Jamesport Vacation Rentals from CA $191: Short-Term Rentals for 2025

Q: What are some of the best vacation home rentals that Jamesport has to offer?

Hamptons Retreat : This vacation home rental outside of Jamesport offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable 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 balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

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Vacation Rentals in Jamesport

Relax in a serene outdoor space with a shaded deck, lounge chairs, and a nearby fire pit.

Stunning beachfront residential area with multi-story buildings and a central park.

"Very nice, clean and cosy place! Highly recommend!"

CA $900 total

includes taxes & fees

Jul 28 - Jul 29

Simple, functional room with a single bed and a window with curtains.

"Trvis and Alice are great host and the property was a great place to stay close to the beach and downtown Sag Harbor."

Stroll through the serene garden, surrounded by lush greenery and a tranquil water feature.

"We had a wonderful vacation at the Fairy Tale Guest Cottage. The location was awesome and we loved the accommodations, especially the fancy bathroom. Mark and Eunyoung are impeccable hosts. Would absolutely stay again!"

Enjoy cooking in this kitchen with a stainless steel range hood, oven, and refrigerator with water dispenser.

"Great property, great views and the owner was terrific in his communication and hospitality.Thank you! "

CA $949 total

includes taxes & fees

Jul 22 - Jul 23

Relax by the serene pool surrounded by tall trees and a well-maintained lawn.

"Great place! Great communication with property owner!"

CA $716 total

includes taxes & fees

Jul 15 - Jul 16

Relax in this serene outdoor space with a glass table, comfortable seating, and a view of the pool.

"Amazing house and location!! Would stay again "

Relax in a serene outdoor oasis with a pool, lounge chairs, and lush greenery.

"Michael's cottage was incredibly well-appointed. The location to Southampton, Coopers Beach and neighboring townships made this very convenient for my trip. The true star of this cottage is the upstairs deck which was perfect for relaxing and stargazing. I will certainly return next summer. "

Relax by the serene pool surrounded by lush greenery and comfortable lounge chairs.

"An absolute perfect home for a family looking to enjoy"

Enjoy meals in the well-lit kitchen with a central island and stove, plus a dining area with outdoor views.

"We had a amazing stay and plan to come back next July again"

Relax in this inviting outdoor seating area with a wicker sofa and matching ottoman, surrounded by lush greenery and a stylish glass table.

"The home is cute and cozy--located close enough to attractions and restaurants but off the beaten path."

CA $426 total

includes taxes & fees

Jul 15 - Jul 16

Relax in this stylish living room with a view of the pool, featuring a sofa, coffee table, and dining area.

"Great house, kitchen is well equipped which made dining in very easy. Loved the pool and backyard."

"The property was exactly as posted. The host was great, super helpful and responsive. The pool was awesome for the kids. It was private and a wonderful stay in Sag Harbor. The town was cute and close. We would definitely stay again ! Thanks so much!"

CA $1,697 total

includes taxes & fees

Jul 20 - Jul 21

Relax on the porch with a view of lush greenery, featuring a wicker sofa and a small table.

"We were pleased with our stay. The house was very clean. My contact with the property manager were great. Would stay again."

Relax in this serene bedroom with a large bed, chandelier, and window offering a view of lush greenery.

"We had a fantastic stay! The home was exactly as described — clean and very comfortable. The location was perfect. We loved being close to town. Communication was smooth and easy — Frank was quick to respond. We’d absolutely stay here again and recommend it to anyone visiting the area! "

CA $984 total

includes taxes & fees

Aug 5 - Aug 6

CA $1,303 total

includes taxes & fees

Jul 27 - Jul 28

Enjoy a serene beachside escape with access to the ocean.

"This is a great place to stay in Greenport. It has a private beach and is quiet and friendly. It's a 2-minute drive to town and shops, but you will want to spend your time enjoying the beautiful waterfront views."

Enjoy cooking in the fully equipped kitchen with a refrigerator and adjacent seating area.

"The room was a lot more spacious than I anticipated and everything was very clean. There was some music playing upstairs but it was quiet by nighttime. Check in and check out was very straightforward. Turning into the driveway was a bit difficult when the highway was crowded but was otherwise easy to find "

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Jamesport vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Jamesport vacation rentals we have selected for you start as low as CA $191 per night. Entering your travel dates in the search wizard 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.

