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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Jamesport vacation rentals

A sign for J&S Reeves Cottages with a view of a house and trees.

1. 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.
The price is CA $956
CA $1,298 total
includes taxes & fees
Oct 20 - Oct 21
4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
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.
The price is CA $721
CA $1,740 total
includes taxes & fees
Oct 24 - Oct 25
North Fork Fall Escape—Vineyards, Apple Picking & Greenport
A dining area with a wooden table, chairs, and a decorative wall with a cityscape picture.

3. 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.
The price is CA $204
CA $451 total
includes taxes & fees
Oct 20 - Oct 21
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
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.
The price is CA $636
CA $1,367 total
includes taxes & fees
Oct 20 - Oct 21
Elegant 5-Bedroom Hamptons Home with Private Pool
A covered outdoor seating area with wicker furniture and a view of boats on a lake.

5. 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.
The price is CA $1,057
CA $1,413 total
includes taxes & fees
Oct 20 - Oct 21
3rd of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Terrace/patio

6. 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.
The price is CA $928
CA $1,267 total
includes taxes & fees
Oct 20 - Oct 21
5th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

7. 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.
The price is CA $158
CA $2,374 total
includes taxes & fees
Oct 28 - Oct 29
Jacuzzi year-round - Villa Luz Private Home
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.
The price is CA $107
CA $639 total
includes taxes & fees
Oct 25 - Oct 26
Walk to Beach | Seabreeze Cottage #4
A modern building with large windows overlooking a beach.

9. 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.
The price is CA $160
CA $1,668 total
includes taxes & fees
Oct 27 - Oct 28
Beachfront Jacuzzi All Year - Black Swan Home
A lakeside cottage with a covered porch, a sign for J&S Reeves Cottages, and a grassy lawn with lounge chairs.

10. 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.
The price is CA $1,057
CA $1,413 total
includes taxes & fees
Oct 20 - Oct 21
1st of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
A waterfront property with a grassy lawn, a dock with boats, and a patio area with outdoor furniture.

11. 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.
The price is CA $1,057
CA $1,413 total
includes taxes & fees
Oct 20 - Oct 21
2nd of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
Property grounds

12. Hamptons Oceanfront Oasis - Cozy 1-bedroom cottage

Hamptons Oceanfront Oasis - Cozy 1-bedroom cottage
Hampton Bays
The price is CA $395
CA $516 total
includes taxes & fees
Oct 20 - Oct 21
Hamptons Oceanfront Oasis - Cozy 1-bedroom cottage
Terrace/patio

13. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (297 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is CA $239
CA $430 total
includes taxes & fees
Nov 12 - Nov 13
Cliffside Resort Condominiums
A modern kitchen with white cabinets, a dining area with a round table, and a living area with a sofa and decorative pillows.

14. Cozy Hamptons Escape 3BR Minutes From Beach!

Cozy Hamptons Escape 3BR Minutes From Beach!
Hampton Bays
9.2 out of 10, Wonderful, (7 reviews)
"Great place. It's exactly like the listing! Would stay again!"
United States
Taylor H.
The price is CA $1,697
CA $2,215 total
includes taxes & fees
Oct 20 - Oct 21
Cozy Hamptons Escape 3BR Minutes From Beach!
A backyard with a swimming pool, outdoor furniture, and a house with solar panels.

15. Near the Hamptons - Private Pool, Jacuzzi Retreat

Near the Hamptons - Private Pool, Jacuzzi Retreat
Calverton
6.0 out of 10, (1 review)
"Upon arrival, there was a notice of non payment of almost 4000 from the electric company on the door so I was concerned I would lose electric. The grounds seemedover grown and unkept. There was no TV, no hot water in the kitchen with a brokenhot water knob which would have needed a wrench. Although it had in room air conditioners vented outside, they were taped in place with open air coming inside. One of the open areas actually had live tree vines coming inside which I pulled out. There was...
United States
Theresa M.
The price is CA $1,266
CA $2,104 total
includes taxes & fees
Oct 20 - Oct 21
Near the Hamptons - Private Pool, Jacuzzi Retreat
A modern two-story house with a swimming pool, a covered deck, and a well-maintained lawn.

16. Amazing Southampton Home with Private Heated Pool

Amazing Southampton Home with Private Heated Pool
Southampton
9.0 out of 10, Wonderful, (2 reviews)
"Very cozy house in a great location!"
United States
Serina R.
The price is CA $708
CA $1,625 total
includes taxes & fees
Oct 20 - Oct 21
Amazing Southampton Home with Private Heated Pool
A modern house with a deck, outdoor seating, and a fire pit.

17. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (67 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is CA $414
CA $473 total
includes taxes & fees
Oct 26 - Oct 27
North Fork Resort
A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

18. 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.
The price is CA $382
CA $813 total
includes taxes & fees
Oct 21 - Oct 22
Immaculate Waterfront 2 bedroom!
Roger’s Beach

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

Prime location, walk to all, cozy cottage WHB
Westhampton Beach
10.0 out of 10, Exceptional, (4 reviews)
"Property was in easy walking distance from the village which made morning coffee runs a breeze. Very clean accommodations and large back yard."
United States
Matt S.
The price is CA $424
CA $877 total
includes taxes & fees
Oct 25 - Oct 26
Prime location, walk to all, cozy cottage WHB
A spacious living area with a fireplace, a wooden staircase, and large windows.

20. 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.
The price is CA $468
CA $889 total
includes taxes & fees
Oct 27 - Oct 28
Cozy beach hose minutes from Hamptons
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

The Hampton Maid

The Hampton Maid

10/10 Excellent
"Property and room was incredible. However, didn’t like the restaurant food. It was lacking flavor and the dessert choices weren’t good. Lastly, the pillows weren’t the best."
Delise 2-night trip
Posted 7 hours ago
The Hampton Maid

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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Jamesport vacation rentals we have selected for you start as low as CA $355 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 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. 

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.