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Check prices for these dates

Next weekend
7 Nov - 9 Nov
In two weeks
14 Nov - 16 Nov
In one month
28 Nov - 30 Nov
In two months
26 Dec - 28 Dec

Featured B&B in Southold

IPod dock, MP3 dock
The Captain Stannard
The Captain Stannard
3.0 star property
9.6 out of 10, Exceptional, (253)
"Amazing stay! Everything was perfect and it is clear that the owners love their jobs and their inn. Can't wait to go back! "
United States
Julie
The Captain Stannard
Exterior
The Sagaponack
The Sagaponack
3.0 star property
8.8 out of 10, Excellent, (195)
"An absolute gem of a place to stay. The rooms are full of character and charm, it’s The Hamptons all the way. Great location, too. "
United States
Brad
The price is RM680
RM946 total
includes taxes & fees
30 Oct - 31 Oct
The Sagaponack
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!"
United States
Brian
The price is RM1,373
RM1,725 total
includes taxes & fees
28 Oct - 29 Oct
Mill House Inn
Individually decorated, individually furnished, iron/ironing board
James Pharmacy Bed & Breakfast
James Pharmacy Bed & Breakfast
4.0 star property
9.2 out of 10, Wonderful, (20)
"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!"
United States
Rachel
The price is RM1,276
RM1,416 total
includes taxes & fees
28 Oct - 29 Oct
James Pharmacy Bed & Breakfast
Terrace/patio
Westbrook Inn B&B
Westbrook Inn B&B
3.0 star property
9.8 out of 10, Exceptional, (173)
"Charming, beautiful inn; excellent food and service."
United States
Michael
The price is RM937
RM1,040 total
includes taxes & fees
30 Oct - 31 Oct
Westbrook Inn B&B
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."
United States
Frank
The price is RM718
RM820 total
includes taxes & fees
31 Oct - 1 Nov
Carole's Place B & B
Aerial view
East Hampton Art House Bed & Breakfast
East Hampton Art House Bed & Breakfast
4.0 star property
9.6 out of 10, Exceptional, (65)
"Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. "
United States
Dan
The price is RM1,604
RM1,833 total
includes taxes & fees
28 Oct - 29 Oct
East Hampton Art House Bed & Breakfast
Seasonal outdoor pool
Head of Pond House
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!"
United States
Michèle
The price is RM2,281
RM2,606 total
includes taxes & fees
10 Nov - 11 Nov
Head of Pond House
Egyptian cotton sheets, premium bedding, down duvets, memory-foam beds
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!"
United States
Cynthia
The price is RM1,259
RM1,398 total
includes taxes & fees
30 Oct - 31 Oct
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!"
United States
Dena
The price is RM1,615
RM1,888 total
includes taxes & fees
10 Nov - 11 Nov
The Huntting Inn
Porch
Harpoon House
Harpoon House
3.0 star property
8.4 out of 10, Very good, (146)
"Very cute location- rooms are very spacious. We were able to walk into town. Would definitely stay again. "
United States
Karissa
The price is RM1,432
RM1,636 total
includes taxes & fees
26 Nov - 27 Nov
Harpoon 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 Southold Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"The staff is extremely helpful and polite. The location is wonderful with a beautiful ocean view. I can’t say enough nice things about it!"
Terence 1-night trip
Posted 3 days ago
Water's Edge Resort & Spa

Find out more about Southold

Southold B&B information

Number of reviews
1,167
Accommodation
30 B&B
Lowest Price
RM820
Highest Price
RM2,606

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. Mill House Inn: 10 rooms. 14.3 mi (23.1 km) from the city centre. Enjoy the free cooked 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.