Photo by Shosh

Search Cottages in Port Chester

    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
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 32 Cottages in Port Chester with updated reviews, rates, and availability.

Charming 2-bedroom cottage with WiFi, AC and Parking spot Huntington
Fridge, microwave, oven, stovetop

Charming 2-bedroom cottage with WiFi, AC and Parking spot Huntington

10.0 out of 10, Exceptional, (2)
"We stayed here for a hockey tournament, very nice and cozy!"
Charming 2-bedroom cottage with WiFi, AC and Parking spot Huntington
Trendy 1 bedroom +loft apartment w/ parking
Smart TV

Trendy 1 bedroom +loft apartment w/ parking

10.0 out of 10, Exceptional, (9)
"We really enjoyed this place and location. Everything as advertised. Clean, safe area with great parking, convenient to 95 and all of Stamford, comfortable bed, W/D steps away. "
Trendy 1 bedroom +loft apartment w/ parking
Cos Cob Cottage- Full Kitchen, Pet Friendly
Miscellaneous

Cos Cob Cottage- Full Kitchen, Pet Friendly

10.0 out of 10, Exceptional, (3)
"Great Property. Driveway parking a bit of a challenge"
Cos Cob Cottage- Full Kitchen, Pet Friendly
Beach house cottage steps to private beach in the heart of Bayville
Interior

Beach house cottage steps to private beach in the heart of Bayville

10.0 out of 10, Exceptional, (9)
"Great location. Very clean modern cottage by the sea. Would love to stay again. "
Beach house cottage steps to private beach in the heart of Bayville
Beautiful Waterfront Beach Cottage Sunset Oasis 1hr NYC
Terrace/patio

Beautiful Waterfront Beach Cottage Sunset Oasis 1hr NYC

9.0 out of 10, Wonderful, (7)
"Very cute cottage on the water with a deck and beautiful views. A short walk into town to shops and restaurants. "
Beautiful Waterfront Beach Cottage Sunset Oasis 1hr NYC
Charming 2 Bedroom Cottage in Peaceful New Canaan
Property grounds

Charming 2 Bedroom Cottage in Peaceful New Canaan

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a wonderful Christmas getaway with family at the “Ice Cream Cottage”. It is much more spacious than it looks on the outside.It was clean and had everything we needed. Host was attentive to any questions we had.The fenced in yard was great for our “fur baby” to run around."
Charming 2 Bedroom Cottage in Peaceful New Canaan
South Salem Vacation Rental w/ Furnished Deck!
Miscellaneous

South Salem Vacation Rental w/ Furnished Deck!

10.0 out of 10, Exceptional, (2)
"This was the second time I stayed at this property and really do love it. It is close enough to my family in Ridgefield for me to fee like I am just around the corner, while being in a quiet, peaceful private property. The setup was perfect for myself and my mom, but could also accommodate a larger group. It isn’t a big space, but had everything that we needed. I would highly recommend this property and will definitely be looking to stay here again on another visit. Thank you!"
South Salem Vacation Rental w/ Furnished Deck!
Second floor cottage apartment located in a private community.
Miscellaneous

Second floor cottage apartment located in a private community.

9.6 out of 10, Exceptional, (15)
"What a lovely apartment hidden away on a private street. It is very clean and well-kept, and extra attention is given to making sure guests have what they need. Communication with hosts was easy and straightforward. We were very pleased with our stay. "
Second floor cottage apartment located in a private community.
Charming New York Escape Near Central Park!
Microwave, oven, stovetop, dishwasher

Charming New York Escape Near Central Park!

