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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, 183 reviews
"Wonderful stay and super clean! Can’t wait to come back. "
The price is NZ$521
per night
27 Jun - 28 Jun
Cliffside Resort Condominiums
Airstream Art Studio Sculpture/Nature Preserve
10.0 out of 10, Exceptional, 2 reviews
"This place was one of the best parts of my stay on LI. It is tucked away on a beautiful stretch of property but still close to central locations making it easy to go out for provisions. I "gifted" myself a stay here as a single-mother and former art maker. This was the first time I painted in 10+ years, the environment and the energy filled my cup to overflowing! Thank you so much for having this space available. I will return."
The price is NZ$386
per night
4 Jun - 5 Jun
Airstream Art Studio Sculpture/Nature Preserve
North Fork Escape Near Wineries, Beaches And Hamptons
9.4 out of 10, Exceptional, 18 reviews
"Lovely quaint home. Very clean and spacious. Perfect for a family getaway . Highly recommend."
North Fork Escape Near Wineries, Beaches And Hamptons
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Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, 49 reviews
"Close to the restaurants and beaches. We enjoyed exploring the nearby areas within 15 to 30 mins drive"
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
Location and views! Located directly on Shinnecock Bay!
9.2 out of 10, Wonderful, 12 reviews
"You have the opportunity to attend a graduation party at the Hamptons, where everyone had to find their own accommodations. The location is essentially located to town to the water and beautiful scenic paths. The host insured that the home was exceptionally clean and amenities provided. Not to mention accommodating due to last-minute change in schedule."
Location and views! Located directly on Shinnecock Bay!
Beautiful Family Home Nestled In The Heart Of Sagaponack
10.0 out of 10, Exceptional, 25 reviews
"House was very clean and host was exceptional. Very relaxing place to stay."
Beautiful Family Home Nestled In The Heart Of Sagaponack
New Reno Hamptons Waterfront Beach House wBackyard Pool Oasis, and Private Beach
10.0 out of 10, Exceptional, 1 review
"Our overall expertise was great. Home was very clean and had all the essentials you need for a nice comfortable stay. The beds were very comfy, equipped with great linens and pillows. Home was cozy and comfortable. Can’t wait to stay again."
The price is NZ$3,277
per night
4 Jun - 5 Jun
New Reno Hamptons Waterfront Beach House wBackyard Pool Oasis, and Private Beach
“The Cool House” Waterfront Oasis, 3 Bedrm 2 bath
10.0 out of 10, Exceptional, 9 reviews
"My family and I had wonderful stay at the "Cool House." The host were great and responded in a timely manner. We were down in L.I. for my sons baseball tournament and it was perfect located 20 minutes away from Lasorda Legacy park. It was great to wake up in the morning and see the bay from the deck. House was clean and had all the amenities."
“The Cool House” Waterfront Oasis, 3 Bedrm 2 bath
Gorgeous private Hamptons house with pool and volleyball court
7.8 out of 10, Good, 7 reviews
"This place was nice and roomy for our family of 8 plus 3 littles kiddos. Pretty clean as well. I gave listing accuracy a 5 because it is accurate but that may be because it doesn't tell you much. We were a little short on towels, many light bulbs were burnt out or just missing. We replaced some (they were there) and moved others to balance out the light. No kitchen linens, short on bath towels, short on paper towels and definitely not enough TP. 3 partial rolls and 1 bathroom had none so we had...
Gorgeous private Hamptons house with pool and volleyball court
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
10.0 out of 10, Exceptional, 11 reviews
"We really enjoyed our stay in this house. Very safe and clean place to stay. Plenty of parking spaces, logs for fireplace, kitchen accessories. All china is very good quality."
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
10.0 out of 10, Exceptional, 147 reviews
"In town for a wedding - a large, convenient location that fulfilled the needs we had for that stay."
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.
8.6 out of 10, Excellent, 8 reviews
"The property was clean and large and the outdoor space made for a fun gathering place, especially for the children in our group. It would have been nice to have dedicated spaces to hang towels and clothes, especially as we had so many people staying. The hosts were friendly and accommodating and we would stay again."
20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
10.0 out of 10, Exceptional, 23 reviews
"It was a great weekend"
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.
10.0 out of 10, Exceptional, 47 reviews
"Beautiful property right on Dune road. Stunning beach views, clean, great communication. Overall a wonderful stay!"
Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.
Soundview Beach House: 4BR,Panoramic Views 1.5hrsNYC, Sits Directly on beach
9.8 out of 10, Exceptional, 50 reviews
"Couldn't say enough positive's about this stay. The owner was very responsive from before it was even booked all the way through the stay and after. The house has a gorgeous view and it's cozy for a nice weekend away. We will definitely be back."
Soundview Beach House: 4BR,Panoramic Views 1.5hrsNYC, Sits Directly on beach
Fabulous Waterfront Property in the Heart of Wine Country
10.0 out of 10, Exceptional, 154 reviews
"Lovely home! Beautiful view! House has everything you need."
Fabulous Waterfront Property in the Heart of Wine Country
The Seashell, just a short walk to Long Beach, "Best Sunsets" in the Hamptons
10.0 out of 10, Exceptional, 53 reviews
"Great stuff, loved the house!"
The Seashell, just a short walk to Long Beach, "Best Sunsets" in the Hamptons
HAMPTON BAYS HOME MINUTES FROM SOUTHAMPTON VILLAGE, SHINNECOCK BAY, OCEAN...
10.0 out of 10, Exceptional, 1 review
"The house was perfect and clean. We really enjoyed the screened in patio."
HAMPTON BAYS HOME MINUTES FROM SOUTHAMPTON VILLAGE, SHINNECOCK BAY, OCEAN...
Beachfront Romance: Rustic Home w/ Private Beach
9.2 out of 10, Wonderful, 39 reviews
"The house is small but it has everything you need. The ocean was lovely to watch and good scavenging for rocks and sea glass. Very private place. My pup and I had a good time!"
Beachfront Romance: Rustic Home w/ Private Beach
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
10.0 out of 10, Exceptional, 28 reviews
"The house was beautiful and comfortable. We enjoyed the property and watching the wildlife. The fire pit was great for a group gathering. We didn't cook but the kitchen appeared well stocked. The house was short on paper products. We left a note for the house manager when we left."
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
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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.

