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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct
The Sagaponack
Relax in a serene outdoor space surrounded by lush greenery and a charming house with a gabled roof.

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (166)
"The location was great, the room was clean, and the staff were very friendly and accommodating."
The price is HK$2,748
HK$3,454 total
includes taxes & fees
1 Sept - 2 Sept
The Sagaponack
Harpoon House
Relax on the porch with a comfortable chair and a view of lush greenery.

Harpoon House

3.0 star property
8.4 out of 10, Very good, (126)
"Great location"
Harpoon House
The Huntting Inn
Relax in style on the patio, surrounded by lush greenery and comfortable seating.

The Huntting Inn

3.5 star property
8.8 out of 10, Excellent, (95)
"Great property."
The price is HK$4,537
HK$5,262 total
includes taxes & fees
7 Sept - 8 Sept
The Huntting Inn
The Captain Stannard
Cozy up by the fireplace in this stylish living room, featuring a comfortable sofa, armchair, and decorative artwork.

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (237)
"Everything was fantastic, will stay again!"
The Captain Stannard
The Hedges Inn
Cozy retreat with a four-poster bed, dresser, and nightstand, plus a large mirror and TV for a comfortable stay.

The Hedges Inn

3.5 star property
9.6 out of 10, Exceptional, (71)
"Great staff "
The price is HK$5,645
HK$6,834 total
includes taxes & fees
10 Aug - 11 Aug
The Hedges Inn
Carole's Place B & B
Swimmers can enjoy a refreshing dip in the pool surrounded by a deck and lush greenery.

Carole's Place B & B

3.0 star property
9.8 out of 10, Exceptional, (47)
"It’s a very charming place and well located."
Carole's Place B & B
East Hampton Art House Bed & Breakfast
Relax in a spacious outdoor area with a swimming pool surrounded by gardens and seating arrangements.

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 HK$5,384
HK$6,151 total
includes taxes & fees
5 Sept - 6 Sept
East Hampton Art House Bed & Breakfast
West Neck Guesthouse
Relax in this serene bedroom with a large bed, nightstand, and skylight above.

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 HK$2,461
HK$2,812 total
includes taxes & fees
1 Sept - 2 Sept
West Neck Guesthouse
The Homestead
Relax in a spacious room with a large bed, seating area, and cozy fireplace.

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (82)
"Best breakfast. The little things that were provided (warm bathroom towels, comfortable bed, patio outside our room just for us to enjoy) added to our wonderful 3 day get away in Madison. Don't want to forget the freshly made popcorn in the evening we so enjoyed. "
The Homestead
Vine & Sand
Stairs lead to a spacious interior with a polished floor, patterned wallpaper, and a modern light fixture.

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
Relax in a classic room with a four-poster bed, flat-screen TV, and comfortable armchair.

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (16)
"Great and historic. "
The price is HK$3,235
HK$4,533 total
includes taxes & fees
10 Aug - 11 Aug
James Pharmacy Bed & Breakfast
Mill House Inn
Stately home surrounded by lush greenery and mature trees, offering a serene and atmosphere.

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (70)
"Great experience at a wonderful property!"
The price is HK$7,810
HK$9,816 total
includes taxes & fees
10 Aug - 11 Aug
Mill House Inn
Westbrook Inn B&B
Relax in the serene outdoor patio area, surrounded by lush greenery and comfortable seating options.

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (155)
"My granddaughter and I had a lovely stay."
The price is HK$2,248
HK$2,495 total
includes taxes & fees
26 Aug - 27 Aug
Westbrook Inn B&B
434 on Main
Enjoy a peaceful view of the outdoors from this room's large window, which also illuminates the space.

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (36)
"Great hosts"
434 on Main
Harbor Knoll Bed & Breakfast
Relax in this open-plan living space with a high ceiling and exposed beams, featuring a dining area, seating area, and large windows.

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
Historical Bed and breakfast<br>
Enjoy cooking in this kitchen with a central island and bar seating, featuring stainless steel appliances and large windows.

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>
The 1708 House
Two-story home with a central entrance, double doors, and a front porch supported by white columns.

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
Enjoy a scenic breakfast on the deck overlooking the water, with a table set for a delicious meal.

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
Enjoy meals in this beautifully set dining area with a long table, vase, and candle holder.

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
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

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"We only stayed one night, but the area looked beautiful and tranquil."
Alicia 1-night trip
Posted 10 hours ago
Saybrook Point Resort & Marina

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 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.