3.0 star property
Charming New York Escape Near Central Park!
Charming Mamaroneck Home ~ 22 Mi to Manhattan
Interior

Charming Mamaroneck Home ~ 22 Mi to Manhattan

3.0 star property
6.0 out of 10, (1)
"Great quiet neighborhood, but this is only part of the home (1st floor, basement, and part of the 2nd floor) and the people upstairs are stepping loudly late into the night. The 3rd bathroom is in the basement with no shower curtain and a shower head that must be held during your entire shower. It was the 1 room that was actually dirty and I cleaned it before we used it. Internet info was inaccurate but provided when we requested. TV instructions lacking. Plenty of room for hanging out and...
Charming Mamaroneck Home ~ 22 Mi to Manhattan
Historic Pound Ridge Cottage, 2 Beds, Fully Furnished
Smart TV, computer monitors, printers

Historic Pound Ridge Cottage, 2 Beds, Fully Furnished

9.4 out of 10, Exceptional, (3)
"I spent 2 serene weeks here and hope to return some day! With modern creature comforts in the kitchen, the rest of this home is very rustic. If you are looking for peace and quiet, and are into drawing, cooking or reading books to the sounds of trees rustling and water flowing across the street, you will be in heaven here. For summer months, note that there is only a small portable AC unit in the sunroom. There are several fans and it was manageable in early summer, but I imagine it is quite...
Historic Pound Ridge Cottage, 2 Beds, Fully Furnished
Hudson River Views + Firepit, Patio, Dog Run, Game Room Stone Manor
House (4 Bedrooms) | Interior

Hudson River Views + Firepit, Patio, Dog Run, Game Room Stone Manor

3.0 star property
Hudson River Views + Firepit, Patio, Dog Run, Game Room Stone Manor
3 Mi to Downtown: Spacious White Plains Home
Interior

3 Mi to Downtown: Spacious White Plains Home

3.0 star property
3 Mi to Downtown: Spacious White Plains Home
Charming Bergenfield Retreat: 16 Mi to Manhattan!
Dining

Charming Bergenfield Retreat: 16 Mi to Manhattan!

3.0 star property
Charming Bergenfield Retreat: 16 Mi to Manhattan!
Glen Cove Home: Walk to Boardwalk + Dining!
House (3 Bedrooms) | Interior

Glen Cove Home: Walk to Boardwalk + Dining!

3.0 star property
Glen Cove Home: Walk to Boardwalk + Dining!
2BDRM COTTAGE IN PLEASANTVILLE
Private kitchen

2BDRM COTTAGE IN PLEASANTVILLE

2BDRM COTTAGE IN PLEASANTVILLE
Rowayton beach cottage with views of Long Island Sound
Terrace/patio

Rowayton beach cottage with views of Long Island Sound

Rowayton beach cottage with views of Long Island Sound
Ossining Vacation Rental Near River, Trails & Mta!
House (5 Bedrooms) | Interior

Ossining Vacation Rental Near River, Trails & Mta!

3.0 star property
Ossining Vacation Rental Near River, Trails & Mta!
Pet-friendly Great Neck Home ~ 1 Mi to Kings Point
House (1 Bedroom) | Private kitchen | Microwave, highchair, cookware/dishes/utensils, paper towels

Pet-friendly Great Neck Home ~ 1 Mi to Kings Point

3.0 star property
Pet-friendly Great Neck Home ~ 1 Mi to Kings Point
Glen Head Home w/ Yard ~ 28 Mi to NYC
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Glen Head Home w/ Yard ~ 28 Mi to NYC

3.0 star property
Glen Head Home w/ Yard ~ 28 Mi to NYC
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.
Don't see what you're looking for?
See all available properties in Port Chester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Port Chester

Starlight Hotel
Deluxe Studio Suite | Private kitchen

Starlight Hotel

2.5 star property
8.0 out of 10, Very Good, (480)
"Everything was close by."
The price is AED 529
AED 620 total
includes taxes & fees
13 May - 14 May
Starlight Hotel
Global Luxury Suites at The Arches
Deluxe Studio Suite, 1 King Bed, Balcony | Balcony view

Global Luxury Suites at The Arches

2.5 star property
6.8 out of 10, (424)
"Quiet location "
The price is AED 500
AED 919 total
includes taxes & fees
1 May - 2 May
Global Luxury Suites at The Arches
2 bed condo NYC, Manhattan, Timesquare
Terrace/patio

2 bed condo NYC, Manhattan, Timesquare

2 bed condo NYC, Manhattan, Timesquare
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.