Find 4 Star Hotels in Southold, NY from $282

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

Seasonal outdoor pool, pool umbrellas, sun 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 !! "
$266 nightly
The price is $304
Oct 26 - Oct 27
Total with taxes and fees
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"
$245 nightly
The price is $282
Oct 30 - Oct 31
Total with taxes and fees
Madison Beach Hotel
Exterior
Journey East Hampton
Journey East Hampton
4.0 star property
9.0 out of 10, Wonderful, (151)
"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. "
$282 nightly
The price is $322
Nov 9 - Nov 10
Total with taxes and fees
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."
$453 nightly
The price is $518
Oct 30 - Oct 31
Total with taxes and fees
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!"
Faraway Sag Harbor
Seasonal outdoor pool, pool umbrellas, sun loungers
The Pridwin Hotel
The Pridwin Hotel
4.0 star property
9.6 out of 10, Exceptional, (82)
"Clean room excellent staff"
$417 nightly
The price is $476
Oct 19 - Oct 20
Total with taxes and fees
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. "
$284 nightly
The price is $325
Oct 22 - Oct 23
Total with taxes and fees
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. "
$729 nightly
The price is $833
Nov 5 - Nov 6
Total with taxes and fees
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.."
$279 nightly
The price is $321
Oct 20 - Oct 21
Total with taxes and fees
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"
$832 nightly
The price is $955
Oct 25 - Oct 26
Total with taxes and fees
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 "
$549 nightly
The price is $628
Nov 16 - Nov 17
Total with taxes and fees
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!"
$302 nightly
The price is $335
Oct 19 - Oct 20
Total with taxes and fees
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."
$341 nightly
The price is $444
Oct 20 - Oct 21
Total with taxes and fees
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
Fridge, microwave, oven, stovetop
Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard
Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard
4.0 star property
10.0 out of 10, Exceptional, (11)
"We spent an awesome week at Ray’s house. The pictures were completely accurate and it was so easy to communicate with Ray (and his helpful assistant). Super comfortable beds and great linens. We were traveling with 3 young kids and he went above and beyond - put up a fence around the pool, had a travel crib, high chair and some silicone plates/cups. The location was great. An easy walk to town and the bay beach. Makes a huge difference during high season with all the traffic. Would definitely...
Pool/5 min walk to Beach/Restaurants/Museums- Village House w/backyard
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. "
$422 nightly
The price is $482
Oct 27 - Oct 28
Total with taxes and fees
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"
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 "
The Rams Head Inn
6 bedrooms, desk, iron/ironing board, free WiFi
Historic House Getaway
Historic House Getaway
4.0 star property
9.6 out of 10, Exceptional, (138)
"Property offered a perfect stay... from the beautiful pool and hot tub to the fire pit and Barbecue. House was far more than adequate and we left wanting to return."
Historic House Getaway
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. "
The Farmhouse Bed and Breakfast
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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
$358 nightly
The price is $408 total per night from Oct 27 to Oct 28
$408 total
Oct 27 - Oct 28
Total with taxes and fees
9/10 Wonderful! (70 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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Top Southold Hotel Reviews

Sound View Greenport

Sound View Greenport

10/10 Excellent
"Nice views on sunset"
Genaro 1-night trip
Posted 13 days ago
Sound View Greenport

Find out more about Southold

Southold Four Star Hotel Information

When you need to book a room with luxurious amazing amenities and the best rates, the 4 star hotels in Southold, New York are incredible options. Known for their extra perks, first-rate service, and fantastic locations, each of the Southold 4 star hotels offers the ultimate experience for globe-trotting travelers. Relax in your expertly designed room. Kick back with around-the-clock room service.

Get a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all available when you stay at one of the top book a four star hotels in Southold. What’s more, thanks to Expedia you might even score a cheap great deal on a 4 star hotel in Southold, New York, areas near the hottest attractions, so you can plan a sightseeing adventure and take advantage of unbeatable discounts in one fell swoop.

Whether you’re putting together a serene getaway or want to revel in the most vibrant entertainment district, 4 star Southold hotels offer everything your heart desires.

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Southold?
To book a 4-star hotel in Southold that matches your budget, use Expedia's handy search filters. Take a look at the availability during your vacation dates and use our pricing filter to set your limit. You can also sort your results by the most wallet-friendly stay first.

  • Search for the lowest price from $408

What's the difference between 5-star and 4-star hotels in Southold?
Offering a friendly traveler experience and upscale décor, 4-star hotels are a wonderful option for your Southold escape. These types of stays generally come with loads of useful amenities that make it a breeze to unpack and unwind — think 24-hour room service, pools and restaurants. Or live the high life at a 5-star hotel designed to spoil you with high-end perks and amenities. Full-service health clubs, premium toiletries and gourmet dining are typically included at these deluxe retreats.
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.

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