Photo by Todd Carroll

Search B&B in Jamesport

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

B&B in Jamesport

Exterior
The Sagaponack

The Sagaponack

3.0 star property
Wainscott
8.8 out of 10, Excellent, (211)
"Clean & amenities, staff friendly Thank you "
United States
Archil
The price is AED 547
AED 772 total
includes taxes & fees
15 Dec - 16 Dec
The Sagaponack
Interior entrance
Vine & Sand

Vine & Sand

3.0 star property
Southold
9.6 out of 10, Exceptional, (13)
"This B&B, and its hosts, were simply amazing. I cannot recommend this place enough."
United States
Sandra
Vine & Sand
Seasonal outdoor pool
Head of Pond House

Head of Pond House

3.0 star property
Water Mill
10.0 out of 10, Exceptional, (3)
"Beautiful place with a very kind host. Highly recommend this place!"
United States
Michèle
The price is AED 1,773
AED 2,025 total
includes taxes & fees
5 Jan - 6 January 2026
Head of Pond House
Porch
Harpoon House

Harpoon House

3.0 star property
Southampton
8.4 out of 10, Very Good, (148)
"Very cute location- rooms are very spacious. We were able to walk into town. Would definitely stay again. "
United States
Karissa
Harpoon House
Interior
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub

Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub

Southold
10.0 out of 10, Exceptional, (1)
"Must like historical houses and little sausage-shaped dogs. A seamless blend of old and mod. Room is meticulously shiny clean. Substantial bedding designed for a good night’s sleep. High-end details (furnishings, footed tub with heat lamp and fluffy robes), culture (gallery), included breakfast is simple perfection due to high-quality ingredients/sourcing (fresh pastries, eggs, butter, fruit). Pool and hot tub divine. Our hosts are upbeat and fun and really went beyond for us. There are great...
United States
Jessica P.
The price is AED 1,307
AED 1,691 total
includes taxes & fees
1 Jan - 2 January 2026
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
Pool
The Jahmtons Guest Room

The Jahmtons Guest Room

Ridge
8.6 out of 10, Excellent, (31)
"Very cozy room and nice people who owned the house. We only met Wayne but he was very cordial and kind. The dogs were wonderful as well :)"
United States
Michael
The price is AED 496
AED 768 total
includes taxes & fees
13 Dec - 14 Dec
The Jahmtons Guest Room
Outdoor dining
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
9 Dec - 10 Dec
Large Room w use of pool/tennis in Spacious home
Interior
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower

Southold
10.0 out of 10, Exceptional, (1)
"Great experience. Wonderful hosts. "
United States
Mark L.
The price is AED 1,192
AED 1,542 total
includes taxes & fees
1 Jan - 2 January 2026
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
Exterior
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower

Southold
The price is AED 1,192
AED 1,542 total
includes taxes & fees
1 Jan - 2 January 2026
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
Interior
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower

Southold
The price is AED 1,307
AED 1,691 total
includes taxes & fees
1 Jan - 2 January 2026
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Jamesport Hotel Reviews

Budget Host East End Hotel in Riverhead

Budget Host East End Hotel in Riverhead

10/10 Excellent
"Everything was good "
Monica 1-night trip
Posted 23 hours ago
Budget Host East End Hotel in Riverhead

Frequently asked questions

Searching for B&Bs in Jamesport?
Whether you're passing through town and are looking for an accommodation that's small and charming, or you're traveling solo and hoping to meet fellow tourists, B&Bs can be a great choice for many types of vacationers. When you want to explore some of the destination's attractions, Jason's Vineyard is worth a visit.
How do you know if a B&B is a good option for your stay?
With attentive service, opportunities to interact with the owner, and tasty breakfasts, B&Bs provide a truly one-of-a-kind setting.
What are the best B&Bs in Jamesport?
Here are some B&Bs in the surrounding area: The Sagaponack: 16.6 mi (26.8 km) from the heart of Jamesport.Harpoon House: 9 rooms. 10.8 mi (17.4 km) from the downtown core. Enjoy the bars and unique décor. Head of Pond House: 4 rooms. Situated 11.4 mi (18.4 km) from the heart of Jamesport. Enjoy the outdoor pool and patio area. Harbor Knoll Bed & Breakfast: 3 rooms. 14.9 mi (24 km) from the heart of downtown. Enjoy the in-room pools and private yard. Vine & Sand: 4 rooms. Located 9.6 mi (15.5 km) from the core of Jamesport. Enjoy the free buffet breakfast and designer toiletries.
When should I stay at a B&B in Jamesport?
When you're dreaming of a stay in Jamesport, 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 39°F. Average annual precipitation for Jamesport is 56 inches.
What is there to do in Jamesport?
When you want to explore some things to do in Jamesport, consider a visit to Jason's Vineyard. Jamesport Vineyards and Harbes Family Farm are also some sites to visit if you want to see more of the area.
How can I get to and around Jamesport?
You can map out your trip in and around Jamesport ahead of time with these transportation options. Fly into Westhampton, NY (FOK-Francis S. Gabreski), which is located 8.5 mi (13.7 km) away from the heart of the city. You can also search for flights into East Hampton, NY (HTO), which is 17.2 mi (27.7 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.