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Vacation rentals with a kayak in Ashland

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Top-rated kayak rentals in Ashland

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Cabin in Bradford

5 out of 5 average rating, 4 reviews

Little Red Wing 50s Lake Cabin

Cozy 1950's waterfront cottage on Lake Massasecum! In the Winter - Skiing is close by. Snowmobiling, Ice Fishing, and Cross County Skiing are allowed on the lake. It’s very important to test the ice for safety. In the Summer - Power boats are allowed on Lake Massasecum and it is also the perfect place for canoes, kayaks, great fishing and bird watching! Three kayaks, one canoe, and one paddle board are available for use with cabin rental. Also comes with the use of a private swim platform.

Apartment in Fairlee

4.98 out of 5 average rating, 144 reviews

Kismet Cottage, Perfect for longer stays

Welcome to your home away from home! This charming, fully-furnished 1-bedroom apartment sits right on the lake, offering serene views and a peaceful retreat after a long shift. With four major hospitals located within a 30-minute commute, this is the ideal spot for traveling nurses looking for comfort and convenience. Everything you need is here from a cozy queen bed to a fully equipped kitchen and comfortable living space including a laundry room so you can stay fresh and ready for your shifts.

Home in Henniker

4.76 out of 5 average rating, 180 reviews

Year-round Water Views ,cozy house near ski resort

Look no further than our waterfront house in Henniker, NH! With a full kitchen, 2 bedrooms, and a large living/dining area with a panoramic view of the pond, you'll have everything you need to relax and unwind. And with pond access just a few steps away, you can easily enjoy activities like fishing, kayaking, and hiking. Want to explore the area? We're just minutes away from Pat's Peak Ski Area and the Contoocook river for white water kayaking. And don't forget to spend some time at Weirs Beach!

Home in Shapleigh

5 out of 5 average rating, 4 reviews

Lakefront Home with Sandy Beach! Kayaks, SUP, Peda

Welcome to The Lazy Loon on Square Pong! Wake up to the sounds of loons calling. This home is located on a large lot with about 100 ft of lake frontage. Square Pond is a spring fed body of water known for its sandy beaches, deep and clean waters, and great fishing! It is one of the largest lakes around, however very private due to no usable public boat launch. The expansive, sandy beach area offers a great space for games, grilling out, and relaxing. The large lakeside fireplace is a great spac

Cottage in Northwood

4.93 out of 5 average rating, 109 reviews

Cottage on the lake! Includes kayaks & rowboat!

Super cozy, beautiful cottage right on the lake & dirt roads. Yard: sitting areas, propane fire pit, fenced in yard. Inside includes reading areas, dvds, wifi, books, coloring books, puzzles, games. Enjoy the rowboat & kayaks or bring your own boat. We are on Antique Ally and State Parks are nearby (2 miles away). Enjoy a day at Chucksters, Concord, Portsmouth or the lakes region. Enjoy the LAKE LIFE! No animals (Health concern for cleaner) 4 adults or 2 adults 3 kids. Life jackets provided

Cottage in Fryeburg

5 out of 5 average rating, 14 reviews

Waterfront Cabin close to all the N Conway Fun

Best of both worlds ...lake and mountain fun!! Relax and play with family and friends at this peaceful spot on Lovewell Pond. Sitting on your own 110 feet of waterfront with kayak access right into the Saco River. All this and just minutes to the all the action in North Conway and the Maine lakes region …shopping, restaurants, and mountain fun! Weekly rentals only! 1 King, 2 Queen Access to 4 kayaks/paddleboard Firepit & Grill BYO boat or rent ours, jet ski available to rent as well

Cottage in Wolfeboro

4.89 out of 5 average rating, 76 reviews

🌟Winni Cottage beach, dock, kayaks, SUP & more! 🌈🍸

Great Wolfeboro Winnipesaukee waterfront cottage on Back Bay Wolfeboro. Includes 5 kayaks, 2 canoes, paddle board & row boat ! 3 bedrooms, indoor and outdoor hot showers! Large deck and big grassy lawn and camp fire! Min of 3 nights, weekly in summer. Lovely protected bay, great for novice paddlers. 40 ft dock, beach area. Swim platform, great for swimming to from dock. Bring your own boat or rent one! Walk to town in 5 mins, bring your bikes, great bike trails! Very relaxing quiet spot!

Cottage in Middleton

4.97 out of 5 average rating, 152 reviews

Beautiful Lakeside Cottage

Beautiful, quiet and secluded lakeside cottage. Enjoy amazing sunsets on our pristine lake. Swim, kayak, fish or just relax and take in the natural beauty. COVID UPDATE: We know everyone has different levels of concern regarding the virus. Please know that while we feel our sanitation and cleanliness of the Cottage is exceptional, we have doubled our efforts providing multiple cleanings between guests. This is a NON-SMOKING property. We are sorry, but we cannot accommodate pets.

Cottage in Parsonsfield

4.87 out of 5 average rating, 146 reviews

Riverpine Retreat - clean&bright waterfront home

Tucked away in a small town, minutes away from the New Hampshire border, located 2 minutes off of rt. 25 (direct route from Portland ME to NH) The ultimate family or couples getaway. Plenty of room in the back yard for any and all yard games, while also enjoying the firepit, "game shed" and 75ft of water frontage where you can swim, fish, or launch your kayaks from the dock into the Ossipee River. Wireless internet is available and reaches the back yard. The 'cabin' has 2 bedrooms.

