Vacation rentals with a kayak in Monterey

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Popular amenities for Monterey kayak rentals

House rentals with a kayak

Guest favorite
Home in Otis
4.92 out of 5 average rating, 12 reviews

Berkshires Oasis Retreat: Art Meets Nature

CharlotteRating, 5 stars5 months ago
We had a lovely time with our family! We were with 2 young children and my elderly father who cannot walk well (uses a walker). The house was perfectly designed to accommodate my father and had great living areas for us to spend time together. A very cozy, warm and welcoming home (with lots of amenities!). Yael is a very friendly, responsive host. We’d gladly come back for another winter or perhaps a summer stay! Thank you Yael!
Top guest favorite
Home in Saugerties
4.97 out of 5 average rating, 300 reviews

Creekside Cottage

DylanRating, 5 stars2 weeks ago
We had a great weekend stay at Katherine’s. The Esopus Bend Nature Preserve is only a ten minute drive and we really appreciated the local recommendations provided in the binder!
Top guest favorite
Home in Sandisfield
5 out of 5 average rating, 33 reviews

Waterfront oasis in heart of Berkshires

LisaRating, 5 stars3 days ago
The location was peaceful and beautiful with great local restaurants, farms, and hiking. The reservoir was a nice amenity with the kayaks and canoe. The house was well maintained and comfortable with pretty views on the first floor. We enjoyed our stay
Guest favorite
Home in Pine Plains
4.98 out of 5 average rating, 123 reviews

Twin Island Lake House • Hot Tub

KaiRating, 5 stars2 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 favorite
Home in Valatie
4.97 out of 5 average rating, 32 reviews

Majestic lake front house

PeterRating, 5 stars1 month ago
We had a great time at Francois & Ann's oasis by the lake. It was so relaxing to wake up, look at the lake, and listen to birds chirp. If you are looking for isolation, this place does the trick, We didn't see anyone all week on the lake or at the other cabins until the day we left. The lake has excellent fishing. With little effort, we caught several decent-sized bass and pickerel right off the dock. The location is ideal. You feel like you are out in the country, but are close to great restaurants in Kinderhook and only 25 minutes from Hudson or Albany. It's also only an hour from Mass Moca and 90 minutes to Cooperstown. Francois and Ann were very communicative and quickly responded to questions and comments.
Top guest favorite
Home in Great Barrington
5 out of 5 average rating, 49 reviews

The Yellow Victorian With Chefs Kitchen

BenRating, 5 stars1 month ago
We loved the Yellow Victorian! Danielle was a great host--clear, honest, responsive. The space is gorgeous, with so many large rooms, each with its own flavor. The beds were comfy, the living room cozy. And the best part were the kitchen and garden. It felt really spacious for the family to cook together, dink coffee, sit outside and chill. The kitchen was well stocked with pots and pans and all the glass and servingware you will need--loved how eclectic the choices were, made the stay fun! We are definitely coming back next time we are in south county :-)
Superhost
Home in Monterey
4.94 out of 5 average rating, 17 reviews

Swim Dock, Lake Toys, screen porch, fire pit!

DanielleRating, 5 stars7 months ago
Great spot on the lake! Exactly as described, super cozy, had everything you need. We drove about 20 minutes to monument mountain and did an amazing fall hike. Berkshires are beautiful and I would definitely come back to this place.
Guest favorite
Home in Becket
4.94 out of 5 average rating, 31 reviews

Lakefront Cottage on Private Beach

GillianRating, 5 stars2 weeks ago
Our family had an AMAZING stay in this cottage. It was clean and comfortable, and just what we were looking for. A quiet spot where we could enjoy fishing, kayaking, biking, etc with the comforts of home. Because of all the amenities offered, we didn’t have to pack too much which is always a bonus! We are already talking about our next visit 😊

Cottage rentals with a kayak

Top guest favorite
Cottage in Nassau
4.97 out of 5 average rating, 32 reviews

Hook, Wine and Sinker!