Other types of properties in Jamesport you may be interested in

The Bentley Hotel Southampton
2.0 star property
9.4 out of 10, Exceptional, 76 reviews
"Large room recently updated, didn’t hear other guests "
The price is NZ$341
per night
4 Jun - 5 Jun
The Bentley Hotel Southampton
Hilton Garden Inn Riverhead
3.0 star property
8.6 out of 10, Excellent, 1,004 reviews
"Nice property and service in a great location. "
The price is NZ$267
per night
16 Jun - 17 Jun
Hilton Garden Inn Riverhead
Greenview Inn Riverhead
2.0 star property
6.0 out of 10, 360 reviews
"The inn was a great deal compared to other hotels in the area and room was updated and very clean and comfy."
The price is NZ$192
per night
17 Jun - 18 Jun
Greenview Inn Riverhead
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Jamesport holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Jamesport. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Jamesport. Seeing all the best attractions is bound to make you fall in love with Jamesport. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Jamesport short-term rentals, that won’t be hard to do.

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?

Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!: This holiday home rental outside of Jamesport is located next to a golf course, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 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 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Jamesport stay.

What can I see and do in Jamesport?

Enjoy the area's cultural attractions such as Hallockville Museum Farm, or get outdoors into nature at a spot like Meschutt Beach. In the wider area, you’ll find Jason's Vineyard and Clovis Point.

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.

Recent reviews of Jamesport properties
Expedia verified reviews