Family-friendly holiday rentals in Port Chester

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Top-rated family-friendly rentals in Port Chester

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Guest favourite

Cottage in Fairfield

4.97 out of 5 average rating, 113 reviews

Charming Fairfield Cottage By The Sea

Newly renovated cottage, steps from private beach. Whether you enjoy walking, biking, swimming, fishing, kayaking, or the daunting task of napping in a shady hammock, this is the place is for you. Near Metro North and I-95, just an hour from Manhattan. Bring back memories of childhood summers—put your toes in the sand and your mind at ease, while enjoying the tranquility of this spectacular Long Island Sound getaway in Fairfield. Also, we have added Amazon Alexa and Fire Stick to our smart TV.

Guest favourite

Home in Cold Spring

4.95 out of 5 average rating, 153 reviews

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, crib and baby monitor, 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.

Guest favourite

Home in Bayport

4.84 out of 5 average rating, 156 reviews

Exquisite spacious waterfront all modern-sleeps 8

READ THE CONSISTENT FINE REVIEWS! Its heart-warming providing such a nice sanctuary! This MEMORABLE Sayville / Bayport Vacation rental home has a picturesque backyard & amazing water views. 3Br 2 full bath. Enjoy the 2-person steam shower & huge 10-person whirlpool bath for spa-like living. Perfect for quiet getaways. All new furniture w/ coastal chic decor. Feed 6 ducks, 2 swans, 2 cranes. The serenity & one-of-a kind view sets this Sayville vacation home apart from all others.

Guest favourite

Guesthouse in Warwick

4.97 out of 5 average rating, 262 reviews

Bellvale Guest House on Solar Powered Mini-estate

Town of Warwick Short Term Rental Permit #32553 Come spend a relaxing week-end on our 4 acre mini-estate in beautiful Warwick, about one hour from NYC. Our detached 2 bedroom guest apartment is in a secluded setting, yet boasts spectacular views of the Warwick Valley. There are numerous attractions for all tastes including craft breweries and wineries. Close to home, Mt Peter Ski Area is within walking distance and further up the mountain is the nationally famous Bellvale Farms Creamery.

Guest favourite

Home in Greenwood Lake

4.91 out of 5 average rating, 123 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

Cabin in Greenwood Lake

4.96 out of 5 average rating, 392 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

Home in Cornwall-on-Hudson

4.95 out of 5 average rating, 109 reviews

Charming Hudson Valley Home: Minutes to West Point

**Currently booking for West Point Graduation 2025. 5-night minimum** 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

Guest favourite

Guest suite in Baldwin

4.91 out of 5 average rating, 233 reviews

Vintage living.

The space is on the ground level its about 600 square feet. Best part is its right next to the inground pool. The pool is 4-7 feet deep with a lounge area. On the ground floor we have a newly renovated kitchen (no oven), seating for 6-7 people, small dinner table, Flatscreen TV, Sectional sofa, and full bathroom. The bedroom in the lower level is about 600 sqft. In the bedroom you will find two queen size Memory Foam beds with top of the line linens. We do allow pets with a $75 pet fee.

Guest favourite

Farm stay in Goshen

4.86 out of 5 average rating, 304 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

Home in Milford

4.93 out of 5 average rating, 121 reviews

#2 Milford Beach by Charles Island/Silver Sands Pk

Welcome to your dream beach getaway in Milford, Connecticut! This stunning 2 bedroom, 1 bath first floor apartment is perfectly situated right across the street from a beautiful beach, offering you the ultimate beachfront experience. With its prime location just 100 yards away from Silver Sands State Park, you'll have easy access to miles of pristine sandy shores and breathtaking coastal views.

Superhost

Home in Weehawken

4.82 out of 5 average rating, 136 reviews

NYC area Historic A+ Family friendly 2BR house Apt

Charming first floor 1,000+ sq.ft apt in a two family house literally steps from midtown Manhattan and as close to the center of the universe as you can get without being there...Antique style apt. with all modern amenities...Children are welcome, as a family lives on the second floor...Truly a delightful and comfortable environment to spend time in....You will not be disappointed...

Guest favourite

Cabin in Putnam Valley

4.96 out of 5 average rating, 157 reviews

Furthermore Cabin: your mountaintop escape

Our treetop hideaway is filled with plants. Our home is open for you and your loved ones to connect and be cozy together. Well stocked kitchen, stylish vibe, and seasonal access to 2 beaches down the mountain. Enjoy the lake view from hammocks on the double decker decks. 20 minutes to the Hudson Valley's best hiking. 15 minutes from the Taconic Pkwy and Peekskill Metro North.