Find 4 Star Hotels in Southold, NY from AED 657

  • 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

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 AED 692
AED 869 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 AED 777
AED 976 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 AED 590
AED 755 total
includes taxes & fees
25 Mar - 26 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 AED 933
AED 1,073 total
includes taxes & fees
20 Mar - 21 Mar
Madison Beach Hotel
Topping Rose House
Outdoor pool

Topping Rose House

4.5 star property
9.2 out of 10, Wonderful, (127)
"Very modern and beautiful rooms. Great design. Nice and peaceful. Perfect weekend vacation. "
The price is AED 1,545
AED 1,778 total
includes taxes & fees
18 Mar - 19 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)
"Wonderful stay!"
The price is AED 716
AED 818 total
includes taxes & fees
13 Mar - 14 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 AED 1,818
AED 2,202 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 AED 867
AED 1,185 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 AED 2,553
AED 3,062 total
includes taxes & fees
13 Mar - 14 Mar
The Roundtree, Amagansett
Copper Beech Inn
Breakfast and dinner served

Copper Beech Inn

4.0 star property
8.6 out of 10, Excellent, (492)
"Excellent - highly recommended. Staff were all great! "
The price is AED 1,025
AED 1,178 total
includes taxes & fees
13 Mar - 14 Mar
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)
"Beautiful grounds, pool and hot tub! Beautiful breakfast!"
The price is AED 1,551
AED 1,772 total
includes taxes & fees
13 Mar - 14 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 AED 1,074
AED 1,227 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 AED 5,325
AED 7,540 total
includes taxes & fees
13 Mar - 14 Mar
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 AED 1,110
AED 1,673 total
includes taxes & fees
1 Apr - 2 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
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 Mar 16 to Mar 17
AED 918
AED 1,154 total
includes taxes & fees
16 Mar - 17 Mar
8.8/10 Excellent! (67 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.

Learn more about Southold

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

See all hotels in Southold

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.