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Jamesport Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Jamesport vacation rentals

Smart TV
Seabreeze #3: Cozy Cottage by the beach

Cottage in Hampton Bays

Seabreeze #3: Cozy Cottage by the beach
10.0 out of 10, Exceptional, (1)
The price is ￥8,552
￥71,059 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Seabreeze #3: Cozy Cottage by the beach
Terrace/patio
South Shore Studio in Mastic

Apartment in Mastic

South Shore Studio in Mastic
2.0 star property
10.0 out of 10, Exceptional, (2)
"Great stay! Super comfy and clean😊"
United States
ERIN
The price is ￥16,793
￥29,848 total
includes taxes & fees
Dec 13 - Dec 14
South Shore Studio in Mastic
Terrace/patio
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Vacation Home in Hampon Bays

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
9.6 out of 10, Exceptional, (22)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is ￥15,394
￥197,722 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Beach
Seabreeze #4: Charming Cottage Footsteps to the Beach

Cottage in Hampton Bays

Seabreeze #4: Charming Cottage Footsteps to the Beach
8.8 out of 10, Excellent, (3)
"Great stay. Would stay again. "
United States
Weston B.
The price is ￥8,552
￥71,059 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Seabreeze #4: Charming Cottage Footsteps to the Beach
Fridge, microwave, stovetop, dishwasher
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Cottage in Greenport

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
10.0 out of 10, Exceptional, (1)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is ￥35,042
￥78,648 total
includes taxes & fees
Dec 14 - Dec 15
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Property grounds
Walk to Beach 2BR Near Dining & Shopping

Apartment in Rocky Point

Walk to Beach 2BR Near Dining & Shopping
6.8 out of 10, (26)
"Great location, great host, and nice rental especially for the price! Everything went smoothly and we will be returning next year."
United States
Joshua W.
The price is ￥12,595
￥36,063 total
includes taxes & fees
Dec 13 - Dec 14
Walk to Beach 2BR Near Dining & Shopping
Fridge, microwave, oven, stovetop
Modern Vacation home. Close to The Hamptons

Vacation Home in Shirley

Modern Vacation home. Close to The Hamptons
10.0 out of 10, Exceptional, (3)
"good time"
United States
Roy T.
The price is ￥51,553
￥96,385 total
includes taxes & fees
Dec 14 - Dec 15
Modern Vacation home. Close to The Hamptons
Outdoor spa tub
Hottub, ⛳️, htd pool, Sauna, Basketball

Vacation Home in Mastic

Hottub, ⛳️, htd pool, Sauna, Basketball
10.0 out of 10, Exceptional, (27)
"Stayed here for my wedding weekends and absolutely loved the house! Very spacious and beautiful yard! Had so much fun "
United States
Tiffany I.
The price is ￥31,148
￥172,773 total
includes taxes & fees
Dec 14 - Dec 15
Hottub, ⛳️, htd pool, Sauna, Basketball
Terrace/patio
American Beech in Greenport - Petite King Room 7

Vacation Home in Greenport

American Beech in Greenport - Petite King Room 7
9.0 out of 10, Wonderful, (4)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is ￥27,833
￥43,346 total
includes taxes & fees
Dec 18 - Dec 19
American Beech in Greenport - Petite King Room 7
Fridge, microwave, oven, stovetop
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Vacation Home in Rocky Point

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
10.0 out of 10, Exceptional, (23)
"Pet friendly "
United States
Steven
The price is ￥41,671
￥84,030 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Smart TV, fireplace, video games, stereo
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026

Cottage in Center Moriches

East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026
10.0 out of 10, Exceptional, (110)
"Amazing stay! Everything was super clean and beautiful "
United States
Liannys P.
The price is ￥45,870
￥95,041 total
includes taxes & fees
Jan 5 - Jan 6, 2026
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026
Oven, stovetop, dishwasher
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Vacation Home in Calverton

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
2.0 star property
8.6 out of 10, Excellent, (8)
"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.
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Front of property
Canoe Place Waterfront Residences

Condo in Hampton Bays

Canoe Place Waterfront Residences
4.0 star property
10.0 out of 10, Exceptional, (1)
The price is ￥259,640
￥314,437 total
includes taxes & fees
Dec 28 - Dec 29
Canoe Place Waterfront Residences
Fridge, microwave, oven, stovetop
Serene East Hampton Escape

Vacation Home in East Hampton North

Serene East Hampton Escape
2.0 star property
The price is ￥77,870
￥165,327 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Serene East Hampton Escape
Terrace/patio
Immaculate Waterfront 2 bedroom!

Vacation Home in Hampton Bays

Immaculate Waterfront 2 bedroom!
10.0 out of 10, Exceptional, (5)
"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 ￥50,534
￥99,840 total
includes taxes & fees
Dec 24 - Dec 25
Immaculate Waterfront 2 bedroom!
Interior
Cozy Hamptons Escape 3BR Minutes From Beach!

Vacation Home in Hampton Bays

Cozy Hamptons Escape 3BR Minutes From Beach!
9.2 out of 10, Wonderful, (5)
"Great place. It's exactly like the listing! Would stay again!"
United States
Taylor H.
The price is ￥108,843
￥142,121 total
includes taxes & fees
Dec 13 - Dec 14
Cozy Hamptons Escape 3BR Minutes From Beach!
Fridge, microwave, oven, stovetop
4-bedroom beach house minutes from Hamptons

Vacation Home in Calverton

4-bedroom beach house minutes from Hamptons
2.0 star property
The price is ￥48,979
￥103,567 total
includes taxes & fees
Dec 15 - Dec 16
4-bedroom beach house minutes from Hamptons
Fridge, microwave, oven, stovetop
Charming Northfork Townhouse- walk to all

Vacation Home in Greenport

Charming Northfork Townhouse- walk to all
10.0 out of 10, Exceptional, (5)
"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.
The price is ￥51,394
￥103,734 total
includes taxes & fees
Dec 13 - Dec 14
Charming Northfork Townhouse- walk to all
Fridge, microwave, oven, stovetop
Northfork Townhouse- walk to all/ newly renovated

Vacation Home in Greenport

Northfork Townhouse- walk to all/ newly renovated
9.6 out of 10, Exceptional, (9)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
The price is ￥56,845
￥110,851 total
includes taxes & fees
Dec 14 - Dec 15
Northfork Townhouse- walk to all/ newly renovated
Fridge, microwave, oven, stovetop
Minutes from the beach, brand new 4 bedroom

Vacation Home in Southampton

Minutes from the beach, brand new 4 bedroom
10.0 out of 10, Exceptional, (3)
"perfect for families"
United States
Okito H.
The price is ￥69,971
￥172,496 total
includes taxes & fees
Dec 23 - Dec 24
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

Home2 Suites by Hilton Long Island Brookhaven

Home2 Suites by Hilton Long Island Brookhaven

10/10 Excellent
"Clean rooms and common areas and staff that is extremely helpful and courteous."
Craig 4-night trip
Posted 2 days ago
Home2 Suites by Hilton Long Island Brookhaven

Find out more about Jamesport

Search for holiday rentals in Jamesport on Expedia! You can easily find your home rentals, villas, holiday apartments in Jamesport using one of the methods below:

  • View our selection of featured holiday rentals in Jamesport
  • Use the map to find apartments and other holiday homes in the Jamesport neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Jamesport while they last

Look no further and take a look at our great range of rental properties in Jamesport!

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?

9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub: 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 9 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 Splish Splash Water Park, or get outside and enjoy nature at Tiana 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.