We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in Port Jefferson, NY and nearby

Payment Protection
Use a credit card to book with our Peace of Mind Protection.Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
All 28 Rentals in the Port Jefferson Area
loading...
From
$350
Per Night
1 / 24
Payment Protection
Port Jefferson
5 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Inquiry
From
$195
Per Night
1 / 8
Port Jefferson
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (13) Make Inquiry

The following rentals are within 10 miles of Port Jefferson, New York.

From
$91
Per Night
1 / 23
Payment Protection
Port Jefferson Station
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Inquiry
From
$250
Per Night
1 / 24
Payment Protection
Rocky Point
3 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Internet Access
  • Private Beach
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Quaint 3 bedroom, 1 bath home, with beautiful views of the long island sound from the kitchen, dining area, bedroom, and back yard. Central air conditioning, cable, internet, phone. electric stove, fireplace, lovely enclosed front porch, large backyard, big gas barbeque grill. 3 minute walk to... View all property information
Make Inquiry
5 of 5 stars Reviewed July 30, 2014
First off the house was very clean, very cozy and the view was amazing. When I showed up and my friends showed up we were all amazed of how nice the place was. Everything we...
5 of 5 stars Reviewed July 15, 2014
Our first time on eastern Long Island - the trip out from the hectic pace of NYC slowly turns from urban to beautiful parkland, finally ending at quaint Rocky Point LI. The home...
See all reviews
From
$250
Per Night
1 / 7
Payment Protection
Southold
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Fireplace
  • Garden or Yard
  • Internet Access
  • Private Beach
  • Private Fishing...
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • Wheelchair access
  • Elder access
  • ?
About this property
This ranch house is beautifully located on a freshwater lake in the heart of Long Island's wine country, just minutes from the beach. Enjoy abundant bird life in a garden setting. The lake is perfect for swimming, fishing, kayaking or canoeing. Swimming in Long Island Sound is just six blocks away... View all property information
Make Inquiry
From
$300
Per Night
1 / 15
Payment Protection
Southold
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
3 bedrooms, 2 full bathrooms, sleeps 6 Pristine, year round, vacation getaway, within short walk to two white, sandy, Sound beaches. Nestled in the North Fork wine country, this home away from home is everything you need to make your stay memorable. A very comfortable, clean, smoke free home.... View all property information
Make Inquiry
From
$295
Per Night
1 / 17
Payment Protection
Southold
3 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (11) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Garden or Yard
  • Grill
  • Internet Access
  • Private Beach
  • Private Fishing...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Bright private sunny renovated three bedroom waterfront house on private street adjoining Arshamamague Pond. The sun is out and all we need is you to complete the picture. Join us at our three bedroom one bath renovated house. Private waterfront. Central AC. Beautiful hardwood floors and... View all property information
Make Inquiry
5 of 5 stars Reviewed August 28, 2014
We had such a wonderful time in Maureen and Alan's cottage. First and foremost, it's on Arshamomaque Pond, which looks like a lake but is actually an inlet of Peconic Bay. It's...
5 of 5 stars Reviewed July 13, 2014
My family was very pleased with these accommodations. We were all very comfortable. The place was very clean and well equipped for our 5 day stay. The location is absolutely...
See all reviews
From
$225
Per Night
1 / 12
Payment Protection
Southold
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Make Inquiry
Amenities & Details
  • Garden or Yard
  • Grill
  • Internet Access
  • Private Beach
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • Wheelchair access
  • Elder access
  • x
About this property
This cottage is beautifully located on Great Pond on one-half acre in the heart of Long Island's North Fork. The lakefront is secluded from neighboring properties and is superb for swimming, boating and fishing. Swimming in Long Island Sound is just six blocks away at Kenney's Beach. Dine on the... View all property information
Make Inquiry
From
$257
Per Night
1 / 17
Payment Protection
Sound Beach
5 Bedrooms, 2 Bathrooms, Sleeps 10
Details Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Located directly on the Long Island Sound, this home offers breathtaking panoramic water views. 5 bedrooms: 3 twins, 2 queens, and a king (in addition to a pull out queen sleeper sofa in the living room) 2 full bathrooms This home is ideal for unwinding and relaxing, the perfect place to find... View all property information
Make Inquiry
From
$300
Per Night
1 / 40
Payment Protection
Southold
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Garden or Yard
  • Grill
  • Internet Access
  • Private Beach
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
Come experience a Northfork summer, golfing, biking, beaching, Estate sale hunting, in the Heart of Wine Country, Long Island. Centrally Located in the Town of Southold, South of the main road, 3 houses from the water in the elite Founders Landing section of North Fork, The cottage is minutes'... View all property information
Make Inquiry
