Holiday rentals with a kayak in Cumberland

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Popular amenities for Cumberland kayak rentals

Holiday 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!
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 Wakefield
4.96 out of 5 average rating, 28 reviews

In the Trees - NH w/ Lake Access

AmyRating, 5 stars1 week ago
We had a wonderful stay at this cozy, comfortable, and peaceful home—perfect for our family of five! The space was quiet, private, and truly felt like a home away from home. It's in a beautiful location right by Lake Province, and we had almost everything we needed for our 3-night Easter weekend stay. Our older children attend UNH, and this was the perfect spot for us all to be together, relax, play games, and enjoy quality family time. We love to cook, and the brand new kitchen was gorgeous and a joy to use—we prepared three amazing meals together! Just a heads-up for fellow cooks: the kitchen is stocked with the basics, so if you're planning more elaborate meals, you might want to bring a few extra tools. The outdoor space was also a highlight! With beautiful weather all three days, we spent a lot of time outside enjoying the fire pit, string lights, grilling, eating al fresco, and just being together. We truly loved our stay and are already looking forward to coming back.
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.
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!
Guest favourite
Home in Sanford
4.88 out of 5 average rating, 40 reviews

Waterfront Condo- Maine village retreat

DiannaRating, 5 stars5 months ago
We had a great stay! Loved the views and hot tub. It was so close to town but felt private with the privacy fence. Owners were very responsive! Thanks for a great stay

Cottages with a kayak

Superhost
Cottage in Conway
4.89 out of 5 average rating, 108 reviews

Cozy Pondside Retreat with direct water access!

TeraRating, 5 stars6 months ago
This place was really nice! Its on a beautiful lake with a lot to do! Jessica had plenty of kayaks, canoes, and life vests. The surrounding is beautiful and peaceful. The location is great with plenty of restaurants and shopping nearby. It's also very close to many great hiking areas Mt Washington.
Guest favourite
Cottage in Windham
4.82 out of 5 average rating, 137 reviews

Cozy camp near highland lake

TyRating, 5 stars4 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, 333 reviews

20ft from the Water with Mountain View!

ElizabethRating, 5 stars2 weeks ago
my partner and i stayed here to just get away from reality for a couple days! this lakeside cottage is the perfect place to do so. we couldn’t decide if we wanted to go out and about or stay right in the cabin, it was so peaceful! thank you for hosting!
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.
Guest favourite
Cottage in Buxton
4.98 out of 5 average rating, 142 reviews

Peaceful Cottage on Maine Flower Farm

RaeganRating, 5 stars6 months ago
Perfect fall cottage so close to Portland! The cottage is so peaceful and quiet. But so close to Portland but you wouldn’t even know it. The farm is lovely and we took a walk down to the river on the property, it was so peaceful and so much land! If you are looking for a get away from a city, but want to be able to explore Portland and Kennybunks, this was the perfect spot. I don’t know if I’ve slept that good all year. Would definitely come back again. And we love Trooper the dog!
Guest favourite
Cottage in Middleton
4.96 out of 5 average rating, 183 reviews

☀ Fox & Loon lake house: hot tub/pedal boat/kayaks

CourtneyRating, 5 stars1 week ago
My family and I had such a WONDERFUL long weekened away at Fox & Loon! It was so relaxing and peaceful, and exactly what we needed! The house was the perfect setup for our family of 4. It was so open and bright, and had everything we needed. We got tons of use out of the hot tub, and fished every day from the dock! The sunsets were gorgeous! Sheri and Adam were the perfect hosts! Right from the beginning, they were extremely responsive and answered every question I had (which was a lot!). They even went out of their way to find out some additional information I requested. We would absolutely, without a doubt, stay here again! Thank you Sheri and Adam!

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 stars3 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.
Guest favourite
Cabin in China
4.89 out of 5 average rating, 171 reviews

Rustic Family Cabin on China Lake

JackieRating, 5 stars7 months ago
I loved this place! Enjoying coffee and meals outside on the deck overlooking the lake and beautiful surroundings of nature. I felt safe there and was a charming neighborhood. I loved that there were boats to use and a dock to watch sunset an autumn harvest moon over lake! Jess was the perfect host and made sure everything was great when I arrived. She was very helpful when I had any questions and I am looking so forward to going back there again! Thank you Jess for sharing this wonderful place!!!
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 stars3 days ago
As advertised, but perhaps a bit smaller than it appears. Great location, and the host was responsive.

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