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Check availability on Southold 4 Star Hotels

Top Southold 4 Star Hotels

Sound View Greenport
Seasonal outdoor pool, pool umbrellas, pool loungers

Sound View Greenport

4.0 star property
8.4 out of 10, Very good, (561)
"Great location "
The price is 7.612.060 ₫
9.983.507 ₫ total
includes taxes & fees
9 Sept - 10 Sept
Sound View Greenport
Baron's Cove
Front of property – evening/night

Baron's Cove

4.0 star property
9.0 out of 10, Wonderful, (283)
"Great location Rooms are very small but still amazing "
The price is 17.063.508 ₫
21.444.610 ₫ total
includes taxes & fees
28 Aug - 29 Aug
Baron's Cove
The Pridwin Hotel
Seasonal outdoor pool, pool umbrellas, pool loungers

The Pridwin Hotel

4.0 star property
9.6 out of 10, Exceptional, (70)
"Lovely hotel/ resort. Look forward to going again!"
The Pridwin Hotel
Journey East Hampton
Exterior

Journey East Hampton

4.0 star property
9.2 out of 10, Wonderful, (143)
"We had a good stay at The Journey. Can’t wait to come back! "
The price is 11.704.176 ₫
14.709.264 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Journey East Hampton
Canoe Place Inn and Cottages
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

Canoe Place Inn and Cottages

4.0 star property
9.8 out of 10, Exceptional, (55)
"Wonderful stay! "
Canoe Place Inn and Cottages
Silver Sands Motel & Beach Bungalows
Beach bar

Silver Sands Motel & Beach Bungalows

4.0 star property
9.8 out of 10, Exceptional, (113)
"Wonderful location and hotel "
Silver Sands Motel & Beach Bungalows
Madison Beach Hotel
Exterior

Madison Beach Hotel

4.0 star property
9.4 out of 10, Exceptional, (312)
"Great stay!! "
The price is 11.187.931 ₫
12.866.121 ₫ total
includes taxes & fees
4 Sept - 5 Sept
Madison Beach Hotel
Copper Beech Inn
Breakfast and dinner served

Copper Beech Inn

4.0 star property
8.6 out of 10, Excellent, (503)
"Had a fantastic room 324 in the newer building.. Breakfast was delicious and service terrific.."
The price is 7.329.888 ₫
8.429.371 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Copper Beech Inn
East Hampton Art House Bed & Breakfast
Aerial view

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (63)
"Very profesional, very good experiencia , the host the best , the property beatiful 100 porcent recomended"
The price is 18.017.338 ₫
20.584.638 ₫ total
includes taxes & fees
3 Sept - 4 Sept
East Hampton Art House Bed & Breakfast
The Maidstone
Front of property – evening/night

The Maidstone

4.0 star property
8.0 out of 10, Very good, (142)
"The details in this beautiful spot is what makes it so special and magical. "
The Maidstone
The Roundtree, Amagansett
Beach nearby, white sand, sun-loungers, beach umbrellas

The Roundtree, Amagansett

4.5 star property
9.8 out of 10, Exceptional, (89)
"The Roundtree was one of the most peaceful hotels we’ve ever stayed in. I highly recommend for a romantic getaway. "
The price is 28.767.840 ₫
34.510.570 ₫ total
includes taxes & fees
3 Sept - 4 Sept
The Roundtree, Amagansett
Topping Rose House
Outdoor pool

Topping Rose House

4.5 star property
9.2 out of 10, Wonderful, (133)
"Great location and very comfortable "
The price is 14.068.656 ₫
16.165.391 ₫ total
includes taxes & fees
9 Sept - 10 Sept
Topping Rose House
The 1770 House Restaurant & Inn
Garden

The 1770 House Restaurant & Inn

4.0 star property
9.8 out of 10, Exceptional, (157)
"The staff was incredibly genuine and the property felt intimate and comfortable."
The price is 15.106.400 ₫
20.651.631 ₫ total
includes taxes & fees
7 Sept - 8 Sept
The 1770 House Restaurant & Inn
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)
"Beautiful property in a great location, convenient to everything.Our room was clean and comfortable."
The price is 9.285.050 ₫
11.882.825 ₫ total
includes taxes & fees
1 Sept - 2 Sept
James Pharmacy Bed & Breakfast
434 on Main
Reception hall

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (36)
"Great hosts"
434 on Main
Canoe Place Waterfront Residences
Front of property

Canoe Place Waterfront Residences

4.0 star property
10.0 out of 10, Exceptional, (1)
Canoe Place Waterfront Residences
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
The Farmhouse Bed and Breakfast
Living area

The Farmhouse Bed and Breakfast

4.0 star property
10.0 out of 10, Exceptional, (13)
"very comfortable stay. "
The Farmhouse Bed and Breakfast
The Baker House 1650
Outdoor dining

The Baker House 1650

4.5 star property
9.4 out of 10, Exceptional, (33)
"Absolutely best place to stay in East Hampton! Charming B&B with incredible staff. "
The Baker House 1650
Jedediah Hawkins Inn
Food and drink

Jedediah Hawkins Inn

4.0 star property
9.8 out of 10, Exceptional, (18)
"It was our first time in this hotel and the area,it was very relaxing. Great service"
Jedediah Hawkins Inn
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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 15.631.840 ₫ per night from 1 Sept to 2 Sept
15.631.840 ₫
19.645.151 ₫ total
1 Sept - 2 Sept
includes taxes & fees
9/10 Wonderful! (70 reviews)
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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.

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.

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Top Southold Hotel Reviews

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 15.631.840 ₫

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.