Photo by Nina Dinoff

Search Cottages in Jamesport

    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

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Cottages in Jamesport and around

Our top choices for Jamesport cottages

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

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

9.8 out of 10, Exceptional, (93)
"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 .
East End cottage on water! Outdoor tub&shower! Minutes from Hamptons & wineries.
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (95)
"Great indoor and outdoor spaces to hang out. Took SUP on the water - so nice and calm. "
The price is €526
includes taxes & fees
3 Sept - 4 Sept
East End cottage on water! Outdoor tub&shower! Minutes from Hamptons & wineries.
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 €856
includes taxes & fees
24 Aug - 25 Aug
Southampton cozy cottage by the beach
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."
The price is €521
includes taxes & fees
22 Sept - 23 Sept
Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!
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!
Pet-friendly Home w/ Hot Tub Near the Hamptons!
House (1 Bedroom) | Interior

Pet-friendly Home w/ Hot Tub Near the Hamptons!

3.0 star property
Pet-friendly Home w/ Hot Tub Near the Hamptons!
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, (14)
"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
Fairy Tale Guest Cottage in Magic Garden by Pool
Property grounds

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (71)
"In the Hamptons working a Vintage market so I barely got to enjoy this incredibly gorgeous home, but it was perfect for just me and the host were absolutely delightful so friendly and accommodating they even let me sleep in which I haven’t had a chance to do in sometime so that was much appreciated I rested better than I have in months in this sweet cottage on a beautiful property. They made sure I was taken care of while giving me speciation enjoy some much needed quiet time. It’s a stunning...
Fairy Tale Guest Cottage in Magic Garden by Pool
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)!
Hidden gem! Southampton beach cottage
Smart TV

Hidden gem! Southampton beach cottage

10.0 out of 10, Exceptional, (1)
Hidden gem! Southampton beach cottage
Lovely Cottage in the Heart of Long Island Wine country
Sun-loungers

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
Cottage on Beach front Estate with Dockage .Walk to Village
Interior

Cottage on Beach front Estate with Dockage .Walk to Village

10.0 out of 10, Exceptional, (70)
"Myself my BF and my dog had a wonderful time."
Cottage on Beach front Estate with Dockage .Walk to Village
Charming 3-Bedroom Cottage, Steps to Sandy Beach & Restaurant in Wine Country.
Sun-loungers, beach towels

Charming 3-Bedroom Cottage, Steps to Sandy Beach & Restaurant in Wine Country.

Charming 3-Bedroom Cottage, Steps to Sandy Beach & Restaurant in Wine Country.
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!
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!
Town walking distance-Bridgehampton Cottage
Beach nearby

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
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!
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!
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!
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 Jamesport Hotel Reviews

The Pridwin Hotel

The Pridwin Hotel

10/10 Excellent
"We had such an amazing stay at the Pridwin! Their staff truly goes above and beyond to make your experience positive. Phenomenal food/ drinks great views. Couldn’t ask for a better trip! Can’t wait to go back!"
Brendan 1-night trip
Posted 17 hours ago
The Pridwin Hotel

Frequently asked questions

Are there any family-friendly cottages in Jamesport?
Yes, there certainly are! Take a look at Villa Gavin, a great base for exploring the outdoors in Jamesport. This family-friendly cottage has a 3.5-star rating and comes with amenities like WiFi and laundry facilities. Jamesport has loads of family-friendly attractions to visit that'll entertain the kids. Splish Splash Water Park and The Hamptons Beaches promise a fun-filled day for everyone.
Why book your cottage in Jamesport with Expedia?
Reserving a cottage in Jamesport is as simple as clicking on your travel dates and selecting an ideal place for a holiday in nature. From chic retreats to inexpensive properties and cottages that have perks like a pool, Expedia has something for all traveller tastes. As for unbeatable deals? We have them too!
How can I find cheap cottages in Jamesport?
Expedia is here to help you look for cheap cottages in Jamesport. To lock in a terrific stay in a few quick keystrokes, simply use our handy filter tool to refine your search by budget, star rating and amenities.