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Holiday houses in Port Chester

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Quick stats about holiday rentals in Port Chester

  • Total holiday rentals

    Explore 20 holiday rentals in Port Chester

  • Nightly prices starting at

    Port Chester holiday rentals start at $144 AUD per night before taxes and fees

  • Verified guest reviews

    Over 900 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Port Chester holiday rentals include Wi-Fi 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!

Top-rated holiday rentals in Port Chester

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A modernist house is surrounded by vibrant autumn foliage, showcasing a blend of red, orange, and green leaves. The structure features large glass windows and a roof that floats above the walls, offering scenic views of the lush forest.
Home in Rye
4.91 out of 5 average rating, 143 reviews

1956 House of the Year Award. Easy commute to NYC.

Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!

FamilyValueNearby

Guest favourite
A white anchor, inscribed with 'BYRAM SHORE BOAT CLUB,' is positioned prominently in a landscaped area. It is surrounded by greenery and colorful blooming flowers, set against a backdrop of finely textured gravel.
Home in Port Chester
4.82 out of 5 average rating, 123 reviews

Greenwich abode Close to Just about Everything

2 - Bedroom apartment in a duplex. 4 - Minutes to Greenwich Avenue Shopping 6 - Minutes to Port Chester restaurants 8 - Minutes to Rye town and restaurants. 5 - Minutes to The Capital Theater 5 - Minutes to Byram Beach 10- Minutes to Tod's Point Beach 4 - Minutes by car to Greenwich and Port Chester Metro North Station 1 - Twin Air Mattress, SERTA auto inflate, 15inch raised {UPON REQUEST } Private and cozy retreat, steps away from one of Greenwich's Top Beaches - Byram Shore Beach Club.

LocationValueAccess

Guest favourite
A spacious living room featuring a comfortable sectional sofa adorned with decorative pillows. A large area rug anchors the seating arrangement, which includes two lounge chairs. Natural light filters through multiple windows, highlighting the neutral color palette and decorative wall art.
Home in White Plains
4.91 out of 5 average rating, 171 reviews

Spacious 3b/3b Mediterranean in White Plains

Bring the whole family to this great place with lots of room for fun, relaxation or hosting! This 3bed/3bath Mediterranean is freshly renovated with stylish touches & comfy furniture. The main floor of this multi family serves as a great spot to bring the family while visiting the area. The house boasts an oversized living room, formal dining room, large chef's kitchen, and plenty of sleeping space. With heat & AC throughout the entire 2k sf unit, this house is great for anything& everything!

ValueLocationIndoor spaces

Guest favourite
Apartment in Greenwich
4.76 out of 5 average rating, 421 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.

LocationFamilyShared spaces

Guest favourite
The inviting living room displays a neutral color palette with a large area rug featuring blue and white patterns. Two comfortable sofas, a decorative coffee table, and a fireplace are visible, accompanied by natural light from the windows, creating a calm and spacious atmosphere.
Home in Port Chester
4.93 out of 5 average rating, 27 reviews

3br + game rm abt 45min drive or easy train to NYC

This cozy 3-bedroom Port Chester house (accommodates up to 11 people), offers excellent value, spacious living, and proximity to NYC and Greenwich, CT. A short 10-min walk brings you to the center, the historic Capitol Theatre, & the train to NYC. It's a quick drive to key landmarks and attractions, about 40 mins to NYC, with a train ride to Grand Central taking 45-60 mins. 11-min walk to Capitol Theatre. Perfect for those seeking a quiet, safe neighborhood close to the vibrant city centers.

LocationFamilyWi-Fi

Top Guest favourite
A cozy living room features a large flat-screen TV mounted on the wall, accompanied by a sleek entertainment unit. A comfortable couch is draped with a soft blanket, and an armchair is positioned nearby. Natural light enters through two windows, brightening the neutral decor.
Guesthouse in Mamaroneck
4.97 out of 5 average rating, 111 reviews

Spacious guest suite near water

Welcome to your perfect home away from home! Enjoy a spacious and newly renovated basement suite with windows and separate entrance in a private house, perfect for up to four guests. Ideal for couples, small families, or business travelers. This cozy retreat, combines privacy and comfort in a quiet neighborhood. Whether you’re here for a short trip or an extended stay, this apartment offers everything you need for a comfortable and relaxing experience. Book now and start planning your visit.

LocationFamilyIndoor spaces

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 Greenwich
4.9 out of 5 average rating, 165 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.

