Holiday houses in Ashland

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Top-rated holiday rentals in Ashland

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A cozy sleeping area features a spacious bed positioned by large picture windows that frame the vibrant outdoor foliage. The wooden walls add a natural touch, while soft bedding is complemented by a warm throw blanket, creating a serene atmosphere for relaxation.
Tiny home in Dorchester
4.97 out of 5 average rating, 213 reviews

Trailside Stays - Tiny House in the Woods-Escape to Nature. Snow Owl

This charming and elegant little cabin will transport you into nature. The feeling of camping outdoors with indoor amenities. Part of the brand-new campsite, Trailside Stays that is conveniently located alongside the ski and mountain bike trails at Green Woodlands. This tiny house features 1 high quality queen-size bed, linens, kitchenette, large picture windows, bathroom with shower, heating and A/C, outdoor seating and grill top fire pit. Don't see your dates available? Check the other cabins!

Guest favourite
A cabin nestled among vibrant autumn foliage displays a charming exterior with a bright red roof. Surrounding trees showcase a mix of red, orange, and yellow leaves, highlighting the serene natural landscape. A well-maintained driveway leads to the welcoming entrance of the home.
Cabin in Holderness
4.98 out of 5 average rating, 43 reviews

Cotton Lake Cabin- Amazing Views of Squam & Mtains

Come enjoy amazing views in this uniquely peaceful and secluded hill-top cabin overlooking Squam Lake and surrounding mountains at the end of a dirt road with absolutely no neighbors in sight! A hiker paradise with your personal trail head right behind the cabin. You can walk down to the Lake in ~5 min and will have easy access to endless activities among which: - Ashland Beach on Little Squam (7-min drive) - Boat ramp and marina to rent a boat (~3-min) - All the Whites have to offer (~25min)

Top Guest favourite
A welcoming exterior view of a vacation home surrounded by trees, featuring a spacious deck with seating. A circular fire pit with Adirondack chairs is situated in a gravel area, creating an inviting outdoor space for gatherings.
Home in Ashland
5 out of 5 average rating, 70 reviews

"HillTop Hideaway"

YOUR LAKES REGION/ MOUNTAIN RETREAT Welcome to your perfect getaway. This brand new home is nestled into the hillside of a private 5 acre lot. On a quiet back road in Ashland NH, you can enjoy all the Lakes Region and White Mountains have to offer. The home is tastefully decorated. Easy access to all the ski resorts and incredible hiking trails. Right off 93. 10 minutes to Holderness. 10 minutes to Plymouth with great shops and restaurants. This lovely new retreat is very family oriented.

Top Guest favourite
The exterior of a round, two-bedroom house is nestled among trees, featuring a wraparound deck accessible by a stone staircase. Large boulders and landscaped areas enhance the natural surroundings, with autumn colors visible in the foliage.
Cabin in Bristol
4.96 out of 5 average rating, 51 reviews

The Round House

~Experience The Round House. This unique 12 sided, 2 bedroom, 1 bath wooded home is nestled above the lake like a tree house with beautiful views of the crystal clear lake and mountains. Sit and enjoy the view on the wraparound deck. The patio has a fire pit and grill, perfect for a summer night. Limited access is available for kayak launch across the street or visit two town beaches within 1 mile of the house. Shackett store is just steps away serving fresh donuts and ice cream daily!

Guest favourite
The cozy bedroom features warm wooden walls accented by decorative wall art and vintage memorabilia. A spacious bed, layered with a soft blanket and decorative pillows, invites relaxation. Elegant curtains frame the windows, allowing natural light to filter in.
Cabin in Meredith
5 out of 5 average rating, 41 reviews

Lake Access | Prime Location | Designer Cabin

Enjoy a spotless, beautifully decorated stay at Camp Waukewan. This cozy cabin offers AC and a gas fireplace for year-round relaxation. Relax by the firepit with peek-a-boo lake views and stargazing. Direct access to Corridor 8 for snowmobiling. A short walk to a peaceful lake access point—perfect for kayaking, paddleboarding, or floating while enjoying loons and wildlife. Just 5 minutes to Waukewan Beach with boat launch & restrooms. Only 1 mile to Lake Winnipesaukee and Downtown Meredith.

Top Guest favourite
Cabin in Alexandria
4.98 out of 5 average rating, 313 reviews

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.

Top Guest favourite
Cabin in Campton
4.99 out of 5 average rating, 184 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 favourite
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.

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 favourite
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, 181 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 favourite
Dome in Sutton
4.96 out of 5 average rating, 151 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.

Top Guest favourite
A charming white house is framed by a large green tree. A gravel pathway leads to a deck with outdoor seating, while manicured shrubs and flowers enhance the front landscape. The home's exterior features large windows and a welcoming entrance.
Guest suite in Meredith
4.99 out of 5 average rating, 121 reviews

Charming Village Suite

This property is within a 4 minute walk from restaurants, Church Landing, parks, hotels & the town docks. It features private parking, a bocce court, decks, and a very central location. The suite has a large bedroom with queen mattress, private bath, and a large sitting room with YouTube TV, Netflix, and Apple TV. We provide towels, toiletries, and free wifi.

Popular amenities for Ashland holiday rentals

When is the best time to visit Ashland?

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Avg. price$377 AUD$386 AUD$373 AUD$346 AUD$369 AUD$427 AUD$438 AUD$427 AUD$396 AUD$409 AUD$341 AUD$356 AUD
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Ashland?

    Ashland has more than 50 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in cabin rentals in Ashland?

    Experience the best of Ashland with our cabin rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Ashland?

    Four-legged friends are welcome in Ashland. Choose from more than 50 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Ashland?

    Yes! Work meets play with ease at over 20 vacation rentals in Ashland featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do bed and breakfast rentals in Ashland have air conditioning?

    Absolutely! We offer over 20 bed and breakfast rentals with air conditioning in Ashland. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Ashland have a kitchen?

    Absolutely! We offer over 30 house rentals with a kitchen in Ashland. Enjoy a tailored experience with all the comforts you desire.

  • Do cabin rentals in Ashland have wifi?

    Absolutely! We offer over 10 cabin rentals with wifi in Ashland. Enjoy a tailored experience with all the comforts you desire.

  • Do bed and breakfast rentals in Ashland have free parking?

    Absolutely! We offer over 20 bed and breakfast rentals with free parking in Ashland. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Ashland

  • Total holiday rentals

    Explore 100 holiday rentals in Ashland

  • Nightly prices starting at

    Ashland holiday rentals start at $101 AUD per night before taxes and fees

  • Verified guest reviews

    Over 2,020 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    100 of Ashland holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Ashland rentals

  • 4.8 Average rating

    Ashland stays are highly rated by guests—averaging 4.8 out of 5!

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