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

Port Chester Vacation Rentals

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Our top choices for Port Chester vacation rentals

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 CA $313
CA $596 total
includes taxes & fees
Jun 29 - Jun 30
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Welcoming 1 bedroom apartment in beautiful harbor village.

Welcoming 1 bedroom apartment in beautiful harbor village.
Northport
The price is CA $270
CA $443 total
includes taxes & fees
Jul 1 - Jul 2
Welcoming 1 bedroom apartment in beautiful harbor village.

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 CA $263
CA $530 total
includes taxes & fees
Jul 20 - Jul 21
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

Luxe Provincial Style Studio w/ Patio & Parking

Luxe Provincial Style Studio w/ Patio & Parking
Huntington Station
10.0 out of 10, Exceptional, (3 reviews)
The price is CA $278
CA $548 total
includes taxes & fees
Jul 13 - Jul 14
Luxe Provincial Style Studio w/ Patio & Parking

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 CA $292
CA $564 total
includes taxes & fees
Jul 8 - Jul 9
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

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 CA $683
CA $994 total
includes taxes & fees
Jul 7 - Jul 8
Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village

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.
The price is CA $1,032
CA $1,794 total
includes taxes & fees
Jul 7 - Jul 8
Spacious Family Home

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 CA $641
CA $1,196 total
includes taxes & fees
Jul 13 - Jul 14
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

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)
"A true port in the storm"
United States
Trey S.
The price is CA $534
CA $994 total
includes taxes & fees
Jul 7 - Jul 8
Captain's Cottage - Cold Spring Harbor Water Views

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 CA $442
CA $508 total
includes taxes & fees
Jul 6 - Jul 7
Guesthouse at Norwalk Inn

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.
The price is CA $425
CA $547 total
includes taxes & fees
Jul 1 - Jul 2
King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

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 CA $132
CA $226 total
includes taxes & fees
Jun 29 - Jun 30
Cozy 1-bedroom apartment in Hicksville with WiFi, AC

Modern Masters Bedroom with Cozy Vibes

Modern Masters Bedroom with Cozy Vibes
Hicksville
The price is CA $278
CA $426 total
includes taxes & fees
Jul 6 - Jul 7
Modern Masters Bedroom with Cozy Vibes

2-bedroom apartment No cleaning Fee

2-bedroom apartment No cleaning Fee
West Norwalk
The price is CA $320
CA $412 total
includes taxes & fees
Jul 1 - Jul 2
2-bedroom apartment No cleaning Fee

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 CA $497
CA $967 total
includes taxes & fees
Jul 20 - Jul 21
Designer Treehouse with Spa Bath

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.
The price is CA $1,559
CA $2,705 total
includes taxes & fees
Jun 29 - Jun 30
Newly Stunningly Updated 4-bedroom house in lovely Hicksville with WiFi, AC.

Spacious 4-bedroom house in charming Hicksville with AC

Spacious 4-bedroom house in charming Hicksville with AC
Hicksville
The price is CA $1,290
CA $2,369 total
includes taxes & fees
Jul 26 - Jul 27
Spacious 4-bedroom house in charming Hicksville with AC

Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
The price is CA $629
CA $1,200 total
includes taxes & fees
Jun 28 - Jun 29
Spacious Retreat with Game Room and Fire Pit

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 CA $799
CA $1,515 total
includes taxes & fees
Jul 22 - Jul 23
Waterview House Walking Distance from Cove Beach

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.
The price is CA $776
CA $1,487 total
includes taxes & fees
Jun 26 - Jun 27
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

Find out more about Port Chester

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Port Chester. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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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.