Photo by Nina Dinoff

Holiday Rentals in Jamesport

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Holiday Rentals in Jamesport

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

10.0 out of 10, Exceptional, (5)
"Perfect getaway for a group of ladies spending a snowy night catching up away from our spouses and kids. Cozy fireplace, beautiful home, ample space and in a great location. Highly recommend!"
The price is €926
includes taxes & fees
4 Mar - 5 Mar
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

9.6 out of 10, Exceptional, (31)
"The mansion is beautiful, with large rooms in the upstairs bedrooms. The 2 bedrooms in the basement were a bit small and a bit Spartan. The fireplace room had 4 remotes, none of which worked the large screen tv, and half of the bedrooms had remotes that did not work the tv's. The kitchen silverware drawer was filthy, requiring my wife to clean the draw and was the silverware. The pocket door in the kitchen was off the track (not a big issue), however it requires repairing, The lower draw in the...
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

10 Bedroom Hampton House with a regulation size Pickleball

10.0 out of 10, Exceptional, (25)
"Had so much fun this weekend in Hampton Bays! House was perfect for a group of friends - many bedrooms, bathrooms, great pool with tons of outdoor games, and even the arcade room inside! So close to the beach, and a number of great restaurants. Highly recommend this house, and appreciate how helpful our host was with making sure we had everything we need and more!"
10 Bedroom Hampton House with a regulation size Pickleball

Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

2.0 star property
7.4 out of 10, Good, (3)
"I had so much fun with my friends"
Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

Stunning Hampton Holiday Family Fantasy for your Team

9.8 out of 10, Exceptional, (66)
"Great home"
Stunning Hampton Holiday Family Fantasy for your Team

WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

10.0 out of 10, Exceptional, (168)
"We had a wonderful stay. The house was great and check in and check out were both easy. We definition would love to stay again."
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

Unique location fenced in private beach

10.0 out of 10, Exceptional, (6)
"In town for a funeral. Provided everything we needed for this unforeseen situation. Very clean. "
The price is €731
includes taxes & fees
23 Feb - 24 Feb
Unique location fenced in private beach

Hottub, ⛳️,firepits, heated pool, pool table, Basketball court.

10.0 out of 10, Exceptional, (21)
"It was a very nice experience staying there. The owner replied to our questions pretty fast. I love the backyard, but unfortunately, it is too cold to stay outside during the winter. I would definitely recommend this house and we will try and go back in a warmer season!"
Hottub, ⛳️,firepits, heated pool, pool table, Basketball court.

Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖

10.0 out of 10, Exceptional, (98)
"Pam was very communicative prior to our stay and a welcoming host. The house was clean, centrally located, and spacious. "
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖

Summer 2025 Now Available! Wolffer Vineyard Close!

10.0 out of 10, Exceptional, (83)
"Our stay was amazing! The house was fabulous, beautifully appointed, very clean, private and secluded. Lots to do in the area. Jay was very responsive and helpful when we had questions. Would definitely stay again. "
Summer 2025 Now Available! Wolffer Vineyard Close!

Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!

10.0 out of 10, Exceptional, (41)
"This is the most magical property with a gorgeous pool, beautiful large trees, a pond and a badmitten court. My two children loved it. The property was a 3-4 minute drive from everything and yet felt totally isolated and removed from everything. I will say that the house was more cozy than we expected as the bedrooms upstairs were a steep walk and there was only one bathroom for the entire house. But we made do and had a lovely time."
Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!

Bayfront 5 bedrooms family home. Panoramic sea view from all rooms

10.0 out of 10, Exceptional, (29)
"We enjoyed a year end visit at Jean Marc's beautiful home. There were incredible water views from the floor to ceiling windows in the living room and the master bedroom. The house was clean, comfortable and well furnished. In particular, the kitchen was stocked with everything you need for preparing family meals. Jean Marc was a very responsive and accommodative host!"
Bayfront 5 bedrooms family home. Panoramic sea view from all rooms

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

9.6 out of 10, Exceptional, (127)
"Wonderful throw back beach house..nothing fancy but very comfortable and the views are amazing! Loved spending our Christmas Holiday relaxing by the bay..and the year round hot tub was up and running when we got there! Perfect spot..will definitely go back next year! "
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.

