
Holiday rentals with a kayak in Great Barrington
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Top-rated rentals with kayak in Great Barrington
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House rentals with a kayak

Lakefront close to ski & shopping
GO TO COPAKE LAKE!!! This past weekend my best friends and I rented out Sara & Mikes place to celebrate my bachelorette. It was nothing short of a dream. Our breaths were taken away the moment we walked into the house and saw the view of the lake. The house was cozy with beautiful decorations and we were supplied with plenty of amenities, we especially could not get over the amount of floaties, kayaks, and SUPs available to use in the boathouse! Our lake day on Friday was paradise, then on Saturday we ventured out to Hudson to shop, enjoy local breweries, and make our own candles and perfumes at Poured Candle Bar. Only a 25 minute drive from Copake Lake - perfect. Our last day on Sunday we went to Kaaterskill falls, the highest cascading waterfall in New York State. This weekend was quintessential and I am so glad I found this gem of an Air BnB. We cannot wait to be back! Thank you, Sara & Mike!

Everything on one floor 2 Bdrm/1.5 Bth & Pets Ok
We had a wonderful stay at Allie's cottage on the lake! The home was just as described, super clean with more than everything we needed for a great stay! My husband loves to cook and the kitchen was beautifully stocked and organized. There is so much to do right at the house, we ended up spending most of our time enjoying the lake and the huge yard! Such a wonderful Airbnb with thoughtful touches (welcome basket), yard games and kayaks. So nice to feel right at home! We only wish we would have stayed longer! Thank you for sharing your beautiful cottage on the gorgeous lake!

Escape to Lakefront Leisure—Amazing views!
We had the BEST TIME at this fantastic Lakeside house in Valatie! The house itself has 3 good bedrooms – 2 large bedrooms upstairs with a nice bathroom and tub. The downstairs has the other cute bedroom, another full bathroom, a good sized kitchen open to a great and large living and dining area. The VIEW from the main room is stunning and was our ‘TV’ for the week. The lake is just gorgeous! It has a little dock with kayaks and plenty of nice seating and lounge chairs. It’s great to have a full grass lawn ! The pups loved the house and the yard and the lake! The house was super clean and roomy but cozy in it’s feel. So many great little towns nearby – it was just the perfect house to get away from the city! The community was chill, even tho it was Memorial Day weekend. Thanks to Michael who was super responsive (not that we needed anything!) but if we had a question. Etc. Thank you Michael ! We hope to be back for another visit !!!

Twin Island Lake House • Hot Tub
We had a wonderful stay at this location during my daughter’s graduation from Bard College. The location has beautiful views of the lake and the layout of the property was perfect for the family to gather and celebrate, while also giving everyone the space for their own quiet time or rest. I would definitely recommend this location and hope to have the opportunity to stay again.

Private Lakehouse in the heart of the Berkshires
We had a lovely thanksgiving getaway at Christopher's place. The neighborhood was blanketed in snow turning it into a winter wonderland. The house was cozy, and we especially enjoyed the sun room with its beautiful views. Christopher was very responsive the entire time. Thanks for a great stay!

Direct Lakefront Home on Otis Reservoir Giant Yard
Beautiful house and great location right on the lake. With the large yard there was plenty of space for outdoor activities! House was very clean and spacious.

Cozy, peaceful lake house close to Jiminy Peak
We loved staying in this lovely cabin right on the lake. It was spacious, comfortable, private and so peaceful. Wonderful stay! We will be back for sure!

Artsy lake house on an island
We had a great time in Vladimir & Annie’s house. The house was clean & comfortable. The balcony of the lake’s view was amazing. We spent a fantastic time by having some morning breakfast on it and listening the birds songs… Special thanks for their flexibility with checking in & out. Highly recommended this house for our friends and family and looking forward to be back 😊
Cottage rentals with a kayak

Lakefront Retreat on Robinson Pond
The house and location are beautiful with direct access to the lake and an amazing view. The house is comfortable and well appointed. We loved the canoe! Vince and Natasha are great hosts, very responsive and helpful. Would definitely recommend this house and hope to stay again sometime.

Cottage with Private Deck on 8 acres of Woods
The stay at Ashlie’s was just perfect. The cabin is so intimate and secluded, but very close to everything you might wanna check out! Ashlie was very friendly, I would definitely stay again!!

