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Aug 15 - Aug 17
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In two months
Oct 3 - Oct 5

B&B in Jamesport

The Sagaponack
Exterior

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 1 - Sep 2
Total includes taxes and fees
The Sagaponack
Harpoon House
Porch

Harpoon House

3.0 star property
8.4 out of 10, Very Good, (125)
"Great location"
$272 nightly
The price is $311
Sep 4 - Sep 5
Total includes taxes and fees
Harpoon House
Carole's Place B & B
Property grounds

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
Vine & Sand
Interior entrance

Vine & Sand

3.0 star property
10.0 out of 10, Exceptional, (7)
"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
West Neck Guesthouse
Deluxe Room, 1 King Bed | Premium bedding, iron/ironing board, free WiFi, bed sheets

West Neck Guesthouse

3.5 star property
8.0 out of 10, Very Good, (33)
"Very convenient location next to Cresent Beach and Leon 1909 restaurant which is fantastic! "
$314 nightly
The price is $358
Aug 21 - Aug 22
Total includes taxes and fees
West Neck Guesthouse
The Jahmtons Guest Room
Pool

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 11 - Aug 12
Total includes taxes and fees
The Jahmtons Guest Room
Stirling House Bed & Breakfast
Beach/ocean view

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
Living area

The Farmhouse Bed and Breakfast

4.0 star property
10.0 out of 10, Exceptional, (13)
"very comfortable stay. "
The Farmhouse Bed and Breakfast
Harbor Knoll Bed & Breakfast
Living area

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
The 1708 House
Exterior

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
Historical Bed and breakfast<br>
Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils

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>
Arbor View House B&B
Exterior

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
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
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent 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
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite 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
Large Room w use of pool/tennis in Spacious home
Outdoor dining

Large Room w use of pool/tennis in Spacious home

$794 nightly
The price is $907
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
Interior

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
Microwave, oven, stovetop, dishwasher

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
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 Jamesport Hotel Reviews

Sound View Greenport

Sound View Greenport

10/10 Excellent
"Our stay was everything we were looking for, waterfront, easy on/off the beach from our room, lounge chairs and umbrellas on the beach and nearby pool. Sunsets were amazing, lobster rolls in the piano bar were incredible. One day there was an issue with the kitchen and they brough complimentary spread to the pool area. July is expensive but it was definitely worth it. We live on Long Island and didn't have to deal with flying issues. Just a 2 hour drive and 4 days of relaxing sun....."
Brian 3-night trip
Posted 22 hours ago
Sound View Greenport

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.