ValueFamilyBathroom

Top Guest favourite
The exterior of the guest house is framed by manicured gardens, featuring two decorative statues positioned beside a pea gravel walkway. A small patio area includes a round table with two chairs, creating a serene spot for outdoor relaxation.
Guesthouse in Waccabuc
4.99 out of 5 average rating, 140 reviews

French Estate Guest House on Private Lake

A private, European-inspired guest house set on an eight-acre gated French estate, just 60 minutes from NYC. Surrounded by manicured gardens, 18th-century statuary, and a private lake, the setting feels transportive—a French countryside retreat. Designed by architect David Easton, the space blends classic elegance with modern comfort: heated stone floors, a heated towel rack, fine linens, curated finishes, and a private entrance. Perfect for a refined weekend escape or a quiet reset.

LocationValueLayout

Top Guest favourite
A welcoming entryway is highlighted by a wooden bench and wall hooks, ideal for hanging coats. The view leads into a modern kitchen, featuring sleek cabinetry and an open layout. Soft lighting and warm wood floors create an inviting atmosphere.
Home in Greenwich
4.96 out of 5 average rating, 53 reviews

1Bd Cottage 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 @dacasabypriscilla. 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.

ValueFamilyCondition

Top Guest favourite
Apartment in Greenwich
4.96 out of 5 average rating, 114 reviews

Cozy 2 BR Greenwich Apt. with easy access to NYC

Cozy two bedroom apartment on a quiet street in Greenwich with brand new appliances. Walking distance to Metro North train station, beach, park, tennis court, pickle ball court, restaurants, shops. Just 38 minutes from NYC. Few minutes drive to downtown. Fully stocked kitchen and laundry with everything you may need. Living room with 65" Smart TV. Master BR with 45" Smart TV. The apartment is professionally cleaned & sanitized up to CDC guidelines & inspected before each stay.

LocationFamilyHospitality

Guest favourite
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 Port Chester
4.79 out of 5 average rating, 89 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.

LocationValueLayout

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
4.83 out of 5 average rating, 12 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!

LocationValueComfort

Popular amenities for Port Chester holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Port Chester

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
4.94 out of 5 average rating, 121 reviews

The Cottage in Greenwich

FamilyLocationAmenities

Guest favourite
An open living area features a comfortable gray sectional sofa beside a light area rug. The modern kitchen includes wooden cabinetry, stainless steel appliances, and a countertop with bar seating. A large TV is mounted on the wall, providing entertainment within the inviting space.
Townhouse in Port Chester
4.93 out of 5 average rating, 89 reviews

Quaint duplex + pvt yard-Walk to town/train/beach!

ValueFamilyKitchen

Home in Port Chester
5 out of 5 average rating, 3 reviews

Mid-century modern nature preserve near NYC

LocationComfortGetting around

Top Guest favourite
A modern kitchen features sleek white cabinetry and stainless steel appliances, including an oven, microwave, and refrigerator. A double laundry unit is positioned beside the cooking area. Light reflects off the geometric backsplash, and natural light enters through a nearby window.
Home in Mamaroneck
5 out of 5 average rating, 70 reviews

Newly renovated modern private guest wing

ValueLocationAccuracy

Guest favourite
Apartment in Rye
5 out of 5 average rating, 6 reviews

Rye City Oasis | Cozy Downtown Rye Apartment

LocationAir conditioningComfort

Guest favourite
An open-concept living area showcases a modern sectional sofa and two accent chairs, arranged around a coffee table. The kitchen features a large island with barstools, and ample natural light floods in through multiple windows, highlighting the spacious layout and clean finishes.
Apartment in Greenwich
5 out of 5 average rating, 13 reviews

Hot New 2 Bedroom walk to train

FamilyLocationNearby

Superhost
Barn in Mount Kisco
New place to stay

Idyllic Retreat

FamilyLocationNearby

Top Guest favourite
Home in Greenwich
4.97 out of 5 average rating, 68 reviews

Cozy Riverfront Cottage•Pool•Hot Tub•35 min NYC

LocationFamilyView

When is the best time to visit Port Chester?

MonthJanFebMarAprMayJuneJulyAugSeptOctNovDec
Avg. price$360 AUD$373 AUD$431 AUD$360 AUD$372 AUD$405 AUD$419 AUD$380 AUD$402 AUD$418 AUD$423 AUD$428 AUD
Avg. temp1°C2°C6°C12°C18°C23°C26°C25°C22°C15°C10°C4°C

Frequently Asked Questions

  • What are the best places to stay in Port Chester?

