Find 4 Star Hotels in Southold, NY from SAR 1,047

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check availability on Southold 4 Star Hotels

Compare Southold 4 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Baron's Cove
Front of property - evening/night

Baron's Cove

4.0 star property
9.0 out of 10, Wonderful, (252)
"Great location in the heart of town Walk to everything Amazing breakfast too "
Baron's Cove
Silver Sands Motel & Beach Bungalows
Beach/ocean view

Silver Sands Motel & Beach Bungalows

4.0 star property
9.8 out of 10, Exceptional, (97)
"The rooms were remodeled and well decorated. The restaurant was amazing."
Silver Sands Motel & Beach Bungalows
Sound View Greenport
Seasonal outdoor pool, pool umbrellas, sun loungers

Sound View Greenport

4.0 star property
8.4 out of 10, Very Good, (527)
"For the short break we wanted it was perfect "
The price is SAR 1,648
SAR 2,075 total
includes taxes & fees
2 Jul - 3 Jul
Sound View Greenport
Canoe Place Inn and Cottages
Garden

Canoe Place Inn and Cottages

4.0 star property
10.0 out of 10, Exceptional, (43)
"The staff were super nice and accommodating. This place beautiful & clean. Really enjoyed our stay. "
Canoe Place Inn and Cottages
Journey East Hampton
Exterior

Journey East Hampton

4.0 star property
9.0 out of 10, Wonderful, (136)
"Great property! Staff is great and personable. I’ve stayed multiple times and will definitely be back again. "
The price is SAR 1,671
SAR 2,101 total
includes taxes & fees
29 Jun - 30 Jun
Journey East Hampton
The Pridwin Hotel
Seasonal outdoor pool, pool umbrellas, sun loungers

The Pridwin Hotel

4.0 star property
9.6 out of 10, Exceptional, (59)
"WELL APPOINTED"
The Pridwin Hotel
Madison Beach Hotel
Front of property - evening/night

Madison Beach Hotel

4.0 star property
9.4 out of 10, Exceptional, (295)
"I loved everything about the property "
The price is SAR 1,910
SAR 2,197 total
includes taxes & fees
24 Jun - 25 Jun
Madison Beach Hotel
The Maidstone
Front of property - evening/night

The Maidstone

4.0 star property
8.0 out of 10, Very Good, (132)
"Excellent stay!"
The price is SAR 1,435
SAR 1,640 total
includes taxes & fees
22 Jun - 23 Jun
The Maidstone
The Roundtree, Amagansett
Free daily continental breakfast

The Roundtree, Amagansett

4.5 star property
9.8 out of 10, Exceptional, (86)
"Fantastic hotel, great location."
The price is SAR 3,733
SAR 4,478 total
includes taxes & fees
22 Jun - 23 Jun
The Roundtree, Amagansett
Copper Beech Inn
Breakfast and dinner served

Copper Beech Inn

4.0 star property
8.6 out of 10, Excellent, (496)
"Peaceful, quiet, well appointed room. Attentive staff. Delicious breakfast!"
The price is SAR 1,047
SAR 1,204 total
includes taxes & fees
19 Jun - 20 Jun
Copper Beech Inn
The 1770 House Restaurant & Inn
Reception

The 1770 House Restaurant & Inn

4.0 star property
9.8 out of 10, Exceptional, (152)
"Nice, quiet & quaint bed and breakfast near all, friendly staff"
The price is SAR 2,157
SAR 2,949 total
includes taxes & fees
19 Jun - 20 Jun
The 1770 House Restaurant & Inn
Topping Rose House
Outdoor pool

Topping Rose House

4.5 star property
9.2 out of 10, Wonderful, (131)
"Had an excellent stay at Topping Rose House! Can’t wait to be back soon!"
The price is SAR 4,026
SAR 4,613 total
includes taxes & fees
25 Jun - 26 Jun
Topping Rose House
Canoe Place Waterfront Residences
Front of property

