Family-friendly vacation rentals in Port Chester

Carriage House -on historic estate-one of kind exp

Relax in an enchanting retreat appx 20 miles from New York City.The cozy 3-bedroom carriage house offers a unique blend of vintage charm and modern comfort on a historic private estate, a one of a kind American gem. Conde Nast Traveler hailed it one of the "Best Airbnbs in New Jersey." Ideal for any occasion: relocation, working remote, “Fam Travel”, wedding base, business travelers, remodeling, traveling doctors/nurses, events MetLife/Pru Center, sightseeing in NYC, tranquil escape from NYC.

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

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.

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.

Cozy, Modern Retreat in the Woods of Cold Spring

Newly renovated with modern style and amenities yet retaining all of its rustic warmth and charm, our home is perfect for your next get away. Outdoors, enjoy the salt water pool, patio, grill and fire pit in our secluded setting. Indoors we offer a sauna, steam shower, central heat and air, a woodburning fire place, ping pong table, washer and dryer, and a fully loaded kitchen. Located 7 minutes drive from charming Cold Spring and just across the river from West Point.

Charming Hudson Valley Home: Minutes to West Point

Located in the Lower Village of Cornwall on Hudson, 5 miles from West Point, 4 miles from Storm King Arts Center and minutes from amazing hiking trails. This charming house offers everything you need for a relaxing getaway. Spacious deck makes it the perfect spot for a relaxing evening outside. The beautiful Hudson Valley and this charming house can't wait to welcome you! **Home does not have a washer/dryer available

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).

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.

Exquisite Studio and Perfect location

Newly renovated apartment August 2022 A half-block walk to the bus stop and BAM ! 10 minutes later you’ll be in Times Square. The renowned Weehawken boardwalk is only 3 blocks away where you will experience some of the most breathtaking views of the Manhattan skyline.