A calm lake with a forest in the background during sunset.

Southold 4 Stars Hotels

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Check availability on Southold 4 Star Hotels

This weekend
Jul 31 - Aug 2
Next weekend
Aug 7 - Aug 9

Our top choices for Southold 4-star hotels

Resort view

1. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very Good, (672 reviews)
"Beautiful location, adequate facility and room to enjoy location"
United States
Dan
The price is NT$11,375
NT$15,778 total
includes taxes & fees
Aug 18 - Aug 19
Sound View Greenport
Terrace/patio

2. The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (95 reviews)
"Stunning hotel! Will def stay again!"
United States
Anna
The price is NT$21,950
NT$27,586 total
includes taxes & fees
Aug 31 - Sep 1
The Pridwin Hotel
Seasonal outdoor pool, cabanas (surcharge), pool umbrellas

3. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (299 reviews)
"Great location in the heart of town Walk to everything Amazing breakfast too "
United States
Michael
The price is NT$32,861
NT$41,297 total
includes taxes & fees
Aug 2 - Aug 3
Faraway Sag Harbor
Exterior

4. Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.4 out of 10, Exceptional, (379 reviews)
"Wonderful in every way."
United States
Meg
The price is NT$15,535
NT$17,865 total
includes taxes & fees
Aug 31 - Sep 1
Madison Beach Hotel
Property entrance

5. The Maidstone

The Maidstone
4.0 star property
East Hampton
8.2 out of 10, Very Good, (166 reviews)
"It was very fantastic and the staff was very helpful. Late last night, my companion had need of feminine products and the staff was able to assist by giving her own. She was a lifesaver."
United States
Min
The price is NT$19,967
NT$23,953 total
includes taxes & fees
Aug 31 - Sep 1
The Maidstone
Beach bar

6. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
10.0 out of 10, Exceptional, (161 reviews)
"This was my first time in the North fork and this hotel was a total surprise It was absolutely wonderful The accommodations the service the food everything was a delight and we cannot wait to come back"
United States
Sol
Silver Sands Motel & Beach Bungalows
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

7. Canoe Place Inn and Cottages

Canoe Place Inn and Cottages
4.0 star property
Hampton Bays
9.8 out of 10, Exceptional, (68 reviews)
"Very beautiful hotel .no complains"
United States
Jason
Canoe Place Inn and Cottages
Breakfast and dinner served

8. Copper Beech Inn

Copper Beech Inn
4.0 star property
Ivoryton
8.6 out of 10, Excellent, (520 reviews)
"It could use an upgrade for the Breakfast menu."
United States
EUGENE
The price is NT$9,033
NT$10,388 total
includes taxes & fees
Aug 5 - Aug 6
Copper Beech Inn
Outdoor pool

9. Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.0 out of 10, Wonderful, (155 reviews)
"Amazing"
United Kingdom
Ming Da
The price is NT$31,906
NT$36,565 total
includes taxes & fees
Aug 4 - Aug 5
Topping Rose House
Beach nearby, white sand, sun loungers, beach umbrellas

10. The Roundtree, Amagansett

The Roundtree, Amagansett
4.5 star property
Amagansett North
9.8 out of 10, Exceptional, (98 reviews)
"Fantastic hotel, great location."
United States
Tunca
The price is NT$48,401
NT$58,063 total
includes taxes & fees
Aug 3 - Aug 4
The Roundtree, Amagansett
Villa, 3 Bedrooms, Pets Allowed, Pool View | Exterior

11. Serenity at Shorewood

Serenity at Shorewood
4.0 star property
East Hampton
Serenity at Shorewood
Miss Anna James Room | Iron/ironing board, WiFi (free), individually decorated

12. James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast
4.0 star property
Old Saybrook Center
9.2 out of 10, Wonderful, (26 reviews)
"Great location for an overnight stay"
United States
Diane
James Pharmacy Bed & Breakfast
Reception hall

13. 434 on Main

434 on Main
4.0 star property
Amagansett North
10.0 out of 10, Exceptional, (38 reviews)
"Great hosts"
United States
David
434 on Main
Outdoor dining

14. The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
4.0 star property
East Hampton
9.8 out of 10, Exceptional, (171 reviews)
"Beautiful property, we had a wonderful stay. Staff were very friendly and helpful, and the location is an easy walk to shops and restaurants."
United States
Lisa
The 1770 House Restaurant & Inn
Front of property

15. The Farmhouse Bed and Breakfast

The Farmhouse Bed and Breakfast
4.0 star property
Cutchogue
10.0 out of 10, Exceptional, (15 reviews)
"The place is lovely. We loved the garden the house the host th alpacas and the beach parking pass. It is really expensive to stay in that area but the place is great"
United States
Bent
The Farmhouse Bed and Breakfast
Exterior

16. The Baker House 1650

The Baker House 1650
4.5 star property
East Hampton
9.4 out of 10, Exceptional, (33 reviews)
"Absolutely best place to stay in East Hampton! Charming B&B with incredible staff. "
United States
Marcelle
The Baker House 1650
Aerial view

17. East Hampton Art House Bed & Breakfast

East Hampton Art House Bed & Breakfast
4.0 star property
Clearwater Beach
9.6 out of 10, Exceptional, (65 reviews)
"The hosts were really nice and the breakfast is excellent!"
United States
IVAN
The price is NT$36,254
NT$41,420 total
includes taxes & fees
Aug 2 - Aug 3
East Hampton Art House Bed & Breakfast
Superior Villa, Pool View | Living room

18. PinkWood PlayHouse

PinkWood PlayHouse
4.0 star property
East Hampton
PinkWood PlayHouse
Front of property

19. Jedediah Hawkins Inn

Jedediah Hawkins Inn
4.0 star property
Jamesport
9.8 out of 10, Exceptional, (18 reviews)
"It was our first time in this hotel and the area,it was very relaxing. Great service"
United States
OMAR
Jedediah Hawkins Inn
Mini-fridge, freezer

20. The Mainstay

The Mainstay
4.0 star property
Southampton
The Mainstay
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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 NT$32,213 per night from Aug 12 to Aug 13
NT$32,213
NT$53,575 total
Aug 12 - Aug 13
includes taxes & fees
9/10 Wonderful! (88 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.

See all hotels in Southold
A pebbled beach at sunset with the sun reflecting on the water.
Photo by Benny Goh
Open Photo by Benny Goh

Top Southold Hotel Reviews

Sound View Greenport

Sound View Greenport

10/10 Excellent
"My family and I recently stayed at the Sound View Hotel and had a wonderful experience all thanks to their front desk staffer named Adrianne. While our trip was off to a rough start regarding the initial room we were assigned, the moment I voiced my complaints to Adrianne she stepped in and went above and beyond to ensure we were more than happy with our room, and our overall stay at the hotel. If you want a wonderful getaway in Greenport, look no further!...Adrianne, thank you again for all that you did to make our trip so special. We are so grateful!"
Lauren 2-night trip
Posted 2 days ago
Sound View Greenport

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.

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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.

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