South Jamesport Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in South Jamesport

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

Westhampton Beach
10.0 out of 10, Exceptional, (195)
"My family and I thoroughly enjoyed our stay! The house is very spacious and the outdoor area/pool are beautiful. Check-in was a breeze and the host was very friendly and responsive to all our questions about the home as well as offering wonderful suggestions for restaurants and beaches in the area. Would definitely recommend for a family vacation!"
United States
livinann
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

Cliffside Resort Condominiums

3.0 star property
Greenport
9.0 out of 10, Wonderful, (249)
"Great stay - beautiful place"
United States
Rebecca
Cliffside Resort Condominiums

Modern Vacation home. Close to The Hamptons

Shirley
10.0 out of 10, Exceptional, (3)
"good time"
United States
Roy T.
The price is AU$950
includes taxes & fees
8 Dec - 9 Dec
Modern Vacation home. Close to The Hamptons

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

Sag Harbor
10.0 out of 10, Exceptional, (89)
"House that has everything you need for a wonderful getaway! Excellent communication with the property owner. Thank you Jay for everything and your hospitality! "
United States
Maria R.
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

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.
The price is AU$356
includes taxes & fees
8 Dec - 9 Dec
Walk to Beach 2BR Near Dining & Shopping

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

Center Moriches
10.0 out of 10, Exceptional, (110)
"Amazing stay! Everything was super clean and beautiful "
United States
Liannys P.
The price is AU$1,143
includes taxes & fees
29 Dec - 30 Dec
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026

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.
The price is AU$1,012
includes taxes & fees
8 Dec - 9 Dec
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

10 Bedroom Hampton House with a regulation size Pickleball court

Hampton Bays
10.0 out of 10, Exceptional, (32)
"Location of this property is impeccable."
United States
Stephen M.
10 Bedroom Hampton House with a regulation size Pickleball court

Private One Bedroom Apartment with full kitchen, living room and full bath.

Ridge
9.4 out of 10, Exceptional, (9)
"Tammy was a lovely host. She provided very detailed instructions on how to get to the Vrbo, parking location, and access in advance. Vrbo was just as pictured too! "
United States
Kristyn R.
Private One Bedroom Apartment with full kitchen, living room and full bath.

Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

Hampton Bays
9.4 out of 10, Exceptional, (75)
"Great Hamptons break with family. We had an amazing time with great pool, tennis, firepit and beautiful house. Very relaxing and close to fantastic beaches and nice ice cream spots and beach bars."
United Kingdom
Jack T.
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

Minutes from the beach, brand new 4 bedroom

Southampton
10.0 out of 10, Exceptional, (3)
"perfect for families"
United States
Okito H.
The price is AU$1,689
includes taxes & fees
12 Dec - 13 Dec
Minutes from the beach, brand new 4 bedroom

The SandPiper

Pipes Cove
9.8 out of 10, Exceptional, (30)
"Our stay in Greenport at the Sandpiper was wonderful! Location was perfect: easy walk into town and to the ferry to shelter island. Ten out of ten!"
United States
paris t.
The SandPiper

Stunning Hampton Holiday Family Fantasy for your Team

East Hampton
9.8 out of 10, Exceptional, (74)
"Outstanding house, beautifully maintained and well stocked, with great location."
United States
Jason C.
Stunning Hampton Holiday Family Fantasy for your Team

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Southampton
9.8 out of 10, Exceptional, (32)
"This place was so nice and so close to so many fun places! "
United States
Daniella L.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

Eastport
9.6 out of 10, Exceptional, (34)
"We had a amazing stay and plan to come back next July again"
United States
Gina G.
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

A Quiet Place in the Hamptons

East Quogue
9.6 out of 10, Exceptional, (39)
"Fantastic house for the extended family ! We loved the pool , enjoyed bbq grilling and hanging out together! "
United States
Anonymous traveller
A Quiet Place in the Hamptons

Safari Tent Glamping,S5-CedarPt, East Hampton, NY

East Hampton
8.6 out of 10, Excellent, (4)
"Had a nice peaceful evening eating our pizza and relaxing while watching the sunset. Nice way to celebrate our 30th, back to the woods❤️"
United States
Ellen
Safari Tent Glamping,S5-CedarPt, East Hampton, NY

Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!

Calverton
9.4 out of 10, Exceptional, (42)
"The description and photos are accurate. The beach is close."
United States
L A.
Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!

5 bedroom Private Family Get Away w/ Heated Pool

Westhampton Beach
10.0 out of 10, Exceptional, (18)
"Family friendly. Lovely pool. Nice area"
United States
Ruth
5 bedroom Private Family Get Away w/ Heated Pool

Work and Play Special! Extended Stay Discount

Shelter Island
10.0 out of 10, Exceptional, (53)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
Work and Play Special! Extended Stay Discount
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.
Save an average of 15% on thousands of hotels when you're signed in

Top South Jamesport Hotel Reviews

Find out more about South Jamesport

Everything you need to know about South Jamesport holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the South Jamesport holiday rental for you. At Expedia, you can take your pick from private holiday 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 South Jamesport holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

South Jamesport holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Jamesport holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Jamesport holiday rentals we have selected for you start as low as AU$356 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on South Jamesport rentals

At Expedia, we put the best South Jamesport holiday 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 holiday.

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 holiday rentals in South Jamesport?

Yes, there are holiday rentals close to the most popular sights in South Jamesport, or you can select a more secluded option if you're looking for a relaxing stay. South Jamesport is known for its beaches.

How many holiday rentals are there in South Jamesport?

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

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

While exploring the area, visit family-friendly sights like Splish Splash Water Park, or get outside and enjoy nature at South Jamesport Park. Jamesport Vineyards and Harbes Family Farm are a couple of places you'll find in the wider area.

What’s a holiday rental in South Jamesport like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in South Jamesport. Holiday rentals offer amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy front desks while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a family trip or a small group gathering.