South Jamesport Vacation Rentals

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Our top choices for South Jamesport vacation rentals

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (249 reviews)
"Great stay - beautiful place"
United States
Rebecca
The price is CA $199
CA $288 total
includes taxes & fees
Apr 29 - Apr 30
Cliffside Resort Condominiums

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is CA $257
CA $294 total
includes taxes & fees
Apr 26 - Apr 27
North Fork Cottages & RV Resort

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Calverton
8.6 out of 10, Excellent, (8 reviews)
"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 CA $621
CA $1,171 total
includes taxes & fees
Apr 14 - Apr 15
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Rocky Point
10.0 out of 10, Exceptional, (25 reviews)
"It was perfect for what we needed and the hostess made it very simple and easy to check in and check out and answer any questions thank you"
United States
ken g.
The price is CA $370
CA $750 total
includes taxes & fees
Apr 14 - Apr 15
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Newly Renovated Sag Harbor Beach House with Pool

Newly Renovated Sag Harbor Beach House with Pool
Sag Harbor
The price is CA $367
CA $931 total
includes taxes & fees
Apr 12 - Apr 13
Newly Renovated Sag Harbor Beach House with Pool

Tranquil Stay

Tranquil Stay
Shirley
8.0 out of 10, Very good, (10 reviews)
"The property was spacious, clean and well kept. We only stayed one night but enjoyed our time. We definitely would stay again. "
United States
Ellen C.
The price is CA $484
CA $871 total
includes taxes & fees
Apr 14 - Apr 15
Tranquil Stay

Cozy Hamptons Escape 3BR Minutes From Beach!

Cozy Hamptons Escape 3BR Minutes From Beach!
Hampton Bays
9.2 out of 10, Wonderful, (5 reviews)
"Great place. It's exactly like the listing! Would stay again!"
United States
Taylor H.
The price is CA $967
CA $1,263 total
includes taxes & fees
Apr 15 - Apr 16
Cozy Hamptons Escape 3BR Minutes From Beach!

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
Mastic
10.0 out of 10, Exceptional, (28 reviews)
"Lovely time with so many fun games and activities on the property, highly recommend!"
United States
Logan S.
The price is CA $415
CA $1,263 total
includes taxes & fees
Apr 14 - Apr 15
Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.

Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (53 reviews)
"This place is a perfect oasis in an already special environment. The host was wonderful and thoughtful. The cottage was magical and had everything to offer that one could want. "
United States
Adam M.
The price is CA $995
CA $1,826 total
includes taxes & fees
Apr 14 - Apr 15
Work and Play Special! Extended Stay Discount

Modern Vacation home. Close to The Hamptons

Modern Vacation home. Close to The Hamptons
Shirley
10.0 out of 10, Exceptional, (4 reviews)
"5/5 I enjoyed my stay , very clean and spacious. "
United States
Quywana F.
The price is CA $524
CA $943 total
includes taxes & fees
Apr 29 - Apr 30
Modern Vacation home. Close to The Hamptons

South Shore Studio in Mastic

South Shore Studio in Mastic
Mastic
10.0 out of 10, Exceptional, (3 reviews)
"Great stay! Super comfy and clean😊"
United States
ERIN
The price is CA $187
CA $313 total
includes taxes & fees
Apr 14 - Apr 15
South Shore Studio in Mastic

Black Swan Beachfront Home with Jacuzzi year round

Black Swan Beachfront Home with Jacuzzi year round
Hampton Bays
9.8 out of 10, Exceptional, (16 reviews)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is CA $289
CA $1,324 total
includes taxes & fees
Apr 12 - Apr 13
Black Swan Beachfront Home with Jacuzzi year round

Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Contemporary Southampton Village Home Walking Distance to Town, Pool,...
Southampton
10.0 out of 10, Exceptional, (15 reviews)
"We loved our stay here it was a lovely, warm and beautifully appointed home with a great pool and walkable to town. We hope to be able to return here again soon!"
United States
Deborah V.
The price is CA $1,748
CA $2,406 total
includes taxes & fees
Apr 15 - Apr 16
Contemporary Southampton Village Home Walking Distance to Town, Pool,...

Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition
Wainscott
The price is CA $2,064
CA $2,674 total
includes taxes & fees
Apr 15 - Apr 16
Cozy 5 Bedroom With Wi-fi And Air Condition

Seabreeze #4: Charming Cottage Footsteps to Beach

Seabreeze #4: Charming Cottage Footsteps to Beach
Hampton Bays
8.8 out of 10, Excellent, (3 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is CA $289
CA $856 total
includes taxes & fees
May 6 - May 7
Seabreeze #4: Charming Cottage Footsteps to Beach

Cozy beach hose minutes from Hamptons

Cozy beach hose minutes from Hamptons
Calverton
10.0 out of 10, Exceptional, (1 review)
"Beautiful home and location. Owner was very helpful. Would love to rent again!"
United States
Evelyn D.
The price is CA $579
CA $1,109 total
includes taxes & fees
Apr 15 - Apr 16
Cozy beach hose minutes from Hamptons

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
The price is CA $964
CA $1,778 total
includes taxes & fees
Apr 14 - Apr 15
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (4 reviews)
"perfect for families"
United States
Okito H.
The price is CA $1,244
CA $2,327 total
includes taxes & fees
Apr 15 - Apr 16
Minutes from the beach, brand new 4 bedroom

Sag Harbor Water View w Dock 1.5ml from town

Sag Harbor Water View w Dock 1.5ml from town
Bay Point
The price is CA $2,487
CA $3,937 total
includes taxes & fees
Apr 15 - Apr 16
Sag Harbor Water View w Dock 1.5ml from town

New Construction Greenport Pool House - 3 Blocks from Town

New Construction Greenport Pool House - 3 Blocks from Town
Greenport
10.0 out of 10, Exceptional, (3 reviews)
"This was a great house for a large group! It was clean, and the backyard was perfect for our group to enjoy. The host was quick to respond to any questions we had. "
United States
Alexis P.
New Construction Greenport Pool House - 3 Blocks from Town
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with South Jamesport. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!: This vacation home rental near South Jamesport is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 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 are there in South Jamesport?

Choose from 12 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.