CaylorRating, 5 stars3 days 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 stars2 weeks ago
Cozy, quaint, cute space. Perfect for a couple or a single adventurer. Gorgeous location and amenities. Would happily re-book!
Top guest favorite
Cottage in Valatie
4.99 out of 5 average rating, 142 reviews

Kinderhook Lakefront Retreat-private, kayaks, ac

DuncanRating, 5 stars2 days ago
Amazing place. Lisa & Steve's cottage made for an amazing weekend. We had pretty bad weather but it was still a great weekend. The lake is so peaceful and the set up of the cottage is perfect. The cottage has everything you need, as well as everything you didnt know you needed! We'll definitely be back. Ate at The Aviary, The Smokehouse & The Maker (Hudson) - all very different but incredible.
Top guest favorite
Cottage in Otis
5 out of 5 average rating, 17 reviews

Lake Escape: Lakefront Cottage in the Berkshires

JeanneRating, 5 stars8 months ago
My husband and I had a wonderful stay. The cottage was clean and comfortable. The hosts thought of everything and made us feel right at home. We could not have been more pleased and would highly recommend this property.
Guest favorite
Cottage in New Marlborough
4.9 out of 5 average rating, 39 reviews

Pet friendly Cottage on Lake; Hike, Swim, Kayak

KunalRating, 5 stars1 month 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 stars2 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 favorite
Cottage in Ulster Park
4.91 out of 5 average rating, 180 reviews

Romantic House on a Magical Lake

VidhiRating, 5 stars2 months ago
Comfortable and clean with beautiful scenery - on clear days, you get a Mountain view across the lake! Highly recommend.
Guest favorite
Cottage in Lanesborough
4.84 out of 5 average rating, 279 reviews

Wildlife Lakeside Cottage; views/wildlife

SonyaRating, 5 stars3 weeks 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.

Cabin rentals with a kayak

Superhost
Cabin in Otis
4.8 out of 5 average rating, 20 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 favorite
Cabin in Climax
4.91 out of 5 average rating, 33 reviews

Catskills Lake Cabin on 100 Wooded Acres

SamRating, 5 stars1 week ago
Great little home on a great property! Would definitely recommend
Top guest favorite
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 stars2 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 favorite
Cabin in Colebrook
4.94 out of 5 average rating, 94 reviews

Rustic Cabin+ Private Beach Pond, Stars & Wildlife

EdwardRating, 5 stars1 week 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 favorite
Cabin in Red Hook
4.97 out of 5 average rating, 87 reviews

Secluded luxury: modern riverfront fishing cabin

JamesRating, 5 stars3 weeks ago
Beautiful & peaceful weekend getaway. I highly recommend Samuel & Catherine’s cabin and will be coming back in the near future.
Guest favorite
Cabin in Saugerties
4.87 out of 5 average rating, 185 reviews

Private Woodstock Getaway w Hot Tub

ErinRating, 5 stars3 days 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 favorite
Cabin in Athens
4.94 out of 5 average rating, 101 reviews

Charming Lakefront Cabin with Hot Tub

EimearRating, 5 stars1 week ago
We had an amazing time at Ruth’s home and we loved the cabin feel. Between the hot tub, lake, and lawn games our time went by so quickly. The home was very clean and had all the essentials. We will definitely be back again!
Top guest favorite
Cabin in Kingston
5 out of 5 average rating, 211 reviews

Lakeside Cottage: Boulder's Bluff

AlexRating, 5 stars7 months ago
We loved our stay at Ed's cabin. it is a real gem and perfect for a long weekend away. we loved the fireplace, the rocking chairs, the windows with views out onto the lake that make you feel like you're right over the lake and in the trees. there were nice restaurants and hikes in the area, but we were perfectly content watching the lake and reading from the cabin. Ed was perfectly accommodating and extremely generous with his space, couldn't recommend more highly.

Quick stats about vacation rentals with a kayak in Monterey

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ588 before taxes and fees

  • Total number of reviews

    950 reviews

  • Family-friendly rentals

    20 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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