Search Bed and Breakfast in Southold

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
3 Oct - 5 Oct
In two weeks
10 Oct - 12 Oct
In one month
24 Oct - 26 Oct
In two months
21 Nov - 23 Nov

Featured B&B in Southold

The Sagaponack
Exterior

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (180)
"Great stay!"
The price is S$321
includes taxes & fees
14 Oct - 15 Oct
The Sagaponack
The Huntting Inn
Garden

The Huntting Inn

3.5 star property
9.0 out of 10, Wonderful, (102)
"What a wonderful place to stay! The room was beautiful. The bed was comfortable and the staff were welcoming and helpful. We loved how close it was to town. We also enjoyed the breakfast every morning. The Palm restaurant downstairs was nice to have on property and the food was great. We will definitely stay again!"
The price is S$723
includes taxes & fees
9 Oct - 10 Oct
The Huntting Inn
Harpoon House
Porch

Harpoon House

3.0 star property
8.4 out of 10, Very good, (141)
"Cute spot"
Harpoon House
The Captain Stannard
IPod dock, MP3 dock

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (247)
"Everything was fantastic, will stay again!"
The Captain Stannard
The Hedges Inn
Egyptian cotton sheets, premium bedding, in-room safe

The Hedges Inn

3.5 star property
9.6 out of 10, Exceptional, (71)
"Great staff "
The price is S$1,127
includes taxes & fees
27 Sept - 28 Sept
The Hedges Inn
Westbrook Inn B&B
Terrace/patio

Westbrook Inn B&B

3.0 star property
9.8 out of 10, Exceptional, (170)
"Charming, beautiful inn; excellent food and service."
The price is S$312
includes taxes & fees
1 Oct - 2 Oct
Westbrook Inn B&B
The Homestead
Egyptian cotton sheets, premium bedding, down duvets, memory-foam beds

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (87)
"This is our 2nd year staying at the Homestead B & B. We absolutely love it here! Great food, amenities galore, and just an awesome getaway!"
The price is S$428
includes taxes & fees
26 Oct - 27 Oct
The Homestead
James Pharmacy Bed & Breakfast
Individually decorated, individually furnished, iron/ironing board

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (18)
"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!"
The price is S$391
includes taxes & fees
6 Oct - 7 Oct
James Pharmacy Bed & Breakfast
Mill House Inn
Front of property – evening/night

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (70)
"Great experience at a wonderful property!"
The price is S$447
includes taxes & fees
27 Oct - 28 Oct
Mill House Inn
Carole's Place B & B
Property grounds

Carole's Place B & B

3.0 star property
9.8 out of 10, Exceptional, (56)
"Very clean and quiet, super comfortable bed, good central location to get around on Long Island, and an great host."
The price is S$222
includes taxes & fees
1 Oct - 2 Oct
Carole's Place B & B
East Hampton Art House Bed & Breakfast
Aerial view

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. "
The price is S$562
includes taxes & fees
27 Oct - 28 Oct
East Hampton Art House Bed & Breakfast
Vine & Sand
Interior entrance

Vine & Sand

3.0 star property
10.0 out of 10, Exceptional, (11)
"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
West Neck Guesthouse
Premium bedding, iron/ironing board, free WiFi, bed sheets

West Neck Guesthouse

3.5 star property
8.0 out of 10, Very good, (37)
"Great property! Close to beach and super clean. "
The price is S$464
includes taxes & fees
2 Oct - 3 Oct
West Neck Guesthouse
Stirling House Bed & Breakfast
Beach/ocean view

Stirling House Bed & Breakfast

3.0 star property
9.8 out of 10, Exceptional, (24)
"Our stay was only 2 nights but felt like 5. Well rested 3 days. Would return in a Heart Beat. Clay was awesome and the breakfasts were over the top !"
The price is S$710
includes taxes & fees
25 Oct - 26 Oct
Stirling House Bed & Breakfast
Arbor View House B&B
Exterior

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
434 on Main
Reception hall

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (36)
"Great hosts"
434 on Main
The 1708 House
Exterior

The 1708 House

3.0 star property
10.0 out of 10, Exceptional, (2)
"We absolutely loved our stay here. The house is stunning, the service is fabulous. The best bed ever to sleep in! Great location and a fabulous breakfast. Thank you. "
The 1708 House
Harbor Knoll Bed & Breakfast
Living area

Harbor Knoll Bed & Breakfast

3.0 star property
9.2 out of 10, Wonderful, (11)
"It was very pleasant. We would stay again someday. Very convenient to restaurants in town and ferry. "
Harbor Knoll Bed & Breakfast
Head of Pond House
Exterior

Head of Pond House

3.0 star property
10.0 out of 10, Exceptional, (2)
"Beautiful place with a very kind host. Highly recommend this place!"
Head of Pond House
The Farmhouse Bed and Breakfast
Living area

The Farmhouse Bed and Breakfast

4.0 star property
10.0 out of 10, Exceptional, (13)
"very comfortable stay. "
The Farmhouse Bed and Breakfast
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southold Hotel Reviews

Greenview Inn Riverhead

Greenview Inn Riverhead

10/10 Excellent
"Serene environment, very neat and clean. "
Dennis 2-night trip
Posted 2 days ago
Greenview Inn Riverhead

Find out more about Southold

Find out more about Southold

Southold B&B information

Number of reviews
1,345
Accommodation
30 B&B
Lowest Price
S$222
Highest Price
S$1,127

Frequently asked questions

Searching for B&Bs in Southold?
If you're interested in something a little more offbeat than your standard hotel experience, a stay at a bed and breakfast might be the perfect option for your getaway. If you'd like to spend some time by the water during your time in Southold, McCabe's Beach and Horton Lane Beach are worth a stop.
How do you know if a B&B is the right choice for your stay?
With attentive service, opportunities to socialise with other guests and of course a full breakfast to start the day, B&Bs offer a truly one-of-a-kind setting.
What are the top B&Bs in Southold?
Here are some well-liked B&Bs in the area: Vine & Sand: 4 rooms. 1.3 mi (2.1 km) from the heart of Southold. Enjoy the free buffet breakfast and designer toiletries. The Sagaponack: 12 mi (19.3 km) from the city centre. East Hampton Art House Bed & Breakfast: 2 rooms. Situated 13.9 mi (22.3 km) from the heart of Southold. Enjoy the free full breakfast and fitness centre. James Pharmacy Bed & Breakfast: 3 rooms. 15.5 mi (25 km) from the city centre. Enjoy the local cuisine breakfast and designer toiletries. Harpoon House: 9 rooms. Located 12.4 mi (19.9 km) from the core of Southold. Enjoy the bars and unique decor.
How many bed & breakfasts will I find in Southold?
Expedia has 5 B&Bs for your time in Southold.
When is the best time to book my B&B in Southold?
When you're dreaming of a escape to Southold, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Southold is 1452 mm.
What is there to do in Southold?
If you're looking for some activities to entertain you on your trip, consider visiting Sparkling Pointe and Croteaux Vineyards. You should put Osprey's Dominion and Sannino's Bella Vita Vineyard on your list if you want to see more of the area.
How can I get to and around Southold?
Mapping out your trip in and around Southold is easy with these transportation options. Fly into East Hampton, NY (HTO), which is located 11.8 mi (18.9 km) from the heart of the city. Otherwise, you can search for flights to Westhampton, NY (FOK-Francis S. Gabreski), which is 19 mi (30.6 km) away. If you'd like to venture out around the area, consider renting a car to explore more sights.

Explore a world of travel with Expedia

Explore a world of travel with Expedia