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Vacation rentals with a kayak in Pioneer Valley

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Popular amenities for Pioneer Valley kayak rentals

House rentals with a kayak

Top guest favorite
Home in Granby
5 out of 5 average rating, 7 reviews

Lake house retreat Granby CT

DianeRating, 5 stars2 weeks ago
We were in the area to meet our son's fiance's extended family. Nathania's home was perfect! We had 7 adults and 5 little boys ages 9, 7, 5, 2, and 2 months. There was plenty of space to spread out and enjoy the time together. The hot tub, kayaks, and foosball table were especially popular! We were able to host a family dinner with guests which was wonderful. Everything we needed for preparation was readily available. Lots of beautiful parks, playgrounds, hiking areas. Plenty to keep everyone entertained! Nathania was extremely kind, gracious, and responsive to questions. We had absolutely zero issues. So grateful for a wonderful vacation. Thank you for sharing your idyllic home with us. We hope to visit again!!!
Guest favorite
Home in Becket
4.92 out of 5 average rating, 77 reviews

Little Longbow Lakefront Chalet

JensRating, 5 stars2 months ago
We went in February. Even with snow no problem to drive to the house. It is perfectly located. Remote but still close enough to everything. It is close to nice hikes. We would love to come back in the Summer or so as it has its own lake access. Kitchen is perfectly equipped if you like to cook. I always like if you have a separate dinning table - to eat, work, talk. All very clean with personal touches. We can just recommend the place highly. And Jaclyn was a great host - she gave us some flexibility with checkout but also was vey responsive. Thanks a lot!
Guest favorite
Home in Williamsburg
4.85 out of 5 average rating, 40 reviews

Cute and Cozy Lake Cottage

SharonRating, 5 stars6 months ago
Felt right at home at this cozy cottage! Pleased with the amenities, comfortable beds and great space to hang out in! Would definitely return!
Guest favorite
Home in Pittsfield
4.95 out of 5 average rating, 62 reviews

Family Fun at Hygge House on Richmond Pond

KatrinaRating, 5 stars6 months ago
The Hygge House was a lovely spot to spend my birthday weekend with my family and friends. We took advantage of so many close-by activities. But the highlights were at the house itself - paddling the canoe and kayak through the water, outdoor dinner, and s’mores at the fire pit. Jessica was also so easy to communicate with and super accommodating during a personal emergency we experienced. We loved our stay and would love to come back again soon.
Guest favorite
Home in Tolland
4.95 out of 5 average rating, 57 reviews

Spacious Home w/ Hot Tub in Private Lake Community

AuraRating, 5 stars2 weeks ago
The place was incredibly beautiful. The photos did not do it justice. It is in the middle of nowhere. Tina was very detailed in her instruction and one of them was that you must bring groceries because the closest grocery store is 30 minutes away. If you decide to book this place, read her detailed instructions. They are very helpful. The home offered a full kitchen which made it so easy for us to prepared our family's meals without struggling. The hot tub was such a treat. The basement had lots of games, a couch to launch and another TV. Perfect if you come with children. We were seven adults and we did not feel that we where on top of each other. The high ceiling truly made one of our boys (the giant) feel at home. Even the basement had a high ceiling. Pretty cool. Tina was incredibly nice and flexible. Check in is at 4 pm and we arrived earlier. We decided to contact her to see if it would be okay to check in earlier and she accommodated us. Thank you soooo much.
Guest favorite
Home in Becket
4.93 out of 5 average rating, 29 reviews

Lakefront Cottage on Private Beach

DaveRating, 5 stars5 months ago
Daphne is a thoughtful and wonderful host. The property was clean, comfortable and very well appointed with everything I would need, especially in the kitchen. I highly recommend this 5-star property. It is quiet, peaceful and full of nature everywhere the eye can see.
Guest favorite
Home in Wilmington
4.88 out of 5 average rating, 105 reviews

MtSnow * HotTub * Pool * Air Hockey * PingPong * Darts

JamesRating, 5 stars2 weeks ago
Place was great! Less than 10 minutes to Mount Snow. We had fun playing ping-pong, air hokey, pool, and darts! Relaxed by the wood burning stove. Lots of rooms and beds.
Guest favorite
Home in Sturbridge
4.96 out of 5 average rating, 168 reviews

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

JillRating, 5 stars6 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!

Cottage rentals with a kayak

Top guest favorite
Cottage in Warwick
4.99 out of 5 average rating, 87 reviews

Corkscrew: Lakeside Cozy Cottage in Warwick, MA

FelixRating, 5 stars1 week ago
We spent a weekend in this beautiful house in early spring. The house is amazing and has everything you need. The view is amazing and the pond invites you to fish or watch birds. It‘s calm and relaxing. Would love to come back here soon and spend more time. Kelly and Claire have been amazing hosts and a nice contact.
Top guest favorite
Cottage in Orange
4.99 out of 5 average rating, 78 reviews

Lake House with view of mountain

JonathanRating, 5 stars7 months ago
Great Lake side cottage charm. Fully stocked kitchen. Lots of fun water toys to use. Great views and peaceful!
Guest favorite
Cottage in Becket
4.81 out of 5 average rating, 53 reviews

