A pebbled beach at sunset with a calm sea and a clear sky.

Jamesport Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Jamesport vacation rentals

A dining area with a wooden table, chairs, and a decorative wall with a cityscape picture.

1. Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,

Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
Flanders
10.0 out of 10, Exceptional, (6 reviews)
"The host was very welcoming and the house was very clean"
United States
James W.
$279 nightly
The price is $319
Oct 20 - Oct 21
Total with taxes and fees
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
A rocky beach with clear water and a forested hillside in the background.

2. North Fork Fall Escape—Vineyards, Apple Picking & Greenport

North Fork Fall Escape—Vineyards, Apple Picking & Greenport
Mattituck
9.6 out of 10, Exceptional, (7 reviews)
"Stayed with several friends for a wedding in Jamesport"
United States
Glenn F.
$1,200 nightly
The price is $1,371
Oct 24 - Oct 25
Total with taxes and fees
North Fork Fall Escape—Vineyards, Apple Picking & Greenport
A sign for J&S Reeves Cottages with a view of a house and trees.

3. 6th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

6th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Riverhead
10.0 out of 10, Exceptional, (12 reviews)
"We enjoyed our stay. Very quiet and relaxing. Excellent location to many wineries. Would definitely stay again."
United States
Donna M.
$849 nightly
The price is $864
Oct 8 - Oct 9
Total with taxes and fees
6th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

4. Elegant 5-Bedroom Hamptons Home with Private Pool

Elegant 5-Bedroom Hamptons Home with Private Pool
Hampton Bays
9.4 out of 10, Exceptional, (43 reviews)
"The house was great. Pool was beautiful and everything was a 10 minute drive! Great place to relax"
United States
Judith M.
$857 nightly
The price is $979
Oct 8 - Oct 9
Total with taxes and fees
Elegant 5-Bedroom Hamptons Home with Private Pool
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

5. Jacuzzi year-round - Villa Luz Private Home

Jacuzzi year-round - Villa Luz Private Home
Hampon Bays
9.6 out of 10, Exceptional, (27 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
$1,573 nightly
The price is $1,666
Oct 12 - Oct 13
Total with taxes and fees
Jacuzzi year-round - Villa Luz Private Home
Terrace/patio

6. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (295 reviews)
"Great place!"
United States
Christine
$266 nightly
The price is $304
Nov 1 - Nov 2
Total with taxes and fees
Cliffside Resort Condominiums
A modern building with large windows overlooking a beach.

7. Beachfront Jacuzzi All Year - Black Swan Home

Beachfront Jacuzzi All Year - Black Swan Home
Hampton Bays
9.4 out of 10, Exceptional, (21 reviews)
"Views are incredible. Lucky enough to have had great weather before Memorial Day weekend! Our family loved it! Hot tub was wonderful."
United States
Donald J.
$1,161 nightly
The price is $1,233
Oct 12 - Oct 13
Total with taxes and fees
Beachfront Jacuzzi All Year - Black Swan Home
A beach with footprints leading to the water, a sunset in the background, and a clear sky.

8. Steps to the beach | Seabreeze Cottage #3

Steps to the beach | Seabreeze Cottage #3
Hampton Bays
6.0 out of 10, (3 reviews)
"The property needs a major cleaning and repairs. The floors were sticky, and the carpet was dirty. Furniture was dirty and soiled. There was dried food on the utensils. The pipes groaned at all hours, several times an hour. The bed creaked with every movement. Bedroom blinds were broken and wouldn’t close all the way. The bedside lamp on the wall was falling off. The last straw was the huge spider that jumped down from the closet onto me. We ended up leaving after less than 24 hours and...
United States
Lydia
$430 nightly
The price is $458
Oct 11 - Oct 12
Total with taxes and fees
Steps to the beach | Seabreeze Cottage #3
A sign for J&S Reeves Cottages with a view of a house and trees.

9. 4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Aquebogue
9.8 out of 10, Exceptional, (19 reviews)
"Great cottage on amazing grounds! We loved the screened in porch. Sandy and john are great hosts. We also loved using the kayaks and checking out the bay."
United States
Richard C.
$915 nightly
The price is $931
Oct 8 - Oct 9
Total with taxes and fees
4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Terrace/patio

10. 5th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

5th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Aquebogue
10.0 out of 10, Exceptional, (3 reviews)
"Fantastic experience. Cabin was clean and quiet. Beautiful mornings on the water."
United States
Leah O.
$893 nightly
The price is $908
Oct 8 - Oct 9
Total with taxes and fees
5th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
A modern house with a deck, outdoor seating, and a fire pit.

11. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (62 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
$228 nightly
The price is $260
Oct 8 - Oct 9
Total with taxes and fees
North Fork Resort
A covered outdoor seating area with wicker furniture and a view of boats on a lake.

12. 3rd of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

3rd of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Aquebogue
8.6 out of 10, Excellent, (7 reviews)
"We loved everything about our stay at the cottage. Such beautiful property and surroundings. If you’re looking to spend some quality time with family in a quiet setting with beautiful surroundings , look no further. Thanks Sandy. We will be Back."
United States
Wendy B.
$996 nightly
The price is $1,014
Oct 8 - Oct 9
Total with taxes and fees
3rd of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
A lakeside cottage with a covered porch, a sign for J&S Reeves Cottages, and a grassy lawn with lounge chairs.

13. 1st of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

1st of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Aquebogue
9.0 out of 10, Wonderful, (7 reviews)
"Nice scenery. Spartan kitchen furnishings and bathroom toiletries. Paid booking (including all ocuppants and pets) and was invoiced by vrbo. Received addtional invoice from the owner adding 250 dolars pet fee (125x2 pets) which was not listed on the property description that only mentions "pet friendly"."
United States
Simon C.
$996 nightly
The price is $1,014
Oct 8 - Oct 9
Total with taxes and fees
1st of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

14. Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!
Hampton Bays
10.0 out of 10, Exceptional, (5 reviews)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
$503 nightly
The price is $575
Oct 8 - Oct 9
Total with taxes and fees
Immaculate Waterfront 2 bedroom!
Roger’s Beach

15. Prime location, walk to all, cozy cottage WHB

Prime location, walk to all, cozy cottage WHB
Westhampton Beach
10.0 out of 10, Exceptional, (3 reviews)
"Erica was very communicative and helpful. Very cozy with a great location."
United States
Chris J.
$657 nightly
The price is $751
Oct 19 - Oct 20
Total with taxes and fees
Prime location, walk to all, cozy cottage WHB
A waterfront property with a grassy lawn, a dock with boats, and a patio area with outdoor furniture.

16. 2nd of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork

2nd of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Aquebogue
9.6 out of 10, Exceptional, (5 reviews)
"Great rental experience. Owners friendly and available"
United States
Patricia and Michael F.
$996 nightly
The price is $1,014
Oct 8 - Oct 9
Total with taxes and fees
2nd of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

17. Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
$523 nightly
The price is $598
Oct 11 - Oct 12
Total with taxes and fees
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A beach with footprints leading to the water, a sunset in the background, and a clear sky.

18. Walk to Beach | Seabreeze Cottage #4

Walk to Beach | Seabreeze Cottage #4
Hampton Bays
8.6 out of 10, Excellent, (8 reviews)
"Great stay. Would stay again. "
United States
Weston B.
$436 nightly
The price is $465
Oct 18 - Oct 19
Total with taxes and fees
Walk to Beach | Seabreeze Cottage #4
A spacious living area with a fireplace, a wooden staircase, and large windows.

19. Cozy beach hose minutes from Hamptons

Cozy beach hose minutes from Hamptons
Calverton
8.2 out of 10, Very good, (11 reviews)
"Very responsive host and a beautiful house."
United States
Robin M.
$641 nightly
The price is $733
Oct 13 - Oct 14
Total with taxes and fees
Cozy beach hose minutes from Hamptons
A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

20. Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (6 reviews)
"perfect for families"
United States
Okito H.
$971 nightly
The price is $1,109
Oct 8 - Oct 9
Total with taxes and fees
Minutes from the beach, brand new 4 bedroom
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

Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"Parking wasn’t convenient."
Carl 1-night trip
Posted 13 hours ago
Hyatt Place Long Island East End

Find out more about Jamesport

Everything you need to know about Jamesport vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Jamesport vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Jamesport vacation 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 low season months. For more hustle and bustle, you may prefer to visit Jamesport in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $260 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Jamesport rentals

At Expedia, we put the best Jamesport vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Jamesport?

Yes, we have vacation rentals near the most popular sights in Jamesport, or you can go with a more remote option if you're looking for a relaxing stay. Jamesport is known for its beaches and wineries.

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

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly: This vacation home rental outside of Jamesport offers an outdoor pool, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Jamesport?

With 6 Expedia vacation rentals, you're sure 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 Safari Adventure, or get outside and enjoy nature at Meschutt Beach. In the larger area, you’ll find Jason's Vineyard and Jamesport Vineyards.

What are vacation rentals like in Jamesport?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Jamesport. Vacation rentals feature extras such as hot tubs, fire pits, and patios to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for small groups.