Canoe Place Waterfront Residences

4.0 star property
The price is SAR 6,437
SAR 7,795 total
includes taxes & fees
26 Jun - 27 Jun
Canoe Place Waterfront Residences
434 on Main
Reception hall

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (35)
"Great hosts"
434 on Main
Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard
Fridge, microwave, oven, stovetop

Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard

4.0 star property
10.0 out of 10, Exceptional, (2)
"This place is an absolute gem. Four big bedrooms, a brand new kitchen and washer/dryer, lovely renovated interior, and huge fluffy towels in excess! A huge backyard with plenty of toys for little ones and a big patio table and chairs to enjoy amazing grilled dinners from the new gas BBQ grill was a huge plus. Also lots of beach chairs, beach towels, umbrella available for use! The owner was extremely communicative, thoughtful, and an excellent host. This house is on a QUIET street in busy Sag...
Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard
East Hampton Art House Bed & Breakfast
Aerial view

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (61)
"The hosts were really nice and the breakfast is excellent!"
The price is SAR 2,859
SAR 3,266 total
includes taxes & fees
19 Jun - 20 Jun
East Hampton Art House Bed & Breakfast
The Farmhouse Bed and Breakfast
Living area

The Farmhouse Bed and Breakfast

4.0 star property
10.0 out of 10, Exceptional, (11)
"Lovely B&B run by a lovely couple"
The Farmhouse Bed and Breakfast
James Pharmacy Bed & Breakfast
Miss Anna James Room | 1 bedroom, individually decorated, individually furnished

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (16)
"Great and historic. "
The price is SAR 1,546
SAR 2,167 total
includes taxes & fees
22 Jun - 23 Jun
James Pharmacy Bed & Breakfast
NORTHFORK COTTAGE with POOL & HOT TUB
Outdoor spa tub

NORTHFORK COTTAGE with POOL & HOT TUB

4.0 star property
9.8 out of 10, Exceptional, (128)
"Loved our stay and will be back"
NORTHFORK COTTAGE with POOL & HOT TUB
The Rams Head Inn
Exterior

The Rams Head Inn

4.0 star property
7.6 out of 10, Good, (18)
"Beautiful views and lovely service "
The Rams Head Inn
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Southold.
Mill House Inn

Mill House Inn

31 North Main Street, East Hampton, NY
The price is SAR 2,983 per night from Jun 23 to Jun 24
SAR 2,983
SAR 3,749 total
23 Jun - 24 Jun
includes taxes & fees
9/10 Wonderful! (69 reviews)
Still don't see what you're looking for?
See all properties in Southold.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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.

Learn more about Southold

Vineyards and farm stands dot the landscape of this North Fork gem, inviting visitors to sample local wines and fresh produce. Stroll along the pebble beaches, explore historic lighthouses, or take a ferry to nearby Shelter Island for a day trip.

See all hotels in Southold

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Southold?
With Expedia's sort and search filters, bagging a great deal on a 4-star hotel in Southold just got simpler. Start by keying in your chosen arrival date and length of your escape. Then list the results by price and choose a hotel that best suits your style and budget.
  • Search for the lowest price from SAR 2,983

What's the difference between 5-star and 4-star hotels in Southold?
If you choose to book a stay at a 4-star hotel in Southold, you'll usually find loads of amenities to make sure you're comfortable, such as a restaurant, gym and pool. You can enjoy excellent service and upscale surroundings. Opt for a 5-star hotel and you'll have access to a few extra bells and whistles --- think on-site spas, around-the-clock concierge and indulgent turndown services. You're likely to get extra amenities and first-rate services at a 5-star retreat, though both are fabulous options for luxury guests.
Does Southold have any 4-star all-inclusive resorts?
Use our "All inclusive" filter to search for your next escape in Southold where just about everything is taken care of, from your meals to your room, activities and entertainment. We can also help you find standard 4-star stays in and around this much-loved destination.