Home in Milton

5 out of 5 average rating, 29 reviews

NH Lake House w/Private Beach, Hottub, & Lg Deck

Perfect for family or friend getaways. Privacy, luxury, and abundant amenities. - Formal open-concept living room & entertainment rooms - 120ft covered deck overlooking lake - Remodeled modern kitchen - Private beach (big enough for volleyball games!) - Walkout finished basement (with bar) - Tiki Bar on beach - 8-person outdoor hottub to watch sunsets - 50ft dock for large boat - Firepit, kayaks - Windows throughout house; every room has a terrific view of the water & sunsets.

Cottage in Croydon

5 out of 5 average rating, 10 reviews

Charming Lakefront cottage with beautiful views

Make memories with family or friends at our perfectly situated waterfront getaway. Enjoy the tranquility of waking up to peaceful mornings with a cup of coffee on your bedroom balcony. Take a leisurely tour of the lake in our kayaks or paddleboat. In the evenings, enjoy toasting smores on the camp fire. Our spacious dock is great for fishing or sitting in the Adirondack chairs with your favorite beverage. We look forward to offering our guests a vacation to remember.

Cottage in Middleton

4.96 out of 5 average rating, 168 reviews

☀ Fox & Loon lake house: hot tub/pedal boat/kayaks

Escape to a peaceful, lakeside retreat with a secluded sun-lit deck and private dock with incredible views of Sunrise Lake, plus a 4-person hot tub, and seasonal amenities like a pedal boat, two kayaks, a SUP board, gas fire table, central A/C, a pellet stove, and snowshoes. Enjoy nearby activities like hiking, leaf peeping, skiing, and visiting scenic towns, local vineyards and breweries — or simply relaxing in a beautiful lakefront setting!

Vacation rentals for every style

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Popular amenities for Ashland kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in Northwood

4.94 out of 5 average rating, 17 reviews

Lakeside cabin w/ beach & dock

Home in Wakefield

5 out of 5 average rating, 21 reviews

In the Trees - NH w/ Lake Access

Home in Laconia

4.92 out of 5 average rating, 236 reviews

Waterfront w firepit, game room, close to gunstock

Home in Alton

4.89 out of 5 average rating, 145 reviews

Ice runway is open & right in front of our house!

Home in Barnstead

4.89 out of 5 average rating, 119 reviews

Lakefront home /3BR 2BA/ Dock/ Game room/ Garage

Home in ENFIELD

4.93 out of 5 average rating, 41 reviews

Home overlooking Mascoma Lake, Dock, Boat Slip

Home in Wakefield

4.88 out of 5 average rating, 16 reviews

Lakefront Retreat! Dog Friendly!

Home in Wakefield

5 out of 5 average rating, 8 reviews

The lake at your back door!

Cottage rentals with a kayak

Cottage in Conway

4.89 out of 5 average rating, 108 reviews

Cozy Pondside Retreat with direct water access!

Cottage in Alton

4.98 out of 5 average rating, 120 reviews

“Stay Awhile in the Lake's Region”

Cottage in Alton

4.91 out of 5 average rating, 11 reviews

The Lakeside Cottage

Cottage in Thornton

4.95 out of 5 average rating, 149 reviews

Cottage with antique charm view & river HSI Wi-Fi

Cottage in Springfield

4.97 out of 5 average rating, 78 reviews

Kolelemook Cottage!

Cottage in Conway

4.94 out of 5 average rating, 325 reviews

20ft from the Water with Mountain View!

Cottage in Gilmanton

4.96 out of 5 average rating, 112 reviews

Minutes to Gunstock MT - Family Lakeside Getaway

Cottage in Freedom

4.79 out of 5 average rating, 465 reviews

Lakefront, Beach Private, Amazing Views, & pets!

Cabin rentals with a kayak

Cabin in Andover

4.94 out of 5 average rating, 108 reviews

Little House on the Lake in the Forest

Cabin in Holderness

4.86 out of 5 average rating, 102 reviews

Beautiful private cabin on Big Squam Lake

Cabin in Barnstead

4.95 out of 5 average rating, 204 reviews

Scenic Lake and Ski Chalet: Hot Tub & Dreamy Views

Cabin in Conway

4.96 out of 5 average rating, 137 reviews

The Conscious Cabin

Cabin in Fairlee

4.95 out of 5 average rating, 132 reviews

Fairlee Log Cabin

Cabin in Sunapee

4.97 out of 5 average rating, 116 reviews

Cozy waterfront cabin Perkins Pond

Cabin in Warren

4.91 out of 5 average rating, 100 reviews

Breezy Moose - A Frame Cabin/ Pet friendly

Cabin in Madison

4.91 out of 5 average rating, 120 reviews

Bear Cabin

Quick stats about vacation rentals with a kayak in Ashland

Total rentals
40 properties
Nightly prices starting at
G$27,161 GYD before taxes and fees
Total number of reviews
550 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Wifi availability
40 properties include access to wifi

Destinations to explore