Find a Bed and Breakfast in Town of Southold Town

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Check prices for these dates

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Aug 15 - Aug 17
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Aug 22 - Aug 24
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Sep 5 - Sep 7
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Oct 3 - Oct 5

Top Cities in Town of Southold Town

B&BB&B

Greenport

Greenport

Featured B&B in Town of Southold Town

Vine & Sand
Stairs lead to a spacious interior with a polished floor, patterned wallpaper, and a modern light fixture.

Vine & Sand

3.0 star property
10.0 out of 10, Exceptional, (9)
"We enjoyed an amazing wine weekend at Vine and Sand. Beautiful home and relaxing, enjoyable stay. Great location for visiting vineyards as well as the villages of Southold and Greenport. "
Vine & Sand
Harbor Knoll Bed & Breakfast
Relax in this open-plan living space with a high ceiling and exposed beams, featuring a dining area, seating area, and large windows.

Harbor Knoll Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (10)
"Beautiful bed and breakfast with gorgeous views. Close to shops and restaurants but far enough to be private and quiet. Will definitely be coming back"
Harbor Knoll Bed & Breakfast
Stirling House Bed & Breakfast
Enjoy a scenic breakfast on the deck overlooking the water, with a table set for a delicious meal.

Stirling House Bed & Breakfast

3.0 star property
9.8 out of 10, Exceptional, (23)
"Very comfortable king size bed. Excellent gourmet breakfast, discreet host. Older house, but all the comforts. Absolutely every need provided for. "
Stirling House Bed & Breakfast
The Farmhouse Bed and Breakfast
Enjoy meals in this beautifully set dining area with a long table, vase, and candle holder.

The Farmhouse Bed and Breakfast

4.0 star property
10.0 out of 10, Exceptional, (13)
"very comfortable stay. "
The Farmhouse Bed and Breakfast
Arbor View House B&B
Enjoy a serene beach experience with calm seas and a picturesque view.

Arbor View House B&B

3.5 star property
9.2 out of 10, Wonderful, (15)
"Two mid age couples just had a good and relaxing time with great hospitality. "
Arbor View House B&B
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
Stunning hallway with polished floor, staircase, and large window offering a view of lush greenery.

Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
Stunning two-story home with a central entrance and covered porch, surrounded by a beautifully manicured lawn.

Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
Stunning hallway with a herringbone floor pattern leading to a staircase and a door with a glass panel offering a view of the outdoors.

Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
Stroll through the hallway to an open door, offering a glimpse of lush greenery outside.

Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub

10.0 out of 10, Exceptional, (1)
"Must like historical houses and little sausage-shaped dogs. A seamless blend of old and mod. Room is meticulously shiny clean. Substantial bedding designed for a good night’s sleep. High-end details (furnishings, footed tub with heat lamp and fluffy robes), culture (gallery), included breakfast is simple perfection due to high-quality ingredients/sourcing (fresh pastries, eggs, butter, fruit). Pool and hot tub divine. Our hosts are upbeat and fun and really went beyond for us. There are great...
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
Fordham House
Stroll through the beautifully maintained gardens to the charming colonial-style house with a spacious porch and wrap-around balcony.

Fordham House

3.0 star property
10.0 out of 10, Exceptional, (16)
Fordham House
North Fork Guest House
Stunning two-story house with a central entrance and symmetrical facade, surrounded by a serene winter landscape.

North Fork Guest House

3.5 star property
9.8 out of 10, Exceptional, (10)
"Beautifully renovated b & b within walking distance of at least 4 wineries. Our hosts were attentive without being intrusive, made off the charts breakfast and were super knowledgeable about the area. The house was modern and comfortable. I left envious of the fresh, warm decor. We would love to come back in the spring or summer! Highly, highly recommended."
North Fork Guest House
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.
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Top Town of Southold Town Hotel Reviews

The Menhaden

The Menhaden

10/10 Excellent
"Staff was excellent. "
edward 2-night trip
Posted 2 days ago
The Menhaden

Frequently asked questions

Searching for B&Bs in Town of Southold Town?
Whether you're passing through town and are looking for an accommodation that's small and charming, or you're traveling solo and hoping to meet fellow tourists, a B&B can be a good choice for many different types of travelers. If your ideal vacation to Town of Southold Town includes spending lots of time outside, Norman E. Klipp Marine Park and Orient Beach State Park are good spots to enjoy the scenery.
Why consider a B&B versus a traditional hotel?
Every B&B has a unique charm— whether it's a picturesque garden or a beautiful breakfast room, the small details are what make bed and breakfasts a fun place to get away.
What are the best B&Bs in Town of Southold Town?
Check out these B&Bs in Town of Southold Town: Shorecrest Bed and Breakfast: 3.5 stars, 5 rooms. Enjoy the free full breakfast and library. Shinn Estate Vineyards and Farmhouse: 4 stars, 4 rooms. Enjoy the free full breakfast and designer toiletries. Stirling House Bed & Breakfast: 3 stars, 3 rooms. Enjoy the free full breakfast and designer toiletries. Harbor Knoll Bed & Breakfast: 3 stars, 3 rooms. Enjoy the bar/lounge and outdoor pool. Arbor View House Bed and Breakfast: 3.5 stars, 4 rooms. Enjoy the free full breakfast and spa tub.
How many Bed & Breakfasts can I expect to find in Town of Southold Town?
Expedia has 8 B&Bs for your time in Town of Southold Town.
What's the best time of year to stay at a B&B in Town of Southold Town?
When you're planning your trip to Town of Southold Town, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 33°F. The snowiest months in Town of Southold Town are February, December, January, and November, with each month seeing an average of 8 inches of snowfall.
What is there to do in Town of Southold Town?
If you're looking for some activities to entertain you on your trip, consider visiting Island's End Golf and Country Club and Kontokosta Winery. You might put Truman's Beach and 67 Steps Beach on your list if you want to see more of the area.
How can I get to and around Town of Southold Town?
You can plan your excursions in and around Town of Southold Town ahead of time with these transportation options. Fly into MacArthur Airport (ISP), which is located 45.9 mi (73.8 km) from the heart of the city. Otherwise, look for flights into New Haven, CT (HVN-Tweed - New Haven Regional), which is 29.9 mi (48.1 km) away. If you'd like to explore around the area, you may want a rental car for your journey.