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Check prices for these dates

Next weekend
5 Sept - 7 Sept
In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct

Featured B&B in Southold and around

The Sagaponack
Exterior

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (171)
"Great stay!"
The price is €349
includes taxes & fees
10 Sept - 11 Sept
The Sagaponack
Harpoon House
Porch

Harpoon House

3.0 star property
8.4 out of 10, Very good, (131)
"Pop Up Rocco was excellent—bed was crisp & comfortable "
Harpoon House
The Huntting Inn
Garden

The Huntting Inn

3.5 star property
8.8 out of 10, Excellent, (99)
"Great property."
The price is €572
includes taxes & fees
8 Sept - 9 Sept
The Huntting Inn
The Captain Stannard
IPod dock, MP3 dock

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (243)
"Everything was fantastic, will stay again!"
The Captain Stannard
The Hedges Inn
Room One: Large Queen Guestroom

The Hedges Inn

3.5 star property
9.6 out of 10, Exceptional, (71)
"Great staff "
The price is €480
includes taxes & fees
2 Sept - 3 Sept
The Hedges Inn
Westbrook Inn B&B
Terrace/patio

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (159)
"Charming, beautiful inn; excellent food and service."
The price is €210
includes taxes & fees
23 Sept - 24 Sept
Westbrook Inn 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, (63)
"Very profesional, very good experiencia , the host the best , the property beatiful 100 porcent recomended"
The price is €669
includes taxes & fees
2 Sept - 3 Sept
East Hampton Art House Bed & Breakfast
Carole's Place B & B
Property grounds

Carole's Place B & B

3.0 star property
9.8 out of 10, Exceptional, (50)
"That is our second time there and we had a blast again , Carole’s is so kind , and always make sure we are okay with what she will offer for breakfast, great location , so clean and the property has a good care , definitely coming back again ! "
Carole's Place B & B
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 €638
includes taxes & fees
3 Sept - 4 Sept
Mill House Inn
West Neck Guesthouse
Deluxe Room, 1 King Bed

West Neck Guesthouse

3.5 star property
8.2 out of 10, Very good, (36)
"Great property! Close to beach and super clean. "
The price is €306
includes taxes & fees
1 Sept - 2 Sept
West Neck Guesthouse
Vine & Sand
Interior entrance

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
The Homestead
Room, 1 King Bed, Patio, Ground Floor (7)

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (84)
"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 €320
includes taxes & fees
26 Aug - 27 Aug
The Homestead
James Pharmacy Bed & Breakfast
Miss Anna James Room

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (16)
"Beautiful property in a great location, convenient to everything.Our room was clean and comfortable."
The price is €386
includes taxes & fees
26 Aug - 27 Aug
James Pharmacy Bed & Breakfast
434 on Main
Reception hall

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (36)
"Great hosts"
434 on Main
Harbor Knoll Bed & Breakfast
Living area

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
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
Stirling House Bed & Breakfast
Beach/ocean view

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 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
Head of Pond House
Exterior

Head of Pond House

3.0 star property
Head of Pond House
Historical Bed and breakfast<br>
Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils

Historical Bed and breakfast<br>

8.8 out of 10, Excellent, (5)
"Very great house , Owner was amazing and was very easy to contact and gave us early check in . Would definitely do it agian"
Historical Bed and breakfast<br>
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 Southold Hotel Reviews

The Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"Great location ,beautiful hotel,nice staff"
ROBERT 1-night trip
Posted 18 hours ago
The Harbor Front Inn

Find out more about Southold

Find out more about Southold

Southold B&B information

Number of reviews
1,287
Accommodation
38 B&B
Lowest Price
€210
Highest Price
€669

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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. The Captain Stannard: 11 rooms. Situated 15.2 mi (24.4 km) from the heart of Southold. Enjoy the private garden and unique decor. Harpoon House: 9 rooms. 12.4 mi (19.9 km) from the city centre. Enjoy the bars and unique decor. East Hampton Art House Bed & Breakfast: 2 rooms. Located 13.9 mi (22.3 km) from the core of Southold. Enjoy the free full breakfast and fitness centre.
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 Corey Creek Winery and Osprey's Dominion 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.