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 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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 6 - Oct 7
Total with taxes and fees
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

2. 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.
$1,584 nightly
The price is $1,679
Oct 4 - Oct 5
Total with taxes and fees
Jacuzzi year-round - Villa Luz Private Home
A spacious living room with a large sofa, a round coffee table, and a television. A kitchen with a refrigerator and cabinets is visible in the background.

3. 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
$406 nightly
The price is $432
Oct 4 - Oct 5
Total with taxes and fees
Steps to the beach | Seabreeze Cottage #3
A modern building with large windows overlooking a beach.

4. Beachfront Jacuzzi All Year - Black Swan Home

Beachfront Jacuzzi All Year - Black Swan Home
Hampton Bays
9.4 out of 10, Exceptional, (20 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 4 - Oct 5
Total with taxes and fees
Beachfront Jacuzzi All Year - Black Swan Home
A modern house with a deck, outdoor seating, and a fire pit.

5. 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
$225 nightly
The price is $257
Oct 4 - Oct 5
Total with taxes and fees
North Fork Resort
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 sign for J&S Reeves Cottages with a view of a house and trees.

7. 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.
$794 nightly
The price is $808
Oct 3 - Oct 4
Total with taxes and fees
6th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
A beach with footprints leading to the water, a sunset in the background, and a clear sky.

8. 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.
$434 nightly
The price is $463
Oct 12 - Oct 13
Total with taxes and fees
Walk to Beach | Seabreeze Cottage #4
A rocky beach with clear water and a forested hillside in the background.

9. 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 modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

10. 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!
A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

11. 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)
"My family and I really enjoyed this home. Everything you can think of is provided for you. We would definitely stay here again!"
United States
Sarah A.
$857 nightly
The price is $979
Oct 4 - Oct 5
Total with taxes and fees
Elegant 5-Bedroom Hamptons Home with Private Pool
A suburban house with a driveway and parked cars.

12. Beautiful Private Studio Apartment!

Beautiful Private Studio Apartment!
Ridge
9.6 out of 10, Exceptional, (22 reviews)
"Clean and comfortable. Very quiet and pleasant place to stay."
United States
Gene
$267 nightly
The price is $305
Oct 19 - Oct 20
Total with taxes and fees
Beautiful Private Studio Apartment!
A covered patio with a table and chairs, large windows, and a view of greenery.

13. Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6

Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
Southampton
9.6 out of 10, Exceptional, (10 reviews)
"Very nice place and super responsive host. "
United States
Angelo D.
$514 nightly
The price is $587
Oct 4 - Oct 5
Total with taxes and fees
Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
Roger’s Beach

14. 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.
$629 nightly
The price is $719
Oct 19 - Oct 20
Total with taxes and fees
Prime location, walk to all, cozy cottage WHB
A doorway with a "WELCOME" mat, a small potted plant on each side, and a hallway leading to a living room with a couch and a lamp.

15. Comfy, private one Bedroom Apartment with full kitchen, living room, full bath.

Comfy, private one Bedroom Apartment with full kitchen, living room, full bath.
Ridge
9.4 out of 10, Exceptional, (21 reviews)
"Super clean had everything we needed and super close to east wind!"
United States
Karina R.
$299 nightly
The price is $342
Oct 15 - Oct 16
Total with taxes and fees
Comfy, private one Bedroom Apartment with full kitchen, living room, full bath.
Terrace/patio

16. 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.
$836 nightly
The price is $851
Oct 3 - Oct 4
Total with taxes and fees
5th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
A beach with people relaxing on chairs and sunbathing.

17. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (26 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
$222 nightly
The price is $254
Nov 1 - Nov 2
Total with taxes and fees
Harbor Heights
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

18. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (52 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
$220 nightly
The price is $251
Nov 2 - Nov 3
Total with taxes and fees
The SandPiper
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
8.0 out of 10, Very good, (10 reviews)
"Very responsive host and a beautiful house."
United States
Robin M.
$637 nightly
The price is $728
Oct 6 - Oct 7
Total with taxes and fees
Cozy beach hose minutes from Hamptons
A sign for J&S Reeves Cottages with a view of a house and trees.

20. 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.
$857 nightly
The price is $872
Oct 4 - Oct 5
Total with taxes and fees
4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
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

Zey Hotel

Zey Hotel

10/10 Excellent
"Had a great stay here. James was very welcoming and a great host. The town is great with nice shops and restaurants."
Michael 1-night trip
Posted 5 hours ago
Zey Hotel

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 $251 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.