9.8 out of 10, Exceptional, (57)
"My friends, partner and I stayed over Columbus day weekend and were pleasantly surprised with the heated pool still being open, which was a huge highlight. The house was super clean and had everything you would need. We did have a minor issue with the hot water not working in the cottage, but other than that everything was great and we would defintely stay again!"
Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.

20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.

8.6 out of 10, Excellent, (10)
"The place was nice for our time with family for a holiday celebration. Our favorite space was the kitchen dining area which was large and well equipped. There was an issue with the heat upstairs; the hosts endeavored to respond to the problem in a timely manner. (Owners were on site for some of our stay, but it did not affect our activities.) Furniture comfortable....most rooms very lightly furnished. I would recommend bringing extra bedding as most beds only had a light quilt without sheets or...
20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.

Beautiful Hamptons home close to beaches, shopping, & restaurants!

10.0 out of 10, Exceptional, (8)
"Had a great stay! Everything about the stay was perfect. Place was all that we expected and more. Host was easy to reach and very responsive. "
Beautiful Hamptons home close to beaches, shopping, & restaurants!

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

10.0 out of 10, Exceptional, (18)
"My friends and I stayed at this house for a few days around New Year's. The house is very spacious, and the grounds are lovely. We had a group of 5 and had lots of room to congregate and disappear if we needed alone time. The hot tub was exactly what some of us needed, while the kitchen provided others with much comfort. The one bummer was when we arrived; it looked like someone had just had a party outside so that first made for a bit of cleanup. That little bump shouldn't stop you from...
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Private Waterfront on Peconic Bay in Hampton Bays - Southampton - Fall Special!

9.8 out of 10, Exceptional, (17)
"The house was clean and the location was magnificent. Jake was great, offered us early check in and late check out. The neighborhood was lovely, walked my pup and admired all of the beautiful homes. Definitely will stay there again. "
Private Waterfront on Peconic Bay in Hampton Bays - Southampton - Fall Special!

Beautiful resort style backyard with newly added professional PICKLEBALL COURT.

9.8 out of 10, Exceptional, (54)
"The house was exactly as described. Excellent stay and the house was super friendly! Highly recommend for any group of friends looking to stay in the Hamptons! Pool was very nice and pickleball courts in excellent condition! Host was super friendly and helped with any questions. Bedrooms were nice and spacious! Nothing But good things to say about my stay "
Beautiful resort style backyard with newly added professional PICKLEBALL COURT.

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

9.4 out of 10, Exceptional, (64)
"We had an incredible time at this house!!! It literally felt like we were staying at a luxury resort and had everything we could have possibly needed for our getaway. Our group included young kids and adults all of whom had an amazing stay. The tennis and basketball court was in great condition and provided endless fun activities. The pool was a great size and the heater worked well when it was needed. There is a ton of space to play sports and games as well as a fire pit which was a great way...
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
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.
Don't see what you're looking for?
See all available properties in Jamesport
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Jamesport you may be interested in

Hyatt Place Long Island East End

3.0 star property
9.2 out of 10, Wonderful, (1000)
"Great property and nice staff."
The price is €127
includes taxes & fees
23 Feb - 24 Feb
Hyatt Place Long Island East End

Residence Inn by Marriott New York Long Island East End

3.0 star property
9.0 out of 10, Wonderful, (907)
"Lovely breakfast and enjoyed the hot tub!"
The price is €137
includes taxes & fees
16 Mar - 17 Mar
Residence Inn by Marriott New York Long Island East End

Sound View Greenport

4.0 star property
8.4 out of 10, Very good, (503)
"It was difficult to find the entrance in the dark, they need lights to indicate where the lobby is."
The price is €187
includes taxes & fees
5 Mar - 6 Mar
Sound View Greenport
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.

Frequently asked questions

Are there holiday rentals in Jamesport?

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

What are some of the best holiday rentals that Jamesport has to offer?

10 Bedroom Hampton House with a regulation size Pickleball: This holiday home rental outside of Jamesport is located near the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 10 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals will I find in Jamesport?

With 5 Expedia holiday rentals, you're guaranteed 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 Meschutt Beach. In the wider area, you’ll find Jason's Vineyard and Clovis Point.

What are holiday rentals like in Jamesport?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Jamesport. Holiday rentals offer extras such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for small groups.