Vacation rentals with a kayak in Cumberland

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Top-rated kayak rentals in Cumberland

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Guest favorite

Guest suite in New Gloucester

4.98 out of 5 average rating, 173 reviews

Peaceful Lakeside Suite w/Firepit and Kayaks

Open the double doors of your suite for direct access to a beautiful Maine lake. With a private entrance, the open concept apartment is in the walk-out basement of our log-cabin style home. Includes a kitchenette, private bathroom, enclosed unheated porch, large flat screen TV with DirecTV, washer & dryer. A patio with firepit is available (except when snow-covered). You may swim and use our kayaks and other boats, in season, at your own risk. Nice views. Quiet and peaceful. Enjoy star-gazing.

Jul 23 – 28

G$27,187 GYD per night

Guest favorite

Cottage in Topsham

4.95 out of 5 average rating, 212 reviews

Cozy waterfront home on Merrymeeting Bay.

Our cozy cottage is the perfect romantic getaway or quiet retreat in any season. Located on a private rd with scenic waterfront view. Guests can enjoy sitting on the dock (May- October) or the jetty, watch the eagles and Osprey, use our kayaks, do some fishing, walking or biking. Sit by the propane fueled fireplace on a chilly night. Brunswick, home of Bowdoin College and a # of great restaurants and unique shops is just 5 mi. Travel by bus or train to/from Boston. Portland is @ 30 min away.

Oct 29 – Nov 5

G$33,633 GYD per night

Guest favorite

Cabin in Dresden

4.98 out of 5 average rating, 213 reviews

Merrymeeting Midcoast Cabin

RUSTIC-no running water! cabin perfect for exploring all mid-coast Maine has to offer: 3 hours from Boston or Acadia, 1 hour to Portland and Maine’s gorgeous beaches. 10-30 minute drive to Hiking, swim spots, farm-stands, nationally recognized dairy farms, breweries, restaurants. 5 minute walk from a pickleball court. Stargaze in the hammock by campfire, Grill dinner, check out local tide charts to float in canoe or kayak on the Eastern river. Wood fired oven can be rented for additional fee.

Jun 18 – 25

G$19,617 GYD per night

Guest favorite

Loft in West Gardiner

4.98 out of 5 average rating, 113 reviews

Cozy, Efficiency Apartment with Hot Tub

Keep it simple at this peaceful, centrally-located efficiency apartment. 15 minutes to Gardiner and Augusta, 15 minutes to I95/295. Less than one hour from Portland. Walk along the stream, listen to the loons or enjoy relaxing in the hot tub. If you want to paddle in a kayak, you can do that too! Eagles regularly soar overhead. Queen size bed, love seat and room enough for a pack and pay or twin air mattress. A/C, full kitchen, Keurig, microwave, toaster, dishes. Wifi and cable. Roomy parking.

Jun 25 – Jul 2

G$25,257 GYD per night

Guest favorite

Farm stay in Norway

4.96 out of 5 average rating, 152 reviews

Waterfront Home on Norway Lake - Hillcrest Farm

Serene parklike setting on 11-acres with 1,300-ft of frontage on Norway Lake. Newly renovated 1 bedroom apartment with full kitchen in historic farmhouse has separate access for complete independence. Only 35 min to Sunday River & 1 mile to downtown Norway. Direct connection to miles of hiking, biking & ski trails on Shepherd's Farm Preserve. Fish from our dock, use our canoes and kayaks, rent boats from the local marina or watch abundant wildlife from the deck - unlimited outdoor activities!

Apr 1 – 8

G$36,740 GYD per night

Guest favorite

Guest suite in Scarborough

4.88 out of 5 average rating, 125 reviews

Moose Creek Lodge & Cabin

Located 5 mi. from Pine Point Beach in Scarborough near kayaking and Frith Farm with fresh food & pick-your-own flowers. Close to Portland, Portland Head Light, L.L. Bean, or Kittery outlets; 3-hrs to Acadia National Park. Hosts live in an upper Suite in the house with separate entrances. Lower Suite includes (kitchen, 1 bath), salt-water Hot Tub, picnic table, Cabin, & parking next to the house surrounded by beautiful gardens & woods. VACATIONLAND! Dogs allowed but not cats due to allergies.

Apr 17 – 24

G$37,962 GYD per night

Guest favorite

Guest suite in Freeport

4.96 out of 5 average rating, 186 reviews

Waterfront Private Apartment just 5 min to LL Bean

Guest apartment with private entrances, king bed, pull out sofa, kitchenette, walk-in shower, and porch facing the water providing the perfect relaxing coastal Maine experience! Custom built home on 7.5 acres tucked away in the woods with waterfront access to Harraseeket Cove & South Freeport Harbor, great for kayaking! Located 5 minutes from LL Bean and Freeport's many shops, restaurants, bars, etc. Wolfes Neck State Park and its stunning coastal trails and forests are less than a mile away.

Jan 14 – 21

G$29,546 GYD per night

Guest favorite

Guest suite in Westbrook

4.93 out of 5 average rating, 208 reviews

Awesome open space in Westbrook near Portland, ME!

Welcome!! We're excited to share our house with you! You'll get the whole ground level of the house - two very large clean modern rooms with a private entrance, bathroom, and direct yard access to the hammock, fire pit, and wildlife. Off-street parking for 2 cars, kitchenette, 300Mbit wifi, smart TV, heat, ping pong, darts, and much more! 15 mins downtown Portland ($15 Uber) 1 mile from I-95 11 mins from the airport We will give you awesome tips on everything in the area and beyond!

Nov 14 – 21

G$25,026 GYD per night

Guest favorite

Cabin in Raymond

4.93 out of 5 average rating, 144 reviews

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

Step out of the screened in patio to lakeside relaxation. Dive into crystal waters, snorkel or float with a cool beverage. Kayak or canoe out to Turtle Cove and enjoy the wildlife in this natural waterway teeming with birds to include our resident Blue Heron, ducks, geese, and loons who make this place their home. We have the fortune of bald eagle pairs in several tall pines. Turtles sunning on doting rocks and lily pads in bloom greet us each day. It is a natural water landscape.

Oct 2 – 9

G$38,408 GYD per night

Guest favorite

Treehouse in Georgetown

4.98 out of 5 average rating, 404 reviews

Modern Tree Dwelling w/Water Views+Cedar Hot Tub

Stay in our custom designed tree dwelling w/ wood-fired cedar hot tub up among the trees! This unique structure is perched atop a 21-acre wooded hill sloping to water views. Enjoy stunning views from the King size bed through a wall of windows. Located in a classic coastal Maine village w/ Reid State Park's miles of beaches + famed Five Islands Lobster Co. (See 2 other tree dwellings on our 21 acre property listed on AirBnb as "Tree Dwelling w/Water Views." See our reviews!).

Dec 14 – 21

G$70,850 GYD per night

Guest favorite

Home in Hollis

4.98 out of 5 average rating, 360 reviews

Birch Ledge Guesthouse--Four Season Maine Getaway

Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

Oct 6 – 13

G$38,197 GYD per night

Guest favorite

Cottage in Buxton

5.0 out of 5 average rating, 119 reviews

Peaceful Cottage Retreat on Maine Flower Farm

Come stay among the flowers! The Cottage at Ferris Farm is a beautifully restored cottage where guests can relax, explore nature, and experience staying on a working flower farm. Enjoy a cup of coffee overlooking the flower fields and spend the afternoon kayaking the Saco River. Located in Buxton, the Cottage is centrally located between the wonderful restaurant and brewery scene of Portland and the popular coastline beaches of Old Orchard/Saco.

Dec 5 – 12

G$48,638 GYD per night