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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$16,725 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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Superhost
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

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!

FamilyKitchenHospitality

4.94 out of 5 average rating, 154 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 spacesFamilyHospitality

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

Indoor spacesFamilyOutdoor spaces

5.0 out of 5 average rating, 102 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

FamilyKitchenCleanliness

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 spacesFamilyView

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!

Indoor spacesKitchenValue

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 spacesFamilyNearby

4.99 out of 5 average rating, 184 reviews
Guest favorite
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.

FamilyIndoor spacesView

4.91 out of 5 average rating, 312 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.

FamilyIndoor spacesAir conditioning

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!

Indoor spacesKitchenView

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!

Indoor spacesKitchenWalkability

4.98 out of 5 average rating, 221 reviews
Top guest favorite
The exterior of the farmhouse features a well-maintained white siding facade and a welcoming yellow front door. A neatly landscaped yard is present, showcasing a mix of greenery and colorful flowers. Stone pathways and a low stone wall add rustic charm to the serene setting.
Home in Hebron

Hebron Historic Farmhouse

The farmhouse was built between 1795 and 1800 by the ancestors of the owner. We renovated it in 2017 and added 600 square feet to the original structure. The space combines the charm of the old with the convenience of the new. We know you will love this relaxing, quiet country setting with views over a lovely meadow to the south, and Mount Crosby to the north.

KitchenIndoor spacesHiking

4.98 out of 5 average rating, 302 reviews

Popular amenities for Ashland family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
A hobbit house is nestled among lush green trees, with a sloping earth-covered roof adorned with grass and ferns. The rounded front features a large window framed in white, complemented by a natural stone border, emphasizing the home's connection with its woodland surroundings.
Earthen home in Sanford

Luxury Year-round Hobbit House w/ private hot tub

Indoor spacesFamilyAccuracy

4.92 out of 5 average rating, 132 reviews
Superhost
A covered wooden deck is highlighted by a hot tub, steam rising gently from its surface. Cozy seating is arranged nearby, facing a lush green backyard surrounded by trees. Soft lighting is provided by string lights overhead, creating a relaxed outdoor space.
Home in Holderness

20mins BNH Pavilion- Large Home, Hot Tub, Firepit

FamilyKitchenNearby

4.88 out of 5 average rating, 105 reviews
Top guest favorite
Home in Sugar Hill

Sugar Hill Hideaway | Theater~Games~Hot Tub~Sauna

KitchenFamilySleep quality

4.97 out of 5 average rating, 109 reviews
Guest favorite
A spacious living area features comfortable seating arrangements including a sectional sofa and two armchairs. Natural light fills the room through multiple windows. A wooden coffee table sits at the center, surrounded by a textured area rug and light hardwood flooring.
Cabin in Campton

Spacious cabin in the heart of White Mountains

Indoor spacesFamilyGrill

4.91 out of 5 average rating, 127 reviews
Top guest favorite
An open-concept kitchen features a central island with a light-colored countertop. Wooden beams and paneled walls add warmth to the space. Large windows provide natural light, displaying views of the surrounding trees. A rustic dining table is positioned nearby, enhancing the inviting atmosphere.
Cabin in Thornton

3 BR Cozy + Renovated Cabin in the White Mountains

Indoor spacesFamilyTV

4.97 out of 5 average rating, 169 reviews
Top guest favorite
The living area features a stone fireplace as a focal point, accompanied by a comfortable dark sofa and armchair. A wooden coffee table is centered on a patterned rug. A flat-screen TV is mounted on the wall, while decorative accents like a wall-mounted ladder and artwork complement the space.
Condo in Campton

The Alpine Oasis

FamilyKitchenView

4.91 out of 5 average rating, 338 reviews
Guest favorite
A modern home is set within a lush green landscape, featuring a spacious deck that wraps around the building. The structure has large windows and a unique upper dormer, complementing the natural surroundings. A gravel driveway leads to the entrance, nestled in a tranquil wooded area.
Chalet in Campton

Large vacation home with a view

FamilyKitchenBiking

4.89 out of 5 average rating, 158 reviews
Top guest favorite
Tiny home in Woodstock

Luxury Tiny Home Getaway- IRIS Home

KitchenFamilySleep quality

4.98 out of 5 average rating, 103 reviews

Family- and pet-friendly home rentals

Top guest favorite
A well-maintained outdoor area features a stone patio surrounded by colorful adirondack chairs in blue, green, purple, and pink. A circular fire pit sits at the center, with a scenic view of the tranquil water and lush greenery in the background.
Apartment in Laconia

Waterfront on Opechee

FamilyKitchenAir conditioning

4.85 out of 5 average rating, 378 reviews
Guest favorite
Cabin in Campton

Cozy Cottage w/ Mountain Views & Two Outdoor Decks

Indoor spacesFamilyGetting around

4.9 out of 5 average rating, 214 reviews
Top guest favorite
A red cabin with a sloped roof is situated among tall trees adorned with autumn leaves. The front porch features white railings and a welcoming wreath on the door. A grassy area surrounding the cabin extends into a natural wooded landscape.
Home in Thornton

