Family-friendly vacation rentals in Keene

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Top-rated family-friendly rentals in Keene

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

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Guest favorite

Home in Ludlow

4.89 out of 5 average rating, 132 reviews

1st floor, Okemo contemporary country 3 BR 2 BA

Family-friendly, pet-friendly, clean, comfortable, contemporary country ski cabin on Okema shuttle buss route in Ludlow, VT, a few minutes from mountain. Very easy access to outdoor activities: skiing, hiking, lakes, boating, hunting, snowmobiling, fly-fishing. Updated, comfortable, light filled ambiance. Great location, 10 minute walk to downtown (2 minute drive). Great for groups, couples, families. Recently renovated. New butcher block counter-tops and island, all new kitchen, new bathrooms.

Guest favorite

Cottage in Newbury

4.87 out of 5 average rating, 113 reviews

Country Cottage

Charming cottage with 3 bedrooms just a small walk to Sunapee lake. You can enjoy swimming off the dock or explore one of the many harbors on the lake. Mount Sunapee is just around the corner (2 minute drive) and offers many fun activities for the whole family. Including zip lines, mtn biking and much more. Sunapee State beach is also within walking distance or just a short drive away. Offers large sandy beach. This rustic cottage is a perfect place to make memories with family and friends.

Superhost

Cottage in Chester

4.9 out of 5 average rating, 156 reviews

Green Mountain Country Cottage

Four bedroom cottage centrally located within less than 35 min. of 4 ski resorts, and next to the former Tater Hill golf club. Access to snowmobile trail on site, X-country skiing, hiking, fishing, shopping, restaurants, state parks nearby. In summer and fall mushroom foraging is very productive. For history buffs there is a revolutionary war era cemetery next to the property. Sleeps 10 to 12. The cottage is only available to family groups or responsible adults over 25. NO PARTYING ALLOWED.

Guest favorite

Home in Weston

4.86 out of 5 average rating, 108 reviews

4 Bedroom Family Ski House w/ WiFi, cable!

This family heirloom sits tucked away in the trees just off of Chester Mountain Road. Short trips to Bromley, Okemo, Stratton and Magic Mountains. Sleeps 8 comfortably with room for up to 10 on pull out couches. You will fall in love with the retro feel of this house, it's straight out of the 1980's, and has kept that charm over the years. We have consistently updated it with all of the amenities needed to relax, including Air Conditioning, High Speed wifi, Cable, big screen TV and sound bar.

Superhost

Condo in Ludlow

4.79 out of 5 average rating, 164 reviews

Winter Paradise —Ski-ON/Ski-OFF Okemo Getaway

Perched on Okemo mountain, step to the trails and start your day with no need to ski to the base. You will be on the best ski/on-ski/off location directly to Sunburst 6 Bubble, Sachem or South Ridge Quads & boarding park lifts; while having everything you might need for a cosy and convenient family stay. That includes a fully-equipped kitchen and a living room with games for your entertainment, a private balcony, laundry facilities and shared resort-style amenities at Winterplace with pool.

Guest favorite

Cabin in Sunapee

4.97 out of 5 average rating, 115 reviews

Cozy waterfront cabin Perkins Pond

Come relax, unwind and enjoy the year round beauty and fun at our cabin on Perkins Pond! Many activities to enjoy with each season.. Kayak, canoe, fish and swim or float, nap on the hammock in summer months.. Walk, hike and enjoy the awe of Fall color.. Snowshoe, skate, ice fish, cross country ski on the frozen pond during winter and enjoy downhill at Mt Sunapee just 8 min away or just relax by the wood stove!! Make special memories with your family and friends here at our special place!!

Guest favorite

Home in Jamaica

4.86 out of 5 average rating, 277 reviews

Yellow Sweetie at the Base of Stratton

Our adorable home, The Yellow Sweetie, is located in a quiet setting at the base of Stratton Mountain, just 1 minute to the Stratton Resort access road and 8 mins to the slopes. Explore Vermont's many historic towns with classic architecture and covered bridges, as well as its breathtaking mountains, rivers and lakes. The Yellow Sweetie offers stylish country living-meets-shabby chic comfort and coziness. Escape to the fresh Vermont mountain air where life feels a little bit simpler!

Guest favorite

Home in Westminster

4.93 out of 5 average rating, 125 reviews

Wachusett Mountain Get-Away

This family home is spacious and accommodating for those looking to relax while away from the ski slopes or simply wanting to get away from the city. Situated nearby a plethora of hiking and mountain biking trails, lakes for fishing and paddling, the home is perfect for those craving the great outdoors. The home is 6 min from Wachusett Mountain Ski Resort, 3 min from the Wachusett Brewery, and 1 min from the 1761 Old Mill Restaurant.

Guest favorite

Rental unit in Chester

4.89 out of 5 average rating, 491 reviews

Beautiful 2 Bedrooms in Mountains w/ full kitchen

Ready for a Vermont getaway? In heart of ski area w/ A+restaurants & charming villages are two cozy bedrooms on 2nd fl of larger apt complex. Each bedroom has separate toilet/sink room, shared shower room for your and your guests alone. Hallway living room at one end with 2 couches, desk and TV Other end is full compact kitchen with dishwasher, stove and over, full size refrigerator, coffee maker and microwave.

Guest favorite

Home in Ludlow

4.97 out of 5 average rating, 151 reviews

Ski Chalet with Hot Tub on Okemo Mountain

Much of the house newly renovated in the Fall, 2023. Relax in this 3-level (1700+ sq. ft) ski chalet that's a 4 min drive to the Okemo Mountain Resort and the center of town, and a 6 min drive to Jackson Gore. Take in the 180-degree views of your wooded backyard with floor-to-ceiling windows and unwind in front of the fireplace or relax in the Jacuzzi hot tub in your private oasis on the mountain.

Guest favorite

Rental unit in Ludlow

4.91 out of 5 average rating, 141 reviews

Great Downtown, walk to everything

Get the best of both worlds with this completely renovated Village apartment. Surrounded by the best restaurants and shopping . . . On Okemo's free winter shuttle route for hassle-free skiing. Welcoming and comfortable space with gas fireplace, full kitchen, master bedroom, private entrance. One queen, one full futon in the living room provide additional sleeping for guests.

Guest favorite

Home in Dover

4.87 out of 5 average rating, 237 reviews

Mt Snow retreat, ski & summer

Warm and welcoming space for relaxation and play, your home base for VT recreation. 7 min. drive to Mount Snow, convenient location. Easy access to hiking, mountain biking, x-c skiing, golf course, and more! Sleeps 5 easily. ~10 min. walk to Moover, 7-11, restaurants. INTERNET - There is a fiber optic connection and the plan speed is 50Mbps down / 30Mbps up.