Recent reviews of Jamesport properties

5/5 Excellent

"Great location in heart of Sag Harbor. With 5 minutes walk to center of town. We had a great stay for our family of 4 over the ;th of July weekend."

A verified traveller stayed at Sag Harbor Inn

Posted 11 hours ago

5/5 Excellent

"Right on the water. Private beach with chair and umbrellas.they will serve you right on the beach bye getting you food and drinks also has a outdoor swimming pool..nice staff..nothing special about the continental breakfast..bagels, fruit, small croissants, small danish and some hard boiled eggs..coffee and oj..i was pleased with my stay. King deluxe room..small table with chairs on the shared deck..could sit outside til about 2pm and the sun starts to beat on you but no biggy..was very humid out when my wife and i was there..a/ c really could not cool the room as much as we would have liked. Nothing wrong with the a/c it just because the sun beating on the hotel all day..luckily i brought a couple of small usb fans to help keep cool at night while we slept did the trick..overall i enjoy my stay and you could not ask for anything more when it comes to the scenery.. "

A verified traveller stayed at Sound View Greenport

Posted 3 days ago

5/5 Excellent

"Took a chance on a last minute two night family getaway and I am so glad we did. Check in could not have been faster and kinder, shout out to Daren you are a treasure of a human! It’s a really cute, updated motel/hotel, the grounds are beautiful and clean as are the rooms. Compared to other places like this, this was absolutely more spacious and had more amenities. Deck, and sand area were great to hangout on, we played some games and had a blast. Day one we hung around at the pool and did the generous $10 beach pass from the Bayview the 2nd day and spent a great day at the beach. You need a car here in order to go to local resturants, coffee places (although there is morning coffee in the communal lounge and a coffee maker in the room) Mini fridge and microwave was a huge help with young kids. They really make this place easy to be a guest at, are happy to give extra towels and everyone was super friendly. If anyone is complaining here I would not understand why. We will be back!"

A verified traveller stayed at Bayview Resort

Posted 5 days ago

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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?

Hamptons Retreat: This vacation home rental outside of Jamesport offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable 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 balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals will I find in Jamesport?

With 5 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 Out East Family Fun, 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.

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Jamesport Vacation Rentals

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Vacation Rentals in Jamesport

Northfork Ranch Style Cottage walking distance to beach & Wineries

Northfork Ranch Style Cottage walking distance to beach & Wineries

Cliffside Resort Condominiums

Cliffside Resort Condominiums

Canoe Place Waterfront Residences

Canoe Place Waterfront Residences

Sag Harbor Suite by the Beach

Sag Harbor Suite by the Beach

Hamptons Retreat

Hamptons Retreat

Fairy Tale Guest Cottage in Magic Garden by Pool

Fairy Tale Guest Cottage in Magic Garden by Pool

East End cottage on water! Outdoor tub&shower! Minutes from Hamptons & wineries.

East End cottage on water! Outdoor tub&shower! Minutes from Hamptons & wineries.

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Escape to Sag Harbor

Escape to Sag Harbor

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

July Flash Sale: Luxury Beach House, Heated Pool, Dune Rd beaches, pets ok

July Flash Sale: Luxury Beach House, Heated Pool, Dune Rd beaches, pets ok

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

Walk to Beach 2BR Near Dining & Shopping

Walk to Beach 2BR Near Dining & Shopping

Heated pool/5 min walk to Beach/Beautiful Sag Harbor Village /Restaurant/Museum

Heated pool/5 min walk to Beach/Beautiful Sag Harbor Village /Restaurant/Museum

Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach

Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach

Lovely North Fork Beach Cottage (2 BR/2 bath)!

Lovely North Fork Beach Cottage (2 BR/2 bath)!

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

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

Southampton cozy cottage by the beach

Southampton cozy cottage by the beach

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

Hamptons apartment getaway

Hamptons apartment getaway

Find out more about Jamesport

Find out more about Jamesport

Recent reviews of Jamesport properties

Recent reviews of Jamesport properties

Sag Harbor Inn

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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Frequently asked questions