The Little Red Retreat - No Adt. Cleaning Fee

KitchenFamilyDecor

4.99 out of 5 average rating, 132 reviews
Guest favorite
The exterior of the cabin is framed by tall trees, showcasing a wooden facade and a covered porch. Two rocking chairs are positioned on the porch, while a large boulder and log stumps are visible in the grassy yard.
Home in Thornton

The Niche...crafted & forged

FamilyIndoor spacesAir conditioning

4.93 out of 5 average rating, 637 reviews
Guest favorite
A three-story lodge is nestled among lush greenery, featuring a spacious balcony with wooden railing. Natural stone leads to the entrance, framed by trees, emphasizing the serene woodland setting. Sunlight filters through the leaves, brightening the facade.
Home in Campton

Come in & Cozy up in Waterville Valley Estates

KitchenIndoor spacesBackyard

4.83 out of 5 average rating, 295 reviews
Top guest favorite
A covered porch offers a spacious outdoor setting with wooden rocking chairs and a bench. Scenic views of fall foliage and rolling mountains are visible in the background, providing a serene environment for relaxation.
Chalet in Franconia

Bear Ridge Lodge

Indoor spacesFamilyGrill

4.95 out of 5 average rating, 354 reviews
Top guest favorite
A warm and inviting living area showcases a stone fireplace framed by soft lighting. Two plush armchairs are positioned near a wooden coffee table. A cozy sofa adorned with a colorful blanket complements the wooden beams and walls, creating a tranquil atmosphere.
Cabin in Conway

The Conscious Cabin | Getaways + Retreats

KitchenIndoor spacesView

4.96 out of 5 average rating, 201 reviews
Guest favorite
Cabin in Sandwich

Coolidge Cabin

FamilyKitchenComfort

4.93 out of 5 average rating, 198 reviews

Family-friendly home rentals with a pool

Guest favorite
A cozy living area is illuminated by a lamp, featuring a comfortable sofa and armchair positioned around a coffee table. A television stands on a cabinet beside a stone fireplace. A dining table with wooden chairs is nearby, set against a floral window treatment.
Condo in Woodstock

Loon Mountain Area Rental - 2Br/2Ba

FamilyIndoor spacesHeating

4.91 out of 5 average rating, 243 reviews
Top guest favorite
A small red cabin with a green metal roof is surrounded by trees and rocks. Flower boxes are mounted under the windows, adding a touch of color. A patio area is visible nearby, featuring chairs and an umbrella for shade.
Tiny home in Thornton

Basecamp in the White mountains

Indoor spacesFamilyLocation

4.98 out of 5 average rating, 258 reviews
Guest favorite
A spacious living area is depicted, featuring a soft sectional sofa oriented towards a light-colored area rug. A modern kitchen with white cabinetry and stainless steel appliances can be seen in the background. Natural light floods through sheer curtains, enhancing the inviting space.
Condo in Laconia

Great night sleep is our specialty!

Indoor spacesKitchenAir conditioning

4.88 out of 5 average rating, 121 reviews
Top guest favorite
The living area is highlighted by a spacious sectional sofa and a wooden spiral staircase leading to the upper level. Natural light fills the space, accentuating the wooden flooring and cozy decor. A coffee table sits centrally, complementing the overall inviting atmosphere.
Condo in Bartlett

An Amazing Mountain Getaway!

FamilyKitchenAir conditioning

4.94 out of 5 average rating, 341 reviews
Top guest favorite
A cozy studio features a spacious bed with a checkered blanket, complemented by a neutral-toned ottoman at its foot. A small dining area and kitchen appliances are visible in the background, while soft lighting from bedside lamps creates a warm ambiance.
Condo in Lincoln

Loon Mountain Cozy Condo

FamilyKitchenAmenities

4.94 out of 5 average rating, 295 reviews
Guest favorite
A modern kitchen displays sleek cabinetry and a white countertop with three wooden stools positioned at the bar. Open shelving holds decorative items and kitchen essentials. Natural light enters through a window, while a microwave and dishwasher are conveniently integrated into the design.
Vacation home in Gilford

Marty'sBay-RetroCondo, Private Beach, Concert Path

Indoor spacesFamilyAir conditioning

4.93 out of 5 average rating, 322 reviews
Guest favorite
A spacious living area features a stone fireplace, surrounded by windows offering views of the snowy landscape. Natural wood accents and warm tones create a cozy environment, while a comfortable chair and woolen blanket invite relaxation.
Chalet in Campton

Mountain cabin with views, privacy, and more.

Indoor spacesFamilyParks

4.9 out of 5 average rating, 449 reviews
Guest favorite
A serene landscape features a vibrant sunset with shades of pink and purple reflecting on the surface of a lake. Mist envelops the mountains in the background, while a cozy building is nestled among lush greenery, creating a calm and peaceful setting.
Condo in Waterville Valley

1BR PetFriendly Condo W/ Pool. Tennis, Golf nearby

KitchenIndoor spacesBiking

4.89 out of 5 average rating, 101 reviews

When is the best time to visit Ashland?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$66,272 GYDG$66,272 GYDG$59,582 GYDG$59,582 GYDG$65,435 GYDG$68,153 GYDG$72,543 GYDG$70,453 GYDG$60,000 GYDG$65,435 GYDG$62,718 GYDG$66,272 GYD
Avg. temp-5°C-4°C1°C7°C14°C19°C22°C21°C16°C10°C4°C-2°C

Destinations to explore