Photo by Nina Dinoff

Jamesport Holiday Rentals

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Holiday Rentals in Jamesport

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (240)
"Great view of the water and nice amenities with the beach and pool."
The price is AU$682
includes taxes & fees
15 Sept - 16 Sept
Cliffside Resort Condominiums

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.6 out of 10, Exceptional, (13)
"Tucked away in a quiet residential area. Rooms were clean and kitchenette was well equipped. Private parking spot in the driveway next to the cottage was a bonus. Highly recommended!"
The price is AU$752
includes taxes & fees
1 Oct - 2 Oct
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

10.0 out of 10, Exceptional, (186)
"House was more then I can imagine , host was great , house literally have anything you forgot at home . "
The price is AU$1,346
includes taxes & fees
2 Oct - 3 Oct
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (73)
"We had an AMAZING stay at Eunyoung and Mark's magical cottage. The property was exactly as described. Eunyoung and Mark are delightful people. Tranquil, quiet, peaceful. "
Fairy Tale Guest Cottage in Magic Garden by Pool

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

9.8 out of 10, Exceptional, (31)
"Our trip was amazing, the pool was in perfect condition and the house had everything we needed. Would definitely stay here again!!"
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

East End Cottage Retreat - Dock, Fireplace, Beaches, Wineries & More!

10.0 out of 10, Exceptional, (96)
"Great indoor and outdoor spaces to hang out. Took SUP on the water - so nice and calm. "
The price is AU$978
includes taxes & fees
2 Oct - 3 Oct
East End Cottage Retreat - Dock, Fireplace, Beaches, Wineries & More!

Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

9.8 out of 10, Exceptional, (53)
"Our family (16) spent a week at the property and found the house and property in good order, comfortable and convenient to the bay and other attractions. I would definitely recommend it as a great family vacation."
Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

Southampton cozy cottage by the beach

10.0 out of 10, Exceptional, (1)
"Great stay. Would stay again. "
Southampton cozy cottage by the beach

Fabulous Waterfront Property in the Heart of Wine Country

10.0 out of 10, Exceptional, (181)
"Beautiful and cozy lakeside retreat. Super serene and peaceful place to stay."
Fabulous Waterfront Property in the Heart of Wine Country

10 Bedroom Hampton House with a regulation size Pickleball court

10.0 out of 10, Exceptional, (32)
"Had so much fun this weekend in Hampton Bays! House was perfect for a group of friends - many bedrooms, bathrooms, great pool with tons of outdoor games, and even the arcade room inside! So close to the beach, and a number of great restaurants. Highly recommend this house, and appreciate how helpful our host was with making sure we had everything we need and more!"
10 Bedroom Hampton House with a regulation size Pickleball court

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

Hamptons Retreat

Hamptons Retreat

Stunning Hampton Holiday Family Fantasy for your Team

10.0 out of 10, Exceptional, (72)
"We loved the house. We had a large party and did alot of cooking - the kitchen was top notch. Great supplies - lots of room and all appliances were excellent. All the rooms were great beds comfy towels great. "
Stunning Hampton Holiday Family Fantasy for your Team

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

9.8 out of 10, Exceptional, (97)
"This is a great place to stay in Greenport. It has a private beach and is quiet and friendly. It's a 2-minute drive to town and shops, but you will want to spend your time enjoying the beautiful waterfront views."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .

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

9.6 out of 10, Exceptional, (135)
"Perfect property to hangout and stay entertained for hours"
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Summer getaway

8.8 out of 10, Excellent, (13)
"Beautiful home with a beautiful pool"
Summer getaway

Yellowstone In The Hamptons ~ 18-Acre Estate Surrounded By A Nature Preserve

10.0 out of 10, Exceptional, (20)
"We had an amazing weekend at Jill’s ranch. There were 7 of us - 4 adults and 3 teens. Everything was clean and well equipped - whether making meals, watching movies, enjoying morning coffee on the porch while watching horses, it was lovely. Jill and her property manager were available at check-in and for any questions. Highly recommend staying here."
Yellowstone In The Hamptons ~ 18-Acre Estate Surrounded By A Nature Preserve

Safari Tent Glamping,S6-CedarPt, East Hampton, NY

8.8 out of 10, Excellent, (3)
"We loved the surroundings, the pizza restaurant with live music and ping pong, and the friendly, warm atmosphere and kind staff. We do wish the bathrooms and especially the showers were cleaner."
The price is AU$441
includes taxes & fees
18 Sept - 19 Sept
Safari Tent Glamping,S6-CedarPt, East Hampton, NY

Walk to Beach 2BR Near Dining & Shopping

6.4 out of 10, (19)
"The beach is private and you need to be a Brookhaven resident to be admitted. This is not specified anywhere on the listing. Communication about this with the owner via app was rather poor. "
The price is AU$462
includes taxes & fees
15 Sept - 16 Sept
Walk to Beach 2BR Near Dining & Shopping

Charming Sag Harbor Retreat with Private Pool, Minutes to Beaches and Town

Charming Sag Harbor Retreat with Private Pool, Minutes to Beaches and Town
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Jamesport Hotel Reviews

Find out more about Jamesport

Find out more about Jamesport

Everything you need to know about Jamesport holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Jamesport holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Jamesport holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Jamesport holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Jamesport. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Jamesport holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Jamesport holiday rentals we have selected for you start as low as AU$441 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Jamesport rentals

At Expedia, we put the best Jamesport holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Jamesport rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Jamesport holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Jamesport. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor : This holiday home rental outside of Jamesport offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a patio, a garden and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Jamesport?

With 6 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 Out East Family Fun, 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.