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 G$16,739 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,210 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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Top guest favorite
A wooden treehouse with large windows and a spiral staircase is surrounded by lush green trees. The structure is elevated, allowing for a view of the forest floor, which is covered in natural earth tones from fallen leaves and pine needles.
Treehouse in Sanford

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

FamilyIndoor spacesCondition

4.91 out of 5 average rating, 604 reviews
Top guest favorite
A bright sleeping area is highlighted by sunlight streaming through three windows. A bed is draped with a floral-patterned coverlet. The view outside features lush greenery, adding a natural touch to the serene ambiance.
Guest suite in Plymouth

Mountain River Suite with private deck and firepit

Close to town and I 93, a rural paradise. You have your own driveway, private deck and your own firepit, with gorgeous views of hills and gardens. The bed is surrounded by two walls of windows-with shades. There is a Hearthstone gas stove, a leather loveseat, and a huge custom shower in the bathroom. The kitchen has a refrigerator, microwave, blender, crock pot and electric skillet. There is a television with cable, Netflix, etc. We stock coffee, and breakfast foods for your convenience.

Indoor spacesFamilyDecor

4.84 out of 5 average rating, 341 reviews
Top guest favorite
An aerial view of the property displays a spacious yard with a well-maintained in-ground saltwater pool surrounded by wooden decking. A barrel sauna and fire pit are positioned nearby, complemented by manicured greenery and tall coniferous trees in the background.
Home in Meredith

1840 Meredith Farmhouse w/ outdoor Sauna & Pool

This beautifully renovated antique 1840 Meredith Farmhouse combines timeless charm with modern comforts. Nestled on over 3 acres in the lakes and mountains, it features a snowmobiling trail in the backyard, easy access to hiking, skiing & lakes, and is less than 10 minutes from Mill Falls in downtown Meredith. Outdoor amenities include a barrel sauna, cozy fire pit, in-ground saltwater pool & a game room. Inside, the chef’s kitchen boasts Thermador appliances, a coffee & tea nook & a bar area

KitchenIndoor spacesView

5.0 out of 5 average rating, 101 reviews
Top guest favorite
A welcoming porch features double blue doors framed by white pillars. An American flag hangs to the left, while light filters through the nearby windows. A bench sits on the wooden deck, inviting guests to enjoy the surrounding greenery.
Home in Plymouth

Lower Intervale Grange; Nat'l Register Hist. Site

One-half mile from the Barn on the Pemi!! A full-house rental, you'll be welcomed by full kitchen, comfy beds, original 1912 tin ceilings, hardwood floors, beadboard walls, piano and great modern amenitites like Wifi and Smart TV. The Grange is an award winning restoration while maintaining its historic elements and charm of this National Register property. The kitchen on the main floor meeting room makes cooking and socializing easy. Sleeps 1 to 7 guests, one large bathroom. License 059528

Indoor spacesKitchenLong stay

4.95 out of 5 average rating, 180 reviews
Top guest favorite
Cabin in Alexandria

Mountain Lodge with Private Sauna

Escape to Darkfrost Mountain Lodge, less than 2 hours from Boston - Gather under the stars by the fire pit & garden - Relax or grill on patio with woodland views - Enjoy a pet-friendly working homestead - Ski at nearby Ragged & Tenney Mountain - Explore hiking, biking & snowshoeing nearby at 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.

Indoor spacesFamilyLayout

4.99 out of 5 average rating, 337 reviews
Top guest favorite
Cabin in Campton

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!

FamilyKitchenTV

5.0 out of 5 average rating, 215 reviews
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

Newfound Lake Log Home | Hot Tub & Lake Views

Escape to Eagle Ridge, a Top 1% Airbnb log home overlooking beautiful Newfound Lake and featured in Log Home Living Magazine. Relax in the private hot tub, enjoy spectacular lake and mountain views, visit the Hebron town beach less than 1/4 mile away, or unwind by the fireplace. Set on 3.5 private acres, Eagle Ridge accommodates up to 6 guests with three bedrooms and two full baths. Enjoy central A/C, a screened porch, large patio, gas grill, high speed WiFi and whole house generator.

