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Family-friendly holiday rentals in Rockland County

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Top-rated family-friendly rentals in Rockland County

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

Guest suite in Piermont
Cozy private apartment with Hudson River views
This cozy apartment just one block from the Hudson River, is on the ground level of a house, with a separate entrance offering complete privacy. This modern space has a fully equipped kitchen, beautiful bathroom, comfy queen bed, reading chair, books galore, and a desk. Located in the adorable town of Piermont, it has the feel of a country retreat, a waterfront town, and it's an easy commute to Manhattan. As of Nov. 2022, the WIFI has been upgraded and it is now RELIABLE & HIGH-SPEED.
10 – 17 Oct
Guest favourite
Apartment in Ossining
Hudson River Peaceful Getaway
Self check-in and private entrance. Peaceful apartment on the Hudson River. Train to NYC (Scarborough Station) is an 8 minute walk through historic neighborhood. Arcadian Mall (Grocery store, Starbucks, etc) 5 minute walk. Rivers views from inside and from three patios (1 on entrance side, 2 on River side). We only allow declawed cats because they can scratch and damage our expensive furniture and carpets. Most house trained dogs are welcome :)
18 – 25 June
Guest favourite
Home in Nyack
Chic Vintage Cottage in Artsy Village of Nyack
Chic, cozy and adorable, our recently renovated 1929 Nyack Village cottage is a one of a kind. Located one block from Main Street and the wonderful dining, shopping and culture downtown Nyack has to offer, our home is the perfect backdrop for a beautiful weekend retreat. Traveling for work? NYC is a quick 30 mile commute with fast access to public transportation. We welcome you to come and be our guests!
5 – 12 Oct

Popular amenities for Rockland County family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Guesthouse in Beacon
Cozy Mountainside Suite - Minutes from Beacon
9 – 16 Mar
Guest favourite
Home in Tomkins Cove
Hudson Valley Victorian with River Views
26 Oct – 2 Nov
Guest favourite
Cottage in Highland Lakes
The Mountaintop Lakehouse that Time Forgot.
24 – 31 Mar
Guest favourite
Apartment in Philipstown
Country apt~chic cabin -hot tub~pool~patio~hiking
30 Mar – 6 Apr
Cabin in Greenwood Lake
Log cabin at Greenwood Lake
14 – 21 Mar
Guest favourite
Chalet in Cold Spring
Mountain View Retreat
3 – 10 Jan
Guest favourite
Home in Cold Spring
Hilltop Hideaway Forest Villa on 13 acres!
5 – 12 Jan
Guest favourite
Home in Beacon
River & Mtn Views - Jacuzzi - near Metro North
31 Aug – 7 Sept
Guest favourite
Villa in Hopewell Junction
The Mission House Sanctuary
22 – 29 Oct
Guest favourite
Home in Cold Spring
1834 Farm House
1 – 8 Feb
Guest favourite
Home in Englewood
Englewood NJ Country Carriage House (15 min NYC)
8 – 15 Jan
Villa in Putnam Valley
Paradise in Hudson Valley-Pool/Gym/1 hr from city
3 – 10 Oct

Family- and pet-friendly home rentals

Guest favourite
Cabin in Greenwood Lake
"Cabinessence" on Greenwood Lake, 60 mi from NYC
30 May – 6 June
Guest favourite
Guesthouse in Warwick
Bellvale Guest House on Solar Powered Mini-estate
12 – 19 Aug
Cottage in Vernon Township
Rustic Chic Lake view cottage 50 miles from NYC
22 – 29 Mar
Guest favourite
Home in West Caldwell
Cozy Designer Cottage -to yourself- one of kind
26 Oct – 2 Nov
Guest favourite
Farm stay in Goshen
Bright Farm House- Tranquil setting
9 – 16 Mar
Guest favourite
Guest suite in Fort Montgomery
West Point - Mountain Top Suite
17 – 24 Nov
Cottage in Putnam Valley
Lakefront Cottage near Hudson Valley
24 – 31 Oct
Guest favourite
Campervan/RV in Cold Spring
Hudson Highlands Base Camp
29 Apr – 6 May
Guest favourite
Farm stay in Fort Montgomery
Secluded overlook cottage near West Point
13 – 20 Mar
Guest favourite
Guest suite in Cold Spring
Cozy getaway in Cold Spring
5 – 12 Dec
Guest favourite
Apartment in Carmel
Private space, with yard
6 – 13 May
Guest favourite
Loft in Yonkers
Blacksmith Bldg Guesthouse Upscale in downtown.
21 – 28 Dec

Family-friendly home rentals with a pool

Guest favourite
Home in Cold Spring
Cozy, Modern Retreat in the Woods of Cold Spring
13 – 20 Nov
Guest favourite
Apartment in Warwick
Farms, wineries, trails, king bed & heated floors
18 – 25 Nov
Guest favourite
Home in Stormville
Private Hudson Valley Country Retreat
31 Oct – 7 Nov
Home in Yorktown Heights
Cozy winter getaway 1 hr from NYC!
25 June – 2 July
Guest favourite
Home in Putnam Valley
Putnam Valley Escape
11 – 18 June
Guest favourite
Cottage in West Orange
Cozy Pool Cottage
6 – 13 Apr
Guest suite in Monroe
Affordable Scape 5 Minutes Walk To The Like
12 – 19 Aug
Guest favourite
Apartment in Clifton
Spacious Apt | 24/7 Onsite Team | Sparkling Clean
25 Mar – 1 Apr
Guest favourite
Home in Highland Falls
Farmhouse with pool/mtn view, 1/2 mi to West Point
9 – 16 Mar
Cottage in New Windsor
Lake Front Property Sauna and Pool Near West Point
7 – 14 June
Guest favourite
Apartment in Florham Park
Resort Community | Spacious 1bd | 24/7 Onsite Team
20 – 27 Apr
Guest favourite
Apartment in West Point
23 – 30 Oct

Destinations to explore