    Many visitors prefer vacation rentals in residential neighborhoods or around the downtown area for easy access to shops, cafes, and live music. The waterfront district also has accommodation options for those seeking scenic views.

  • What are the best things to do in Port Chester with kids?

    Families often explore playgrounds at neighborhood parks, enjoy interactive exhibits at nearby museums, or attend community events in town centers. The waterfront and local theaters sometimes host family-friendly performances or seasonal activities.

  • What are some of the best things to do in Port Chester?

    Explore live music at downtown venues, discover art galleries, and sample dishes at multicultural restaurants in Port Chester. Parks and waterfront areas provide space for a walk or relaxed afternoon outdoors.

  • How is the weather in Port Chester?

    Port Chester has cold winters averaging 29–45°F (-2–7°C), with snowy days and moderate rainfall, while summers bring warm afternoons near 72–86°F (22–30°C), along with occasional rain showers. Spring and fall are milder with moderate rainfall and comfortable temperatures.

  • When is the best time to visit Port Chester?

    Many visitors explore Port Chester from late spring through early fall, when daytime temperatures range from about 56–86°F (13–30°C) and outdoor events are frequently suggested. Expect rainfall throughout the year, so packing layers and rain gear is helpful during any season.

  • What are the best places to visit in Port Chester?

    Port Chester has popular live music venues, art galleries, and locally rooted restaurants in the downtown area. Riverside parks and cultural centers invite visitors to experience performances, outdoor spaces, and neighborhood history.

  • What are some hiking trails in Port Chester?

    Port Chester has small park trails and green spaces that are great for leisurely walks. For longer or wooded hikes, plan to explore nearby nature areas just outside town with more expansive trails.

  • What are some family activities we can do in Port Chester?

    Explore playgrounds, neighborhood parks, and seasonal festivals for family fun in Port Chester. Indoor activity centers, local performances, and interactive museum exhibits nearby are often recommended for children.

  • What are some of the best day trip ideas from Port Chester?

    Many visitors enjoy exploring coastal towns, historic estates, or hiking in nearby nature preserves around Westchester County and the Hudson River Valley. Art museums, botanical gardens, and vibrant city neighborhoods are also popular day trip choices.

  • Are there any pet friendly accommodations available in Port Chester?

    Port Chester has pet-friendly vacation rentals in residential neighborhoods and around downtown. Parks and walking paths make it easy to get outside with your dog during your stay.

  • What are some local tips for visiting Port Chester?

    Locals suggest exploring both the main street and side neighborhoods for distinctive shops and food spots. Checking community calendars can help you discover live music, festivals, and markets happening during your visit.

  • What is Port Chester known for?

    Port Chester is known for its lively arts scene, historic architecture, and diverse dining options reflecting the community’s multicultural roots. Music venues and festivals are frequently suggested experiences here.

  • What are the best hidden gems to explore in Port Chester?

    Port Chester has locally owned bakeries, artisan shops, and small galleries that reflect the community’s creative energy. Outdoor murals and neighborhood markets are often suggested by residents seeking off-the-beaten-path experiences.

  • What are the best foods to try in Port Chester?

    Port Chester’s food scene celebrates Latin American flavors, local seafood, and traditional baked goods. Many visitors explore lively taquerias, Italian eateries, and bakeries serving pastries and breads made with regional ingredients.

  • What should I bring for a trip to Port Chester?

    Pack layers and a waterproof jacket, as Port Chester’s weather can shift from chilly to warm and includes periods of rain throughout the year. Comfortable walking shoes are useful for exploring local parks, attractions, and neighborhoods.

  • What is the nightlife in Port Chester like?

    Port Chester has vibrant nightlife with live music venues, bars, and cozy restaurants around the downtown area. Many visitors explore music performances at local theaters and gather at welcoming lounges for conversation and food.

  • What are the most popular events or festivals in Port Chester?

    Port Chester frequently hosts music concerts, outdoor markets, and cultural festivals, especially during late spring and summer. Community celebrations often take place around holiday weekends and draw visitors from the region.

  • Are there family friendly vacation rentals in Port Chester?

    Port Chester has family-friendly vacation rentals in quiet neighborhoods and near parks, making it convenient for guests traveling with children. Many homes are equipped for comfortable stays and easy access to local attractions.

Destinations to explore