Cozy Cottage on the Lake

PaigeRating, 5 stars4 months ago
The cottage was easy to check into, clean, and very cozy. It was decorated for the holidays which was perfect for our weekend. We enjoyed the fireplace and the games in the cabin as well! I would consider coming back in the summer to enjoy the outdoor area and lake. Ann-Marie and Carl provided really helpful instructions on how to get to the house.
Top guest favorite
Cottage in Hinsdale
4.99 out of 5 average rating, 153 reviews

Cozy Cottage in the Berkshires

SteveRating, 5 stars6 months ago
Thanks for much for an amazing stay! Sonya took extra steps to ensure we enjoyed our time here. It was a cozy little cottage and the perfect little getaway. We will be back!
Guest favorite
Cottage in Holland
4.95 out of 5 average rating, 82 reviews

Cozy Lakefront Cottage

JohnRating, 5 stars6 months ago
Lovely rustic cottage on a picture perfect lake. Dawn was a wonderful host and made sure we had everything we needed to enjoy our stay. Will stay again!
Top guest favorite
Cottage in Vernon
4.97 out of 5 average rating, 108 reviews

Vintage Bolton Lake

JeffRating, 5 stars6 months ago
If you are looking for simplicity (which we were) this is the perfect place to. I’ve always wanted to stay at a lake house. We couldn’t have asked for more. Serene, tranquil, beautiful are the proper descriptions of the house and the area. We came to Connecticut to visit my daughter and family and they ended up coming to our place instead. Jason was extremely helpful when needed. We would definitely stay there again!
Top guest favorite
Cottage in Brimfield
4.98 out of 5 average rating, 66 reviews

Cheerful 2 bedroom cottage with lake access.

DonalRating, 5 stars4 months ago
This place is bright with lots of natural light. Well equipped with very nice sun room and patio. Close to Old Sturbridge Village where the Christmas show was excellent. We had a relaxing and cozy dinner at the Duck. Gwendolyn was a gracious host keenly attentive to our arrival, weather, comfort and more. You will enjoy the cottage.
Top guest favorite
Cottage in Holland
5 out of 5 average rating, 44 reviews

Blissfully Peaceful Cottage nestled on a lake

StephanieRating, 5 stars8 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!

Cabin rentals with a kayak

Top guest favorite
Cabin in Athol
4.99 out of 5 average rating, 68 reviews

Panoramic Sunroom | Soaking Tub | Modern Cabin

KevinRating, 5 stars2 days ago
Can’t say enough good things here. The location is amazing, the home is beautifully decorated. The sunsets are perfect. The hosts are there if you need anything and not if you prefer. Incredible value for the experience. We will be back !
Top guest favorite
Cabin in Whitingham
4.99 out of 5 average rating, 105 reviews

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

KaitlynRating, 5 stars2 months ago
This was our 2nd time staying at Brian's place, the home is perfect for a larger group and has so many toys for the kids, they LOVED it! Everything is very clean, and the kitchen has all the pots/pans needed for cooking. In Feb there was so much snow we got to go sledding in the front yard, and a few from our group made the trip to Stratton for the day. We love going to Wilmington for coffee/lunch. Planning to be back again in 2026!
Guest favorite
Cabin in Petersburgh
4.93 out of 5 average rating, 225 reviews

Cozy Retreat in the Trees

MoRating, 5 stars5 months ago
This place was perfect for a peaceful weekend getaway. On the chilly fall weekend the wood stove and sauna were much enjoyed. We hope to return!
Guest favorite
Cabin in Colebrook
4.93 out of 5 average rating, 92 reviews

Cozy rustic cabin with beach on pond with 7 acres!

Prafful SinghRating, 5 stars2 months ago
We really enjoyed our stay at the cabin. Our pets loved taking long naps by the fireplace. - clean place - responsive host - private and peaceful
Guest favorite
Cabin in Otis
4.88 out of 5 average rating, 51 reviews

Enjoy 43 Acres on Two Ponds!

RebeccaRating, 5 stars3 months ago
We came to Otis with our 3 young children with the plan for them to learn to ski at the nearby ski school/mountain. We had a wonderful time and John and Loren’s house was perfect for us. They are lovely, accessible and accommodating hosts! We had the good luck of a snowy weekend and the cabin and property were just gorgeous. The cabin is simple, but very comfortable and we enjoyed how cozy it felt. Our kids slept well and and had so much fun, so did we!
Guest favorite
Cabin in New Hartford
4.98 out of 5 average rating, 50 reviews

West Hill Cabin

ChrisRating, 5 stars1 week 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 Canaan
4.99 out of 5 average rating, 72 reviews

Beautiful Lake Front Cabin

LouiseRating, 5 stars8 months ago
Mary’s place is truly magical. It’s the perfect spot for a family to enjoy the lake and each other. Most of all, Mary and her family are exceptional people, and we enjoyed getting to know them and felt very lucky to be in their special spot. We cannot recommend this place enough!
Superhost
Cabin in Otis
5 out of 5 average rating, 4 reviews

Berkshires Lakefront Boho Modern Retreat

MelissaRating, 5 stars2 months ago
What a beautiful home in a gorgeous setting. We unfortunately got caught in a winter storm during our stay. Christina went above and beyond to make sure we were taken care of during the inclement weather. We will definitely stay here again!

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