A calm lake with a forest in the background during sunset.

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Check prices for these dates

Next weekend
25 Sep - 27 Sep
In two weeks
2 Oct - 4 Oct
In one month
16 Oct - 18 Oct
In two months
13 Nov - 15 Nov

Our top choices for Southold bed & breakfast

Deluxe Room, 1 King Bed | Premium bedding, iron/ironing board, WiFi (free), bed sheets

1. West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.2 out of 10, Very good, (46 reviews)
"It was great! The location was perfect, plenty of amenities close by as well. Easy ferry access depending on time of day. Room was very clean. Will be staying again!"
United States
Allie
The price is AED 1,151
AED 1,316 total
includes taxes & fees
1 Oct - 2 Oct
West Neck Guesthouse
Property entrance

2. The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (288 reviews)
"everything about the hotel was excellent, prices fair for the Hamptons!"
United States
Jane
The price is AED 842
AED 1,108 total
includes taxes & fees
28 Sep - 29 Sep
The Sagaponack
Interior detail

3. Harpoon House

Harpoon House
3.0 star property
Southampton
8.4 out of 10, Very good, (193 reviews)
"Wonderful place great location I definitely recommend!"
United States
Yuliya V
The price is AED 882
AED 1,007 total
includes taxes & fees
21 Sep - 22 Sep
Harpoon House
Living area

4. The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (282 reviews)
"Had a great stay. Everything was fantastic."
United States
Deborah
The price is AED 808
AED 896 total
includes taxes & fees
22 Sep - 23 Sep
The Captain Stannard
Fireplace

5. Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (203 reviews)
"This place is always the best love the rooms. The staff is excellent place is so clean always feel so comfortable here."
United States
Diane
The price is AED 1,023
AED 1,136 total
includes taxes & fees
29 Sep - 30 Sep
Westbrook Inn B&B
Room, 1 King Bed, Patio, Ground Floor (2) | Terrace/patio

6. The Homestead

The Homestead
3.0 star property
Madison Center
10.0 out of 10, Exceptional, (107 reviews)
"Charming Inn with great staff and an amazing breakfast."
United States
Sherry
The price is AED 815
AED 905 total
includes taxes & fees
23 Sep - 24 Sep
The Homestead
Terrace/patio

7. Large Room w use of pool/tennis in Spacious home

Large Room w use of pool/tennis in Spacious home
Sag Harbor
The price is AED 2,099
AED 3,028 total
includes taxes & fees
26 Sep - 27 Sep
Large Room w use of pool/tennis in Spacious home
Traditional Cottage, 2 Bedrooms, Lake View (Pet not allowed) | Desk, laptop workspace, iron/ironing board, WiFi (free)

8. Head of Pond House

Head of Pond House
3.0 star property
Water Mill
10.0 out of 10, Exceptional, (14 reviews)
"What a wonderful little gem in the heart of Watermill. This was our favorite Hamptons B&B stay and we can’t wait to comeback!"
United States
Liz
The price is AED 3,463
AED 3,957 total
includes taxes & fees
26 Sep - 27 Sep
Head of Pond House
Interior

9. The Scranton Seahorse Inn

The Scranton Seahorse Inn
3.0 star property
Madison Center
9.0 out of 10, Wonderful, (249 reviews)
"The owner Michael and staff were awesome. Michael makes delicious breakfast. We will definitely stay again. Andersens"
United States
Vicki
The price is AED 1,295
AED 1,437 total
includes taxes & fees
22 Sep - 23 Sep
The Scranton Seahorse Inn
Beach nearby

10. The Huntting Inn

The Huntting Inn
3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (130 reviews)
"Good location"
Canada
Josie
The price is AED 1,636
AED 1,905 total
includes taxes & fees
4 Oct - 5 Oct
The Huntting Inn
Beach nearby, sun loungers, beach umbrellas, beach towels

11. The Hedges Inn

The Hedges Inn
3.5 star property
East Hampton
9.6 out of 10, Exceptional, (80 reviews)
"The staff was warm, welcoming, knowledgeable & helpful! The food was superb! The room was impeccable from cleanliness to the amenities provided! We absolutely loved our stay and cannot wait to return. "
United States
Lauren
The price is AED 1,319
AED 1,724 total
includes taxes & fees
21 Sep - 22 Sep
The Hedges Inn
Aerial view

12. East Hampton Art House Bed & Breakfast

East Hampton Art House Bed & Breakfast
4.0 star property
Clearwater Beach
9.6 out of 10, Exceptional, (65 reviews)
"The hosts were really nice and the breakfast is excellent!"
United States
IVAN
The price is AED 2,515
AED 2,873 total
includes taxes & fees
28 Sep - 29 Sep
East Hampton Art House Bed & Breakfast
Property grounds

13. Luxury B&B: Pool, Tennis, Free Local Rides

Luxury B&B: Pool, Tennis, Free Local Rides
Southampton
The price is AED 1,084
AED 1,414 total
includes taxes & fees
21 Sep - 22 Sep
Luxury B&B: Pool, Tennis, Free Local Rides
Front of property - evening/night

14. Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (89 reviews)
"Couldn't have been nicer. Dawn and Tiffany were grcious and accomodating."
Canada
Ronald
The price is AED 3,214
AED 4,645 total
includes taxes & fees
21 Sep - 22 Sep
Mill House Inn
Property grounds

15. Lux Southampton B&B: Pool, Tennis, Gym & Bikes

Lux Southampton B&B: Pool, Tennis, Gym & Bikes
Southampton
The price is AED 1,377
AED 1,787 total
includes taxes & fees
21 Sep - 22 Sep
Lux Southampton B&B: Pool, Tennis, Gym & Bikes
Smart TV, offices

16. Private B&B w/ Pool, Gym, Tennis & Biocharger

Private B&B w/ Pool, Gym, Tennis & Biocharger
Southampton
The price is AED 1,286
AED 1,679 total
includes taxes & fees
21 Sep - 22 Sep
Private B&B w/ Pool, Gym, Tennis & Biocharger
Smart TV, video games, offices

17. B&B Near Shinnecock: Pool, Tennis, Beach Access

B&B Near Shinnecock: Pool, Tennis, Beach Access
Southampton
The price is AED 1,286
AED 1,666 total
includes taxes & fees
21 Sep - 22 Sep
B&B Near Shinnecock: Pool, Tennis, Beach Access
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

Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

10/10 Excellent
"Great place."
Christine 3-night trip
Posted 1 hour ago
Hilton Garden Inn Riverhead

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. Harpoon House: 9 rooms. Situated 12.4 mi (19.9 km) from the heart of Southold. Enjoy the bars and unique décor. The Hedges Inn: 12 rooms. 14.4 mi (23.1 km) from the heart of downtown. Enjoy the free cooked breakfast and designer toiletries. The Homestead: 10 rooms. Located 17.8 mi (28.6 km) from the core of Southold. Enjoy the deli and unique décor.
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 Sannino's Bella Vita Vineyard and The Old Field Vineyards 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.

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