
Holiday rentals with a kayak in Columbia County
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Top-rated Accommodation with a Kayak in Columbia County
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Holiday House Rentals with a Kayak

Modern and Stylish Country Lakeside Cottage
This was my second time staying at Maureen’s beautiful lakeside home and it surely won’t be my last. It’s the coziest, peaceful and inspiring place. Looking forward to future visits!

Modern & Cozy Lake Oasis ~ Hot Tub ~ Games ~ View
We loved Kathryn’s place! It was so peaceful and pretty, we loved having lake access, and it was convenient to drive to several local towns with great restaurants. The whole family enjoyed the kayaks and the community pool and the lovely outdoor space. My favorite part of the stay was the friendly fox who would visit the property in the mornings. Kathryn was also a wonderful host and responsive to our questions/messages. I would definitely stay here again!

Lakeside home with Private dock and more !
We thoroughly enjoyed our weekend stay at your beautiful home. Everything was perfect! As soon as we opened the front door, we were welcomed by the comfortable setting and design of your home. Thoughtful details were everywhere and we felt spoiled by your hospitality. A special thank you for leaving the snack basket and pickleball sets :)

Taconic Hill-a modern retreat on 50 forested acres
We had a wonderful stay at the Taconic Hill home with our young children. It's clean, open, and minimal with an abundance of space and light. There is plenty of space to spread out if you want some privacy, and also welcoming centers to bring the family together. The location is great, with easy access to the activities in neighboring towns, and the hosts provided a helpful guide book that answered all of our questions while we were there (so we didn't need to bother them at all, it was so helpful!). Also the property is great - we went on a long walk through the woods with our children and had a magical time, great to have the convenience of this in the backyard. We'd all love to stay here again!

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 😊

Cozy Lakeside Retreat
This is a great spot, on a dead end street. Very peaceful and a wonderful open space. About 25-30 minutes south of Albany/Troy. Close to a shopping area in Valatie, NY (about 2 miles.) Maura is a fantastic host, who quickly helped with any questions or needs. I highly recommend this house to anyone looking for a serene getaway.

Secluded Mountain and Lake View in Canaan, NY
This is a really special place, full of spectacular artwork, and is a superbly designed space. ..And has a riveting view of Queechy Lake. Though the photos show it well, it is even more beautiful in real life. It is quiet, and close to both Berkshire and Chatham attractions. And Jim is a very responsive and thoughtful host. Definitely recommend for a family getaway.

Cozy Red Cottage on Robinson Pond
Can't say enough of how awesome this place was. Right on a lake. Literally a few minutes to Catamount. Everything available within a few minutes. Even an urgent care that we needed during our trip just around the corner. The house was perfect and cozy. Very homey and very clean. Everything and anything you need is included in this stay. The hostess had gone above and beyond consistently reaching out to me with new ideas or even looking into things, such as ice skating, if locally available. Looking forward to booking the house again for the summer to enjoy the lake and some fishing.
Cottages with a kayak

Secluded Country Getaway on 22 acres
I cannot thank Joyce enough for opening her lovely home to us. We felt relaxed and refreshed from the minute we arrived. Whether it was sipping coffee and reading by the pond or watching our beagle explore the grounds, I don't think the smile left my face. Joyce was so helpful with recommendations and available to answer any questions we might have had. The proximity to Great Barrington and Stockbridge was fantastic but the local Hillsdale attractions should be missed. We'll absolutely stay here again! Love this house.

Lakefront Retreat on Robinson Pond
The lake house is truly gorgeous, especially with the fall foliage. We fell in love with the location and plan to be back soon.

Plan your Berkshires by the lake
I cannot emphasize enough how responsive, helpful and accommodating Julie was before and during our stay. The property is as shown, interior was clean and beds very comfortable. The walk to the lake is a short, peaceful one. It is a lovely setting with quiet neighbors. Highly recommend for anyone visiting nearby Berkshire attractions or for a quiet getaway near a beautiful lake!

Kayak, pet a Highland cow, have dinner in Hudson!
This was our second time staying at Tom’s beautiful property and once again it didn’t disappoint! Great place to relax and catch some fish by the fire. It was clean and comfortable. Lots of wildlife to see; bald eagles, turtles and even a beaver who would show up daily! Tom left us some fresh chicken and quail eggs in the fridge which were delicious. The location is quiet and peaceful but close enough to stores to grab essentials easily. Can’t wait to stay again next year!

