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 SAR 826
SAR 1,563 total
includes taxes & fees
29 Jun - 30 Jun
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Property grounds

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (41 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is SAR 625
SAR 1,184 total
includes taxes & fees
6 Jul - 7 Jul
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
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 SAR 1,203
SAR 1,384 total
includes taxes & fees
8 Jul - 9 Jul
Guesthouse at Norwalk Inn
Property grounds

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.8 out of 10, Exceptional, (15 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is SAR 794
SAR 1,506 total
includes taxes & fees
25 Jun - 26 Jun
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
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 SAR 694
SAR 1,398 total
includes taxes & fees
20 Jul - 21 Jul
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
Smart TV

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
10.0 out of 10, Exceptional, (6 reviews)
"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."
United States
danyelle s.
The price is SAR 1,179
SAR 2,706 total
includes taxes & fees
25 Jun - 26 Jun
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
2 bedrooms, iron/ironing board, WiFi, bed sheets

Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC

Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC
Bronx
9.6 out of 10, Exceptional, (25 reviews)
"Nice home very clean and easy to access transit"
United States
Christina F.
The price is SAR 1,111
SAR 2,154 total
includes taxes & fees
14 Jul - 15 Jul
Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC
House (5 Bedrooms) | Interior

3 Mi to Downtown: Spacious White Plains Home

3 Mi to Downtown: Spacious White Plains Home
3.0 star property
White Plains
The price is SAR 687
SAR 2,670 total
includes taxes & fees
14 Jul - 15 Jul
3 Mi to Downtown: Spacious White Plains Home
Offices

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"loved walking the city. pizza was good."
United States
michelle b.
The price is SAR 541
SAR 1,170 total
includes taxes & fees
28 Jun - 29 Jun
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Property grounds

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Greenwich
7.6 out of 10, Good, (4 reviews)
"This was a warm and inviting space. CC even offered me breakfast. I was a single woman in for a class reunion and had be somewhere on Sat and Sunday mornings. It was lovely coming back to relax and read. The space is small perfect for a couple with a young person. The patio over looks the river. The house is on a cul-de-sac perfect for strolling around the neighborhood. Very quiet and safe. Well lit path at night to the back, private entrance. Small fridge but holds a lot. Microwave, kurgurg...
United States
Kathleen W.
The price is SAR 845
SAR 1,114 total
includes taxes & fees
25 Jun - 26 Jun
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
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 SAR 770
SAR 1,497 total
includes taxes & fees
8 Jul - 9 Jul
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Luxury House | Living area

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
8.0 out of 10, Very Good, (2 reviews)
"Room was cold. No parking lot for vehicle. Only off-street parking was available "
United States
david
The price is SAR 1,689
SAR 2,449 total
includes taxes & fees
25 Jun - 26 Jun
Spacious 3BR Luxe Escape near NYC
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 SAR 348
SAR 598 total
includes taxes & fees
28 Jun - 29 Jun
Cozy 1-bedroom apartment in Hicksville with WiFi, AC
Smart TV

Modern Luxe 1BR Apt in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford
Downtown Stamford
9.6 out of 10, Exceptional, (5 reviews)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
The price is SAR 601
SAR 1,652 total
includes taxes & fees
9 Jul - 10 Jul
Modern Luxe 1BR Apt in Downtown Stamford
Exterior

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (133 reviews)
"Great location, friendly and helpful staff. Good value for money."
United States
ian
The price is SAR 490
SAR 563 total
includes taxes & fees
5 Jul - 6 Jul
Stamford Suites
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 SAR 732
SAR 1,445 total
includes taxes & fees
14 Jul - 15 Jul
Luxe Provincial Style Studio w/ Patio & Parking
Terrace/patio

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
New Rochelle
9.8 out of 10, Exceptional, (7 reviews)
"We had such a nice and peaceful stay! Shelton’s place was super clean, quiet, comfortable, and had everything we needed. Would definitely stay here again! "
United States
Katie M.
The price is SAR 574
SAR 1,310 total
includes taxes & fees
13 Jul - 14 Jul
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
Fridge, microwave, stovetop, coffee/tea maker

The Subterranean Haven

The Subterranean Haven
North Side
8.8 out of 10, Excellent, (10 reviews)
"Great space but anlittle amall, the floor dips a few spots and the space is pretty tight, but perfect for a short term stay!"
United States
Hannah R.
The price is SAR 751
SAR 1,183 total
includes taxes & fees
28 Jun - 29 Jun
The Subterranean Haven
In-room safe, iron/ironing board, travel crib, free WiFi

2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly

2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly
Bryn Mawr
The price is SAR 1,520
SAR 2,798 total
includes taxes & fees
25 Jun - 26 Jun
2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly
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

Crowne Plaza Englewood by IHG

Crowne Plaza Englewood by IHG

10/10 Excellent
"They have just about everything you need as if your were at home"
Luis 2-night trip
Posted less than an hour ago
Crowne Plaza Englewood by IHG

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.