A suspension bridge over a calm river, surrounded by hills and autumn foliage.

Port Chester Vacation Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Port Chester vacation rentals

TV

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (31 reviews)
"Super cute with everything we needed! We had a great time during our stay and this was the perfect spot for a little getaway! Highly recommend!"
United States
Christina
The price is AED 808
AED 1,529 total
includes taxes & fees
29 Jun - 30 Jun
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Interior

Welcoming 1 bedroom apartment in beautiful harbor village.

Welcoming 1 bedroom apartment in beautiful harbor village.
Northport
The price is AED 698
AED 1,154 total
includes taxes & fees
1 Jul - 2 Jul
Welcoming 1 bedroom apartment in beautiful harbor village.
1 bedroom, iron/ironing board, free WiFi, bed sheets

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
Huntington Station
10.0 out of 10, Exceptional, (8 reviews)
"Enjoyed our recent stay!! Would definitely come back "
United States
Donna S.
The price is AED 680
AED 1,368 total
includes taxes & fees
20 Jul - 21 Jul
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
1 bedroom, WiFi

Luxe Provincial Style Studio w/ Patio & Parking

Luxe Provincial Style Studio w/ Patio & Parking
Huntington Station
10.0 out of 10, Exceptional, (3 reviews)
"This stay was perfect for what I needed. The studio was clean, roomy, and had A A/C, which was needed on the muggy hot days there. If I'm in the area again, this will be my spot. "
United States
Elizabeth
The price is AED 716
AED 1,414 total
includes taxes & fees
13 Jul - 14 Jul
Luxe Provincial Style Studio w/ Patio & Parking
Coffee/tea maker, spices

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Huntington
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful time for stay."
United States
Logan M.
The price is AED 753
AED 1,465 total
includes taxes & fees
8 Jul - 9 Jul
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Fridge, microwave, oven, stovetop

Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village

Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village
Huntington
9.2 out of 10, Wonderful, (11 reviews)
"Perfect stay ! Owners were beyond helpful and responsive. Their kindness helpedOur family during a difficult transition between buying and selling a home. "
United States
Christina C.
The price is AED 1,763
AED 2,564 total
includes taxes & fees
8 Jul - 9 Jul
Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village
Private kitchen

Spacious Family Home

Spacious Family Home
Westport
10.0 out of 10, Exceptional, (1 review)
"We had a getaway weekend for a close friend group from college. This location could not have been better! We had everything we needed. Four bedrooms and three full bathrooms and across the street, a bakery, pizza place, fantastically stocked market, and a nice restaurant! A short drive allowed us to enjoy shopping and more food choices, as well as giving our Manhattan friend easy access to the train. Really could not have been a better place for us. Communication with the host was timely,...
United States
Laura B.
Spacious Family Home
Smart TV, fireplace, books, stereo

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Historic District
10.0 out of 10, Exceptional, (12 reviews)
"This house was so lovely, clean, cozy, and well-appointed - everything we could have asked for for a girls' weekend! And so close to the town of Westport with its excellent restaurants and shops. The best!"
United States
Rebecca H.
The price is AED 1,873
AED 3,333 total
includes taxes & fees
27 Jul - 28 Jul
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Marina

Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views
Cold Spring Harbor
10.0 out of 10, Exceptional, (80 reviews)
"Location was perfect!"
United States
Linda J P.
The price is AED 1,708
AED 2,996 total
includes taxes & fees
8 Jul - 9 Jul
Captain's Cottage - Cold Spring Harbor Water Views
Standard Room, 1 King Bed, Main Building | Property entrance

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is AED 1,127
AED 1,297 total
includes taxes & fees
5 Jul - 6 Jul
Guesthouse at Norwalk Inn
Dining

King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
Historic District
10.0 out of 10, Exceptional, (1 review)
"Great "
United States
Ricky W.
King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
1 bedroom, in-room safe, desk, free WiFi

Cozy 1-bedroom apartment in Hicksville with WiFi, AC

Cozy 1-bedroom apartment in Hicksville with WiFi, AC
Hicksville
9.0 out of 10, Wonderful, (12 reviews)
"Had a great stay "
United States
Desiree
The price is AED 347
AED 592 total
includes taxes & fees
28 Jun - 29 Jun
Cozy 1-bedroom apartment in Hicksville with WiFi, AC
Interior

