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Aug 15 - Aug 17
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Sep 5 - Sep 7
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Oct 3 - Oct 5

B&B in Jamesport

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, (165)
"The location was great, the room was clean, and the staff were very friendly and accommodating."
$376 nightly
The price is $430
Sep 8 - Sep 9
Total includes taxes and fees
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"
$269 nightly
The price is $308
Sep 8 - Sep 9
Total includes taxes and fees
Harpoon House
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
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. "
$314 nightly
The price is $358
Aug 21 - Aug 22
Total includes taxes and fees
West Neck Guesthouse
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
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
The Jahmtons Guest Room
Relax in the backyard with a swimming pool, lawn, and outdoor furniture, plus a covered seating area.

The Jahmtons Guest Room

8.6 out of 10, Excellent, (28)
"Really like the place. Nice setting, friendly owners, adorable dogs, comfortable room, and an amazing welcome."
$180 nightly
The price is $206
Aug 13 - Aug 14
Total includes taxes and fees
The Jahmtons Guest Room
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
Arbor View House B&B
Enjoy a serene beach experience with calm seas and a picturesque view.

Arbor View House B&B

3.5 star property
9.2 out of 10, Wonderful, (15)
"Two mid age couples just had a good and relaxing time with great hospitality. "
Arbor View House B&B
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
Stunning hallway with polished floor, staircase, and large window offering a view of lush greenery.

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
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
Stunning two-story home with a central entrance and covered porch, surrounded by a beautifully manicured lawn.

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
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
Stunning hallway with a herringbone floor pattern leading to a staircase and a door with a glass panel offering a view of the outdoors.

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
Large Room w use of pool/tennis in Spacious home
Relax on the deck, surrounded by lush greenery, with lounge chairs and a dining table nearby.

Large Room w use of pool/tennis in Spacious home

$758 nightly
The price is $866
Aug 31 - Sep 1
Total includes taxes and fees
Large Room w use of pool/tennis in Spacious home
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
Stroll through the hallway to an open door, offering a glimpse of lush greenery outside.

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

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...
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
Cozy and Stylish 1 Bedroom Guest Suite
Enjoy cooking in this well-equipped kitchen with a microwave, Keurig machine, and stainless steel sink.

Cozy and Stylish 1 Bedroom Guest Suite

10.0 out of 10, Exceptional, (2)
"The place was clean and the hostess was very accommodating. The only drawback is it is in the basement and overhead you could hear the dogs."
Cozy and Stylish 1 Bedroom Guest Suite
SEVEN - Shelter Island Guest House
Kayaking

SEVEN - Shelter Island Guest House

2.5 star property
9.8 out of 10, Exceptional, (57)
"It was a beautiful place! Under construction however, Beth was Amazing! Amelia was so hospitable. Close to everything and it certainly helped that the weather was spectacular! Will definitely go back another time!"
SEVEN - Shelter Island Guest 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 Jamesport Hotel Reviews

Greenview Inn Riverhead

Greenview Inn Riverhead

10/10 Excellent
" ROOMS ARE VERY COZY ! "
Miguel 2-night trip
Posted 18 hours ago
Greenview Inn Riverhead

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Jamesport?
Prices for B&Bs in Jamesport often vary, but you can find a great deal from $206 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Jamesport B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed & Breakfast in Jamesport?
The best time to book a B&B in Jamesport is during the vibrant summer months, particularly from June to August, when the town comes alive with activities. This peak season draws visitors keen on exploring the charming wineries and scenic landscapes that characterize this delightful region. The warm weather, with temperatures ranging from the mid-70s to the low 90s Fahrenheit, creates a great backdrop for outdoor adventures, including vineyard tours and leisurely strolls through picturesque gardens.

July stands out as the most popular month to visit, offering a bustling atmosphere filled with local events, farmers' markets, and community gatherings. Travelers can soak in the lively spirit of the season while enjoying the rich flavors of local wines and artisanal products.

If you're looking for a more budget-friendly option, consider planning your trip in October. This month showcases the stunning fall foliage, transforming the landscape into a kaleidoscope of colors. The cooler temperatures, generally in the 50s to 70s Fahrenheit, provide a refreshing climate for outdoor exploration, making it an ideal time for scenic drives and leisurely winery visits without the summer crowds.
What is the difference between a Jamesport Bed and Breakfast and a hotel?
Every Jamesport B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Jamesport B&Bs.