
Vacation rentals with a kayak in Oakland
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House rentals with a kayak

Sugarmaple Lakehouse - Sebasticook Lake Newport ME
Enjoyed a wonderful weekend here with our family (5 adults, 1 child, 1 dog). The house is very comfortable & beautifully updated/decorated. The setting is even better in person than we were expecting with an expansive lawn perfect for playing games. We had read other reviews about the neighbors having free roaming pet rabbits and saw them quite a bit. Fortunately our dog is a good listener and left them alone but could prove challenging for other dogs depending on their temperament. The lake was gorgeous and the location within one of the coves felt quiet and private while offering easy access to the rest of the lake via boat, kayak, etc. Enjoyed sitting on the dock & picnic table by the waters edge. Appreciated all the kayaks, games, toiletries & kitchen items provided as well as the large deck with grill & the firepit with chairs. Conveniently close to the boat launch, grocery store, restaurants, gas station, etc. if you need to run out for anything. Thanks for a great stay!

Family Escape w/ Kayaks, Fire Pit, & Water Access
What a whimsical town! In the middle of nowhere So peaceful Yet, Wallace's General Store, right up the road Maybe a mile Amazing food and Sandwiches and just about everything under sun to Need So, just down the road is this Amazing Place! Three Sisters Farm Heaven Awaits Must check out

LUX Designer Private Waterfront
We loved staying at this location! The setting was private and peaceful. The house was beautiful and it seemed like they had thought of everything. It was great to have the canoe and kayaks and of course we also loved the indoor and outdoor showers and indoor and outdoor fire options. This place was a splurge but I would say definitely worth it!

Unique Octagonal House with Private Beach!
Simply magical! Cozy and fun space. We enjoyed watching eagles and ospreys fish, seals pop their heads up, and even an adorable family of foxes from the comfort of the living room! Kitchen had all necessities for cooking most meals at home. A nice trail for walking down the road and an awesome beach where the kids threw stones and searched for seaglass each afternoon. We were all sad to leave!

Cozy Waterfront Home With Breathtaking Views!!!
We had an amazing time. TJ was very responsive and gave his secrets for fishing! He also accommodated a request that was an overlook on my part. I can’t say enough good things about the place itself or how nice TJ was. It was a phenomenal experience all around!

Riverside
This was my 5th time going there and I love it! The house is so cozy & very clean. The property is large and the view is breathtaking over looking the river. They are also pet friendly so we were able to take our Lhasa Apso Revy on vacation with us. Besides how great this Air BnB is, my favorite is the hosts Kent & Tish! They are wonderful people. They are kind & friendly, & have such beautiful souls. They have become family to me! I highly recommend getting this air bnb!! Thank you again Tish & Kent! Ian, Revy, & I are always happy to see you!!

Waterfront Farmhouse with Modern Flair!
We loved our stay (late May, 2025). The weather did not cooperate but the house was perfect. Thank you Debbi!

Lakefront: Private Hot Tub, Sauna & Free Massages!
Me and my friends had a lovely time at this lake house, the beds were comfy and there was more than enough room for sixteen of us. The place is very well taken care of and you can tell there is a lot of thought and work put into the home. All the amenities were amazing from the chair to the sauna everything worked great and the hot tub was to die for. We loved our stay and would 100% come again.
Cottage rentals with a kayak

Lakefront Cottage on Tracy Pond, New Hampshire
This was great cozy, cottage. We we were pleasantly surprised! The inside was very nicely decorated and was definitely enough space for my husband and I, and our two dogs. It was so nice to relax enjoy a sunset and make a fire in the fire pit after a long day. We were greeted by the welcome committee (black cat) numerous times. The cottage had everything we needed. My dog really enjoyed swimming in the lake. Thanks so much and we would definitely consider staying here again

Privacy with spectacular waterfront, Lilla Stuga.
This was our third time at Lilla Stuga and we were once again extremely happy with our stay. We love it there. The privacy, the dock, the house, the sunsets, I could go on and on. There’s a reason we keep coming back 😊 Beth and Steve are incredible hosts and we are always so grateful for their hospitality!

Gorgeous lakefront, sunsets, kayaks, fire pit
Leslie was very responsive and helpful before the trip. The place was even more beautiful than expected. The Google address leads to a few houses before, but the description of the driveway helped us find the right location. It was the perfect location to relax for the weekend.

sunny lakefront cottage in quiet woodsy setting
Very peaceful, quiet and tranquil location on the pond. House was very clean, fully stocked kitchen, great amenities and a very comfortable bed. Even left us a case of water and a Smores kit. Any questions I had were answered within minutes

Hidden Haven A Rustic Retreat In St. George, Maine
Mischele really thinks of a traveler when she sets up her place! The extra touch of orange juice, creamer, coffee, freshly baked breakfast is great! Everything is there. Convenient to many great restaurants.

