Southold Hotel Guide - 4 Stars Hotels in Southold, New York

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Top Southold 4 Star Hotels

Baron's Cove
Front of property – evening/night

Baron's Cove

4.0 star property
9.0 out of 10, Wonderful, (264)
"Great location in the heart of town Walk to everything Amazing breakfast too "
The price is Rp9.065.862
Rp11.393.591 total
includes taxes & fees
12 Aug - 13 Aug
Baron's Cove
Sound View Greenport
Seasonal outdoor pool, pool umbrellas, pool loungers

Sound View Greenport

4.0 star property
8.4 out of 10, Very good, (535)
"We had an overall great stay and will be back. Especially loved nights out on the beach!"
The price is Rp6.996.372
Rp8.827.123 total
includes taxes & fees
28 Jul - 29 Jul
Sound View Greenport
The Pridwin Hotel
Seasonal outdoor pool, pool umbrellas, pool loungers

The Pridwin Hotel

4.0 star property
9.6 out of 10, Exceptional, (64)
"Lovely hotel/ resort. Look forward to going again!"
The Pridwin Hotel
Canoe Place Inn and Cottages
Garden

Canoe Place Inn and Cottages

4.0 star property
10.0 out of 10, Exceptional, (45)
"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, (103)
"Wonderful location and hotel "
Silver Sands Motel & Beach Bungalows
Journey East Hampton
Exterior

Journey East Hampton

4.0 star property
9.0 out of 10, Wonderful, (139)
"We had a good stay at The Journey. Can’t wait to come back! "
Journey East Hampton
The Maidstone
Front of property – evening/night

The Maidstone

4.0 star property
8.0 out of 10, Very good, (139)
"The details in this beautiful spot is what makes it so special and magical. "
The price is Rp11.336.382
Rp12.951.857 total
includes taxes & fees
14 Jul - 15 Jul
The Maidstone
Madison Beach Hotel
Exterior

Madison Beach Hotel

4.0 star property
9.4 out of 10, Exceptional, (301)
"Great stay!! "
The price is Rp7.302.641
Rp8.398.037 total
includes taxes & fees
20 Jul - 21 Jul
Madison Beach Hotel
The Roundtree, Amagansett
Beach nearby, white sand, sun-loungers, beach umbrellas

The Roundtree, Amagansett

4.5 star property
9.8 out of 10, Exceptional, (88)
"The Roundtree was one of the most peaceful hotels we’ve ever stayed in. I highly recommend for a romantic getaway. "
The price is Rp21.002.310
Rp25.194.946 total
includes taxes & fees
27 Jul - 28 Jul
The Roundtree, Amagansett
Copper Beech Inn
Breakfast and dinner served

Copper Beech Inn

4.0 star property
8.6 out of 10, Excellent, (498)
"Tired, expensive needs update"
The price is Rp4.524.822
Rp5.203.545 total
includes taxes & fees
14 Jul - 15 Jul
Copper Beech Inn
Topping Rose House
Outdoor pool

Topping Rose House

4.5 star property
9.2 out of 10, Wonderful, (133)
"Had an excellent stay at Topping Rose House! Can’t wait to be back soon!"
The price is Rp22.624.110
Rp25.904.809 total
includes taxes & fees
15 Jul - 16 Jul
Topping Rose House
The 1770 House Restaurant & Inn
Garden

The 1770 House Restaurant & Inn

4.0 star property
9.8 out of 10, Exceptional, (155)
"The staff was incredibly genuine and the property felt intimate and comfortable."
The price is Rp9.325.350
Rp12.748.483 total
includes taxes & fees
14 Jul - 15 Jul
The 1770 House Restaurant & Inn
Canoe Place Waterfront Residences
Front of property

Canoe Place Waterfront Residences

4.0 star property
Canoe Place Waterfront Residences
East Hampton Art House Bed & Breakfast
Aerial view

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (62)
"The hosts were really nice and the breakfast is excellent!"
The price is Rp16.509.924
Rp18.862.669 total
includes taxes & fees
14 Jul - 15 Jul
East Hampton Art House Bed & 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 Rp6.684.446
Rp9.365.895 total
includes taxes & fees
15 Jul - 16 Jul
James Pharmacy 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
434 on Main
Reception hall

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (35)
"Great hosts"
434 on Main
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 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
The Mainstay
Balcony

The Mainstay

4.0 star property
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 Rp16.136.910 per night from 14 Jul to 15 Jul
Rp16.136.910
Rp20.279.960 total
14 Jul - 15 Jul
includes taxes & fees
9/10 Wonderful! (69 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

Come to Southold and enjoy its wineries, island views and beaches.

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Frequently asked questions

How much does it cost to stay in a 4-star hotel in Southold?
With Expedia's handy filter tool, bagging a terrific deal on a 4-star hotel in Southold just got easier. Start by keying in your chosen travel dates and length of your break. Then list the results by price and choose a property that best suits your style and budget.

  • Search for the lowest price from Rp16.136.910

What's the difference between 5-star and 4-star hotels in Southold?
If you decide to stay at a 4-star hotel in Southold, you'll typically find loads of conveniences to keep you relaxed, such as a restaurant, pool and gym. You can enjoy excellent service and upmarket surroundings. Choose a 5-star hotel and you'll get a few more perks --- think around-the-clock concierge, on-site spas and opulent turndown services. You'll most likely get more amenities and exclusive services at a 5-star stay, though both are fabulous options for luxury guests.
Does Southold have any 4-star all-inclusive resorts?
Finding your dream holiday in Southold is as simple as entering your travel details and clicking on our "All inclusive" filter. Stay and play where everything is already taken care of like your accommodation, food and activities, or choose a standard 4-star resort in or around this much-loved destination.