Waterlily Lakehouse - Modern+Waterfront+Retreat
My friends and I loved our weekend getaway at Vivian's lake house. Vivian was a very responsive host and provided clear instructions that made our stay seamless. The space was super clean, modern, and easily accommodated all 8 of us. The highlight of our trip was spending time on the lake with the provided kayaks and paddle boards. We enjoyed ending the day by grilling and sitting around the fire pit. We wish we had stayed longer!

Lake Front Cottage with Sun Soaked Terraces
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.

Oriole Cottage@Copake Lake:Swim, Kayak, Canoe
My husband, our two elderly parents and I stayed at Oriole Cottage with our young dog during a winter break. Cheryl had been Hannah really friendly and proactive in their communications with us, and when we arrived we found Oriole Cottage cheerful, warm, clean, and with good bedding (fluffy duvets and quite comfortable beds). The living/dining area and kitchen are bright, nice and sunny. We found the kitchen very well appointed, and we each enjoyed the different coffee-making choices available to us (French press, drip, Nespresso etc)… something to suit everyone’s taste. Bathrooms had good hot water and shower pressure (!) Overall, the cottage is a sunny, warm, comfortable and clean place to stay. We’d love to return during a summer month when we can try kayaking and all the activities of a summer lakeside stay.

Huge Lakefront, Cozy Private Cottage in Upstate NY
I can’t say enough positive things about Daniel’s place. The setting was beautiful and serene; It was so quiet and peaceful we almost felt like it was our own private lake! The house was lovely and so tastefully and uniquely decorated. All the windows gave a constant view of the lake. There are many quaint towns to explore within a 30 minute drive, but you may want to spend most of your time enjoying the lake and kayak. We hope to return in the summer.
Cabin rentals with a kayak

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!

Lux Lakefront | Dock | Game Room | Movie Theater
If I could give 6 stars, I would! This house is super clean, great layout, and has everything needed for great stay. Check in and check out were extremely easy. Orlando was very quick to respond to all of our correspondences. He was always kind and professional when communicating with us. We stayed in the house during a snowy, chilly week in December. The house was nice and warm upon our arrival and we immediately felt right at home. The lake views are beautiful from inside the house and deck. Comfortable bed, nice furniture, and a well stocked kitchen. Airbnb photos accurately represent this lovely home. There is plenty to do in the area or you can just stay at the home and enjoy! We already booked another stay for the end of December. Thank you Orlando for sharing your home and making us feel safe and comfortable.

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!

The Cosmo Cottage
look forward to renting again 4 sure

Lakefront | Mountains | Family | Peaceful | Ski
Wonderful house and amenities in a beautiful & peaceful surroundings. Caters for families of all ages.

Cozy Yellow Cabin at the Lake
I highly recommend Tina's yellow cabin by the lake. We had come to Hillsdale as a family for a wedding. I chose Tina's cabin because there was something for the different members of my family. Fishing for my brother and husband. Swimming for my Sister in law and my self. Beautiful big porch to sit and relax. Unfortunately we got stuck in the cabin for the first day and a half due to heavy rain. Never fear we played board games and visited. As the weather broke we were able to fenture outside and enjoy our stay even more. Tina checked on us several times through our our stay, she wanted to be sure we had all we needed. If you are looking for a cute quiet place with plenty to do...check out Tina's yellow cabin by the lake.

Beautiful Lake Front Cabin
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!

Cheerfull 3 bedroom cabin nestled in the woods
It has been an amazing experience staying in this house. Host is amazing with great communication. The place is so nice and cozy. Overall it’s has been awesome. Highly recommending.
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- Hunter Mountain
- Saratoga Race Course
- Howe Caverns
- John Boyd Thacher State Park
- Albany Center Gallery
- 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
- Saratoga Spa State Park
- Mount Greylock Ski Club
- Norman Rockwell Museum
- Beartown State Forest
- Mohawk Mountain Ski Area
- Hancock Shaker Village
- Hunter Mountain Resort
- Opus 40
- Naumkeag
- Brignole Vineyards
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