Get the List
From
$175
Per Night
1 / 21
Payment Protection
Southold
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Come listen to the bands while tasting the local wines (See local vineyards and events). Walk to Southold Village or Beautiful Bay Beaches or just relax on your own patio while overlooking green lawns and mature trees. On the sought after 'Bayside' of the North Fork In the heart of the North... View all property information
Make Inquiry
5 of 5 stars Reviewed June 3, 2014
I rented both units in this cottage a few years back and was pleased to see that the property was lovely as ever. I rented both cottages again this time for a girl’s getaway...
See all reviews
From
$2,400
Per Week
1 / 12
Payment Protection
Southold
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Garden or Yard
  • Grill
  • Internet Access
  • Private Beach
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
**New for 2013 Summer: Central Air, Paver Stone Patio Charming, bright, airy, two-bedroom home sits on cozy lot at the heart of the beautiful North Fork, just a minute walk to Southold's most sought after private community beach (Founders Beach). Our beautiful beach features a playground,... View all property information
Make Inquiry
From
$150
Per Night
1 / 19
Payment Protection
Southold
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Step back in time as you enter a Historic Home in the heart of Southold....the charm of the historic home is clear as you enter the front door of your unit into the inviting hallway and stairs to the entire upstairs of the home. Just part of the charm is the refinished original 1830 floors, lower... View all property information
Make Inquiry
From
$250
Per Night
1 / 18
Payment Protection
Southold
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Internet Access
  • Safe
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Representing the owner's suite is the Unit One apartment in the Historic White Blossom House. Newly renovated, floors, kitchen and bath completely updated. Kitchen updated with period country deep sink and fixtures. You will be very comfortable in this large apartment with living room, family... View all property information
Make Inquiry
From
$172
Per Night
1 / 19
Southold
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (8) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Garden or Yard
  • Grill
  • Internet Access
  • Private Beach
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
This charming farmhouse is just what you’ve been looking for: A beautiful, newly renovated 1890's house with all the modern conveniences, perfectly located a few short blocks to Founders Landing Beach Park, Town Beach and Southold Village. About the House The house is a very bright and airy, and... View all property information
Make Inquiry
5 of 5 stars Reviewed August 18, 2013
This is a beautiful, well maintained house· Decorated and furnished to a very high standard. Fantastically situated for the beach in the lovely town of Southold. We used for our...
See all reviews
From
$500
Per Night
1 / 13
Kings Park
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (3) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This house overlooks the Nissequoge River near where it enters Long Island Sound. There is a nice yard, big trees and immediate access to the water. Bring your canoe or kayaks or rent them locally. The house is ideally located for day trips to all other Long Island locations including the... View all property information
Make Inquiry
5 of 5 stars Reviewed July 29, 2012
My Mom, myself, my two Aunts and best friend, met up here for our yearly summer reunion. My family grew up in Kings Park so it is always nice to go home and stay in familiar...
See all reviews
From
$225
Per Night
1 / 22
Payment Protection
Rocky Point
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (6) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Garden or Yard
  • Grill
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This breathtaking seaside cottage neighbors a 50 acre preserve with trails that lead to scenic views along the bluffs. This house was originally a boathouse that was pulled up from the beach and put onto a lot that was carved out of a huge sand dune. It has been completely renovated with an open... View all property information
Make Inquiry
4 of 5 stars Reviewed July 13, 2014
The house was great, had almost everything, everything easy to use. Enjoyed the Jacuzzi, fire pit, and kayaks. Right in the middle of the island so nothing too far away. The house...
See all reviews
From
$250
Per Night
1 / 11
Southold
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
John Andrew's Cottage is a 'turnkey' experience accommodating two adults and children including: -a cozy bedroom with its full size bed, which beckons you after a sun-filled day at the private beach (within walking distance) which overlooks Shelter Island -a complete kitchen and full bath -a... View all property information
Make Inquiry
4 of 5 stars Reviewed August 22, 2014
my daughter (5 1/2 year old) and i had a great visit here. the cottage was cute and comfortable. having the backyard was great too. the hosts were very friendly and...
5 of 5 stars Reviewed August 26, 2013
We stayed at John Andrew’s cottage for my best friend’s bachelorette getaway and loved it. Karen was extremely helpful, had great recommendations all around (The Blue Canoe!) and...
See all reviews
From
$500
Per Night
1 / 20
Southold
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Garden or Yard
  • Grill
  • Internet Access
  • Private Beach
