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.

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Top guest favourite
A modern living space features a stylish kitchen with white cabinetry and stainless steel appliances. An inviting seating area includes a light-colored sofa and a round coffee table. Natural light streams in, accentuating the neutral color palette and decorative accents, including a floral artwork.
Home in Byram
4.92 out of 5 average rating, 24 reviews

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.

Apartment in Greenwich
4.74 out of 5 average rating, 390 reviews

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.

Top guest favourite
A spacious living area features a large green sectional sofa and a coffee table with decorative items. The open-concept design connects to a modern kitchen, visible in the background. Bright natural light fills the room through large windows, highlighting the contemporary artwork on the walls.
Apartment in White Plains
4.95 out of 5 average rating, 22 reviews

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

Guest favourite
A private deck is displayed with wooden planks, featuring a sun lounger and a small table with two chairs. A large umbrella provides shade, while trees can be seen in the background, enhancing the outdoor experience.
Cabin in Bell Haven
4.9 out of 5 average rating, 145 reviews

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.

Top guest favourite
Guest suite in Norwalk
5 out of 5 average rating, 50 reviews

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!

A modern kitchen island with a white countertop is centrally located, complemented by a floral arrangement in a vase. A cozy seating area with a patterned couch and a flat-screen TV is visible in the background, providing a welcoming environment. Light enhances the open layout.
Home in Rye Brook
4.71 out of 5 average rating, 48 reviews

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.

Top guest favourite
A well-appointed kitchen features wooden cabinetry and modern appliances. A round dining table is set for two, complemented by a vibrant plant centerpiece. The space is illuminated with soft lighting, enhancing the inviting atmosphere while maintaining ample counter space.
Apartment in Harrison
4.96 out of 5 average rating, 310 reviews

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.

Guest favourite
A bright sleeping area features a spacious bed with light bedding, positioned beneath a vaulted ceiling. Floor-to-ceiling windows provide views of the woods, while a small desk and chair are set against one wall for workspace. A television is mounted for entertainment.
Guesthouse in Greenwich
4.95 out of 5 average rating, 105 reviews

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.

Superhost
A sleeping area features a spacious bed with light-colored bedding, accompanied by neatly folded towels. A wall adorned with greenery and string lights adds a cozy ambiance. A television is mounted nearby, with a framed picture featuring a car on the wall.
Apartment in Port Chester
5 out of 5 average rating, 4 reviews

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!

Guest favourite
A cozy living room features a large sectional sofa adorned with decorative pillows. A glass coffee table sits on a soft area rug, while a flat-screen TV is mounted on the wall. Two windows allow natural light to fill the space, enhancing its inviting atmosphere.
Apartment in Port Chester
4.97 out of 5 average rating, 93 reviews

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.

Top guest favourite
Home in West Side
4.99 out of 5 average rating, 181 reviews

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.

Guest favourite
Home in Harbor Point
4.8 out of 5 average rating, 140 reviews

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

When is the best time to visit Port Chester?

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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
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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!