
Vacation rentals in Port Chester
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Top-rated vacation rentals in Port Chester
Guests agree: these stays are highly rated for location, cleanliness, and more.

Cozy&Chic 1Bd in Greenwich | Designer Stay near NY
Modern Designer One-Bedroom Retreat | Near NY & CT Experience luxury and comfort in this stylish one-bedroom apartment designed by a professional interior designer and crafted by a top-tier contractor. Featuring high-end finishes, curated décor, and abundant natural light, this serene hideaway blends modern design with convenience. Nestled in a peaceful setting yet minutes from major highways, it offers easy access to Connecticut and New York—perfect for business travelers or weekend getaways.

Flex Comfort Apts of Greenwich #1
Flex Comfort Apt #1 is 1 BR / 1 BA and sleeps 4. Apt #1 is the bottom floor ('Basement') of a 3 apt building. Private Parking & Entrance. Great mattresses, linens, big screen smart TVs, multiple desks, and clean. Well stocked kitchen to put on a family meal. Get the value of 2 x hotel rooms for the price of one that includes your own kitchen and Family Room. 1 Mile from Greenwich Train station - 45 mins to Grand Central. Easy access to 95 and everything CT & NY have to offer.

The Westchester Gem. Free Parking! No Cleaning fee
This stylish and modern apt is located in a prime White plains location. It’s right in the hearts of downtown white plains and only about 0.6 miles from White plains station, to make your commute into Manhattan a breeze. The apartment is surrounded by lots of supermarkets including Whole foods which is a stone throw away. There is plethora of restaurants, bars, cafes and shops all within walking distance. The apartment itself is super equipped with everything you would need for a great stay

Overlook Cabin in downtown Greenwich CT
Last house on a private road, parking onsite if available, conveniently located walk to train station, Greenwich Avenue in Greenwich CT to the ferry, Sherman Park for beach access. Travel to New York City in 37 minutes with the Metro-North Express train. We are at one of the highest points on the Greenwich Coastline. You can hear the sounds of life: from church bells ringing, the train to NYC and Rt 95 traffic, NO SMOKING NO parties NO events Sorry NO PETS service animals always welcomed.

Cozy 1 Bd Private Entrance In-law Suite & Hot Tub
Charming Getaway in Norwalk, CT - Discover comfort and convenience in this cozy low ceiling short-term rental located just 5 minutes from local markets, dining spots, Norwalk River Valley Trail, Norwalk Hospital and shopping centers. Perfect for single travelers, work related or weekend adventurers, this space offers a warm, inviting atmosphere with modern amenities. Enjoy easy access to local attractions and scenic spots, the perfect base for exploring coastal Connecticut!

Guest Suite w/ Private Entrance
Cozy lower-level studio with private entrance, separate from the main living space. Located just 1.2-1.3 miles from Metro-North stations (Rye & Port Chester) for easy NYC access. Sleeps 4 with a queen bed, 2 twin beds, and a pull-out couch. Full kitchen with essentials. Shared patio (owners' dog may be outside). 1 parking spot on-premises, additional parking nearby. Across from a shopping plaza with grocery, CVS, Dunkin', and restaurants. 1 mile to The Capitol Theater.

Luxury Private Apartment - Walk to Train for NYC!
Luxury Large Private One Bedroom Apartment. With private walkway and entrance. Full Kitchen with New Appliances. King size Bed with Move Projector and Screen. Large couch with Desk in Living room. Updated Bathroom with Bathtub. Walking Distance to Harrison Train Station - Harrison Metro North Train Station access to New York City or Greenwich / Stamford CT. To Grand Central Station. Walking Access to local Parks.

The Cottage in Greenwich
Brand new, light-filled private cottage guesthouse overlooking the woods in the heart of Greenwich, CT. Floor to ceiling windows, radiant heat bathroom floors, queen Casper mattress, a dedicated parking spot, Wi-Fi, TV, kitchenette with full fridge, Keurig coffee maker, microwave, toaster and induction stovetop and all utensils. Perfect for a weekend getaway or a quiet place to work.

Downtown Port Chester near train walk to shops
Cozy, cutely decorated apartment just steps from the Port Chester train and vibrant downtown. Enjoy a full kitchen, fresh linens, and free high-speed Wi-Fi. Coin-operated washer/dryer available on premises. Perfect for work or play, this comfy space is ideal for solo travelers or couples looking to relax and explore. Book your stay today and feel right at home!

Sunny & Cozy Stay by Capitol Theatre/Downtown
Within walking distance of downtown Port Chester, Capitol Theatre, Metro North, and so much more; this 2 bedroom apartment with PRIVATE ENTRANCE provides a comfortable, inviting stay for those visiting the New York City/Metropolitan area. We are centrally located near the I-287, I-95, so commuting to and from the area is easy.

STAMFORD STUDIO CLOSE TO DOWNTOWN AND SHOPPING
Welcome, to newly renovaded small studio for one guest with private entrance, bathroom, small kitchen with microwave, coffee maker and refrigerator. Off the street parking, you have your spot reserved during your stay. One mile from I-95, walk to shopping and restaurants, five minutes drive to Stamford downtown.

Small Studio. Private Entrance and bathroom
Welcome, this is a small and cozy studio for one person located in a quiet and safe area near Harbor Point with a private entrance, private bathroom, and a small kitchenette. 1 miles from downtown and a 3 minutes drive to the train station and I95.
Popular amenities for Port Chester vacation rentals
Other great vacation rentals in Port Chester

Our COZY and convenient home

Sun Room

Freshly updated room

Simon’s Sage Room

Country Cottage

Room near NYC

Cos Cob, Greenwich garden studio

North Stamford Lux - Plush, Comfortable & Quiet
When is the best time to visit Port Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $321 CAD | $329 CAD | $293 CAD | $353 CAD | $364 CAD | $396 CAD | $410 CAD | $372 CAD | $393 CAD | $360 CAD | $343 CAD | $371 CAD |
| Avg. temp | 1 °C | 2 °C | 6 °C | 12 °C | 18 °C | 23 °C | 26 °C | 25 °C | 22 °C | 15 °C | 10 °C | 4 °C |
Frequently Asked Questions
Are there family-friendly vacation rentals in Port Chester?
Port Chester has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Where should I stay in Port Chester?
Make yourself at home in Port Chester by choosing from our most frequently booked neighborhoods. We have over 60 vacation rentals in Tamarack Gardens, over 190 vacation rentals in Pemberwick, and over 140 vacation rentals in Port Chester.
Are there vacation rentals with a dedicated workspace in Port Chester?
Yes! Work meets play with ease at over 10 vacation rentals in Port Chester featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Port Chester?
Four-legged friends are welcome in Port Chester. Choose from more than 10 vacation rentals for guests traveling with pets.
Quick stats about vacation rentals in Port Chester

Total vacation rentals
Explore 20 vacation rentals in Port Chester

Nightly prices starting at
Port Chester vacation rentals start at $85 CAD per night before taxes and fees

Verified guest reviews
Over 830 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Port Chester vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Port Chester rentals

4.9 Average rating
Port Chester stays are highly rated by guests—averaging 4.9 out of 5!
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