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Search Vacation Homes in Port Chester

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Vacation Homes in Port Chester

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
9.6 out of 10, Exceptional, (20)
"Perfect place to rest. Excellent service! "
Mexico
Lucymar
$181 nightly
The price is $205
Nov 9 - Nov 10
Total with taxes and fees
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
10.0 out of 10, Exceptional, (6)
"Exceptional space for our needs. We’d absolutely book again if the opportunity arises. Maritza was communicative and everything was easily accessible"
United States
Joanne
$291 nightly
The price is $329
Nov 7 - Nov 8
Total with taxes and fees
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Captain's Cottage - Cold Spring Harbor Water Views
10.0 out of 10, Exceptional, (70)
"Great home to stay. Beautiful area to explore!"
United States
Randy W.
$405 nightly
The price is $463
Nov 10 - Nov 11
Total with taxes and fees
Captain's Cottage - Cold Spring Harbor Water Views
Private room, 5 min walk to restaurant, 40 min to NYC. 5 min drive to MetroNorth
2.0 star property
$120 nightly
The price is $137
Nov 7 - Nov 8
Total with taxes and fees
Private room, 5 min walk to restaurant, 40 min to NYC. 5 min drive to MetroNorth
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
10.0 out of 10, Exceptional, (5)
"Ahead of my arrival the communication was timely and very detailed. The space was super clean, modern and open. Perfect studio for anyone traveling either alone, a couple or even a family with a baby - plenty of room for all the gear! Everything on ground level, close to town and convenient to the highway. I will definitely be back!!!"
United States
Karen E.
$343 nightly
The price is $392
Nov 9 - Nov 10
Total with taxes and fees
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
2.0 star property
10.0 out of 10, Exceptional, (7)
"We had a very nice family weekend. There was plenty of room, the furniture and beds were comfortable, and the kitchen had everything we needed. Great communication with the owner"
United States
Helen C.
$490 nightly
The price is $555
Nov 9 - Nov 10
Total with taxes and fees
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...
9.2 out of 10, Wonderful, (5)
"It’s nice to have a place for our family of 5 that actually fits us all. Plenty of space and very clean. Thanks "
United States
Katy G.
$487 nightly
The price is $525
Nov 9 - Nov 10
Total with taxes and fees
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...
45 Minutes from NYC, Entire House near Stamford Downtown,
10.0 out of 10, Exceptional, (19)
"Very nice property. Owner was very nice and quickly answered any questions we had. Well stocked pantry and fridge!! We enjoyed our stay and property was very convenient and comfortable. "
United States
Lisa B.
$401 nightly
The price is $454
Nov 10 - Nov 11
Total with taxes and fees
45 Minutes from NYC, Entire House near Stamford Downtown,
Stylish Beach Home near Stamford Downtown/Beach
10.0 out of 10, Exceptional, (23)
"We had an absolutely amazing time during our stay. The house was beautiful, and Elena was super quick & helpful with answering any questions we had. Both the check in and check out processes were easy and smooth. We had a great time and would highly recommend staying here!"
United States
Matthew O.
$801 nightly
The price is $851
Nov 9 - Nov 10
Total with taxes and fees
Stylish Beach Home near Stamford Downtown/Beach
Foliage at Westchester Manor - Near Sleepy Hollow
2.0 star property
$926 nightly
The price is $1,031
Nov 12 - Nov 13
Total with taxes and fees
Foliage at Westchester Manor - Near Sleepy Hollow
6 BR, 4 BA Mansion Close to the City
10.0 out of 10, Exceptional, (1)
"Awesome space, perfect for our fall getaway, close to NYC or small town shopping"
United States
Jennifer L.
$680 nightly
The price is $801
Nov 10 - Nov 11
Total with taxes and fees
6 BR, 4 BA Mansion Close to the City
Spacious 3 Bd Home Pet Friendly, Parking and Laundry
9.4 out of 10, Exceptional, (3)
"the home was nice clean if in the area I would stay here again"
United States
james w.
$487 nightly
The price is $525
Nov 11 - Nov 12
Total with taxes and fees
Spacious 3 Bd Home Pet Friendly, Parking and Laundry
Waterfront Retreat Center for Health & Wellness
9.6 out of 10, Exceptional, (64)
"This historic home was better than I could have hoped for. My extended family thoroughly enjoyed this beautiful home. Every room was a joy to be in. We would go back in a heart beat."
United States
Kathy L.
$2,048 nightly
The price is $2,342
Nov 11 - Nov 12
Total with taxes and fees
Waterfront Retreat Center for Health & Wellness
Cheerful Home in Yonkers NY
7.6 out of 10, Good, (4)
"Nice neighborhood,open concept.Hreat space for my entire family.Kitchen big and spacious. Beds are huge. Definitely will stay here again."
United States
Tanya J.
$487 nightly
The price is $573
Nov 30 - Dec 1
Total with taxes and fees
Cheerful Home in Yonkers NY
Comfortable 1 family home in Tuckahoe that's near train
$629 nightly
The price is $701
Nov 7 - Nov 8
Total with taxes and fees
Comfortable 1 family home in Tuckahoe that's near train
Charming 3-bedroom modern family retreat!
9.6 out of 10, Exceptional, (8)
"Great location & thoughtful amenities."
United States
Joshua
$536 nightly
The price is $612
Dec 3 - Dec 4
Total with taxes and fees
Charming 3-bedroom modern family retreat!
Luxury NY Home with Free Parking
4.0 star property
$558 nightly
The price is $638
Nov 7 - Nov 8
Total with taxes and fees
Luxury NY Home with Free Parking
3BR Prime Luxury near NYC w Arcade Room
2.0 star property
8.0 out of 10, Very Good, (1)
"We thought we rented the entire property, but was half of it. expect a lot of stairs. No bath tubs but two showers. some door knobs and locks need maintenance, but overall nice clean rooms."
United States
Anonymous traveler
$687 nightly
The price is $769
Nov 7 - Nov 8
Total with taxes and fees
3BR Prime Luxury near NYC w Arcade Room
Cozy Waterfront Stay: 30 Min train to NYC, USOpen, Golf, Citifield, MSG & Mets.
10.0 out of 10, Exceptional, (12)
"Everything went so smooth, house well stocked, heater worked perfectly, very clean, safe neighborhood, specious bedrooms and living space, give it the highest recommendation"
United States
Sandi N.
$1,163 nightly
The price is $1,298
Dec 2 - Dec 3
Total with taxes and fees
Cozy Waterfront Stay: 30 Min train to NYC, USOpen, Golf, Citifield, MSG & Mets.
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

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Port Chester Vacation Homes information

Number of reviews
230
Accommodation
369 Vacation Homes
Lowest Price
$205
Highest Price
$2,342

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