Find 4 Star Hotels in Southold, NY from SAR 603

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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, (214)
"Thoroughly enjoyed my stay at Baron's Cove. I stayed late February so the pool was closed, but this was expected. It's a motel style hotel where your door opens to the outside, but given the location of the hotel i felt perfectly safe. The Staff were fantastic, and always helpful. The breakfast was first class too. Sag Harbor is such an iconic place within the Hamptons and this hotel is just as iconic in my eyes. The decor, is photo-worthy. I certainly hope to come back again soon!"
The price is SAR 680
SAR 855 total
includes taxes & fees
25 Mar - 26 Mar
Baron's Cove
Journey East Hampton
Exterior

Journey East Hampton

4.0 star property
9.0 out of 10, Wonderful, (125)
"Great property! Staff is great and personable. I’ve stayed multiple times and will definitely be back again. "
The price is SAR 793
SAR 997 total
includes taxes & fees
18 Mar - 19 Mar
Journey East Hampton
Sound View Greenport
Seasonal outdoor pool, pool umbrellas, sun loungers

Sound View Greenport

4.0 star property
8.4 out of 10, Very Good, (509)
"Amazing location, great staff and very hotel boutique vibes. "
The price is SAR 603
SAR 771 total
includes taxes & fees
24 Mar - 25 Mar
Sound View Greenport
Madison Beach Hotel
Exterior

Madison Beach Hotel

4.0 star property
9.4 out of 10, Exceptional, (277)
"My stay was relaxing and welcoming. The staff went above and beyond to ensure my trip was as enjoyable as possible. I HIGHLY recommend this hotel. You won’t be disappointed. "
The price is SAR 953
SAR 1,096 total
includes taxes & fees
23 Mar - 24 Mar
Madison Beach Hotel
Topping Rose House
Outdoor pool

Topping Rose House

4.5 star property
9.2 out of 10, Wonderful, (127)
"Topping Rose House is beautiful, and the staff is excellent. I am looking forward to returning on my next visit"
The price is SAR 1,482
SAR 1,706 total
includes taxes & fees
12 Mar - 13 Mar
Topping Rose House
Silver Sands Motel & Beach Bungalows
Beach bar

Silver Sands Motel & Beach Bungalows

4.0 star property
9.8 out of 10, Exceptional, (76)
"This property is quaint, thoughtful, decorated with intention. We were there for an overnight trip and it felt like vacation from the moment we stepped foot onto the property. Cant wait to come back in the summer and spend an actual vacation there. "
The price is SAR 732
SAR 836 total
includes taxes & fees
23 Mar - 24 Mar
Silver Sands Motel & Beach Bungalows
Canoe Place Inn and Cottages
Garden

Canoe Place Inn and Cottages

4.0 star property
10.0 out of 10, Exceptional, (38)
"The staff were super nice and accommodating. This place beautiful & clean. Really enjoyed our stay. "
The price is SAR 1,857
SAR 2,249 total
includes taxes & fees
18 Mar - 19 Mar
Canoe Place Inn and Cottages
The 1770 House Restaurant & Inn
Reception

The 1770 House Restaurant & Inn

4.0 star property
9.8 out of 10, Exceptional, (148)
"Property was adorable and the staff very pleasant and helpful!! "
The price is SAR 885
SAR 1,210 total
includes taxes & fees
13 Mar - 14 Mar
The 1770 House Restaurant & Inn
The Roundtree, Amagansett
Beach nearby, white sand, sun loungers, beach umbrellas

The Roundtree, Amagansett

4.5 star property
9.8 out of 10, Exceptional, (85)
"My wife and I stayed a couple nights in October. We felt very pampered. Felix served us up late night snacks with homemade cookies and ice cream! Beautiful and charming hotel with attentive staff."
The price is SAR 2,607
SAR 3,128 total
includes taxes & fees
16 Mar - 17 Mar
The Roundtree, Amagansett
Copper Beech Inn
Breakfast and dinner served

Copper Beech Inn

4.0 star property
8.6 out of 10, Excellent, (491)
"Excellent - highly recommended. Staff were all great! "
The price is SAR 1,047
SAR 1,204 total
includes taxes & fees
8 Apr - 9 Apr
Copper Beech Inn
The Pridwin Hotel
Seasonal outdoor pool, pool umbrellas, sun loungers

The Pridwin Hotel

4.0 star property
9.6 out of 10, Exceptional, (57)
"Fantastic property. Rooms are beautifully appointed, decor is super chic and comfortable. Gorgeous views and amenities. Absolutely enjoyed our second stay at The Pridwin!"
The Pridwin Hotel
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)
"What a beautiful, quiet, peaceful place to stay, even in the dead of winter. The home itself is modern, welcoming, bright, everything you could dream of. The hosts are very active and successful artists who all but gave us a private master class in how their work is imagined and created. I don’t know when we’ve had a more delightful weekend. The walks to the beach were lovely, too. "
The price is SAR 1,585
SAR 1,810 total
includes taxes & fees
12 Mar - 13 Mar
East Hampton Art House Bed & Breakfast
The Maidstone
Front of property - evening/night

The Maidstone

4.0 star property
7.8 out of 10, Good, (120)
"private and elegant"
The price is SAR 1,097
SAR 1,254 total
includes taxes & fees
1 Apr - 2 Apr
The Maidstone
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
434 on Main
Reception hall

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (35)
"Great hosts"
434 on Main
Private beach house - steps to Hamptons & wineries
On the beach

Private beach house - steps to Hamptons & wineries

4.0 star property
The price is SAR 5,439
SAR 7,701 total
includes taxes & fees
10 Apr - 11 Apr
Private beach house - steps to Hamptons & wineries
James Pharmacy Bed & Breakfast
Garden

James Pharmacy Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (14)
"We loved staying in the historic pharmacy. We stayed in the Ann Petry room and it is well appointed, clean and charming. The property sits on the town's main street and is very walkable to shopping and dining. We look forward to our next stay. "
The price is SAR 1,134
SAR 1,709 total
includes taxes & fees
8 Apr - 9 Apr
James Pharmacy Bed & Breakfast
The Farmhouse Bed and Breakfast
Garden

The Farmhouse Bed and Breakfast

4.0 star property
10.0 out of 10, Exceptional, (10)
"Lovely B&B run by a lovely couple"
The Farmhouse Bed and Breakfast
The Baker House 1650
Indoor pool, seasonal outdoor pool, sun loungers

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
Charming 3 Bed/2.5 Bath Cottage In Historic Shelter Island Heights Walk to Ferry
Exterior

Charming 3 Bed/2.5 Bath Cottage In Historic Shelter Island Heights Walk to Ferry

4.0 star property
10.0 out of 10, Exceptional, (2)
"Perfect location for Shelter Island, right next to a few restaurants and coffee shop. Very nice house with an entirely new second floor and beautiful bathroom. We stated here for a wedding instead of staying at The Chequit. Got a better nightly rate and much more space than the hotel. I'd recommend this house to anyone venturing out to Shelter Island."
Charming 3 Bed/2.5 Bath Cottage In Historic Shelter Island Heights Walk to Ferry
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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 SAR 938 per night from Mar 12 to Mar 13
SAR 938
SAR 1,179 total
includes taxes & fees
12 Mar - 13 Mar
8.8/10 Excellent! (67 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 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 938

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.