Find 4 Star Hotels in Southold, NY from SAR 585

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Compare Southold 4 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Sound View Greenport
Poolside bar

Sound View Greenport

4.0 star property
8.4 out of 10, Very Good, (493)
"Amazing view. Would stay here again. Breakfast limited but great croissants. "
The price is SAR 585
SAR 748 total
includes taxes & fees
24 Dec - 25 Dec
Sound View Greenport
Baron's Cove
Exterior

Baron's Cove

4.0 star property
9.0 out of 10, Wonderful, (199)
"The place was great and maintained very well. Staff always helpful. "
The price is SAR 814
SAR 1,022 total
includes taxes & fees
23 Dec - 24 Dec
Baron's Cove
Journey East Hampton
Lobby sitting area

Journey East Hampton

4.0 star property
9.0 out of 10, Wonderful, (121)
"close to amenities. "
The price is SAR 761
SAR 947 total
includes taxes & fees
1 Jan - 2 January 2025
Journey East Hampton
Madison Beach Hotel
Exterior

Madison Beach Hotel

4.0 star property
9.4 out of 10, Exceptional, (267)
"Our stay was really enjoyable. The room and beds were very clean, and we were on the 4th floor, which gave us a great view! The corridors were nice and quiet, we were there on 2 weekday nights. The valets were such pleasant guys. Desk staff was great, when we had an issue with our bathtub, they were on it right away. We can only say good things about the Madison Beach and plan to return in 2025."
The price is SAR 1,123
SAR 1,292 total
includes taxes & fees
22 Dec - 23 Dec
Madison Beach Hotel
Topping Rose House
Exterior

Topping Rose House

4.5 star property
9.2 out of 10, Wonderful, (120)
"Amazing place. "
The price is SAR 1,548
SAR 1,780 total
includes taxes & fees
5 Jan - 6 January 2025
Topping Rose House
Copper Beech Inn
Exterior

Copper Beech Inn

4.0 star property
8.6 out of 10, Excellent, (488)
"I wish every B&B owner would take note of this property! Honestly one of the best experiences. From the moment you drive through the area. Such a quaint New England block with beautiful homes. The foyer had a wonderful scent of Fall. Staff was so friendly. The home is tastefully decorated. Our room was beautiful. Room #4. Very comfortable. Tv,AC, sitting area, incredibly comfortable bed/bedding, ample storage, fully equipped bathroom with plenty of hooks (nothing worse than a bathroom...
The price is SAR 785
SAR 903 total
includes taxes & fees
29 Dec - 30 Dec
Copper Beech Inn
Canoe Place Inn and Cottages
Exterior

Canoe Place Inn and Cottages

4.0 star property
10.0 out of 10, Exceptional, (36)
"Everything is delightful, love all the thoughtful attention to detail and luxuries so much I’ve decided to extend my stay. "
The price is SAR 1,123
SAR 1,346 total
includes taxes & fees
22 Dec - 23 Dec
Canoe Place Inn and Cottages
The 1770 House Restaurant & Inn
Garden

The 1770 House Restaurant & Inn

4.0 star property
9.8 out of 10, Exceptional, (142)
"An excellent place."
The price is SAR 942
SAR 1,287 total
includes taxes & fees
24 Dec - 25 Dec
The 1770 House Restaurant & Inn
Silver Sands Motel & Beach Bungalows
Private kitchen

Silver Sands Motel & Beach Bungalows

4.0 star property
9.8 out of 10, Exceptional, (68)
"Absolutely a beautiful place that you will enjoy & want to come back too! Upscale, clean, wonderful food & service!"
The price is SAR 751
SAR 858 total
includes taxes & fees
22 Dec - 23 Dec
Silver Sands Motel & Beach Bungalows
The Roundtree, Amagansett
Living area

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 2,236
SAR 2,679 total
includes taxes & fees
22 Dec - 23 Dec
The Roundtree, Amagansett
The Maidstone
Front of property

The Maidstone

4.0 star property
7.8 out of 10, Good, (118)
"Cozy bedroom which made my stay comfortable. Nice, easy going staff. "
The price is SAR 1,505
SAR 1,717 total
includes taxes & fees
2 Jan - 3 January 2025
The Maidstone
The Rams Head Inn
Exterior

The Rams Head Inn

4.0 star property
8.0 out of 10, Very Good, (17)
"Beautiful views and lovely service "
The Rams Head Inn
434 on Main
Front of property

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (35)
"Great hosts"
434 on Main
The Pridwin Hotel
Front of property

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, (60)
"Beautiful grounds, pool and hot tub! Beautiful breakfast!"
The price is SAR 1,587
SAR 1,811 total
includes taxes & fees
24 Dec - 25 Dec
East Hampton Art House Bed & Breakfast
The Baker House 1650
Exterior

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
James Pharmacy Bed & Breakfast
Room

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. "
James Pharmacy Bed & Breakfast
The Farmhouse Bed and Breakfast
Front of property

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
Modern, coastal-style home with flooding natural light, a private pool, a...
Pool

Modern, coastal-style home with flooding natural light, a private pool, a...

4.0 star property
10.0 out of 10, Exceptional, (1)
Modern, coastal-style home with flooding natural light, a private pool, a...
The Mainstay
Living room

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 SAR 939 per night from Dec 22 to Dec 23
SAR 939
SAR 1,179 total
includes taxes & fees
22 Dec - 23 Dec
8.8/10 Excellent! (59 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.

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 939

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.