Lake Front Cottage with Sun Soaked Terraces
The waterfront property with kayaks was the winning touch for us. In a quiet neighborhood with a friendly neighbor and plenty of birds to enjoy, it was a great escape from the city. Unrelated, we were a bit surprised at the prices of everything in the area, but maybe that’s just the spread of the Hudson draw.

Pet friendly Cottage on Lake; Hike, Swim, Kayak
Loved the quick weekend getaway from the city! Wanted somewhere we could stretch out into.. which Ayren’s house fully is.. loved playing the many board games provided and watching movies in the late evenings.. plus a few walks down to the lake and drive to town which is less than 15 min away.. A very communicative host with clear instructions and well laid out amenities and basic kitchen condiments.. Thanks again for a great weekend !

LAKE COTTAGE WITH HOT TUB - PAINTED TURTLE
Thank you Ellen for the easeful stay at your cottage with clear instructions. The surroundings are beautiful. We saw an eagle at the lake!

Romantic House on a Magical Lake
Comfortable and clean with beautiful scenery - on clear days, you get a Mountain view across the lake! Highly recommend.

Wildlife Lakeside Cottage; views/wildlife
This is a beautiful and peaceful cottage with easy access to shops and restaurants in the area. It was perfect for a sisters weekend. Highly recommend.

A Magical Spot on Little Robin Lake
Truly a magical spot--in October, the fall colors. Any time, the lake view, and the absolutely lovely sunroom.
Cabin rentals with a kayak

Simple, rustic, cozy get away
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!

Catskills Lake Cabin on 100 Wooded Acres
Great little cabin in the woods. This was exactly what I was looking for. Quaint, quiet, and located on a lake.

Modern hilltop chalet-style cabin @ Copake Lake
Had a great long weekend on Copake Lake! Amazing kitchen, multiple outdoor spaces for relaxing, and honestly the best mattress I’ve ever experienced in an AirBnB. Tobye was very responsive during our stay and made sure everything went smoothly. Thanks so much!

Rustic Cabin+ Private Beach Pond, Stars & Wildlife
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!

Secluded luxury: modern riverfront fishing cabin
My husband and I spent a long weekend at the cabin for our 10th Anniversary and we had the most peaceful, relaxing stay. The location is impeccable - very private, beautiful setting, close to nearby cute towns. We loved falling asleep listening to the creek and seeing the fireflies over the water. The cabin is adorable and well appointed. Finally, Sam and Catherine could not have been better hosts- very easy to communicate with, reached out with tips, and our dogs enjoyed running around together. We will absolutely be back!

Private Woodstock Getaway w Hot Tub
We had a wonderful stay at Marta's house. Everything was spotless, well cared for and thoughtful. The check in process was so simple and the house rules were easy to follow. The record collection was such a nice touch, especially on a rainy Saturday afternoon and the basement with a full media setup and games was perfect for a Saturday night in. The beds were comfortable, plenty of towels and amenities and the hot tub was great as well! The location was also great! Nothing bad to say about this amazing little spot :-)

Charming Lakefront Cabin with Hot Tub
We had a great time here with our 9 month old baby. The pictures don’t do the house justice. Access to the lake for swimming and kayaking and the facilities (pools, beach, basket ball and tennis court) make this a great place for an active vacation. The house has everything you need to travel with a young child (toys, changing table, pack ‘n play and even black out shades). The towns of Athens and Coxsackie are a few minutes away and have decent food and drink options. We would love to come back!

Lakeside Cottage: Boulder's Bluff
we had a wonderful stay with Ed! private lake, extremely peaceful. had fun taking the row boat out and cruising around fishing. Very little preditoral fish wich resulted in massive crappy and bluegill so we still had fun!! Ed was a great host, very responsive and even surprised us with a lil treat for our anniversay. keep in mind it is a lake house so thier were Lots of bugs but would absolutely recommend this location.
Quick stats about holiday rentals with a kayak in Great Barrington
Total rentals
20 properties
Nightly prices starting at
₹2,591 before taxes and fees
Total number of reviews
1.3K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Hunter Mountain
- Six Flags New England
- Thunder Ridge Ski Area
- John Boyd Thacher State Park
- Albany Center Gallery
- Bushnell Park
- Jiminy Peak Mountain Resort
- Taconic State Park
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Zoom Flume
- Windham Mountain
- Kent Falls State Park
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Norman Rockwell Museum
- Mohawk Mountain Ski Area
- Beartown State Forest
- Bright Nights at Forest Park
- Hartford Golf Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Hunter Mountain Resort