
Holiday rentals with a kayak in Ashland
Find and book unique kayak rentals on Airbnb
Quick stats about holiday rentals with a kayak in Ashland

Total holiday rentals
Explore 40 holiday rentals in Ashland

Nightly prices starting at
Ashland holiday rentals start at £96 per night before taxes and fees

Verified guest reviews
Over 830 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
40 of Ashland holiday rentals include wifi 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!
Top-rated rentals with kayak in Ashland
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

Luxury Year-round Hobbit House w/ private hot tub
Fern Hollow 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.

Holderness Hideaway 3BR/2BA Home near Meredith
Holderness Hideaway is the quintessential New Hampshire retreat—perfect for families or friends seeking peaceful escapes. Set back from the road with plenty of space to relax and unwind. It’s minutes from downtown Holderness and only 10 minutes to Meredith and Lake Winnipesaukee. Spend days boating on the lakes, hiking nearby trails, or exploring the Squam Lakes Science Center. Evenings are made for games, s’mores, and cozy nights by the fire. Experience the best of lake life and mountain charm!

Hill Studio
Take it easy at this unique and tranquil getaway. This former Architect’s studio has been set up as a one bedroom guest house. It is a wonderful spot to relax and snuggle up next to the fire with your favorite book, beverage, or a special someone. The studio is very private with only the trees or maybe a visiting moose to see in. We are 30 min. to Ragged Mountain and Newfound Lake. We have a friendly dog and preapproved well-behaved pets are welcome. An all-wheel drive car is needed in winter.

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.

Secluded Waterfront Retreat with Luxe Amenities
Welcome to Hawkins Point, a luxurious waterfront retreat perfectly situated between Lake Winnipesaukee and Squam Lake. Kayak, paddleboard and fish from the dock located on a private peninsula with 360 degree water views. No detail has been overlooked in this stylish, fully-stocked family-friendly home that comfortably sleeps 8. Elevate your stay! Our new concierge can book reservations, arrange transport, and stock groceries before arrival. Contact us after booking for a personalized quote.

Cozy Historic Home on Squam River
Welcome to our beautiful home in Ashland, NH! Nestled on a picturesque acre along Squam River, this cozy home with modern touches offers everything you need for a relaxing vacation no matter the season. Walking distance to restaurants, minutes to Squam and Plymouth State. 10 minutes to hiking trails and 30 minutes to major ski resorts. Keep a window open to hear a waterfall, dine outside and gather around a fire pit, or retreat to a renovated sugar shack. Our Ashland retreat has it all.

Waterfront Cabin on Berry Pond
Waterfront log home along picturesque Berry Pond close to route 25--hiking, skiing, fishing, kayaking, or relaxing on the deep porch with a cup of coffee. We have air conditioning in the summer and a double-sided fireplace for the cooler months. Fully stocked kitchen and dining room table with expansion boards for family dinners and card games--or go on the bug-free screened-in porch! Garage available to keep your toys clean and dry. Great value, traditional cabin style, and a cozy vibe.

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.

Charming Mountain View River Cottage w/ Pvt. Trail
Escape to our secluded cottage, where tranquillity meets adventure, & have access to towns in 10 min. Enjoy mountain views, private hiking/snowshoeing trails & the Pemi River. Unwind by the fireplace & enjoy a book from our library. Spend evenings by the fire pit, relax in the hammock, or swim in the river. Local hiking, skiing, golfing, and fishing spots offer outdoor activities. With HS Wi-Fi & a pet-friendly policy (pet fee $80), your stay is comfortable and convenient!

