Find 4 Star Hotels in Southold, NY from AED 590

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

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, (496)
"The view from the room"
The price is AED 590
AED 754 total
includes taxes & fees
20 Jan - 21 Jan
Sound View Greenport
Baron's Cove
Exterior

Baron's Cove

4.0 star property
9.0 out of 10, Wonderful, (206)
"We had a great time, live music in the lobby bar which is super cute and cozy, we had breakfast in the dining room that was great and loved that it was dog friendly."
Baron's Cove
Madison Beach Hotel
Exterior

Madison Beach Hotel

4.0 star property
9.4 out of 10, Exceptional, (270)
"Nice book store in town worth visiting. "
The price is AED 933
AED 1,074 total
includes taxes & fees
30 Jan - 31 Jan
Madison Beach Hotel
Journey East Hampton
Lobby sitting area

Journey East Hampton

4.0 star property
9.0 out of 10, Wonderful, (122)
"Enjoyed our stay here. Room was spacious. Really friendly staff. "
The price is AED 744
AED 926 total
includes taxes & fees
16 Jan - 17 Jan
Journey East Hampton
Copper Beech Inn
Exterior

Copper Beech Inn

4.0 star property
8.6 out of 10, Excellent, (489)
"Property was very nice and staff upon arrival was very helpful in getting us checked in. The room was very nice and clean, and the building overall was charming. The toilet in the room needed service however as we had to hold down the handle anytime it was used, and check out was not quite as friendly and staff felt short and eager to get us out. Not a bad place by any standard, but not unique for what you get for the cost."
The price is AED 768
AED 883 total
includes taxes & fees
15 Jan - 16 Jan
Copper Beech Inn
Topping Rose House
Exterior

Topping Rose House

4.5 star property
9.2 out of 10, Wonderful, (120)
"Amazing place. "
The price is AED 1,564
AED 1,797 total
includes taxes & fees
7 Jan - 8 Jan
Topping Rose House
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 AED 1,451
AED 1,739 total
includes taxes & fees
5 Jan - 6 Jan
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, (144)
"Wonderful property - exceeded all expectations!"
The price is AED 921
AED 1,258 total
includes taxes & fees
5 Jan - 6 Jan
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, (72)
"Excellent would recommend"
The price is AED 758
AED 865 total
includes taxes & fees
16 Jan - 17 Jan
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 AED 2,185
AED 2,619 total
includes taxes & fees
21 Jan - 22 Jan
The Roundtree, Amagansett
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 Maidstone
Front of property

The Maidstone

4.0 star property
7.8 out of 10, Good, (119)
"private and elegant"
The price is AED 1,471
AED 1,679 total
includes taxes & fees
19 Jan - 20 Jan
The Maidstone
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!"
East Hampton Art House Bed & Breakfast
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 price is AED 1,194
AED 1,362 total
includes taxes & fees
4 Jan - 5 Jan
The Rams Head Inn
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
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
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 AED 918 per night from Jan 8 to Jan 9
AED 918
AED 1,153 total
includes taxes & fees
8 Jan - 9 Jan
8.8/10 Excellent! (60 reviews)
Still don't see what you're looking for?
See all properties in Southold.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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 AED 918

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?
Enjoy a stress-free vacation experience where everything is included in the one rate by using our “All inclusive” filter. Budgeting is a breeze when your accommodations, food and many activities are already taken care of. After something different? Check out the incredible deals on our standard 4-star hotels in and around Southold too.