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Holiday Rentals in Jamesport

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Holiday Rentals in Jamesport

Cottage in Greenport

3.0 star property
9.4 out of 10, Exceptional, (6)
"great place to stay, clean and quiet....loved it"
United States
Darlin
North Fork Cottages & RV Resort

Cottage in Hampton Bays

10.0 out of 10, Exceptional, (1)
The price is €402
includes taxes & fees
4 Dec - 5 Dec
Seabreeze #3: Cozy Cottage by the beach

Holiday Home in Hampton Bays

10.0 out of 10, Exceptional, (12)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is €1,096
includes taxes & fees
7 Dec - 8 Dec
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Cottage in Greenport

10.0 out of 10, Exceptional, (1)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is €474
includes taxes & fees
9 Dec - 10 Dec
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Holiday Home in Rocky Point

10.0 out of 10, Exceptional, (23)
"Pet friendly "
United States
Steven
The price is €478
includes taxes & fees
1 Jan - 2 Jan 2026
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Apartment in Mastic

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great stay! Super comfy and clean😊"
United States
ERIN
The price is €169
includes taxes & fees
3 Dec - 4 Dec
South Shore Studio in Mastic

Apartment in Southampton

2.0 star property
9.0 out of 10, Wonderful, (4)
"Very nice place and super responsive host. "
United States
Angelo D.
Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6

Holiday Home in Shirley

10.0 out of 10, Exceptional, (3)
"good time"
United States
Roy T.
The price is €551
includes taxes & fees
3 Dec - 4 Dec
Modern Vacation home. Close to The Hamptons

Holiday Home in Mastic

10.0 out of 10, Exceptional, (27)
"Stayed here for my wedding weekends and absolutely loved the house! Very spacious and beautiful yard! Had so much fun "
United States
Tiffany I.
The price is €1,101
includes taxes & fees
3 Dec - 4 Dec
Hottub, ⛳️, htd pool, Sauna, Basketball

Holiday Home in Calverton

2.0 star property
8.6 out of 10, Excellent, (8)
"This was a great place to stay! Nice house, great backyard on a river and the house was well stocked with essentials. Owner was accommodating and easy to communicate with."
United States
Nicole A.
The price is €588
includes taxes & fees
3 Dec - 4 Dec
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Holiday Home in Greenport

10.0 out of 10, Exceptional, (5)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
Charming Northfork Townhouse- walk to all

Holiday Home in Hampon Bays

9.6 out of 10, Exceptional, (22)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is €1,153
includes taxes & fees
20 Dec - 21 Dec
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Holiday Home in Southold

10.0 out of 10, Exceptional, (3)
"good experience"
United States
Anonymous traveller
The price is €1,037
includes taxes & fees
8 Dec - 9 Dec
Beautifully farmhouse

Holiday Home in Shelter Island

10.0 out of 10, Exceptional, (53)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
Work and Play Special! Extended Stay Discount

Holiday Home in Greenport

9.6 out of 10, Exceptional, (9)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
Northfork Townhouse- walk to all/ newly renovated

Holiday Home in Calverton

2.0 star property
The price is €529
includes taxes & fees
7 Dec - 8 Dec
4-bedroom beach house minutes from Hamptons

Condo in Hampton Bays

4.0 star property
10.0 out of 10, Exceptional, (1)
The price is €1,673
includes taxes & fees
31 Dec - 1 Jan 2026
Canoe Place Waterfront Residences

Holiday Home in Hampton Bays

10.0 out of 10, Exceptional, (5)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
The price is €567
includes taxes & fees
3 Dec - 4 Dec
Immaculate Waterfront 2 bedroom!

Cottage in Hampton Bays

8.8 out of 10, Excellent, (3)
"Great stay. Would stay again. "
United States
Weston B.
The price is €402
includes taxes & fees
10 Dec - 11 Dec
Seabreeze #4: Charming Cottage Footsteps to the Beach

Holiday Home in Greenport

9.0 out of 10, Wonderful, (4)
"Great job "
United States
emilio
The price is €240
includes taxes & fees
1 Jan - 2 Jan 2026
American Beech in Greenport - Petite King Room 7
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

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, apart-hotels, 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 favorite 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 depends 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 €207 per night. Entering your travel dates in the search wizard you might find 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.

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 Splish Splash Water Park, or get outside and enjoy nature at Tiana 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.