Holiday rentals with a kayak in Great Barrington

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Holiday House Rentals with a Kayak

Top Guest favourite
Home in Hillsdale
5 out of 5 average rating, 59 reviews

Lakefront close to ski & shopping

CayleeRating, 5 stars2 weeks ago
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!
Top Guest favourite
Home in Valatie
5 out of 5 average rating, 115 reviews

Escape to Lakefront Leisure—Amazing views!

BryanRating, 5 stars3 weeks ago
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 !!!  
Top Guest favourite
Home in Pine Plains
5 out of 5 average rating, 7 reviews

Stunningly Designed Historical Icon w/ Hot Tub

NataliaRating, 5 stars3 months ago
Still gleaming from an unforgettable stay at Willow Vale which is hands down a 5-star gem! The design of the house is one-of-kind where every detail piques curiosity and wonder. The library stole our hearts from the start, brimming with an extensive book collection and unique treasures. We sat by the fire here every night. The sunroom was the perfect daytime spot where we napped, worked, ate and played games. It’s impossible not to fall in love with the kitchen…we cooked almost every meal. Enjoying the hot tub under the stars was a highlight. We loved that there was a telescope and took advantage of it. The river was serene with a perfect swimming hole…and cold plunge! The house is secluded and there is so much to do nearby. It’s truly the land of hidden gems. Stissing House for dinner is a MUST. As their home might suggest, Matt and Whitney go above and beyond as hosts. They made this family vacation special for us in every possible way. We cannot wait to return!!!
Guest favourite
Home in Pine Plains
4.98 out of 5 average rating, 123 reviews

Twin Island Lake House • Hot Tub

KaiRating, 5 stars3 weeks ago
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.
Guest favourite
Home in Becket
5 out of 5 average rating, 14 reviews

Private Lakehouse in the heart of the Berkshires

AaronRating, 5 stars8 months ago
I want to say thank you to Christopher and his family for allowing my friends and me to stay in their home. it was clean, beautiful, serene and exactly what it was described to be. Christopher, your suggestions on golf courses for my friends and me were exceptional. I hope we were as good of guests as you were hosts!
Guest favourite
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.
Top Guest favourite
Home in Averill Park
4.96 out of 5 average rating, 163 reviews

Cozy, peaceful lake house close to Jiminy Peak

DaveRating, 5 stars2 weeks ago
The house was exactly as advertised. Clean and neat. Good supply of kitchen utensils, dishes etc. Appliances in good condition. Burden Lake is absolutely beautiful. An adult Bald Eagle flew right by our deck. And Kay's Pizza on the Second Dyke Rd is fabulous
Guest favourite
Home in Becket
4.92 out of 5 average rating, 26 reviews

Lakefront Jewel By: Evergreen Home

KimRating, 5 stars6 days ago
Great place to spend quiet time with loved ones and enjoy nature!

Cottages with a kayak

Top Guest favourite
Cottage in Nassau
4.97 out of 5 average rating, 32 reviews

Hook, Wine and Sinker!

CaylorRating, 5 stars1 week ago
Such a nice, quiet, cozy cabin. Truly does not feel like a cabin. The inside is modern and very clean. Surprisingly spacious! Layout is great. The back porch was the best part. We stayed during a rainy weekend, but sitting on the porch over looking the lake to the sound of the rain was beyond peaceful. Truly a hidden gem. I would stay here again and again! HIGHLY RECOMMEND!!
Superhost
Cottage in Kingston
4.8 out of 5 average rating, 173 reviews

Cottage with Private Deck on 8 acres of Woods

MattRating, 5 stars3 weeks ago
Cozy, quaint, cute space. Perfect for a couple or a single adventurer. Gorgeous location and amenities. Would happily re-book!
Superhost
Cottage in Copake
4.85 out of 5 average rating, 41 reviews

Lake Front Cottage with Sun Soaked Terraces

DanielRating, 5 stars2 months ago
It's hard to beat a place like this if you are looking for a peaceful, quiet, and comfortable stay. The lakefront backyard with kayaks, fireplace, heated porch with swing, and amenities to meet any basic need, made this a wonderful base for our group of four adults, a child, and furry friend to explore the area. It's a beautiful country/lake side escape a short drive from a number of villages and towns providing great eats, good shopping, and sightseeing. Highly recommend.
Guest favourite
Cottage in New Marlborough
4.9 out of 5 average rating, 39 reviews

Pet friendly Cottage on Lake; Hike, Swim, Kayak

KunalRating, 5 stars2 months ago
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 !
Superhost
Cottage in Red Hook
4.9 out of 5 average rating, 206 reviews

LAKE COTTAGE WITH HOT TUB - PAINTED TURTLE

JenniferRating, 5 stars3 weeks ago
Thank you Ellen for the easeful stay at your cottage with clear instructions. The surroundings are beautiful. We saw an eagle at the lake!
Guest favourite
Cottage in Ulster Park
4.91 out of 5 average rating, 180 reviews

Romantic House on a Magical Lake

VidhiRating, 5 stars3 months ago
Comfortable and clean with beautiful scenery - on clear days, you get a Mountain view across the lake! Highly recommend.
Guest favourite
Cottage in Lanesborough
4.84 out of 5 average rating, 279 reviews

Wildlife Lakeside Cottage; views/wildlife

SonyaRating, 5 stars1 month ago
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.
Top Guest favourite
Cottage in Otis
4.98 out of 5 average rating, 54 reviews

Berkshire lakefront cabin with modern luxuries

AileenRating, 5 stars5 days ago
We had a wonderful time! The house is beautiful in a spectacular spot on the lake. We were four adults and a large dog and had enough space. We got to use the kayaks/paddle board and fished endless hours from the dock The kitchen is well equipped and we cooked all our meals at the house I highly recommend this place and would come back if the opportunity arises

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!
Guest favourite
Cabin in Climax
4.89 out of 5 average rating, 35 reviews

Catskills Lake Cabin on 100 Wooded Acres

DesireeRating, 5 stars1 week ago
Great little cabin in the woods. This was exactly what I was looking for. Quaint, quiet, and located on a lake.
Top Guest favourite
Cabin in Hillsdale
4.98 out of 5 average rating, 45 reviews

Modern hilltop chalet-style cabin @ Copake Lake

JeffreyRating, 5 stars1 week ago
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!
Top Guest favourite
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 favourite
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!
Guest favourite
Cabin in Red Hook
4.97 out of 5 average rating, 88 reviews

Secluded luxury: modern riverfront fishing cabin

CaityRating, 5 stars5 days ago
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!
Guest favourite
Cabin in Saugerties
4.87 out of 5 average rating, 185 reviews

Private Woodstock Getaway w Hot Tub

ErinRating, 5 stars1 week ago
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 :-)
Guest favourite
Cabin in Athens
4.94 out of 5 average rating, 103 reviews

Charming Lakefront Cabin with Hot Tub

ModouRating, 5 stars6 days ago
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!

Quick stats about holiday rentals with a kayak in Great Barrington

  • Total rentals

    20 properties

  • Nightly prices starting at

    $46 AUD 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

Destinations to explore