Kid-friendly vacation rentals in Monterey

4.87 out of 5 average rating, 183 reviews

A wooden deck is shown featuring a large umbrella providing shade over a seating area. A patterned rug lies on the floor, accompanied by a potted plant. Two lounge chairs and a small table create a comfortable outdoor space, surrounded by lush greenery.

Cabin in Saugerties

Private Woodstock Getaway w Hot Tub

Relax in this cozy retreat on a private road. Snuggle up by the fire, play some records, relax on the sunny deck, or jump in the hot tub. Cook dinner in the fully stocked kitchen or grill on the deck and enjoy your meal in the screened in porch. The master bedroom has a king-size bed and quality linens, as do the other two bedrooms, one with a queen and one with 2 twins beds. Relax downstairs in the family room, watch a movie, or cozy up by the wood burning stove. Short drive to the town of Woodstock ! Close to skiing, hiking & swim holes! $50 extra for dogs. No cats. Use hot tub at your own risk. The whole home is yours except the garage remains closed. Always available if any issues arise, but not on the property. The house is set back on a private road. It's a genuine retreat, but still only a short drive from the shops and restaurants of Woodstock and Saugerties. Local hikes abound, and venture a little further to find swimming holes and skiing. If you have a small child, I suggest bringing a gate as there are stairs to the basement.

Home in Litchfield County

A charming two-story white house is surrounded by greenery, featuring a welcoming front porch with rocking chairs. The structure showcases large windows and a shingled roof, with a pathway leading to the entrance. The tranquil setting is complemented by the rustic stone bench in front.

4.8 out of 5 average rating, 10 reviews

Charming home ready for fun and/or relaxation!

Enjoy our peaceful (pet friendly) home, at the end of a dead-end road & just a short walk to the center of Norfolk. Great for friends and/or family visits. Board games & puzzles inside; lawn games & fire pit outside. Front & back decks, including screened-in porch, are perfect for relaxing. Access great cafes, shops & cultural delights in Norfolk. The nearby Ellen Battell Stoeckel Estate hosts Yale's Summer Chamber Music Concert series. It’s a home, not a hotel. But, we think you’ll love it!

4.82 out of 5 average rating, 95 reviews

A spacious living area features a large, soft sofa with decorative pillows, facing a rustic coffee table. Natural light fills the room through multiple windows, with a dining table set for six in the background. Soft, neutral tones create a serene atmosphere.

Home in Cornwall

State Forest Getaway

Enjoy our Mountain getaway for year round fun! There are lots of activities close by-Mohawk Ski Mountain, Indian Lake and historic Covered Bridges! Hike in the backyard, cool off in the creek or relax in front of the Wood-burning fireplace or get the whole family together for a fun BBQ on the outdoor deck. We have 4 comfortable bedrooms plus daybed room and 3 bathrooms and a fully equipped Chefs Kitchen. The living room is great for lounging and perfect a movie night watched on the projector

4.96 out of 5 average rating, 195 reviews

Home in Round Top

Escape in the Catskills w/hottub

Escape to the Catskills: Your Mountain Retreat No Cleaning Fee! Immerse yourself in the breathtaking beauty of the Catskills. Our cozy retreat offers the perfect blend of relaxation and adventure, whether you're seeking a romantic getaway, a peaceful remote work haven, or an exciting outdoor adventure. Unwind in the hot tub while enjoying stunning world-class panoramic views. Conveniently located near charming towns with unique shops, delectable dining options, and hidden antique treasures.

4.95 out of 5 average rating, 111 reviews

An enclosed porch features two metal-framed chairs with cushions, positioned near a small table. A decorative rug with vibrant floral patterns covers the floor. A potted plant and a lantern add to the decor, with sunlight streaming through the windows overlooking the water.

Home in Lake Katrine

Waterfront 3BR Home in Hudson Valley, Catskills

Key Residence Features at a glance; Waterfront on the Esopus Creek, Seasonal Kayaks, Rowboat, Dock (approx. Memorial Day weekend-mid October) large yard. Fully equipped kitchen, cable, wireless internet, washer and dryer. Enclosed porch, deck and patio with propane grill and patio furniture. Paved flat driveway, ramp allowing access to first floor, oversize door to first floor bathroom. Three spacious bedrooms with air conditioners. Convenient location close to thruway exits. No boat launch.

5 out of 5 average rating, 149 reviews

A wooden playset is situated in a shaded area, featuring a slide, climbing wall, and swings. Nearby, a grassy space with pebbled pathways leads to a rustic barn surrounded by trees. Natural light filters through the forest canopy, creating a serene atmosphere.

