Vacation rentals with a kayak in Windham

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Top-rated kayak rentals in Windham

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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.

Mar 20 – 27

ﺩ.ﺇ590 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.

Jan 27 – Feb 3

ﺩ.ﺇ438 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!

Nov 27 – Dec 4

ﺩ.ﺇ580 per night

Guest favorite

Guest suite in Freeport

4.96 out of 5 average rating, 187 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 22 – 29

ﺩ.ﺇ427 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!

Dec 22 – 29

ﺩ.ﺇ483 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.

Sep 22 – 29

ﺩ.ﺇ674 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 15 – 22

ﺩ.ﺇ1,244 per night

Guest favorite

Home in Hollis

4.98 out of 5 average rating, 361 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 12 – 19

ﺩ.ﺇ671 per night

Superhost

Cottage in Windham

4.79 out of 5 average rating, 104 reviews

Cozy camp near highland lake

If you're looking for a quiet, cozy get a-way steps from the lake this is the place. Lake is private with no public access so it’s not crowded. Close to everything but far enough away; highway (95), Portland, Sebago Lake Area. Boating, swimming, fishing, hiking at your finger tips. 4 kayaks provided. Big yard, great for games, BBQ or sitting by the fire pit. Listen to the loons from the front deck. Sorry no pets so please don’t ask if you bring one!

Jul 10 – 17

ﺩ.ﺇ792 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.

Oct 13 – 20

ﺩ.ﺇ854 per night

Guest favorite

Guest suite in Conway

5.0 out of 5 average rating, 258 reviews

CloverCroft - "Far from the madding crowd."

CloverCroft, a 200+/- year old farmhouse, is located in the rich farmland of the Saco River Valley at the foot of the White Mountains. We go the extra mile to make your stay enjoyable and comfortable. (Please note our mattress is FIRM and there is a long flight of outdoor stairs to access the suite.) COME ENJOY PRIVACY AND THE GREAT OUTDOORS. There are many summer and winter activities very close by and we look forward to hosting you.

Jun 10 – 17

ﺩ.ﺇ422 per night

Guest favorite

Guest suite in Windham

4.92 out of 5 average rating, 152 reviews

Millers Private Studio on Highland Lake

If you're looking for a quiet, cozy getaway with private Highland Lake access this is the place for you. Private deck to enjoy your morning coffee, close to everything but in a country setting. 15 minutes from 95, Portland ME and Sebago Lake Region. Small boat launch available, Swimming & Fishing . Large back yard and a great window view of the lake. Wifi 100(mbps) for a work from home atmosphere.

Oct 16 – 23

ﺩ.ﺇ423 per night