Family-friendly holiday 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 favourite

Flat

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 favourite

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 favourite

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 favourite

Flat

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 favourite

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 favourite

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

Flat

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 favourite

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 favourite

Guest house

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 favourite

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.

Guest favourite

Guest house

4.96 out of 5 average rating, 189 reviews

Southport, CT across from BEACH

Located at Southport beach on Westport Line, this renovated 1 bedroom apartment totally private located above the garage and includes a full kitchen with new appliance and d/w and central air. Bdrm with queen, fine cotton sheets and towels, marble bath open living room w views.