Vacation rentals with a kayak in Hillsborough County

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Hillsborough County

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Guest favorite

Home in Derry

4.91 out of 5 average rating, 129 reviews

Sanctum by the Lake

Looking for a place to bring the family, or a get-a-away with friends? This is it! From the light and airy design that makes it feel like home to the large pool, hot tub, and lake access, The Sanctum by the Lake has everything you need for a great stay. It is a short 100 yard walk from the lake and a quick drive to Canobie Lake Park and Manchester Airport, 45 minutes to Boston or the NH Seacoast, close to the Lakes Region, White mountains, and great skiing spots as well as the famous NH Outlets.

Superhost

Home in Henniker

4.75 out of 5 average rating, 176 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!

Guest favorite

Cabin in Henniker

4.96 out of 5 average rating, 135 reviews

The SugarShack at Sweetwater

Welcome to our off-the-grid cabin, sleeping 2-4 people with an upstairs loft & downstairs custom Murphy bed. It's equipped with lights, mini-fridge, Bluetooth speakers & an indoor/outdoor bar. Outside you'll find a private fire pit & charcoal grill, a shared outdoor kitchen pavilion w/ gas grill (stocked with cooking supplies) & the outdoor bathroom w/ a real flushing toilet, sink and outdoor shower. Access the Tooky River just steps away and enjoy plenty of space, privacy & beautiful scenery!

Guest favorite

Guest suite in Milford

5 out of 5 average rating, 85 reviews

New England Village Luxury Studio

Kick back and relax in this stylish studio! Our house is in a quiet neighborhood of older homes surrounded by woodlands yet conveniently located downtown, a half mile from our village green (Milford Oval). A short stroll over the river will take you to cafes, restaurants, pubs with live music, post office, library, shops & useful stores such as Rite Aid. Whatever brings you…business, skiing, hiking, antiques, a family gathering or a romantic weekend away…we are looking forward to hosting you!

Superhost

Guest suite in Merrimack

4.86 out of 5 average rating, 142 reviews

Mini-Apartment in Quiet Neighborhood

Located in a quiet, secluded neighborhood, yet only 15min from Nashua and Manchester--you'll be close to everything, yet away from it all. This is the perfect spot for business travelers, short-term medical professionals, or vacationers looking to experience NH. This peaceful spot has access to hiking trails, lakes, Merrimack Outlets, and more. Hosts are a friendly couple happy to provide any recommendations you need! PLEASE NOTE: You will hear active children upstairs during daytime hours.

Guest favorite

Cabin in Rindge

4.98 out of 5 average rating, 121 reviews

Lakeside Log Cabin near Mt Monadnock

Welcome to Cabin at the Cove! This spacious 4-bedroom 2-bathroom log cabin sleeps 10 + up to 2 dogs. The cabin offers rustic charm with modern amenities and is located just a short 2-min walk to a private beach on Lake Contoocook! Vacation on a picturesque lake, hike to leaf peep from the top of beautiful Mount Monadnock, cross-country ski, or curl up with a book by the fire – there is something for everyone year-round. While only 90 minutes from Boston, it feels like a true nature escape.

Superhost

Home in Derry

4.88 out of 5 average rating, 446 reviews

Little Lakehouse, the Lookout

Cozy up during your next trip to southern New Hampshire! The Lookout, situated right next to a serene lake, boasts luxury and spectacular water views. It's a perfect place for a peaceful escape or chance to experience the wide variety of seasonal New England activities from swimming to leaf peeping to ice fishing. The Little Lake house is a short drive to Canobie Lake Park and Manchester Airport, and about an hour to Boston, the NH Seacoast, NH Lakes Region and the White mountains.

Guest favorite

Home in Henniker

4.93 out of 5 average rating, 142 reviews

The Farmhouse at Sweetwater

Welcome to Sweetwater Farm, a historical landmark in Henniker. Our family purchased the Farm in 2006 and recently decided to share it with others. The newly renovated 2 BR farmhouse sleeps 4-5 people. You'll have access to the grounds, including 1000 ft of frontage on the Tooky River (great for swimming, kayaking and fishing). We're also located just steps away from Pat's Peak Mountain. Our guests can also purchase our USDA certified beef and farm fresh eggs to enjoy during your stay

Guest favorite

Cottage in Weare

4.99 out of 5 average rating, 80 reviews

Cozy, lakeside cottage; gorgeous view from deck

Come and enjoy a relaxing stay at our peaceful cottage on Daniels Lake. The small, recently-renovated home is in a rural setting but close to restaurants, shopping, parks, ski slopes, golf course, lakes and quaint New England villages. The large deck has a gorgeous view of the lake. Four kayaks, two canoes, standup paddle board and pedal boat are available to use on the lake which is known for its good fishing. Two bedrooms, dining room and living room overlook the lake and woods.

Guest favorite

Home in Northwood

4.99 out of 5 average rating, 130 reviews

Pleasant Lake Paradise - Heaven with a hot tub!

If you’ve contemplated booking - do it now! Our home will be remodeled beginning in August 2025. We love our home away from home...with lake views, two bedrooms, 1.5 baths, and an expansive back deck with hot tub - our peaceful home on Pleasant Lake is sure to please. Boat, swim, kayak, hike, ice fish...or simply relax. In all seasons, this charming home has it all. And, we love your 4 legged friend! Dogs welcome. Looking to stay again? Message me for priority booking.

Guest favorite

Cabin in Winchendon

5 out of 5 average rating, 11 reviews

The little house on Mirror Pond

Escape to our fully renovated tiny pond house on the serene Mirror Pond. Perfect for up to 4 guests, enjoy swimming, kayaking, or floating on tubes. Unwind by the fire pit, barbecue on the deck, or cozy up by the fireplace currrently noy hooked up) with board games on cooler days. With great WiFi, it’s also ideal for a peaceful work retreat. Whether you're here to relax, or get some work done, this tranquil hideaway offers the perfect blend of adventure and relaxation.

Guest favorite

Vacation home in Derry

4.97 out of 5 average rating, 117 reviews

Little Lake House-Kayaking, Swimming & more

Welcome to our home away from home. This cozy lake get away just minutes over the border from Massachusetts is the perfect place to connect with friends and family. Enjoy days out on the water which is right outside your back door! Or nights at the fire pit enjoying the stars. We have wifi, tv w/ streaming services, laundry, a/c & heat, and kayaks to make your stay as comfortable and fun as possible. We're family friendly and have a crib for infant/baby.