Vacation rentals with a kayak in Windham

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Popular amenities for Windham kayak rentals

House rentals with a kayak

Top guest favourite
Home in Gardiner
4.98 out of 5 average rating, 45 reviews

2 Acre Waterfront w/Canoes & Kayaks, Game Room

LivRating, 5 stars1 month ago
I love coming to Maine, and this was my first time staying at Rob's place—it was beautiful! Rob was more than accommodating and incredibly hospitable. The home is gorgeous, super clean, cozy, and very private. The game room was such a fun bonus! It was the perfect little getaway. Thank you so much, Rob, for everything! I will definitely be keeping this place in mind for future visits!
Guest favourite
Home in Fayette
4.9 out of 5 average rating, 21 reviews

Lakehouse with 100ft of private waterfront

GeorgeRating, 5 stars6 months ago
My wife and I spent our first year anniversary in this wonderful home. We had a great time enjoying the fall colors and over looking the beautiful pond, especially in the morning as the fog broke. Within 15 minutes there were several grocery shopping options, restaurants, and breweries. Perfect balance of being in a quiet setting but having amenities nearby. Would recommend and hope to go back next autumn!
Superhost
Home in Tamworth
4.82 out of 5 average rating, 96 reviews

Lakefront HotTub, Fireplace, Shop, Ski, Hike, Swim

ShaunaRating, 5 stars2 months ago
The place is clearly well taken care of with attention to detail. This would be a great place any time of year. Miriam and the home were very accommodating. I would return to this location with great peace of mind.
Top guest favourite
Home in Norway
4.99 out of 5 average rating, 83 reviews

Open concept 4 bedroom Lakehouse

ErikRating, 5 stars1 month ago
Great winter weekend stay in Maine, the house was very cozy and perfect for our group. The location is perfect for access to the ski mountains and the town as well. Overall highly recommend Roman’s place, I’m sure it is just as beautiful in the summer!
Guest favourite
Home in Newfield
4.97 out of 5 average rating, 30 reviews

Peaceful 4 bedroom lakehouse retreat

JessicaRating, 5 stars3 months ago
We had a fantastic time staying at Justin’s home!
Guest favourite
Home in West Gardiner
4.96 out of 5 average rating, 26 reviews

2 BR Waterfront house with stunning view.

KristenRating, 5 stars7 months ago
This was a really nice house on a beautiful lake. The beds were comfortable and there were enough to accommodate us. It was very clean and easy to enjoy your stay. We really enjoyed our stay.
Superhost
Home in Barnstead
4.89 out of 5 average rating, 121 reviews

Lakefront home /3BR 2BA/ Dock/ Game room/ Garage

AdamRating, 5 stars2 months ago
Great house, quiet and peaceful. Ivars was very responsive. Enjoyed our stay!
Guest favourite
Home in Shapleigh
4.96 out of 5 average rating, 146 reviews

Secluded Lakehouse/2 private docks*Hottub*big yard

CarlyRating, 5 stars1 month ago
We had a wonderful stay at this home for a mother daughter weekend end of March. Great location for each of us coming from different states in New England. The home was very clean, each of us commented on how comfortable the beds were, also loved the good quality linens. The huge dining table was unique for a rental and was awesome for sharing meals and doing arts & crafts. Lots of space and seating in the living room as well. Highly recommend staying here!

Cottage rentals with a kayak

Top guest favourite
Cottage in Alton
4.98 out of 5 average rating, 125 reviews

“Stay Awhile in the Lake's Region”

NetanyaRating, 5 stars1 month ago
I reached out to Bob about allowing one of my company crews to stay at his home, he allowed it which was awesome! The home was just as described, the crew were able to relax after working at a jobsite in the area and really enjoyed the home and the area. Bob was very responsive and easy to talk to. I will definitely be booking with Bob again when the crew needs to go back to the job site!
Top guest favourite
Cottage in Belgrade
5 out of 5 average rating, 103 reviews

Lakefront Home, Sandy Beach, Belgrade Lakes Maine

SarahRating, 5 stars5 months ago
This property was awesome we were all very happy with the location, amenities, price and host. Hillary was polite and very helpful. This trip almost didn’t happen as our previous reservation was canceled 12 hours before check in from a different host. Luckily Hillary saved the week with her quick response time and answering questions about sleeping situations etc. would stay here again in a heart beat highly recommend!
Guest favourite
Cottage in Windham
4.82 out of 5 average rating, 136 reviews

Cozy camp near highland lake

TyRating, 5 stars3 days ago
My stay here was absolutely awesome—cozy, charming, and full of thoughtful touches that made it feel like a home away from home. Tucked away in a quiet spot, it had just the right mix of comfort and style, with a super comfy bed, a well-equipped little kitchen, and warm lighting that made evenings feel magical. The host went above and beyond, leaving local tips and a welcome treat that totally made my day. I honestly didn’t want to leave! And the view to the lake was so beautiful especially the sunsets for the cabin overlooking everything was just so awesome!
Guest favourite
Cottage in Conway
4.95 out of 5 average rating, 332 reviews

20ft from the Water with Mountain View!

