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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 Belchertown
4.98 out of 5 average rating, 63 reviews

Moonstone Lake House – romance and serenity

EmilyRating, 5 stars3 weeks ago
We had a great time here, and the relaxed and eclectic decor was interesting and welcoming!
Top guest favorite
Home in Dummerston
4.99 out of 5 average rating, 346 reviews

Pinecone Pond

EugeneRating, 5 stars2 months ago
My family and I just returned home from a wonderful ski vacation! The home was just as pictured and the surroundings were absolutely beautiful!The house was immaculate and the ambiance was warm and welcoming. We had a great time skiing at Mt.Snow (30 minutes),exploring Brattleboro (12 minutes),preparing meals together and just spending quality time with each other! On another note….. Cat and Ed were very responsive and were always available if we had any questions! My family and I are already looking forward to returning next year ! Thank you again for EVERYTHING! Carol and Gene
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!
Top guest favorite
Home in Goshen
5 out of 5 average rating, 14 reviews

Waterfront Wonderland | Luxe Log Cabin (Sauna/Gym)

AshleighRating, 5 stars2 weeks ago
Wow, I can't recommend Elle's place enough! Beautiful setting and the cabin felt cozy but had more than ample room and privacy for our large party. Everything was spotless and the beds were very comfortable. Elle was a wonderful host and had a huge basket of snacks waiting for us! Checkout was a breeze. We were very appreciative that checkout did not include a list of chores to do! We also loved the sauna. 10 stars!!!
Guest favorite
Home in Becket
4.96 out of 5 average rating, 25 reviews

New Shaw Pond Skytop Retreat in the Berkshires

NancyRating, 5 stars4 months ago
We stayed here on our way to Stowe to break up our long drive with an 8 and 2 year old. It ended up being a wonderful mini trip that we didn't want to leave. The house exceeded our expectations in terms of quality, cleanliness, and amenities. And the location was excellent - about 10 to 12 min to the nearest grocery store and downtown with restaurants, Edith Wharton's estate about 20 min away, and Great Barrington/Stockbridge were easily accessible for day trips. We plan to come back for skiing, and to take advantage of the lake activities in the summer. The only downside was the busy road, as mentioned in the listing, but the traffic quieted down in the evening and it didn't affect our sleep at night with the bedrooms located in the back of the house (husband is a very light sleeper; we did bring and use sound machines just in case).
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 Wilmington
4.88 out of 5 average rating, 105 reviews

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

JamesRating, 5 stars1 week 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.
Top guest favorite
Home in Agawam
4.98 out of 5 average rating, 166 reviews

Sunrise on the Water's Edge - Riverside Bungalow

BrianRating, 5 stars2 days ago
Great time with friends here. Even on a rainy day sitting out on the enclosed back porch was beautiful.

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 stars3 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 stars7 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, 67 reviews

Panoramic Sunroom | Soaking Tub | Modern Cabin

KevinRating, 5 starstoday
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 stars1 month 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!
Superhost
Cabin in Ashford
4.85 out of 5 average rating, 78 reviews

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

AnaRating, 5 stars5 days ago
We enjoyed staying at this cabin very much! We didn’t want to travel far this time. Sometimes it’s hard to find places like this, in the early spring, without having to hike half way down south. Where we can enjoy the peace and quiet yet have a lake/beach etc, with decent weather. Joe’s cabin is very cool. If you enjoy traveling back in time, there are plenty of antiques all over the cabin!
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!
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!
Superhost
Cabin in Hinsdale
4.95 out of 5 average rating, 38 reviews

Relaxing Berkshire cabin on Lake Ashmere

BiancaRating, 5 stars9 months ago
Had a great stay here! Really enjoyed spending time in the lake, on the deck, and at the fire pit. Beds were pretty comfortable. As other reviews have noted, only one bedroom has a door and both have an opening into the downstairs so it isn’t the most private, but it worked fine for our stay. Would likely stay here again!

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