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Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Featured B&B in Southold

The Sagaponack
Exterior

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (170)
"Great stay!"
The price is P23,579
P29,221 total
includes taxes & fees
Sep 7 - Sep 8
The Sagaponack
Harpoon House
Porch

Harpoon House

3.0 star property
8.4 out of 10, Very Good, (129)
"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, (98)
"Great property."
The price is P32,991
P38,263 total
includes taxes & fees
Sep 2 - Sep 3
The Huntting Inn
The Captain Stannard
IPod dock, MP3 dock

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (238)
"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 P41,044
P49,690 total
includes taxes & fees
Sep 1 - Sep 2
The Hedges Inn
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
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 P39,143
P44,721 total
includes taxes & fees
Sep 2 - Sep 3
East Hampton Art House Bed & Breakfast
West Neck Guesthouse
Premium bedding, iron/ironing board, free WiFi, bed sheets

West Neck Guesthouse

3.5 star property
8.2 out of 10, Very Good, (34)
"Great property! Close to beach and super clean. "
The price is P17,894
P20,444 total
includes taxes & fees
Aug 21 - Aug 22
West Neck Guesthouse
The Homestead
1 bedroom, Egyptian cotton sheets, premium bedding, down comforters

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (83)
"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 P19,263
P21,383 total
includes taxes & fees
Aug 20 - Aug 21
The Homestead
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
James Pharmacy Bed & Breakfast
1 bedroom, individually decorated, individually furnished

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (16)
"Great and historic. "
The price is P22,414
P24,879 total
includes taxes & fees
Aug 18 - Aug 19
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 P33,961
P42,680 total
includes taxes & fees
Sep 1 - Sep 2
Mill House Inn
Westbrook Inn B&B
Terrace/patio

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (157)
"Charming, beautiful inn; excellent food and service."
The price is P11,749
P13,042 total
includes taxes & fees
Sep 2 - Sep 3
Westbrook Inn 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
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
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
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 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
Head of Pond House
Exterior

Head of Pond House

3.0 star property
Head of Pond House
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
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

Greenporter Hotel

Greenporter Hotel

10/10 Excellent
"Great location, clean, staff very nice"
Karen 2-night trip
Posted 2 days ago
Greenporter Hotel

Frequently asked questions

Searching for B&Bs in Southold?
If you're looking for something a little different than your standard hotel experience, a stay at a bed and breakfast could be a great option for your trip. 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 interact with the owner, and breakfast served on site, B&Bs provide a unique 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 downtown core. The Captain Stannard: 11 rooms. Situated 15.2 mi (24.4 km) from the heart of Southold. Enjoy the private yard and unique décor. Harpoon House: 9 rooms. 12.4 mi (19.9 km) from the heart of downtown. Enjoy the bars and unique décor. 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 center.
How many Bed & Breakfasts will I be able to find in Southold?
Expedia has 5 B&Bs for your stay in Southold.
When should I 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 temp of 70°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Southold is 57 inches.
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 might 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?
Planning your excursions in and around Southold is easier with these transportation options. Fly into East Hampton, NY (HTO), which is located 11.8 mi (18.9 km) away from the heart of the city. You can also search for flights into Westhampton, NY (FOK-Francis S. Gabreski), which is 19 mi (30.6 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.