2-bedroom apartment No cleaning Fee

2-bedroom apartment No cleaning Fee
West Norwalk
The price is AED 826
AED 1,068 total
includes taxes & fees
29 Jun - 30 Jun
2-bedroom apartment No cleaning Fee
Interior

Designer Treehouse with Spa Bath

Designer Treehouse with Spa Bath
Wilton
10.0 out of 10, Exceptional, (1 review)
"We came to stay near our son at Sacred Heart. The neighborhood is cute, the house is a perfect size and the location was close to everything we needed."
United States
Sarah M.
The price is AED 1,293
AED 2,482 total
includes taxes & fees
20 Jul - 21 Jul
Designer Treehouse with Spa Bath
Dining

Newly Stunningly Updated 4-bedroom house in lovely Hicksville with WiFi, AC.

Newly Stunningly Updated 4-bedroom house in lovely Hicksville with WiFi, AC.
Hicksville
9.4 out of 10, Exceptional, (3 reviews)
"My family and I absolutely loved this home! It had everything we needed and plenty of room for everyone! We def recommend this home"
United States
Erin D.
Newly Stunningly Updated 4-bedroom house in lovely Hicksville with WiFi, AC.
Interior

Spacious 4-bedroom house in charming Hicksville with AC

Spacious 4-bedroom house in charming Hicksville with AC
Hicksville
10.0 out of 10, Exceptional, (1 review)
"Place was nice and clean. Nice and peaceful neighborhood. Had a great time during our family vacation."
United States
Sarwan R.
The price is AED 3,199
AED 5,904 total
includes taxes & fees
28 Jul - 29 Jul
Spacious 4-bedroom house in charming Hicksville with AC
Fridge, microwave, oven, stovetop

Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
The price is AED 1,273
AED 2,611 total
includes taxes & fees
28 Jun - 29 Jun
Spacious Retreat with Game Room and Fire Pit
Interior

Waterview House Walking Distance from Cove Beach

Waterview House Walking Distance from Cove Beach
Cove - East Side - Shippan
9.4 out of 10, Exceptional, (28 reviews)
"House was amazing, with a wonderful view. Hosts were responsive and helpful. Will need to come back in summer!"
United States
Scott H.
The price is AED 2,061
AED 3,861 total
includes taxes & fees
22 Jul - 23 Jul
Waterview House Walking Distance from Cove Beach
Fridge, microwave, oven, stovetop

Stylish Beach Home near Stamford Downtown/Beach

Stylish Beach Home near Stamford Downtown/Beach
Cove - East Side - Shippan
9.8 out of 10, Exceptional, (26 reviews)
"The house was perfect! Plenty of bedding and the kitchen was well appointed. We were there for my fathers memorial and the living room provided a great space for us to connect and talk together. "
United States
Maury A.
Stylish Beach Home near Stamford Downtown/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.
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Top Port Chester Hotel Reviews

New York LaGuardia Airport Marriott

New York LaGuardia Airport Marriott

10/10 Excellent
"Great customer service"
Margo 1-night trip
Posted less than an hour ago
New York LaGuardia Airport Marriott

Frequently asked questions

Can I find a vacation rental in Port Chester?

Yes, you can find vacation rentals in Port Chester close to Clay Art Center Gallery, or you can select a secluded option if you're looking for extra privacy while you relax. Port Chester is known for its live music and entertainment choices. Make sure you have time to check out the theaters and waterfront during your trip.

What are some of the best vacation rentals that Port Chester has to offer?

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: Visitors like this Port Chester vacation home rental. It is equipped with a garden, air-conditioning, and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals will I find in Port Chester?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Port Chester stay.

What can I see and do in Port Chester?

Enjoy the area's cultural attractions such as Capitol Theatre, or get outdoors into nature at a spot like Greenwich Point Park. While here, Clay Art Center Gallery and Capitol Theatre - Garcia’s are other places worth a visit.

What are vacation rentals like in Port Chester?

Vacation rentals are privately owned properties you can book for a couple days or more in Port Chester. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for family trips or small group gatherings.