Family-friendly vacation rentals in Ashland

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Ashland

  • Total vacation rentals

    Explore 50 vacation rentals in Ashland

  • Nightly prices starting at

    Ashland vacation rentals start at ﺩ.ﺇ 294 per night before taxes and fees

  • Verified guest reviews

    Over 1,190 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Ashland vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Ashland rentals

  • 4.9 Average rating

    Ashland stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated family-friendly rentals in Ashland

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

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Guest favorite
An A-frame cabin showcases a wooden exterior with large glass windows, allowing natural light indoors. The deck features four Adirondack chairs arranged around a circular fire pit. Surrounding greenery and autumnal trees enhance the serene outdoor setting.
Cabin in Danbury
4.95 out of 5 average rating, 144 reviews

Cozy A Frame Cabin

Discover Your Dream Getaway at Our Enchanting A-Frame Cabin in Danbury, NH! Hike lush forest trails, paddle across sparkling lakes, or hit the nearby slopes for seasonal adventure. After a day outdoors, kick back on the spacious deck, fire up the grill, and dine under the stars. Whether you're planning a romantic escape or a fun-filled family getaway, this hidden gem offers the perfect blend of comfort, charm, and natural beauty. Escape the ordinary—book your unforgettable Danbury retreat today!

Guest favorite
A rustic cabin is nestled among the trees, showcasing its wooden exterior and a metal roof. Tall windows allow natural light to fill the space. Surrounding greenery, including ferns and bushes, adds to the secluded atmosphere. A stone wall and picnic table can be seen in front.
Cabin in Sharon
4.93 out of 5 average rating, 298 reviews

forest retreat; off-grid writers cabin

Secluded rustic charm, circa 1900 cabin in the woods getaway, spend time in nature surrounded by forest, brook, wildlife, hiking trails, fall foliage, mountain biking skiing. Sauna, Cold Plunge, Outdoor Shower & Hot Bath (seasonal) Unwind from the outside world and reconnect with your self or your loved ones and the natural world around you. Loft with real beds, well stocked kitchen, grill, outhouse, Glamping! Close to Woodstock, VT and Killington, S. Royalton, White River, Lebanon & Hanover NH

Top guest favorite
Cabin in Corinth
4.96 out of 5 average rating, 132 reviews

Cabin Hill at Taplin Hill Farm in Corinth, Vermont

Amazing White Mountain views on the peak of the farm. Private cozy cabin, perfect romantic vacation getaway, ideal for writers/artists, or like the owners, nomads looking to nature to inspire creativity and relaxation. One-room cabin with a full bathroom, kitchenette, and BBQ grill sits high on a ridge known as Cabin Hill. Expansive views of the White Mountains are seen from large windows and the deck. Outfitted with tasteful linens and bath amenities. Furry friends are welcome - NO Pet fees!!

Guest favorite
A serene outdoor space features a fire pit surrounded by natural stone. Lush greenery extends to distant mountain views under a partly cloudy sky, creating a peaceful setting for relaxation and outdoor gatherings.
Cabin in Tamworth
4.9 out of 5 average rating, 576 reviews

Secluded Mountain View Cabin • Private Sauna

A real cabin in the North Woods secluded, private, and surrounded by open sky and sweeping mountain views that remind you why you came. This log-style retreat sits deep in the woods above Tamworth, fully equipped for comfort without sacrificing the rugged feel. Hike local trails, stargaze in near-zero light pollution, or sit by the fire pit with the mountains in front of you. The optional wood-fired sauna steps from the door is the perfect end to the day. Sauna available as a one-time add-on.

Guest favorite
The exterior of a two-story house is surrounded by fallen leaves in autumn colors. A wooden structure is visible to the left, and the house features large windows that allow natural light. A well-maintained lawn complements the serene setting.
Guest suite in Plymouth
4.87 out of 5 average rating, 245 reviews

Cozy White Mountain Getaway - Walk to PSU

Private sitting room, bedroom and full bath, separated from main house. 5-minute walk to Plymouth State University. Close to Waterville Valley, Loon, and other ski resorts. Also close to lakes and hiking trails. Bedroom has a king size bed and reclining chair. Sitting room has a daybed with a trundle bed underneath. The sitting room also has a table with four chairs, a mini fridge, microwave oven, and Kreurig coffee maker. Plates, cups, silverware are also provided. Parking for three cars.

