Search South Jamesport Cottage Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Cottages in South Jamesport

Our top choices for South Jamesport cottages

Southampton cozy cottage by the beach
Beach

Southampton cozy cottage by the beach

10.0 out of 10, Exceptional, (1)
"Great stay. Would stay again. "
The price is ￥44,225
￥105,955 total
includes taxes & fees
Aug 20 - Aug 21
Southampton cozy cottage by the beach
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
Property grounds

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

9.8 out of 10, Exceptional, (92)
"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."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
Location and views! Located directly on Shinnecock Bay!
Smart TV

Location and views! Located directly on Shinnecock Bay!

9.0 out of 10, Wonderful, (28)
"Cute beach bungalow vibe. The outdoor space, grill, and firepit made this property worthwhile! Lori's a wonderful, accomodating host."
Location and views! Located directly on Shinnecock Bay!
Fairy Tale Guest Cottage in Magic Garden by Pool
Exterior

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (71)
"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!"
Fairy Tale Guest Cottage in Magic Garden by Pool
East End cottage on water! Outdoor tub&shower! Minutes from Hamptons & wineries.
Property grounds

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

10.0 out of 10, Exceptional, (93)
"Great indoor and outdoor spaces to hang out. Took SUP on the water - so nice and calm. "
The price is ￥62,862
￥114,406 total
includes taxes & fees
Sep 16 - Sep 17
East End cottage on water! Outdoor tub&shower! Minutes from Hamptons & wineries.
Baiting Hollow Cozy Cottage w/Walk-to beach, Wineries, farmstands. horsefarms!
Beach nearby, sun loungers

Baiting Hollow Cozy Cottage w/Walk-to beach, Wineries, farmstands. horsefarms!

9.6 out of 10, Exceptional, (9)
"Great location near good dining options (Cooperage, Desmond's), vineyards, walk to beach. Comfortable bed. It's a cabin in the woods so damp and musty smell, like a cabin in the woods."
Baiting Hollow Cozy Cottage w/Walk-to beach, Wineries, farmstands. horsefarms!
Lovely North Fork Beach Cottage (2 BR/2 bath)!
Terrace/patio

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

10.0 out of 10, Exceptional, (115)
"Lovely cottage on the Peconic Bay. We enjoyed our stay; found more than everything we needed. "
Lovely North Fork Beach Cottage (2 BR/2 bath)!
Lovely Cottage in the Heart of Long Island Wine country
Exterior

Lovely Cottage in the Heart of Long Island Wine country

9.8 out of 10, Exceptional, (26)
"Our family stayed at this quaint cottage in the North Fork. The cottage has a nice kitchen, gas fireplace, and well appointed bedrooms. I would love to visit in summer, it must be wonderful!"
Lovely Cottage in the Heart of Long Island Wine country
CHARMING WATERFRONT ENGLISH COTTAGE WITH PRIVATE BAY BEACH IN A NATURE PRESERVE
Property grounds

CHARMING WATERFRONT ENGLISH COTTAGE WITH PRIVATE BAY BEACH IN A NATURE PRESERVE

10.0 out of 10, Exceptional, (13)
"We had a wonderful stay here while visiting for a wedding. the bedrooms were both upstairs, FYI which I wasn't aware of from the listing but we made it work. The grounds were beautiful and lots of birds to enjoy. "
CHARMING WATERFRONT ENGLISH COTTAGE WITH PRIVATE BAY BEACH IN A NATURE PRESERVE
Town walking distance-Bridgehampton Cottage
Exterior

Town walking distance-Bridgehampton Cottage

9.4 out of 10, Exceptional, (10)
"Walking distance to Bridgehampton and a short drive to sag harbor. Great for 2 couples."
Town walking distance-Bridgehampton Cottage
Hidden gem! Southampton beach cottage
Smart TV

Hidden gem! Southampton beach cottage

10.0 out of 10, Exceptional, (1)
The price is ￥44,225
￥105,955 total
includes taxes & fees
Aug 20 - Aug 21
Hidden gem! Southampton beach cottage
Hamptons Vacation Rental w/ Seasonal Pool!
Cottage (3 Bedrooms) | Interior

Hamptons Vacation Rental w/ Seasonal Pool!

3.0 star property
Hamptons Vacation Rental w/ Seasonal Pool!
Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!
Sun loungers, beach towels

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

9.6 out of 10, Exceptional, (40)
"Really enjoyed our stay here and had a wonderful time exploring the area."
Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!
Charming and Bright Cottage with Salt Water Pool
Smart TV

Charming and Bright Cottage with Salt Water Pool

10.0 out of 10, Exceptional, (8)
"What a beautiful cottage. Clean and bright. Would definitely stay again!"
Charming and Bright Cottage with Salt Water Pool
Renovated 2 BR Cottage-Perfect for North Fork Beach,Vineyard,Wedding Vacations!
Exterior

Renovated 2 BR Cottage-Perfect for North Fork Beach,Vineyard,Wedding Vacations!

10.0 out of 10, Exceptional, (12)
"What a great little get away weekend in a beautiful cottage in the middle of wine country. Great host a lovely accommodations"
Renovated 2 BR Cottage-Perfect for North Fork Beach,Vineyard,Wedding Vacations!
Amazing Rocky Point Retreat Overlooking the Sound!
House (3 Bedrooms) | Interior

Amazing Rocky Point Retreat Overlooking the Sound!

3.0 star property
Amazing Rocky Point Retreat Overlooking the Sound!
Waterfront Home w/ Large Deck & Dock on Narrow Bay
House (3 Bedrooms) | Interior

Waterfront Home w/ Large Deck & Dock on Narrow Bay

3.0 star property
Waterfront Home w/ Large Deck & Dock on Narrow Bay
Charming Rocky Point Home ~ 1 Mi to Beach!
House (3 Bedrooms) | Interior

Charming Rocky Point Home ~ 1 Mi to Beach!

3.0 star property
Charming Rocky Point Home ~ 1 Mi to Beach!
Walk to Love Lane! Immaculately renovated private cottage.
Property grounds

Walk to Love Lane! Immaculately renovated private cottage.

10.0 out of 10, Exceptional, (18)
"My wife and I stayed for the weekend for our Anniversary and this was the perfect location. Quaint and quite hideout with tons to do nearby."
Walk to Love Lane! Immaculately renovated private cottage.
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Fridge, microwave, oven, stovetop

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

10.0 out of 10, Exceptional, (27)
"The property was clean, exactly as advertised and extremely cozy and convenient. The host was super helpful and quick to respond!"
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
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
Sign in
Sign up, it's free

Top South Jamesport Hotel Reviews

Hampton's Vacation Inn

Hampton's Vacation Inn

10/10 Excellent
"Our stay at Hampton’s Vacation Inn was excellent. The cottage was awesome, the staff was amazing, and the room was clean and very accessible to everything. I would definitely stay here again and highly recommend it to others."
Athanassios 3-night trip
Posted 1 day ago
Hampton's Vacation Inn