South Jamesport Vacation Rentals

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Our top choices for South Jamesport vacation rentals

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Water Mill
10.0 out of 10, Exceptional, (6)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
$6,393 nightly
The price is $7,304
Jan 6 - Jan 7
Total with taxes and fees
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

Seabreeze #3: Cozy Cottage by the beach

Seabreeze #3: Cozy Cottage by the beach
Hampton Bays
10.0 out of 10, Exceptional, (1)
$390 nightly
The price is $446
Jan 12 - Jan 13
Total with taxes and fees
Seabreeze #3: Cozy Cottage by the beach

Spacious 5-bedroom house with water views and 2 houses from the bay.

Spacious 5-bedroom house with water views and 2 houses from the bay.
Sag Harbor
$5,636 nightly
The price is $6,439
Jan 10 - Jan 11
Total with taxes and fees
Spacious 5-bedroom house with water views and 2 houses from the bay.

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Hampon Bays
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.
$1,170 nightly
The price is $1,337
Jan 7 - Jan 8
Total with taxes and fees
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Sag Harbor Water View w Dock 1.5ml from town

Sag Harbor Water View w Dock 1.5ml from town
Bay Point
$5,557 nightly
The price is $6,349
Jan 8 - Jan 9
Total with taxes and fees
Sag Harbor Water View w Dock 1.5ml from town

South Shore Studio in Mastic

South Shore Studio in Mastic
2.0 star property
Mastic
10.0 out of 10, Exceptional, (3)
"Great stay! Super comfy and clean😊"
United States
ERIN
$195 nightly
The price is $223
Jan 6 - Jan 7
Total with taxes and fees
South Shore Studio in Mastic

Cozy and Modern 2-bedroom apartment in lovely Yaphank

Cozy and Modern 2-bedroom apartment in lovely Yaphank
2.0 star property
Yaphank
10.0 out of 10, Exceptional, (1)
$366 nightly
The price is $418
Jan 6 - Jan 7
Total with taxes and fees
Cozy and Modern 2-bedroom apartment in lovely Yaphank

Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Hampton Bays
9.6 out of 10, Exceptional, (14)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
$1,114 nightly
The price is $1,273
Jan 14 - Jan 15
Total with taxes and fees
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
2.0 star property
Calverton
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.
$577 nightly
The price is $659
Jan 6 - Jan 7
Total with taxes and fees
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.0 out of 10, Wonderful, (4)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
$216 nightly
The price is $247
Jan 6 - Jan 7
Total with taxes and fees
American Beech in Greenport - Petite King Room 7

MUST LOVE DOGS! Pet friendly separate entrance apartment. Safe cul de sac

MUST LOVE DOGS! Pet friendly separate entrance apartment. Safe cul de sac
2.0 star property
Manorville
$173 nightly
The price is $198
Jan 6 - Jan 7
Total with taxes and fees
MUST LOVE DOGS! Pet friendly separate entrance apartment. Safe cul de sac

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)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
$454 nightly
The price is $519
Jan 11 - Jan 12
Total with taxes and fees
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Cozy Hamptons Escape 3BR Minutes From Beach!

Cozy Hamptons Escape 3BR Minutes From Beach!
Hampton Bays
9.2 out of 10, Wonderful, (5)
"Great place. It's exactly like the listing! Would stay again!"
United States
Taylor H.
$1,371 nightly
The price is $1,566
Jan 7 - Jan 8
Total with taxes and fees
Cozy Hamptons Escape 3BR Minutes From Beach!

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

Beach cottage, private road, private beach, private mooring, private parking.
2.5 star property
Laurel
10.0 out of 10, Exceptional, (1)
$743 nightly
The price is $849
Jan 19 - Jan 20
Total with taxes and fees
Beach cottage, private road, private beach, private mooring, private parking.

Seabreeze #4: Charming Cottage Footsteps to the Beach

Seabreeze #4: Charming Cottage Footsteps to the Beach
Hampton Bays
8.8 out of 10, Excellent, (3)
"Great stay. Would stay again. "
United States
Weston B.
$396 nightly
The price is $452
Jan 20 - Jan 21
Total with taxes and fees
Seabreeze #4: Charming Cottage Footsteps to the Beach

East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026

East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026
Center Moriches
10.0 out of 10, Exceptional, (111)
"Amazing stay! Everything was super clean and beautiful "
United States
Liannys P.
$537 nightly
The price is $614
Jan 11 - Jan 12
Total with taxes and fees
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026

Beautifully farmhouse

Beautifully farmhouse
Southold
10.0 out of 10, Exceptional, (3)
"good experience"
United States
Anonymous traveler
$1,028 nightly
The price is $1,175
Jan 7 - Jan 8
Total with taxes and fees
Beautifully farmhouse

Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!
Hampton Bays
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.
$562 nightly
The price is $642
Jan 7 - Jan 8
Total with taxes and fees
Immaculate Waterfront 2 bedroom!

Walk to Beach 2BR Near Dining & Shopping

Walk to Beach 2BR Near Dining & Shopping
Rocky Point
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.
$198 nightly
The price is $226
Jan 11 - Jan 12
Total with taxes and fees
Walk to Beach 2BR Near Dining & Shopping

Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition
Wainscott
$1,707 nightly
The price is $1,950
Jan 6 - Jan 7
Total with taxes and fees
Cozy 5 Bedroom With Wi-fi And Air Condition
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 South Jamesport Hotel Reviews

Find out more about South Jamesport

Everything you need to know about South 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 South 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 South Jamesport vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

South Jamesport vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South 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 South 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 $226 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 South Jamesport rentals

At Expedia, we put the best South 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 South 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 South 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 South 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

Can I find vacation rentals in South Jamesport?

Yes, we give you a choice of vacation rentals near well known attractions in South Jamesport, or you can select a secluded option if you'd like a relaxing place to stay. South Jamesport is known for its beaches.

What's the top vacation rental in South Jamesport?

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr: This vacation home rental near South 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 are there in South Jamesport?

Choose from 11 Expedia vacation rentals in South Jamesport for a memorable vacation.

What’s there to see and do in South Jamesport?

While exploring the area, visit family-friendly sights like Safari Adventure, or get outside and enjoy nature at South Jamesport Park. Jamesport Vineyards and Martha Clara Vineyards are a couple of places you'll find in the larger area.

What’s a vacation rental in South Jamesport like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in South Jamesport. Vacation rentals feature extras like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for family trips.