Indoor spacesFamilyDecor

4.99 out of 5 average rating, 184 reviews
Superhost
The exterior of a two-story house is displayed, featuring a brown wooden façade and a large deck with a welcoming entrance. Two garage doors are visible beneath the deck, alongside a landscaped area with greenery, and a driveway leads to the home.
Home in Ashland

Quiet and large Squam Lake House. Lake Region

Squam Lake, large family friendly house, 40'x50' deck with great 20'x20' screened-in section, hot tub (seasonal), lots of hiking trails local, great Foliage, Many Lakes Region attractions close. Foosball, corn hole, movie room, games, etc. Mini splits for AC and heat in all bedrooms and common area. Short walk down the road to a shared separate 40' Beach with swim docks and kayaks (5 min walk). Close to many ski mountains and other winter activities. Loon, Waterville, Gunstock, etc.

KitchenIndoor spacesGrill

4.91 out of 5 average rating, 312 reviews
Top guest favorite
The studio apartment features a queen size bed with a striped duvet and two large leather chairs. A wooden desk is positioned near a window, while the warm wooden floor adds to the inviting feel of the space.
Apartment in Wakefield

Clean, quaint studio apartment on small farm

Enjoy the Old Farm cottage, a studio apartment on our small homestead in the beautiful Lakes Region. It’s a perfect spot for couples, small families, or traveling nurses. We are within 20 minutes to many beaches, including Lake Winnipesaukee, and provide easy access to head south to the ocean or north to the mountains. You will have your own separate parking/entrance, but are welcome to enjoy our cozy fire pit, stylish treehouse, and backyard access to the network of snowmobile trails.

FamilyKitchenNearby

4.98 out of 5 average rating, 127 reviews
Top guest favorite
The exterior of a two-story apartment is shown, featuring a welcoming porch with red accents and greenery alongside a gravel pathway. A red barn is visible nearby, complemented by lush trees in the background, enhancing the peaceful, natural surroundings.
Apartment in New Hampton

Cozy Post and Beam, New Hampton, one mile off 93

Beautiful, cozy, two-story post and beam private apartment at rear of historic home includes large southern exposure picture windows in living room and master bedroom, looking out on private woods and barn, as well as private porch entrance. One mile off I-93. Easy to Newfound Lake, Bristol, Meredith, Lake Winnipesaukee, Plymouth, Ragged Mtn. Resort. TV in living room has Netflix and Sling. No smoking or vaping on property. Open flame only away from building structure.

KitchenFamilySkiing

4.98 out of 5 average rating, 189 reviews
Guest favorite
A modern two-story home is surrounded by green lawns and tall trees. It features a mix of white and dark exterior elements, with large windows allowing natural light. Soft outdoor lighting highlights the landscaped area, creating a serene evening ambiance.
Home in Thornton

Luxury Retreat in the Mountains! Gas Fireplace

Welcome to the White Mountains! Enjoy winter skiing , direct access to snowmobiling, and explore the mountains and rivers, or golf at nearby Owl's Nest in the summer. Our brand new designer luxury home has been thoughtfully designed with guests in mind, featuring all of the comforts of home. Centrally located between Loon Mountain and Waterville Valley, the home is situated to serve as your gateway to year round recreation in the White Mountains. The amenities are endless!

KitchenFamilyAccuracy

4.91 out of 5 average rating, 103 reviews
Top guest favorite
Cabin in Conway

Modern A-frame w/ Mountain Views - North Conway

Welcome to our cozy 3-bedroom A-frame cabin, nestled in the heart of North Conway. Originally built by our grandparents in the 1960's, this A-frame serves as the perfect home-base for adventuring and exploring all that the White Mountains have to offer; skiing, snowshoeing, snowmobiling, hiking, biking, breweries, dining, floating the Saco, leaf-peeping and the like!

KitchenIndoor spacesQuiet

4.98 out of 5 average rating, 221 reviews

Popular amenities for Ashland family-friendly rentals

When is the best time to visit Ashland?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$66,329 GYDG$66,329 GYDG$59,633 GYDG$59,633 GYDG$65,492 GYDG$68,212 GYDG$72,606 GYDG$70,513 GYDG$60,051 GYDG$65,492 GYDG$62,772 GYDG$66,329 GYD
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