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

Jamesport Vacation Rentals

Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Jamesport vacation rentals

A hammock under a tree by a lake with boats in the background and a sign for J&S Reeves Cottages.

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.
$920 nightly
The price is $936
Aug 23 - Aug 24
Total with taxes and fees
4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
A hammock under a tree by a lake with boats in the background and a sign for J&S Reeves Cottages.

2. 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.
$726 nightly
The price is $739
Sep 14 - Sep 15
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.

3. Elegant 5-Bedroom Hamptons Home with Private Pool

Elegant 5-Bedroom Hamptons Home with Private Pool
Hampton Bays
9.4 out of 10, Exceptional, (41 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.
$1,151 nightly
The price is $1,315
Aug 30 - Aug 31
Total with taxes and fees
Elegant 5-Bedroom Hamptons Home with Private Pool

4. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (285 reviews)
"Great place!"
United States
Christine
$385 nightly
The price is $439
Sep 9 - Sep 10
Total with taxes and fees
Cliffside Resort Condominiums

5. 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.
$920 nightly
The price is $936
Aug 26 - Aug 27
Total with taxes and fees
5th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
A dining area with a wooden table, chairs, and a decorative wall with a cityscape picture.

6. 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
Sep 17 - Sep 18
Total with taxes and fees
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
A modern house with a deck, outdoor seating, and a fire pit.

7. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (50 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
$273 nightly
The price is $312
Sep 7 - Sep 8
Total with taxes and fees
North Fork Resort
A covered patio area with a white sofa, wooden chairs, and a ceiling fan.

8. Villa Luz Family Home w/ heated pool & jacuzzi

Villa Luz Family Home w/ heated pool & jacuzzi
Hampon Bays
9.6 out of 10, Exceptional, (26 reviews)
"Everything was in order. When there were a couple of very minor glitches, the manager of the property was immediately responsive - and glitch gone, fast. This was one of the smoothest VRBO experiences we've had, and we've had many."
United States
Carola C.
$1,921 nightly
The price is $2,050
Sep 8 - Sep 9
Total with taxes and fees
Villa Luz Family Home w/ heated pool & jacuzzi
A beach with footprints leading to the water, a sunset in the background, and a clear sky.

9. Seabreeze 4 Charming Cottage footsteps to beach

Seabreeze 4 Charming Cottage footsteps to beach
Hampton Bays
9.4 out of 10, Exceptional, (6 reviews)
"Great stay. Would stay again. "
United States
Weston B.
$572 nightly
The price is $615
Sep 7 - Sep 8
Total with taxes and fees
Seabreeze 4 Charming Cottage footsteps to beach
A modern kitchen with white cabinetry, a large island with bar stools, stainless steel appliances, and pendant lighting.

10. Best location! Cozy and Chic Retreat 5 min to beach and close to town, peaceful!

Best location! Cozy and Chic Retreat 5 min to beach and close to town, peaceful!
Hampton Bays
9.0 out of 10, Wonderful, (12 reviews)
"Great property with ease of access! Plenty of amenities and very kind host!"
United States
Travis A.
Best location! Cozy and Chic Retreat 5 min to beach and close to town, peaceful!
A modern kitchen with white cabinets, a dining area with a round table, and a living area with a sofa and decorative pillows.

11. 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.
$1,371 nightly
The price is $1,566
Aug 23 - Aug 24
Total with taxes and fees
Cozy Hamptons Escape 3BR Minutes From Beach!

12. Hamptons Tiana Bay Oasis

Hamptons Tiana Bay Oasis
Hampton Bays
10.0 out of 10, Exceptional, (4 reviews)
"We thoroughly enjoyed this newly renovated home and had a wonderful time. Beautiful pool and grounds. "
United States
Anonymous traveler
$1,503 nightly
The price is $1,615
Sep 2 - Sep 3
Total with taxes and fees
Hamptons Tiana Bay Oasis
A backyard with a swimming pool, outdoor furniture, and a house with solar panels.

13. 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.
$1,257 nightly
The price is $1,436
Aug 21 - Aug 22
Total with taxes and fees
Near the Hamptons - Private Pool, Jacuzzi Retreat
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.
$806 nightly
The price is $921
Sep 1 - Sep 2
Total with taxes and fees
Immaculate Waterfront 2 bedroom!
A sandy beach with footprints leading to the water, a wooden bench, and a pair of shoes on the ground.

15. Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants

Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants
Southampton
10.0 out of 10, Exceptional, (2 reviews)
"Had a great stay for a long weekend in the Hamptons. House was cozy and comfortable and in a good location."
United States
Beverly J.
$913 nightly
The price is $1,043
Sep 14 - Sep 15
Total with taxes and fees
Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants
A covered patio with a table and chairs, large windows, and a view of greenery.

16. 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)
"great experience"
United States
Jordan
$514 nightly
The price is $587
Aug 31 - Sep 1
Total with taxes and fees
Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
A two-story building with a prominent sign reading 'Ivy Restaurant & Bar' on the front window.

17. Prime location, walk to all, cozy cottage WHB, 30 minutes from Shinnecock Hills

Prime location, walk to all, cozy cottage WHB, 30 minutes from Shinnecock Hills
Westhampton Beach
10.0 out of 10, Exceptional, (2 reviews)
"Adorable cottage in a perfect location to walk into West Hampton town and the beaches. Easy check-in with great communication. Plenty of amenities, including bikes, beach chairs, towels, and all you need to have a BBQ. Peaceful backyard - perfect to relax and read or enjoy an outside BBQ with family. I was with 2 girls friends and it was great for our needs."
United States
Cindy M.
$514 nightly
The price is $587
Sep 7 - Sep 8
Total with taxes and fees
Prime location, walk to all, cozy cottage WHB, 30 minutes from Shinnecock Hills
A sandy beach path leading to the ocean with grass on either side.

18. Town walking distance-Bridgehampton Cottage

Town walking distance-Bridgehampton Cottage
Bridgehampton
9.6 out of 10, Exceptional, (12 reviews)
"Walking distance to Bridgehampton and a short drive to sag harbor. Great for 2 couples."
United States
Jim M.
Town walking distance-Bridgehampton Cottage
A driveway with a parked car, surrounded by trees and illuminated pathway lights.

19. Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.

Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
Bridgehampton
10.0 out of 10, Exceptional, (1 review)
"We thoroughly enjoyed our stay. The property was exactly as described, very well maintained, comfortable, and welcoming. The location is ideal for exploring the Hamptons, with convenient access to Sag Harbor, East Hampton, and Bridgehampton. We would definitely recommend this property to others visiting the area."
United States
Robert R.
$514 nightly
The price is $587
Sep 20 - Sep 21
Total with taxes and fees
Bridgehampton, NY cottage near Sag Harbor, NY. Elegant and modern.
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
7.8 out of 10, Good, (7 reviews)
"Beautiful home and location. Owner was very helpful. Would love to rent again!"
United States
Evelyn D.
$779 nightly
The price is $890
Sep 14 - Sep 15
Total with taxes and fees
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

Home2 Suites by Hilton Long Island Brookhaven

Home2 Suites by Hilton Long Island Brookhaven

10/10 Excellent
"My short stay (one night) at this Hilton location was great! Everything was very clean, all staff were very pleasant. There was a complimentary continental breakfast in the morning as well!"
madeleine 1-night trip
Posted 3 hours ago
Home2 Suites by Hilton Long Island Brookhaven

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 $298 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?

Bayfront 5 bedrooms family home. Panoramic sea view from all rooms: This vacation home rental outside of Jamesport is located by the ocean and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 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 books.

How many vacation rentals will I find in Jamesport?

With 7 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.