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

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Check availability on Southold 4 Star Hotels

Top Southold 4 Star Hotels

Seasonal outdoor pool, pool umbrellas, pool loungers
Sound View Greenport
Sound View Greenport
4.0 star property
8.4 out of 10, Very good, (579)
"Loved everything about my stay at the Sound view !! "
Sabrina
The price is Rp3.702.040
Rp5.041.121 total
includes taxes & fees
26 Oct - 27 Oct
Sound View Greenport
Exterior
Madison Beach Hotel
Madison Beach Hotel
4.0 star property
9.4 out of 10, Exceptional, (323)
"the staff was exceptional and our dinner was very good"
john
The price is Rp4.065.330
Rp4.675.129 total
includes taxes & fees
30 Oct - 31 Oct
Madison Beach Hotel
Exterior
Journey East Hampton
Journey East Hampton
4.0 star property
9.0 out of 10, Wonderful, (152)
"We were able to access many beaches with the beach pass that came with the stay. That was the main reason we wanted to stay there. The rooms were very nice, spacious and comfortable. "
Sarah
The price is Rp4.255.335
Rp5.347.973 total
includes taxes & fees
9 Nov - 10 Nov
Journey East Hampton
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Canoe Place Inn and Cottages
Canoe Place Inn and Cottages
4.0 star property
9.8 out of 10, Exceptional, (58)
"Amazing property. Really enjoyed our stay."
Dave
Canoe Place Inn and Cottages
Restaurant
Faraway Sag Harbor
Faraway Sag Harbor
4.0 star property
9.0 out of 10, Wonderful, (291)
"staff seemed tired and fed up of people staying!"
andrew
Faraway Sag Harbor
Seasonal outdoor pool, pool umbrellas, pool loungers
The Pridwin Hotel
The Pridwin Hotel
4.0 star property
9.6 out of 10, Exceptional, (82)
"Clean room excellent staff"
Concetta
The Pridwin Hotel
Beach bar
Silver Sands Motel & Beach Bungalows
Silver Sands Motel & Beach Bungalows
4.0 star property
9.8 out of 10, Exceptional, (136)
"Great hotel and location. "
Lyn
Silver Sands Motel & Beach Bungalows
Beach nearby, white sand, sun-loungers, beach umbrellas
The Roundtree, Amagansett
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. "
Sabrina
The price is Rp11.523.795
Rp13.824.202 total
includes taxes & fees
2 Nov - 3 Nov
The Roundtree, Amagansett
Breakfast and dinner served
Copper Beech Inn
Copper Beech Inn
4.0 star property
8.6 out of 10, Excellent, (504)
"Had a fantastic room 324 in the newer building.. Breakfast was delicious and service terrific.."
Anita
The price is Rp4.626.099
Rp5.320.014 total
includes taxes & fees
20 Oct - 21 Oct
Copper Beech Inn
Outdoor pool
Topping Rose House
Topping Rose House
4.5 star property
9.2 out of 10, Wonderful, (135)
"Great rooms, staff and food"
Alexandra
The price is Rp8.879.125
Rp10.202.434 total
includes taxes & fees
20 Oct - 21 Oct
Topping Rose House
Front of property – evening/night
The Maidstone
The Maidstone
4.0 star property
8.0 out of 10, Very good, (150)
"We had a wonderful stay "
Sabrina
The price is Rp9.795.226
Rp11.191.046 total
includes taxes & fees
28 Oct - 29 Oct
The Maidstone
Miss Anna James Room | Individually decorated, individually furnished, iron/ironing board
James Pharmacy Bed & Breakfast
James Pharmacy Bed & Breakfast
4.0 star property
9.2 out of 10, Wonderful, (19)
"My husband and I stayed here for a quick weekend getaway and loved our experience! The location was perfect - located near restaurants, shops, and the beach - and the room was clean and charming. We will definitely be back!"
Rachel
The price is Rp5.008.623
Rp5.559.572 total
includes taxes & fees
23 Oct - 24 Oct
James Pharmacy Bed & Breakfast
Garden
The 1770 House Restaurant & Inn
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."
Aniya
The price is Rp5.223.015
Rp7.140.276 total
includes taxes & fees
27 Oct - 28 Oct
The 1770 House Restaurant & Inn
Front of property
Canoe Place Waterfront Residences
Canoe Place Waterfront Residences
4.0 star property
10.0 out of 10, Exceptional, (1)
Canoe Place Waterfront Residences
Aerial view
East Hampton Art House Bed & Breakfast
East Hampton Art House Bed & Breakfast
4.0 star property
9.6 out of 10, Exceptional, (64)
"Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. "
Dan
The price is Rp6.297.464
Rp7.194.828 total
includes taxes & fees
28 Oct - 29 Oct
East Hampton Art House Bed & Breakfast
Reception hall
434 on Main
434 on Main
4.0 star property
10.0 out of 10, Exceptional, (36)
"Great hosts"
David
434 on Main
Exterior
The Rams Head Inn
The Rams Head Inn
4.0 star property
7.6 out of 10, Good, (18)
"Beautiful views and lovely service "
Lana
The Rams Head Inn
Living area
The Farmhouse Bed and Breakfast
The Farmhouse Bed and Breakfast
4.0 star property
10.0 out of 10, Exceptional, (13)
"very comfortable stay. "
Valentine
The Farmhouse Bed and Breakfast
Outdoor dining
The Baker House 1650
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. "
Marcelle
The Baker House 1650
Food and drink
Jedediah Hawkins Inn
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"
OMAR
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 Rp5.388.825 per night from 27 Oct to 28 Oct
Rp5.388.825
Rp6.772.509 total
27 Oct - 28 Oct
includes taxes & fees
9/10 Wonderful! (70 reviews)
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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 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.

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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.