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Easy to reach, hard to leave! Relax in this charming setting overlooking one of the most beautiful vineyards on The North Fork, complete with a stunning and private sugar sand beach on Southold Bay, one of the best beaches anywhere on the North Fork or The Hamptons, yours to enjoy throughout your... View all property information
Make Inquiry
4 of 5 stars Reviewed June 16, 2014
We found the farmhouse to be charming and spacious for our seven family members. The location was beautiful with the vineyards and private beach, and it was also very handy for...
See all reviews
From
$250
Per Night
1 / 14
Saint James
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Beautiful 4 bedroom 2 bath Long Island home nestled in the historic village of Saint James on the North Shore. This space is the main floor of a ranch house located a convenient 60 miles away from New York City but a world away in vacation experience. It is easily accessible by car or train.... View all property information
Make Inquiry
From
$250
Per Night
1 / 12
Southold
3 Bedrooms, 2 Bathrooms, Sleeps 7
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Our immaculate waterview beach house is located in a beach and boating community in Southold, New York, only a mile from the historic village of Greenport. It's the perfect place to relax and take in the North Fork's pristine beaches, award-winning wineries, antique shops, art galleries, and... View all property information
Make Inquiry
From
$499
Per Night
1 / 8
Southold
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Stunning views, master suite, deck, sunrooms, private lane and beaches Completely renovated and enlarged to double the footprint this winter with new kitchen, two and a half new bathrooms with tubs and showers and large master bedroom suite overlooking the Ashamomaque inlet in Southold, with... View all property information
Make Inquiry
From
$200
Per Night
1 / 8
Southold
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This charming summer cottage is unique in the sense that it is located in the private community of Reydon Shores, and is just walking distance to a private beach and marina. The special feature is its wrap around enclosed porch with a view of the Peconic Bay. If you enjoy the peaceful country... View all property information
Make Inquiry
From
$321
Per Night
1 / 5
Southold
4 Bedrooms, 4 Bathrooms, Sleeps 10
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This Home is located minutes from beautiful Long Island sound beaches, wineries, and historic Greenport village. Whether you enjoy the sun or antiquing everything is hereby. The house was built in 2009, having all modern conveniences but still holding the North Fork charm. The home has a central... View all property information
Make Inquiry
From
$295
Per Night
1 / 11
Southold
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Walk to our private beach just houses away, kick back with a local bottle of pinot in our beautiful sunroom, barbecue in the backyard or cook your favorites in our new kitchen and dine al fresco on the patio, dining room or eat at the counter and entertain the cook. We provide 2 comfortable... View all property information
Make Inquiry
From
$295
Per Night
1 / 10
Southold
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Newly renovated waterfront cottage with detached studio This property consists of two separate buildings, a two bedroom house and a detached studio cottage . From September through June only the studio (sleeps 2) is available for rent. In July and August both the 2 bedroom cottage and the studio... View all property information
Make Inquiry
From
$167
Per Night
1 / 16
Southold
3 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Idyllic retreat in North Fork beach and wine country. Quiet and peaceful, at the end of a private road, our charming, renovated 1830's farmhouse features lots of sunlight, a stainless steel kitchen, all wooden floors, jacuzzi bathtub, mudroom, washer/dryer, wifi, cable tv, air conditioning and... View all property information
Make Inquiry
Inquire for rates
1 / 21
Payment Protection
Southold
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Garden or Yard
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
About this property
Come listen to the bands while tasting the local wines (See local vineyards and events). Walk to Southold Village or Beautiful Bay Beaches or just relax on your own patio while overlooking green lawns and mature trees. On the sought after 'Bayside' of the North Fork In the heart of the North Fork... View all property information
Make Inquiry
5 of 5 stars Reviewed October 14, 2014
Mark & Mona's historic apartment was a delight. It was small but cozy and clean. Our only surprise was that we didn't realize the bathroom was located inside one of the bedrooms...
See all reviews
Go to map view
Book Online(15)
Use filters to find the best results!

Suitability

  • Wheelchair access (4)
  • Elder access (12)
  • Suitable for children (12)
  • Pet friendly (12)
  • Smoking allowed (2)

Amenities

  • Internet (25)
  • Other outdoor space (25)
  • Parking (23)
  • Air Conditioning (22)
  • Grill (21)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Nearby cities
Filter search results by:
Book Online(15)

Suitability

  • Wheelchair access (4)
  • Elder access (12)
  • Suitable for children (12)
  • Pet friendly (12)
  • Smoking allowed (2)

Amenities

  • Internet (25)
  • Other outdoor space (25)
  • Parking (23)
  • Air Conditioning (22)
  • Grill (21)
  • View all amenities