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Vacation rentals with a kayak in Pioneer Valley

Find and book unique kayak rentals on Airbnb

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Popular amenities for Pioneer Valley kayak rentals

House rentals with a kayak

Guest favorite
Home in Woodstock
4.85 out of 5 average rating, 116 reviews

Secluded 2 Acre Lake Front Home!

PeterRating, 5 stars1 week ago
Beautiful place. We caught fish off the dock. Loved sitting in the kitchen,catching up with friends.
Top guest favorite
Home in Dummerston
4.99 out of 5 average rating, 347 reviews

Pinecone Pond

KathyRating, 5 stars2 weeks ago
We had the most lovely stay at Pincone Pond. The house is absolutely spotless and well stocked with everything you need in the kitchen, shampoo and condition in the bathrooms and throw blankets for the cool evenings. The house is so homey and comfortable and the grounds are stunning. Beautiful yard and pond which were well cared for. Catherine has thought of everything including chairs for sitting by the pond or fire pit. Just a lovely, peaceful spot.
Superhost
Home in Monterey
4.83 out of 5 average rating, 80 reviews

Rustic 3bd Lake Front Country Cottage

SarahRating, 5 stars1 week ago
Very rustic, private, peaceful kind of like a camp but with air conditioning and excellent wifi. Bald eagle sat over the lake outside. Kayaks were fun. Tons of great hikes and historical things to see. Town of Great Barrington and Sheffield have great antiquing both high and low end. I would go back any time.
Guest favorite
Home in Williamsburg
4.85 out of 5 average rating, 41 reviews

Cute and Cozy Lake Cottage

BarbaraRating, 5 stars1 month ago
While the weather was not optimal (sometimes western MA spring is slow to come), we loved the cottage. It is perfect for walking, hiking, reading and other quiet activities. But, you have access easily to Northampton or other local towns for a meal or night out. Debra was easy to reach but not at all intrusive. Check in was smooth. All in all, a lovely experience.
Guest favorite
Home in West Brookfield
4.89 out of 5 average rating, 66 reviews

Hillside Hideaway

JoannaRating, 5 stars2 weeks ago
What a gem of a place! Perfectly located to our daughter’s boarding school. We spent both parent’s weekends and graduation here, staying with multi-generations of our family. It has enough space in the great room for a small gathering. Just a wonderful spot that we highly recommend.
Guest favorite
Home in Otis
4.96 out of 5 average rating, 111 reviews

Direct Lakefront Home on Otis Reservoir Giant Yard

ChrisRating, 5 stars1 month ago
Adam's place was the perfect location for our annual spring fishing trip. Plenty of space for everyone to relax their own way let still be connected to the group. Kitchen is well equipped for anything you would want to cook with other extras like coffee maker and blender. It's a short walk to the docks which makes fishing for a full day convenient to take breaks / have lunch etc. The boathouse is a nice added amenity which allows storage of coolers, drinks and ice which is also very close proximity to the fire pit. We are already looking forward to next year's trip.
Guest favorite
Home in Sturbridge
4.96 out of 5 average rating, 169 reviews

Cedar Lake 3 Bed 3 1/2 Bath Home Sturbridge MA

JillRating, 5 stars8 months ago
This was our second time to stay. It had a gorgeous view surrounded by beautiful trees. It was so peaceful and relaxing with everything we needed. James is so easy to work with and very responsive. Highly recommended!
Guest favorite
Home in Holland
4.92 out of 5 average rating, 93 reviews

D. Chief's Lodge Cheerful Cabin at the Camp

DanielRating, 5 stars3 weeks ago
Susan was a great host. We loved kayaking on the grounds. Bed was very comfortable. Would stay again.

Cottage rentals with a kayak

Guest favorite
Cottage in Holland
4.91 out of 5 average rating, 44 reviews

The Maybrook: Lake & Sauna

DonnaRating, 5 stars1 week ago
This place was everything it was said to be. it was clean and very cozy. Kyle had a booklet with useful information about the cottage, restaurants and local attractions.
Guest favorite
Cottage in Warwick
4.95 out of 5 average rating, 38 reviews

By Still Waters Cottage

GilRating, 5 stars1 week ago
Just before we left for our short vacation, Daddy read to Mommy every night from a book about an enchanted April at the “San Salvatore” castle in Portofino, Italy. That was a magical place that touched the souls of its guests. So is the By Still Waters Cottage, which we now call “our San Salvatore” and plan to return to as soon as possible. --Sasha, a German Shepherd Mix rescue from Belarus; a world traveler, I look forward to frolicking again in Moore’s Pond.
Guest favorite
Cottage in Orange
4.99 out of 5 average rating, 78 reviews

Lake House with view of mountain

JonathanRating, 5 stars8 months ago
Great Lake side cottage charm. Fully stocked kitchen. Lots of fun water toys to use. Great views and peaceful!
Top guest favorite
Cottage in Otis
5 out of 5 average rating, 17 reviews

Lake Escape: Lakefront Cottage in the Berkshires

JeanneRating, 5 stars8 months ago
My husband and I had a wonderful stay. The cottage was clean and comfortable. The hosts thought of everything and made us feel right at home. We could not have been more pleased and would highly recommend this property.
Top guest favorite
Cottage in Brimfield
4.99 out of 5 average rating, 70 reviews

Cheerful 2 bedroom cottage with lake access.