Top guest favorite
A charming historic house is surrounded by mature trees, showcasing a white exterior and a welcoming front porch with rocking chairs. A well-maintained picket fence frames the property, while colorful flower arrangements are seen near the windows, enhancing the peaceful outdoor setting.
Cottage in Plymouth
4.91 out of 5 average rating, 430 reviews

Plymouth's Historic Doll House; A tiny house

The Doll House has everything you’ll need at under 700 square feet. This fully-outfitted, historic, full-house rental has a complete kitchen, living room, two-bedrooms, bath, back sitting room, front farmer's porch and beautiful gardens and sitting areas. The Doll House is within easy walking distance to the Town Common, great restaurants and shopping, the Flying Monkey, and PSU. We are just a few minutes' drive to the Barn on the Pemi and Holderness School. NH Rooms Tax; License #059528.

Top guest favorite
Cabin in Campton
4.99 out of 5 average rating, 186 reviews

Stickney Hill Cottage

Stickney Hill Cottage is nestled up and away from the hustle of daily life. A quiet get-away for you to reconnect and make new treasured memories with a loved one. Located close to amenities in Campton, NH at the base of the White Mountains, this unique handcrafted cottage has been lovingly built using local wood , much of it from the property it is built on! Whether this is your base for adventure or you plan to stay in the entire visit, Stickney Hill is your special get-away location!

Top guest favorite
A renovated studio cabin features a cozy sleeping area with a patterned bedspread. A small kitchenette is visible in the background, alongside a wall-mounted TV. Natural light fills the space through a window, while exposed wooden beams add a rustic touch.
Cabin in Campton
5 out of 5 average rating, 274 reviews

Sleepy Hollow Cabins 2

Come enjoy a fun filled getaway at this centrally-located studio Cabin in the foothills of the White Mountains. Whether you are looking for outdoor adventures ranging from hiking, skiing, kayaking to birdwatching, we are close to it all. Then, in the evening, relax at the propane fire table with a glass of wine or build your own fire at the wood firepit (wood provided) and take advantage of the spectacular stargazing. The cabin has a smart TV and high-speed internet provided.

Top guest favorite
Cabin in Alexandria
4.98 out of 5 average rating, 104 reviews

Modern Rustic Cabin with Sauna near Lake and Hike

Escape to Black Dog Cabin, less than 2 hours from Boston: - Gather under the stars by the fire pit - Relax or grill on the huge back deck & sauna - Enjoy our pet-friendly working homestead - Ski at nearby Ragged & Tenney Mountain resorts - Hike, bike & snowshoe at nearby Wellington, Cardigan Mountain State Parks, AMC Cardigan Lodge Looking for options? Visit my Airbnb Host Profile to explore our 3 available cabins: Millmoon A-Frame, Black Dog Cabin, Darkfrost Lodge.

Superhost
A spacious farmhouse is set among lush greenery, featuring a well-maintained lawn. A combination of porches and seating areas, including red adirondack chairs, are visible. The exterior showcases a charming white facade with a star accent, surrounded by tall trees.
Home in Ashland
4.87 out of 5 average rating, 211 reviews

Squam Lake Farmhouse, Beach Access, Winter Skiing

Quiet Large Farmhouse at Squam Lake. Five bedrooms, large kitchen, family room, and living room provide lots of space for large groups. Themed bedrooms, pool table, ping pong, cornhole, firepit, etc. Large yard. Lots of hiking trails local, great foliage, and many other Lakes Region attractions are close. Separate shared 40' Beach with swim docks and kayaks (5 min walk). Close to many ski mountains and other winter activities. Loon, Waterville, Gunstock,etc

Top guest favorite
The living area features a high, wooden ceiling with large windows that provide natural light and views of the surroundings. A stone fireplace is positioned centrally, flanked by comfortable seating. A dining area and modern kitchen appliances are visible in the background.
Home in Hebron
4.99 out of 5 average rating, 182 reviews

Luxurious Eagle Ridge Log Home at Newfound Lake

This stunning one of a kind log home, featured in Log Home Living Magazine, built in 2020 is located at the end of a tree lined driveway on 3.5 acres overlooking beautiful Newfound Lake, NH. This 1,586 Sq Ft home can house a MAX of 6 guests in 3 bedrooms. Amenities are 100 mbs Wi-Fi, TV, gas fireplace, gas grill, hot tub, whole house generator, central A/C, screened porch and huge patio. Parking pass to the private town beach that is less than 1/4 mile away.

Top guest favorite
Dome in Sutton
4.96 out of 5 average rating, 159 reviews

Luxury Glamping NH - Geodome Sanctuary

Escape to a private luxury sanctuary retreat tucked behind a charming Christmas tree farm in Sutton, New Hampshire. This adults-only geodome features a private hot tub, wood-fired cedar sauna, cold plunge, and fire pit beneath a sky full of stars. Created for couples seeking rest, connection, and renewal, it’s the perfect place to slow down, reconnect, and experience the beauty of New Hampshire. Just 90 minutes from Boston, yet a world away.

Popular amenities for Ashland family-friendly rentals