
$193 total
Jan 8 - Jan 9
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! (601 reviews)
Great room with amazing views! Staff was fantastic and the food was great too

Reviewed on Nov 28, 2025

Opens in a new windowSound View Greenport
Canoe Place Inn and Cottages

Canoe Place Inn and Cottages

4 out of 5
239 E Montauk Hwy Hampton Bays NY
$652 nightly
The price is $745 total per night from Jan 10 to Jan 11
$745 total
Jan 10 - Jan 11
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! (60 reviews)
Staff was amazing, food was delicious, decor and ambiance was beautiful, and the room was spotless. Check in and valet was so helpful. I will definitely be returning!

Reviewed on Nov 17, 2025

Opens in a new windowCanoe Place Inn and Cottages
Journey East Hampton

Journey East Hampton

4 out of 5
490 Pantigo Road East Hampton NY
$193 nightly
The price is $221 total per night from Jan 8 to Jan 9
$221 total
Jan 8 - Jan 9
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! (160 reviews)
Clean and simple

Reviewed on Dec 1, 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
$218 nightly
The price is $250 total per night from Jan 4 to Jan 5
$250 total
Jan 4 - Jan 5
Total with taxes and fees
This smoke-free hotel features a private beach, a full-service spa, and 3 restaurants. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...
9.8/10 Exceptional! (143 reviews)
Everything was excellent, best hotel on the north fork.

Reviewed on Jan 1, 2026

Opens in a new windowSilver Sands Motel & Beach Bungalows
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 Jan 4 to Jan 5
$713 total
Jan 4 - Jan 5
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! (91 reviews)
Very nice property, very nice food, and very nice service. Although the room was very nice and clean there was some maintenance needed in the bathroom area

Reviewed on Nov 13, 2025

Opens in a new windowThe Roundtree, Amagansett
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 Jan 4 to Jan 5
$321 total
Jan 4 - Jan 5
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! (474 reviews)
Very nice property. Very clean. Staff was very nice - very good breakfast.

Reviewed on Oct 27, 2025

Opens in a new windowCopper Beech Inn
The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn

4 out of 5
143 Main Street East Hampton NY
$263 nightly
The price is $343 total per night from Jan 4 to Jan 5
$343 total
Jan 4 - Jan 5
Total with 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, ...
9.8/10 Exceptional! (161 reviews)
Couldn’t ask for anything more. Make sure to have a burger at the downstairs Tavern

Reviewed on Nov 4, 2025

Opens in a new windowThe 1770 House Restaurant & Inn
Topping Rose House

Topping Rose House

4.5 out of 5
One Bridgehampton - Sag Harbor Turnpike Bridgehampton NY
$524 nightly
The price is $603 total per night from Jan 15 to Jan 16
$603 total
Jan 15 - Jan 16
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! (138 reviews)
Our second home :)

Reviewed on Dec 27, 2025

Opens in a new windowTopping Rose House
The Maidstone

The Maidstone

4 out of 5
207 Main Street East Hampton NY
Fully refundableReserve now, pay when you stay
$257 nightly
The price is $294 total per night from Jan 3 to Jan 4
$294 total
Jan 3 - Jan 4
Total with taxes and fees
A restaurant and a bar/lounge are featured at this hotel. Free perks include continental breakfast, free self parking, and a beach shuttle. Free WiFi in public ...
7.8/10 Good! (150 reviews)
We had a wonderful stay

Reviewed on Sep 9, 2025

Opens in a new windowThe Maidstone
Don't see what you're looking for?
See all available properties in Southold
View all properties
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.

Recent Southold hotel reviews by fellow wanderers