KathleenRating, 5 stars2 weeks ago
This was the perfect spot for our mini vacation with our adult son and dog. The house was adorable and comfortable...the beds were especially comfy. The fenced in patio area and sun porch was so relaxing and although no one actually slept on it, the daybed was very comfortable as well. We enjoyed our day trip to Boston and multiple trips to Treehouse Brewery. Gwen's communication was awesome...such a terrific host! Hoping to stay again.
Top guest favorite
Cottage in Holland
5 out of 5 average rating, 44 reviews

Blissfully Peaceful Cottage nestled on a lake

StephanieRating, 5 stars9 months ago
What an amazing stay! The place had great games and the porch was such a treat. The view from the fire pit was so relaxing and we enjoyed toasting smores while overlooking the lake. We ended up taking the folding chairs and playing catch by the lake, which was only a short walk away. Robert was responsive when we asked where to get firewood. We also enjoyed the Sturbridge coffee house and Maine Lobster (we liked it so much, we went twice)! We ended up going to the farmers market and flea market, which were great finds. Overall, a great stay with the kitchen utensils, bathroom necessities that you’d need. Close by the lake and a great neighborhood!
Top guest favorite
Cottage in Wilmington
5 out of 5 average rating, 38 reviews

Emerald Cottage @ Harriman Reservoir

EvanRating, 5 stars3 months ago
We really enjoyed our stay at Michelle’s place. Overlooking a lake in a peaceful location, this was perfect for a small group looking for a reasonably priced Airbnb to stay while skiing at Mount Snow. The location was cool and I can definitely see this house being great for warmer seasons as well. One thing that stood out was the clarity of instructions provided by the host. Both the description of the property and what to expect, and the check in/out instructions are very accurate and helpful.
Top guest favorite
Cottage in Jaffrey
4.97 out of 5 average rating, 32 reviews

The Boathouse - A rustic and cozy lakeside cottage

CindyRating, 5 stars3 weeks ago
This was the perfect spot for us. The cabin was all we hoped for! Everything was so clean and well thought out. We felt at home immediately! Chris always responded to our questions. Honestly, I can’t think of anything that would have made it a better stay! If you are looking for an “in the woods” experience, this is the place!

Cabin rentals with a kayak

Superhost
Cabin in Otis
4.81 out of 5 average rating, 21 reviews

Simple, rustic, cozy get away

ChrisRating, 5 stars9 months ago
It was a perfect price. With the ABNB it was double+. I would rather pay John more for the one night personally, than what I did. And have done twice. I have always left the place the same or better than I found it. I understand the cleaning fee, but kills single fathers like me for a 1 night trip. That being said. Walker cabin is great! Kayaks, all safety gear, fully outfitted down to toothpicks, brushes, floss, ect. You think you forgot it. It’s there. Baby monitors!
Top guest favorite
Cabin in Athol
4.97 out of 5 average rating, 77 reviews

Panoramic Sunroom | Soaking Tub | Modern Cabin

GiaRating, 5 stars3 days ago
Amanda and Jake were so nice with us, they helped us a lot with everything we needed and even more, the place was clean, and with everything we could need, we would love to come back in the future !!
Top guest favorite
Cabin in Whitingham
4.99 out of 5 average rating, 107 reviews

Cozy Cabin ~16 Mi. to Slopes on 10 Acres of Woods!

CoreyRating, 5 stars3 weeks ago
Beautiful house, perfect for our family retreat. After another host cancelled on us last minute, we found Brian's place and were very happy we did! Brian was very responsive to our needs, and was very helpful throughout the weekend. the kids loved the game room, we set a new record on the Pacman machine. We made s'mores on the front porch in rainy weather, and visited some of the local breweries nearby. We were very pleased with the home, and it was perfect for our long weekend.
Guest favorite
Cabin in Colebrook
4.94 out of 5 average rating, 95 reviews

Rustic Cabin+ Private Beach Pond, Stars & Wildlife

EdwardRating, 5 stars2 weeks ago
Amazing cabin!! My third visit. Was there with friends for fishing and I love the cabin so much that I booked my anniversary weekend and my wife is also in love with the property. Relaxing Birding Fishing Kayaking Fire pit Romantic This place has it all! Book it now! You won’t regret it!
Top guest favorite
Cabin in Dummerston
4.96 out of 5 average rating, 50 reviews

Cozy Riverfront Cabin-Ski, Swim, Fish, Float, Hike

JanessaRating, 5 stars3 weeks ago
This was our 2nd time staying here and it was lovely! The house is clean and cozy. Great location by the river — lovely spot for an evening fire and morning coffee. Well stocked with kitchen essentials, towels, linens, etc. Thank you! We will be back!
Superhost
Cabin in Otis
4.87 out of 5 average rating, 54 reviews

Enjoy 43 Acres on Two Ponds!

PatrickRating, 5 stars1 month ago
We had a great stay for my daughter’s college graduation. Really enjoyed the house and fire pit. Thanks!
Guest favorite
Cabin in New Hartford
4.98 out of 5 average rating, 50 reviews

West Hill Cabin

ChrisRating, 5 stars2 months ago
Great location near West Hill Lake and Brodie Park; walking distance to public beach, playground, and more. The house is very clean and well provisioned. A great stay!
Guest favorite
Cabin in Otis
5 out of 5 average rating, 6 reviews

Berkshires Lakefront Boho Modern Retreat

LaurenRating, 5 stars6 days ago
Staying at this lake house was peaceful and lovely -- the house is updated, so clean, right on the pond and great for a family. Christina is such a responsive host. We can't wait to come back!

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