Jamesport Vacation Rentals

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Check prices for these dates

In two weeks
Mar 13 - Mar 15
In two months
Apr 24 - Apr 26
In three months
May 22 - May 24
In four months
Jun 19 - Jun 21

Our top choices for Jamesport vacation rentals

Terrace/patio

Cottage on Beach front Estate with Dockage .Walk to Village

Cottage on Beach front Estate with Dockage .Walk to Village
Pipes Cove
10.0 out of 10, Exceptional, (76 reviews)
"Wonderful stay at such a special spot. "
United States
Meg B.
$307 nightly
The price is $351
Feb 28 - Mar 1
Total with taxes and fees
Cottage on Beach front Estate with Dockage .Walk to Village
Exterior detail

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Calverton
8.6 out of 10, Excellent, (8 reviews)
"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.
$554 nightly
The price is $632
Feb 26 - Feb 27
Total with taxes and fees
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Terrace/patio

Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Hampton Bays
9.6 out of 10, Exceptional, (15 reviews)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
$1,056 nightly
The price is $1,207
Feb 26 - Feb 27
Total with taxes and fees
Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Smart TV, books

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Rocky Point
10.0 out of 10, Exceptional, (25 reviews)
"It was perfect for what we needed and the hostess made it very simple and easy to check in and check out and answer any questions thank you"
United States
ken g.
$475 nightly
The price is $543
Feb 26 - Feb 27
Total with taxes and fees
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
1 bedroom, free WiFi, bed sheets

South Shore Studio in Mastic

South Shore Studio in Mastic
Mastic
10.0 out of 10, Exceptional, (3 reviews)
"Great stay! Super comfy and clean😊"
United States
ERIN
$199 nightly
The price is $227
Feb 26 - Feb 27
Total with taxes and fees
South Shore Studio in Mastic
Terrace/patio

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.0 out of 10, Wonderful, (4 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
$175 nightly
The price is $200
Feb 26 - Feb 27
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
Fridge, microwave, oven, stovetop

Modern Vacation home. Close to The Hamptons

Modern Vacation home. Close to The Hamptons
Shirley
10.0 out of 10, Exceptional, (4 reviews)
"5/5 I enjoyed my stay , very clean and spacious. "
United States
Quywana F.
$454 nightly
The price is $518
Mar 1 - Mar 2
Total with taxes and fees
Modern Vacation home. Close to The Hamptons
Exterior

Cozy&Chic Beach Cottage - wineries, beach and perfect for all seasons

Cozy&Chic Beach Cottage - wineries, beach and perfect for all seasons
Southold
$386 nightly
The price is $441
Mar 4 - Mar 5
Total with taxes and fees
Cozy&Chic Beach Cottage - wineries, beach and perfect for all seasons
Terrace/patio

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
Mastic
10.0 out of 10, Exceptional, (28 reviews)
"Lovely time with so many fun games and activities on the property, highly recommend!"
United States
Logan S.
$914 nightly
The price is $1,044
Mar 1 - Mar 2
Total with taxes and fees
Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
Dining

Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
10.0 out of 10, Exceptional, (5 reviews)
"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.
$513 nightly
The price is $586
Mar 3 - Mar 4
Total with taxes and fees
Northfork Townhouse walk to all
Dining

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.
$556 nightly
The price is $635
Feb 26 - Feb 27
Total with taxes and fees
Immaculate Waterfront 2 bedroom!
Interior

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 location. Great host. Easy house, pool and private back yard. It's modest but has it all."
United States
Harry V.
$503 nightly
The price is $574
Feb 26 - Feb 27
Total with taxes and fees
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Sun loungers, beach towels

Cozy beach hose minutes from Hamptons

Cozy beach hose minutes from Hamptons
Calverton
10.0 out of 10, Exceptional, (1 review)
"Beautiful home and location. Owner was very helpful. Would love to rent again!"
United States
Evelyn D.
$609 nightly
The price is $696
Mar 4 - Mar 5
Total with taxes and fees
Cozy beach hose minutes from Hamptons
Smart TV, fireplace

Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (10 reviews)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
$598 nightly
The price is $683
Mar 1 - Mar 2
Total with taxes and fees
Renovated Townhouse walk to all
Property grounds

Walk to Beach 2BR Near Dining & Shopping

Walk to Beach 2BR Near Dining & Shopping
Rocky Point
6.8 out of 10, (28 reviews)
"This is an adequate place to stay. That's about it"
United States
Maureen T.
$206 nightly
The price is $235
Feb 26 - Feb 27
Total with taxes and fees
Walk to Beach 2BR Near Dining & Shopping
Interior

Breakwater Estate… perfect for Large Group Getaways!

Breakwater Estate… perfect for Large Group Getaways!
Mattituck
10.0 out of 10, Exceptional, (35 reviews)
"Beautiful property. Great pool, We had a great time."
United States
william p.
$1,142 nightly
The price is $1,202
Feb 27 - Feb 28
Total with taxes and fees
Breakwater Estate… perfect for Large Group Getaways!
Smart TV, fireplace, stereo

Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (3 reviews)
"perfect for families"
United States
Okito H.
$971 nightly
The price is $1,109
Feb 27 - Feb 28
Total with taxes and fees
Minutes from the beach, brand new 4 bedroom
Smart TV, books

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Greenport
10.0 out of 10, Exceptional, (1 review)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
$549 nightly
The price is $627
Feb 27 - Feb 28
Total with taxes and fees
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Property grounds

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.
$784 nightly
The price is $797
Feb 26 - Feb 27
Total with taxes and fees
4th of 6 Premier Waterfront Vacation Rentals on Long Island NY in Wine Country of Famed North Fork
On the beach, sun loungers, beach towels

Beach cottage, private road, private beach, private mooring, private parking.

Beach cottage, private road, private beach, private mooring, private parking.
Laurel
10.0 out of 10, Exceptional, (1 review)
$743 nightly
The price is $849
Mar 23 - Mar 24
Total with taxes and fees
Beach cottage, private road, private beach, private mooring, private parking.
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

Hotel Indigo East End by IHG

Hotel Indigo East End by IHG

10/10 Excellent
"Courteous staff, par excellence. They answered all my questions, as itinerary was complicated by the Feb.'26 blizzard. Extremely clean room, plus everywhere else on site, is spotless. Temperature of the room, in winter; perfect & adjustable. Varied, healthful and delicious complimentary breakfast. Bistro 72 is superb. Any season, in Riverhead? Hotel Indigo is a winner."
Alison 7-night trip
Posted 2 days ago
Hotel Indigo East End by IHG

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 $351 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?

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!: This vacation home rental outside of Jamesport is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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.