Lovely home, across from lake, walk to Meredith
Hilltop Lakeview Retreat is a quiet and private modern oasis! Across the street from Lake Waukewan and a short walk to Main St in Meredith, NH, this 4 bedroom 3.5 bath home sleeps 12! Well behaved dogs are allowed with a pet fee. A 3 minute drive gets you to the Meredith town docks and Hesky Park. Stroll through the local shops and visit the restaurants for a culinary delight. Take in the Meredith Sculpture Art Walk, or Weirs Beach is only a 10 min drive.

kids hidden room, firepit, Kayaks/Canoes, ev
Relax, recharge, reconnect. Whatever you are looking for from your stay, it would be an honor to host you in The Riverview Haven. Planning a vacation is a big decision but our goal is to do everything we can to create an unforgettable experience with your friends, family, & loved ones. Message us for local event information, trip planning and seasonal discounts! Kayla and Charlie.

New Home Discount! Lakefront|Dock|Fireplace|XBox
Lakefront 4BR home in Meredith, NH—perfect for families! Enjoy private lake access, a dock to bring your boat, fireplace, fully stocked kitchen, Xbox, washer/dryer, and a private office. Every bedroom has lake views; 3 open to a waterside deck. Minutes to downtown Meredith and the shops, ice cream, and dining. Relax, play, and make lifelong memories in the NH Lakes Region!
Popular amenities for kayak rentals in Ashland
House rentals with a kayak

20 Mile Bay - Tuftonboro - Lake View Pet friendly

Enjoy Fall Foliage at the Lake

Eagles Landing with Hot Tub, Boat Slip @ Braun Bay

Immaculate Lake House Perfect for Entire Family

Camp Oscar Waterfront Lake Winnipesaukee

Winnipesaukee Lakefront Luxury unit #4 w Hot tub

Luxury Lake House +Hot Tub! Waterfront Magic in NH

Gram's House
Cottage rentals with a kayak

Quaint lakefront; firepit, boat, kayaks, hammock

Lovely cottage on Sunrise Lake, Middleton, NH.

Large Private Lake House

Eclectic Lakefront Cottage on Great East Lake

Kolelemook Cottage!

Beautiful Lakeside Cottage

Smokey Pines Camp

Waterfront Cottage Private Dock | Kayaks | Rowboat
Cabin rentals with a kayak

Riverfront cabin between Portland & White Mtns.

Beautiful Serene Lake/Ski House with central AC

Breezy Moose - A Frame Cabin/ Pet friendly

Dreamy Lakefront: Hot Tub, Kayaks, & Kid-friendly

Cozy waterfront cabin Perkins Pond

The Conscious Cabin | Getaways + Retreats

Waterfront,Hot tub,Private dock,Freshly renovated

Little House on the Lake in the Forest
When is the best time to visit Ashland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £233 | £233 | £233 | £233 | £230 | £238 | £240 | £246 | £205 | £230 | £233 | £233 |
| Avg. temp | -5°C | -4°C | 1°C | 7°C | 14°C | 19°C | 22°C | 21°C | 16°C | 10°C | 4°C | -2°C |
Destinations to explore
- Rentals with lake access Ashland
- House rentals Ashland
- Family-friendly rentals Ashland
- Rentals with beach access Ashland
- Pet-friendly rentals Ashland
- Rentals with breakfast Ashland
- Bed and breakfasts Ashland
- Waterfront rentals Ashland
- Rentals with a kayak Grafton County
- Rentals with a kayak New Hampshire
- Rentals with a kayak United States
- White Mountain National Forest
- Squam Lake
- Story Land
- Weirs Beach
- Loon Mountain Resort
- Pats Peak Ski Area
- Mount Washington Cog Railway
- Snhu Arena
- Dartmouth College
- Cranmore Mountain Resort
- Tenney Mountain Resort
- Franconia Notch State Park
- Gunstock Mountain Resort
- Omni Mount Washington Resort
- Pleasant Mountain Ski Area
- Conway Scenic Railroad
- Ragged Mountain Resort
- Bear Brook State Park
- Diana's Baths
- Crawford Notch State Park
- Waterville Valley Resort
- Echo Lake State Park
- Attitash Mountain Resort
- Flume Gorge





