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Check prices for these dates

Next weekend
24 Oct - 26 Oct
In two weeks
31 Oct - 2 Nov
In one month
14 Nov - 16 Nov
In two months
12 Dec - 14 Dec

Featured B&B in Southold and around

IPod dock, MP3 dock
The Captain Stannard
The Captain Stannard
3.0 star property
9.6 out of 10, Exceptional, (250)
"Everything was fantastic, will stay again!"
The Captain Stannard
Property grounds
Carole's Place B & B
Carole's Place B & B
3.0 star property
9.8 out of 10, Exceptional, (60)
"Small B&B with a charming old school vibe. Second time we’ve stayed there and we will return."
The price is €148
includes taxes & fees
27 Oct - 28 Oct
Carole's Place B & B
Exterior
The Sagaponack
The Sagaponack
3.0 star property
8.8 out of 10, Excellent, (190)
"Great stay!"
The price is €202
includes taxes & fees
16 Oct - 17 Oct
The Sagaponack
Terrace/patio
Westbrook Inn B&B
Westbrook Inn B&B
3.0 star property
9.8 out of 10, Exceptional, (171)
"Charming, beautiful inn; excellent food and service."
The price is €212
includes taxes & fees
21 Oct - 22 Oct
Westbrook Inn B&B
Front of property – evening/night
Mill House Inn
Mill House Inn
5.0 star property
9.0 out of 10, Wonderful, (70)
"Great experience at a wonderful property!"
The price is €352
includes taxes & fees
29 Oct - 30 Oct
Mill House Inn
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. "
The price is €374
includes taxes & fees
27 Oct - 28 Oct
East Hampton Art House Bed & Breakfast
Miss Anna James Room
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!"
The price is €289
includes taxes & fees
29 Oct - 30 Oct
James Pharmacy Bed & Breakfast
Room, 1 King Bed, Patio, Ground Floor (7)
The Homestead
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 €285
includes taxes & fees
10 Nov - 11 Nov
The Homestead
Garden
The Huntting Inn
The Huntting Inn
3.5 star property
9.0 out of 10, Wonderful, (103)
"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 €385
includes taxes & fees
9 Nov - 10 Nov
The Huntting Inn
Deluxe Room, 1 King Bed
West Neck Guesthouse
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 €353
includes taxes & fees
17 Oct - 18 Oct
West Neck Guesthouse
Porch
Harpoon House
Harpoon House
3.0 star property
8.4 out of 10, Very good, (143)
"Very cute location- rooms are very spacious. We were able to walk into town. Would definitely stay again. "
The price is €220
includes taxes & fees
18 Oct - 19 Oct
Harpoon House
Outdoor dining
Large Room w use of pool/tennis in Spacious home
Large Room w use of pool/tennis in Spacious home
The price is €714
includes taxes & fees
16 Oct - 17 Oct
Large Room w use of pool/tennis in Spacious home
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

Greenview Inn Riverhead

Greenview Inn Riverhead

10/10 Excellent
"Really clean and new!"
Abdalla 1-night trip
Posted 3 days ago
Greenview Inn Riverhead

Find out more about Southold

Southold B&B information

Number of reviews
1,184
Accommodation
38 B&B
Lowest Price
€148
Highest Price
€714

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. Harpoon House: 9 rooms. 12.4 mi (19.9 km) from the city centre. Enjoy the bars and unique decor. James Pharmacy Bed & Breakfast: 3 rooms. Located 15.5 mi (25 km) from the core of Southold. Enjoy the local cuisine breakfast and designer toiletries.
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.