Home in Saugerties

Upstate Modern Scandinavian Barn in the Catskills

Renovated 1850's barn with 3 bedrooms and an ample loft space that can serve as a fourth. The house also has a large rec room with cathedral ceiling buttressed by hand-hewn beams, well-equipped kitchen, Scandinavian wood stove, sauna, home gym, and projector. Outside: 2 private decks with amazing views of Overlook Mountain, private grill, private hot tub. On property: shared tennis court, swing set, fishing pond, heated pool (summer only). 2 hours from NYC, 10 min. to Woodstock & Saugerties.

4.93 out of 5 average rating, 132 reviews

A designated workspace is visible, featuring a wooden desk with a monitor and a sleek chair, positioned against a gray wall. A cozy living area can be seen through the open doorway, with a comfortable blue sofa and a decorative table, offering an inviting atmosphere.

Home in Kingston

Hightop House: Modern, Uptown, Centrally Located

Hightop House is a newly renovated Victorian home in midtown Kingston. Ideal for a WFH getaway (inhouse and coworking partnership), groups, and families. Enjoy easy access to Kingston and surrounding areas. 3 bedrooms, 2.5 baths. Large open kitchen, contemporary furnishings, brand new appliances. Walk to UPAC / Stockade District, Keegan Ales. <10 min drive to the Rondout district, Hutton Brickyards. 10min to Ashokan Rail Trail, Onteora Lake. 20min drive to Saugerties, Woodstock, Rosendale.

4.84 out of 5 average rating, 170 reviews

The living room features light green walls with large windows allowing natural light to fill the space. A patterned sofa and two armchairs offer seating. A coffee table sits on a layered area rug, while a corner with a small table and a chair adds functionality.

Home in Athens

A Victorian "Lady"

Enjoy an old-fashioned vacation right across the street from the Hudson river. Watch the tides, boats, and barges pass by. Dining, kayaking within walking. Historic Hudson, Olana just 10 min. drive. This is a house to relax, use as a base for other activities. It is not intended as a place to party.. It is a quiet neighborhood. I expect my guests to respect that. There is a weekend special. If you book friday/saturday or saturday/sunday the price is $350.00 for the 2 nights. Thanks

Bungalow in Great Barrington

4.91 out of 5 average rating, 117 reviews

Idyllic Berkshires Getaway

Secluded large ranch in the country on 8 acres with pastoral scenic views, only 7 minutes drive from the center of Great Barrington and Lake Mansfield Beach, 10 minutes to Ski Butternut, 12 minutes to Stockbridge, 20 minutes to Lenox and Tanglewood . Kids playroom and a spectacular jungle gym, perfect for entertaining inside by the fire or outside on the patio with the bbq with beautiful views surrounded by pine trees. Perfect for fall foliage, skiing, spring and summer!

4.97 out of 5 average rating, 70 reviews

A spacious game room features dual large screens for entertainment, along with a sleek shuffleboard table and a pool table. A modern kitchenette is positioned in the corner, and warm wood flooring enhances the inviting atmosphere.

Home in Athens

Lake House with Game Room

Relax with the whole family at this peaceful place. As a guest you'll have access to our Sleepy Hollow Lake community beach area, pools and playgrounds, and pickle-ball, tennis and basketball courts. Athens hosts a gourmet bakery, restaurants and an award-winning brewery. Drive 7 miles to explore historic Catskill, 12 to hip Hudson and for year-round sports enthusiasts - only 30 to Windham and Hunter Mountains. Game room with pool table, shuffleboard and bowling!

4.92 out of 5 average rating, 171 reviews

A spacious backyard is presented, featuring a playground set with a slide and a small playhouse. A wooden deck offers seating, while a shaded area is created by a large tree. A red shed is visible in the background, surrounded by well-maintained grass.

Home in Bristol

Cozy Family Home - Kid & Pet Friendly

3 bedroom house on a quiet street. 5mins down the road from ESPN and Lake Compounce. Kid friendly. Pet friendly. Workspace available. 1 bedroom w/ king bed. 1 bedroom w/ queen bed. 1 bedroom w/ 2 twin beds. Fully finished basement with 60inch TV, kids toys and fitness equipment/stationary bike. Deck and below deck hang out space. Though we aren’t living here full time, it’s still the place we call home, and we will use it when it’s not booked. Long stays welcome.