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Jamesport Holiday Rentals

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Holiday Rentals in Jamesport

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (223)
"After some lengthy travel to get to LI this was an excellent choice to start our vacation. Great accommodations, comfortable and great location. "
The price is NZ$494
includes taxes & fees
6 July - 7 July
Cliffside Resort Condominiums

Canoe Place Waterfront Residences

4.0 star property
The price is NZ$3,791
includes taxes & fees
30 June - 1 July
Canoe Place Waterfront Residences

Escape to Sag Harbor

10.0 out of 10, Exceptional, (47)
"Amazing house and location!! Would stay again "
Escape to Sag Harbor

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (67)
"We had a wonderful vacation at the Fairy Tale Guest Cottage. The location was awesome and we loved the accommodations, especially the fancy bathroom. Mark and Eunyoung are impeccable hosts. Would absolutely stay again!"
Fairy Tale Guest Cottage in Magic Garden by Pool

East End cottage on water! Outdoor tub&shower! Minutes from Hamptons & wineries.

10.0 out of 10, Exceptional, (88)
"Place was beautiful. It was very clean. Easy to get to. Would stay again"
The price is NZ$1,294
includes taxes & fees
21 July - 22 July
East End cottage on water! Outdoor tub&shower! Minutes from Hamptons & wineries.

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

9.6 out of 10, Exceptional, (33)
"We had a amazing stay and plan to come back next July again"
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

Charming East Hampton Home, private yard with fenced in pool, perfect for...

Charming East Hampton Home, private yard with fenced in pool, perfect for...

Lovely North Fork Beach Cottage (2 BR/2 bath)!

10.0 out of 10, Exceptional, (114)
"We were pleased with our stay. The house was very clean. My contact with the property manager were great. Would stay again."
Lovely North Fork Beach Cottage (2 BR/2 bath)!

Southampton cozy cottage by the beach

The price is NZ$1,572
includes taxes & fees
27 July - 28 July
Southampton cozy cottage by the beach

Walk to Beach 2BR Near Dining & Shopping

6.6 out of 10, (13)
"a little hard to find: hint, look for the address on the garbage cans, because the addresses get a bit wonky further down the block, but this is a lovely spot on the north shore if all you're looking for is a clean bed on a quiet street, and the two bedrooms are so much better for friends or families than would be two rooms in the hotel by the highway -- oh, and there's a nice bagel place just north of the Starbucks on the corner of 25A"
The price is NZ$510
includes taxes & fees
2 July - 3 July
Walk to Beach 2BR Near Dining & Shopping

Heated pool/5 min walk to Beach/Beautiful Sag Harbor Village /Restaurant/Museum

10.0 out of 10, Exceptional, (45)
"Great house, kitchen is well equipped which made dining in very easy. Loved the pool and backyard."
Heated pool/5 min walk to Beach/Beautiful Sag Harbor Village /Restaurant/Museum

Stunning Southampton Village Modern Home

The price is NZ$27,469
includes taxes & fees
30 June - 1 July
Stunning Southampton Village Modern Home

Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!

9.6 out of 10, Exceptional, (37)
"Lovely cottage beautifully decorated, close to restaurants, farm stands, and food stores. A least a 15 to 20 minute walk to the beach."
The price is NZ$670
includes taxes & fees
2 July - 3 July
Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!

Meets Modern Comfort in This 3-Bedroom Long Island Sound Retreat

9.0 out of 10, Wonderful, (2)
"We spent two nights at Roman’s house and it was perfect for our needs. He was communicative and helpful when any questions arose and explained everything perfectly to help make our stay a pleasant one. I highly recommend staying here!"
Meets Modern Comfort in This 3-Bedroom Long Island Sound Retreat

Location and views! Located directly on Shinnecock Bay!

9.0 out of 10, Wonderful, (26)
"Stay was relaxing, space was very cozy. we enjoyed our stay. "
The price is NZ$1,188
includes taxes & fees
2 July - 3 July
Location and views! Located directly on Shinnecock Bay!

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

9.6 out of 10, Exceptional, (132)
"Stayed for a blustery President’s Weekend with grandparents, college and high school kids, and dogs. Great house for a multi-generational, pet-friendly vacation with knock-out views. Would love to return in the spring or summer!"
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Summer getaway

9.2 out of 10, Wonderful, (10)
"Beautiful home with a beautiful pool"
Summer getaway

July Flash Sale: Luxury Beach House, Heated Pool, Dune Rd beaches, pets ok

10.0 out of 10, Exceptional, (10)
"An absolute perfect home for a family looking to enjoy"
July Flash Sale: Luxury Beach House, Heated Pool, Dune Rd beaches, pets ok

Work and Play Special! Extended Stay Discount

10.0 out of 10, Exceptional, (43)
"We had a lovely time at Cottage Green. Ingrid was a lovely owner and was very easy to communicate with!"
Work and Play Special! Extended Stay Discount

Hamptons Retreat

Hamptons Retreat
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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Frequently asked questions

Are there holiday rentals in Jamesport?

Yes, there are holiday rentals close to the most popular sights in Jamesport, or you can select a more secluded option if you're looking for a relaxing stay. Jamesport is known for its beaches and wineries.

What are some of the best holiday rentals that Jamesport has to offer?

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr: This holiday home rental outside of Jamesport offers an outdoor pool, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Jamesport?

With 5 Expedia holiday rentals, you're guaranteed to find just the right place for your Jamesport stay.

What can I see and do in Jamesport?

While exploring the area, visit family-friendly sights like Splish Splash Water Park, or get outside and enjoy nature at Meschutt Beach. In the wider area, you’ll find Jason's Vineyard and Jamesport Vineyards.

What are holiday rentals like in Jamesport?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Jamesport. Holiday rentals offer extras such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for small groups.