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 SAR 1,178
SAR 1,345 total
includes taxes & fees
1 Oct - 2 Oct
West Neck Guesthouse
Interior detail

2. Harpoon House

Harpoon House
3.0 star property
Southampton
8.4 out of 10, Very good, (192 reviews)
"Staff was very courteous and the location was perfect. We would book this venue again for our next trip to the hamptons."
United States
Kim
The price is SAR 916
SAR 1,046 total
includes taxes & fees
1 Oct - 2 Oct
Harpoon House
Property entrance

3. The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (287 reviews)
"everything about the hotel was excellent, prices fair for the Hamptons!"
United States
Jane
The price is SAR 855
SAR 1,127 total
includes taxes & fees
18 Oct - 19 Oct
The Sagaponack
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 SAR 817
SAR 907 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 SAR 1,035
SAR 1,149 total
includes taxes & fees
7 Oct - 8 Oct
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, (105 reviews)
"Charming Inn with great staff and an amazing breakfast."
United States
Sherry
The price is SAR 896
SAR 994 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 SAR 2,385
SAR 3,408 total
includes taxes & fees
26 Sep - 27 Sep
Large Room w use of pool/tennis in Spacious home
Interior

8. 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 SAR 1,324
SAR 1,470 total
includes taxes & fees
23 Sep - 24 Sep
The Scranton Seahorse Inn
Property grounds

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

Luxury B&B: Pool, Tennis, Free Local Rides
Southampton
The price is SAR 1,108
SAR 1,446 total
includes taxes & fees
20 Sep - 21 Sep
Luxury B&B: Pool, Tennis, Free Local Rides
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 SAR 1,673
SAR 1,949 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 SAR 1,687
SAR 2,149 total
includes taxes & fees
20 Sep - 21 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 SAR 2,572
SAR 2,939 total
includes taxes & fees
28 Sep - 29 Sep
East Hampton Art House Bed & Breakfast
Front of property - evening/night

13. 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 SAR 3,287
SAR 4,750 total
includes taxes & fees
20 Sep - 21 Sep
Mill House Inn
Property grounds

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

Lux Southampton B&B: Pool, Tennis, Gym & Bikes
Southampton
The price is SAR 1,409
SAR 1,828 total
includes taxes & fees
20 Sep - 21 Sep
Lux Southampton B&B: Pool, Tennis, Gym & Bikes
Smart TV, video games, offices

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

B&B Near Shinnecock: Pool, Tennis, Beach Access
Southampton
The price is SAR 1,315
SAR 1,703 total
includes taxes & fees
20 Sep - 21 Sep
B&B Near Shinnecock: Pool, Tennis, Beach Access
Smart TV, offices

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

Private B&B w/ Pool, Gym, Tennis & Biocharger
Southampton
The price is SAR 1,315
SAR 1,717 total
includes taxes & fees
20 Sep - 21 Sep
Private B&B w/ Pool, Gym, Tennis & Biocharger
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

Zey Hotel

Zey Hotel

10/10 Excellent
"Great time, great stay, great staff! Will definitely be coming back!"
Amanda 2-night trip
Posted 3 hours ago
Zey 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. 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 Huntting Inn: 19 rooms. Located 14.4 mi (23.1 km) from the core of Southold. Enjoy the fireplace in the lobby and bar/lounge.
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.