HannahRating, 5 stars2 weeks ago
Such a beautiful and cozy stay! literally feet from the water. It was incredible to wake up to that view. A cozy cabin feel with modern amenities. such a great space! thank you for having us
Guest favourite
Cottage in Belgrade
4.93 out of 5 average rating, 135 reviews

Near Waterville | Lake Great Pond | Dog Friendly

TammyRating, 5 stars2 days ago
The place was beautiful and exactly what we needed! I would definitely recommend staying here.
Guest favourite
Cottage in Topsham
4.93 out of 5 average rating, 249 reviews

Cozy waterfront home on Merrymeeting Bay.

ElaineRating, 5 stars2 months ago
This is our second stay here and we just love the location. looking out over the river is so relaxing.
Superhost
Cottage in Lyman
4.82 out of 5 average rating, 101 reviews

RK North : All season Waterfront cottage with dock

BrianRating, 5 stars2 weeks ago
It was overall a tremendous experience. I would definitely recommend it!
Guest favourite
Cottage in Livermore
4.95 out of 5 average rating, 149 reviews

Bass Point Lakeside Cottage: Livermore, Maine

BiancaRating, 5 stars6 months ago
I had a wonderful 4 night stay at the lake house and couldn't have asked for a better place to spend the little getaway. It is beautifully located on the lake and has this huge window in the living room from which you have an amazing view. The house has everything you need, even washing machine and dryer in the basement. I would 100% recommend this unique place! Christine has been super helpful throughout my stay.

Cabin rentals with a kayak

Guest favourite
Cabin in Woodstock
4.96 out of 5 average rating, 153 reviews

Sunday River & Lake Chalet, 2 Kitchens, Hot Tub

JenavieveRating, 5 stars1 month ago
My friends and I had a great time relaxing at this beautiful place. Aqeel and Michelle were extremely responsive and helpful when necessary. We would stay again!
Top guest favourite
Cabin in Dresden
4.95 out of 5 average rating, 185 reviews

McKeen's Riverside Retreat

AmberRating, 5 stars2 days ago
I would recommend this place to anyone looking for a comfortable place to stay. It was my son’s wedding and I loved being able to come back from the activities to rest and relax . It was very homey.
Top guest favourite
Cabin in Dresden
4.98 out of 5 average rating, 240 reviews

Merrymeeting Midcoast Cabin

LenaRating, 5 stars5 months ago
Terrill and Charlie‘s cabin is lovely! Great communication, the cabin is well equipped (including lots of board games) and super cozy. We had a really relaxing time and might come back in spring :)
Superhost
Cabin in Raymond
4.93 out of 5 average rating, 154 reviews

Rustic, cozy cabin on Sebago Lake. A hidden gem.

WaltRating, 5 stars6 months ago
Came for the Fall colors; left in love with the place! Small but delightful. Cluttered in the most fantastical way. Nestled in paradise. Bonnie is so nice and friendly! Pay attention to the fact that the toilet is not attached to house. Short walk to privet and very clean!
Guest favourite
Cabin in Harrison
4.99 out of 5 average rating, 125 reviews

Get away at Crystal Lake

GabrielRating, 5 stars3 months ago
Great cabin, location, and hosts. Our group had a great time coming back for our second trip here and would highly recommend. 5 stars all around.
Guest favourite
Cabin in Bridgton
4.93 out of 5 average rating, 123 reviews

Private cabin w hot tub,skiing,firepit & mountains

DanRating, 5 stars2 weeks ago
This is a beautiful home that is very well maintained and cared for. Alexa's cabin was a great place for 5 of us to gather, relax, and enjoy. Kitchen has everything you need, the hot tub is fantastic during a spring snowstorm, the beds were very comfortable, and it provided ample space for us.
Guest favourite
Cabin in Madison
4.92 out of 5 average rating, 130 reviews

Bear Cabin

LilaRating, 5 stars1 month ago
Absolutely beautiful and peaceful stay. John and Cassie’s cabin was just as described and exactly what we were looking for. We drove up during a snow storm but the roads were plowed and well maintained. Very isolated and private but never felt unsafe or uncomfortable. Not too far from things to do but we were content enjoying the cozy relaxing home. John was quick to communicate with us if we needed anything and was very helpful.
Guest favourite
Cabin in Parsonsfield
4.96 out of 5 average rating, 222 reviews

Riverfront cabin between Portland & White Mtns.

ColinRating, 5 stars2 days ago
As advertised, but perhaps a bit smaller than it appears. Great location, and the host was responsive.

Quick stats about vacation rentals with a kayak in Windham

  • Total rentals

    50 properties

  • Nightly prices starting at

    $111 CAD before taxes and fees

  • Total number of reviews

    2K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

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