Family-friendly vacation rentals in Port Chester

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Top-rated family-friendly rentals in Port Chester

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

An open living space is presented, featuring a cozy bed and a comfortable sofa. A dining table with white chairs is visible, complemented by large windows allowing natural light. A flat-screen TV is placed on a console, enhancing the room's functionality.

Apartment

4.89 out of 5 average rating, 319 reviews

Cozy Suite 5 min walk to train/15 min JFK+parking

Gorgeous Fully furnished/quipped and freshly remodeled 1bedroom + living room apartment, at only a 4 minutes walk to Long Island Rail Road (30 min ride to NYC) The apt comes with a fully equipped kitchen, a full bath, 1 cable TV, 2 AC's (from June to Sept) & WI-FI. Guests are provided with dish soap, sponge, shower gel, shampoo, towels, sheets, blankets, silverware pots,pans and kitchen utensils. The open space will allow you to socialize cooking/having dinner without missing any action :))

Guest favorite

A cozy living area features dark upholstered chairs positioned around a light wooden coffee table. A large television is set on a matching media console, while natural light enters through the windows, highlighting the beamed ceiling and trim moldings.

Home

4.92 out of 5 average rating, 131 reviews

Casa del Lago, Boating, Hiking & Grilling!

Welcome to GWL! This 109 year old Arts & Crafts home is charming with high ceilings & beams, trim moldings, porch and original hardwood floors. There is plenty of outdoor space including back yard, a deck, patio & lake deck. Plenty of nooks for you to relax, grill, sip wine from the enclosed porch or watch TV. House faces the lake but you must cross a low traffic street for lake / dock access. Plenty of parking driveway & lakefront. Short walk to the Village, close to all! PERMIT #18-07697

Guest favorite

The exterior of a charming carriage house is surrounded by lush greenery, featuring a dark blue facade with red accents. The well-maintained garden showcases manicured hedges, while trees provide a natural canopy and a serene atmosphere.

Home

4.92 out of 5 average rating, 111 reviews

Carriage House -private historic estate-“best NJ”

Escape to an enchanting retreat appx 20 miles from New York City! Nestled in the heart of suburban New Jersey, this cozy 3-bedroom carriage house offers a unique blend of vintage charm and modern comfort on a historic estate.Conde Nast Traveler hailed as one of the "Best Airbnbs in New Jersey." Ideal for any occasion, this American gem is perfect for relocation, working remote, family vacations/wedding base, business travelers, traveling md/nurses, World Cup/concerts, visiting NYC and more.

Guest favorite

The living room features a dark sofa adorned with cushions, complemented by a light-toned area rug. A mid-century chair with a soft throw and a glass coffee table enhance the cozy ambiance. Green plants bring a touch of nature, while large windows allow ample natural light.

Apartment

4.98 out of 5 average rating, 113 reviews

Family brownstone with backyard

Located in Clinton Hill, a historic Brooklyn neighborhood, with lots of wonderful restaurants, cafes, and markets, our home is a quintessential brownstone. It was built in 1860 and freshly renovated in a way that preserved all of its old charm. The space available is the master bedroom with an en suite bathroom in the owners duplex. The apartment is loved by parents and kids all over the neighborhood, especially the backyard. The subway is just a block away. Discounts for monthly rentals.

Guest favorite

Cabin

4.96 out of 5 average rating, 418 reviews

"Cabinessence" on Greenwood Lake, 60 mi from NYC

"Cabinessence" is Year Round Comfort in a Chestnut Cabin by Greenwood Lake with a little touch of "glamping". Hiking, biking, strolling, paddle boarding, kayaking , canoeing. Restaurants, shopping, Drive-in movies, antiquing in nearby Warwick. Fall color, apple picking, gas fireplace (in season). Winter, ski, snowboard, tubing. Spring is watching the natural world wake up :) Hanging at the cabin- year round- is special here! Every season has its magic! ( + Covid Enhanced cleaning!)

Guest favorite

A bright sunroom features a round table surrounded by two white metal chairs with blue cushions. Large windows allow natural light to fill the space, showcasing a coastal view. Straw hats are hung on the walls, adding a touch of seaside charm.

Cottage

4.97 out of 5 average rating, 119 reviews

Charming Fairfield Beach 3BR Cottage By The Sea

Charming Beach Cottage – Steps from Private Beach! Welcome to our newly renovated seaside retreat—a perfect getaway for families, couples, or anyone looking to relax by the shore. Nestled just steps from a private beach (right across the street!), our charming cottage offers the ideal balance of coastal tranquility and convenient access to town. Whether you enjoy walking, biking, swimming, fishing, kayaking, or simply napping in a shady hammock, this is the place for you.

Superhost

A well-lit bedroom features a spacious bed dressed in white linens. A wooden slatted accent wall adds warmth, while two bedside lamps are positioned on dark nightstands. A closet door and a white curtain frame the scene, enhancing the airy atmosphere.

Apartment

4.88 out of 5 average rating, 112 reviews

Cute & Cozy Family Suite. Close to NYC & EWR

This apartment consists of two gorgeous and luminous bedrooms, kitchen and one bathroom. It is fully equipped with everything you need for a comfortable stay. The kitchen is equipped with all kitchen basics. The living-room is equipped with a comfortable sofa (which sleeps 2 ) , a smart TV, & a PS5. The apt is in the ironbound area of Newark. 7 mins to EWR, 20-60 mins to NYC by train, 10 mins to Newark Penn station, 20 mins to Met Life Stadium & Dream waterpark.

Guest favorite

The farmhouse features a spacious front porch with several seating areas and a central entry door. The light-colored exterior is complemented by white trim and sizeable windows. Landscaping includes plant beds with yellow flowers and a decorative rooster statue on the side.

Farm stay

4.87 out of 5 average rating, 339 reviews

Bright Farm House- Tranquil setting

Secluded 3-bedroom newly renovated late 1800 Farm house on a 50 acre working farm nestled in the Hudson Valley. Only 60 miles from NYC and close to everything the Hudson Valley has to offer. Many farms with seasonal apple picking and pumpkin picking ,West point , Woodbury Commons Premium outlets ,Resorts Casino. Tons of great local breweries ,Hudson Valley Wine Trail .. LegoLand Theme park is just 5 minutes away

Guest favorite

The exterior of the stone garage features natural stone walls, green foliage, and a grass area. Two Adirondack chairs and a chiminea are positioned in the outdoor space, alongside a dining table set for four. Windows allow light to reflect off the stone structure.

Guesthouse

4.96 out of 5 average rating, 133 reviews

Hiking trails steps from your door!

Secluded, renovated apartment in a 100 year old stone garage. Harriman State Park and great walks and hikes are steps away. Ground floor entry and kitchen, with a LR/BR upstairs; main house is 130' away. We accept well-behaved adult dogs for stays of a week or less with a fee of $20 per night, paid separately/later (see details and pet rules below).

Guest favorite

Home

4.99 out of 5 average rating, 107 reviews

Cozy 4 Bed 2 Bath Home 1/4 mile from West Point

Split level floor plan featuring 4 spacious, bright bedrooms and 2 full baths. Newly renovated home with large deck for entertaining. Sleeps 10 with room to spare. Quiet end street 1/4 mile from Thayer Hotel at USMA. Walking distance to several restaurants. Amenities include: Satellite TV/WiFi/Washer-Dryer/Dishwasher/Outdoor grill.