Driftwood Cottage | Lake Great Pond | Dog Friendly
Alana's home was more than we expected. The home was spotless and well equipped for our quick stay. She is very accommodating and responds to questions immediately. We would definitely stay again if we're in her area.

Cozy waterfront home on Merrymeeting Bay.
Loved our time here! It’s about a 40 minute drive from Portland and then 5-10 from Brunswick. The neighborhood is quiet and perfect, exactly what we needed to relax! We loved coming back from Portland and grabbing dinner and gelato in Brunswick, such a nice way to unwind from a long day. Highly recommend and would love to stay here again :)

Classic Lakefront Maine Cabin
What a beautiful location! David is a great host. He made sure we had good directions, tips for the area, and was quick to answer any questions. The lakeside cabin has absolutely everything you need to have a peaceful, relaxing vacation. The view of the lake is spectacular. The cabin is very clean, has a well stocked kitchen, comfortable beds and Echo lake is a gorgeous pristine lake. Every morning, we enjoyed our coffee on the dock. We swam, kayaked, canoed and even tried out the paddle boards that came with the house. We would love to come back! Thanks!
Cabin rentals with a kayak

Lake Cabin in the Trees
We fell in love with this beautiful, magical “tree house”. You couldn’t ask for a more perfect place to share time with friends & family. Beautiful view of the lake & everything you need is there - both inside & outside. This home radiates happiness & reflects the thoughtfulness of the owners. The furnishing are lovely & they have the most comfortable beds I’ve ever slept in. I heartily recommend this cabin the woods. We look forward to returning. Linda

Lakefront Stunning Home, only 35 min to Sugarloaf!
Absolutely beautiful views. Peaceful location. House is very well equipped with board games and basic amenities!

The Getaway- A Cozy Lakeside Cabin
After getting things clean we enjoyed 28 days was not good weather went back to take care of our mothers things was good to have this place to come relax in would rent again even tho it wasn’t cleaned they tried to make things right loved the cabin

McKeen's Riverside Retreat
We have stayed at Jackies place twice now and enjoyed it just as much this time as the last. Even though it rained for two days the house is plenty big enough to spread out. We had to change our reservation days twice because of circumstances and Jackie was very accomidating..

Loon Lodge Canaan,ME
Christine is a seriously helpful and attentive host! The property was as described and the house was SPOTLESS!! Although we only had 5 people with us, the space definitely could hold double that! We will be sure to book again when we are up visiting family again!

Rustic, cozy cabin on Sebago Lake. A hidden gem.
The cabin was cozy, the view of the lake was incredible, and Bonnie was a great host!

Cozy Lakefront Cabin - Hope Floats
We had a wonderful 2-night stay at Hope Floats in Maine with our dog—it was spotless, serene, and exactly what we needed. The peaceful surroundings made it easy to unwind, and the beautifully maintained property gave us plenty of space to relax and reconnect. From morning coffee on the deck to quiet evening strolls, every moment felt like a true escape.

Mill Pond Waterfront Cabin On The Way To Sugarloaf
We had the most wonderful stay! We spent a week, celebrating our 15th anniversary, soaking in the views, enjoying the wild life and cozying up at the camp fire, enjoying one another’s company. The cabin was clean, stocked with necessities and perfectly decorated. The bed was comfortable and all the linens were clean, with very comfy pillows too! Lots of games were provided, and the view from the living room is stunning. You look right out onto the pond. We had some wildlife visit us, and a chipmunk we made friends with. Look for his little house entrance by the fire pit! He also loved perching on the cairns to watch us Explore the property and find some little hidden gems of beauty The locals were super friendly, Jon was very accommodating and responsive. We couldn’t have asked for a more perfect experience Thank you so much. We are looking forward to visiting again!!
Quick stats about vacation rentals with a kayak in Oakland
Total rentals
30 properties
Nightly prices starting at
R1,771 ZAR before taxes and fees
Total number of reviews
960 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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- Samoset Resort
- Pemaquid Beach
- Coastal Maine Botanical Gardens
- Fox Ridge Golf Club
- Brunswick Golf Club
- Belgrade Lakes Golf Club
- Saddleback Ski Mountain Maine
- Sugarloaf Golf Club
- Hermon Mountain Ski Area
- Maine Maritime Museum
- Dragonfly Farm & Winery
- Rockland Breakwater Light
- Eaton Mountain Ski Resort
- Pinnacle Park
- Three Island Beach
- Spragues Beach
- Lost Valley Ski Area
- Bear Island Beach
- The Camden Snow Bowl
- Pebble Beach
- Narrow Place Beach
- Black Mountain of Maine
- Titcomb Mountain
- Martindale Country Club