
Vacation rentals with a kayak in Greenwood
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Top-rated kayak rentals in Greenwood
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LUX Designer Private Waterfront Hot Tub - Secluded
Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

Sunset & Lake View, Theater, HTub, Xbox, Woodstove
Welcome to the Sunday River retreat in our luxury chalet with the best views in Maine. Our sanctuary can comfortably sleep 12 and boasts Lake Christopher panoramic views with Mt. Abram sights. Minutes from Sunday River Resort, a public boat launch and other area attractions. Private hot tub, fire pit, wood stove and deck await your arrival. Enjoy arcade games, Xbox, a movie theatre room, BBQ grill and speakeasy theme bar setup. Don't forget to take a picture in the gondola and to catch a sunset!

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!

Waterfront Gem walkable to Restaurants!
Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

Forest Bathing: Off-Grid Tiny Home, Pond w/ Kayak
Immerse yourself in our forest and serene pond. Quiet 40-acre commune consists of two tiny house cabins + barn on private pond. Book one of the simple yet elegant cabins/barn for more guests. Modern, off-grid, solar-powered retreat. Two solid glass walls to bring you closer to nature while staying in our simple yet elegant tiny house with all comforts of home. 5 min walk to shared fire pits, kayaks, pond & seasonal picnic shelter. AWD SUV or truck required. Off-grid, so no A/C. Pet fee $89.

The Loons' Nest: Lakefront oasis w/ private dock
Welcome to Maine. Enjoy the peace and tranquility of Maines pristine lakes, at our modern Scandinavian lakefront home. On a PRIVATE lake, nestled in the heart of the Maine countryside. This charming retreat offers a peaceful getaway, perfect for those looking to escape the hustle and bustle of city life. The whole group will enjoy easy access to Maines world famous food scene. Enjoy a private dock with stunning views where you can swim, fish, or launch a host-provided kayak or canoe.

Let's Ski! Mins to Slopes, Snow & Fun on the Pond
Winter at Camp Wigwam! Lake cottage on North Pond. Skate, hike, enjoy the firepit in the snow. Stay in comfort with all the amenities. Explore Western Maine or just relax at camp. Watch the nesting pair of bald eagles swoop down to capture fish, listen to the loons. Strong WiFi with Streaming. Enjoy the Wii, 100+ DVDs' and the record turntable. Near Bethel with lovely restaurants, bars and other venues. Great for kids, couples and families. *Bring your 4-footed friend-pet fee applies*

Maine Lakes Region house (private hot tub)
Cozy new construction, Chalet style, year-round house, on 9 wooded acres. Lots of Privacy, Short drive to Ski slopes, snowmobile trails, hiking, or beautiful lake to swim, or kayak. Gage beach a 10-minute drive. Close to great hiking, Also Shawni peak and Sunday River. Great restaurants, Mt Washington, NH shopping outlets. Full Desk / office, 200 mb of streaming. Wi-Fi, Netflix via ROKU, Canines only, NO CATS, NO EXCEPTIONS. Portable generator in the event of a power failure provided.

StreamSide Getaway- HOT TUB / AC/ Wi-Fi
The Streamside Getaway offers a luxurious glamping experience in a new solar and wind-powered Geodome. Equipped with custom furniture, new hot tub,luxury appliances, free high speed wifi, AC/Heat Unit and modern bathroom and kitchen facilities, guests can enjoy a homely and comfortable stay in nature. A glamping site built in 2022 offers a contactless check-in process with a custom key code. Additionally, we have added archery, axe throwing, and kayaks to enhance your outdoor activity!

Private Lakefront Cabin in Woods near Sunday River
Private waterfront Cabin in woods, nestled off private dirt road near Mt. Abrams and Sunday River. Kayak, swim & fish in pristine lake in Summer. Skate, XC Ski, Ice Fish, Snowshoe, Hike in Winter. Fireplace and Fire Pit. Excellent wifi - Private, quiet remote workspace. Rustic modern cozy decor: fully-equipped stainless steel kitchen with full sized appliances, dishes, utensils, coffee maker. Organic linens. Pristine bathroom-large hot shower area, heat lamp, soaking tub.

Waterfront| Outdoor Sauna| Ski| Mountains| Firepit
Escape to Camp Sweden, an eco-friendly waterfront sanctuary in the foothills of the White Mountains. Paddle across the private pond, go for a hike in the Mountains nearby, or jump in the new outdoor panoramic barrel sauna and let your worries evaporate away. Enjoy a unique and rejuvenating experience that connects you to nature without sacrificing comfort. This retreat offers all-season enjoyment for nature lovers and outdoor enthusiasts alike. Experience Maine’s beauty today

Fish Tales Cabin
Everything for your perfect Maine getaway! Use our private dock for your boat, but don't worry about kayaks and paddle boards - use ours. Enjoy a tranquil sunrise, the song of a loon, and the the quaint Bridgton village. Enjoy foliage in the fall and skiing at Pleasant Mountain (formerly Shawnee Peak) only 5 minutes away. White Mountains are very close too! Follow us on FB for more pictures, news and offers! Search for 35 Moose Pond, Bridgton, ME.
Popular amenities for Greenwood kayak rentals
House rentals with a kayak

Witts' End- quiet neighborhood in Knights Hill

Open concept 4 bedroom Lakehouse

Sebago Waterfront with beach, kayaks, + amenities

Lake Home Retreat • Hot Tub • Sleeps 9 • Near Ski

Kayak to the Causeway-50s cottage with modern vibe

Hot Tub Haven: Dog-Friendly Retreat

“A Beary Happy Place” stunning home, views & more

Luxury Sunday River Chalet • Hot Tub•Sleeps 16
Cottage rentals with a kayak

Tranquil waterfront cottage

Charming 3 bedroom cottage on Notched Pond

Lake Front 3 Season House with Private Deck

Thompson Lake, No Cleaning Fee Pine Point Cottage,

Fun 2 bed 2 bath on a private Pequawket Lake.

20ft from the Water with Mountain View!

Loons Rest – Maine Quintessential Cottage

Conway Waterfront Base for Your Family Memories!
Cabin rentals with a kayak

All seasons Lake House next to ski areas

Lakefront Getaway Cabin/Private Sandy Beach!

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

Nordic House | Glamping Cabin w Private Hot Tub

Get away at Crystal Lake

Private cabin w hot tub,skiing,firepit & mountains

A-Frame Glamping Cabin with Sauna onsite

Cozy Ski Cabin #6 W/ Loft, HOT TUB
When is the best time to visit Greenwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,513 | ﺩ.ﺇ1,546 | ﺩ.ﺇ1,315 | ﺩ.ﺇ1,010 | ﺩ.ﺇ1,010 | ﺩ.ﺇ1,105 | ﺩ.ﺇ1,351 | ﺩ.ﺇ1,407 | ﺩ.ﺇ1,194 | ﺩ.ﺇ1,260 | ﺩ.ﺇ1,105 | ﺩ.ﺇ1,520 |
| Avg. temp | -10°C | -9°C | -3°C | 4°C | 11°C | 16°C | 19°C | 18°C | 14°C | 7°C | 1°C | -6°C |
Quick stats about vacation rentals with a kayak in Greenwood

Total vacation rentals
Explore 30 vacation rentals in Greenwood

Nightly prices starting at
Greenwood vacation rentals start at ﺩ.ﺇ551 per night before taxes and fees

Verified guest reviews
Over 1,710 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Greenwood vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Greenwood rentals

4.9 Average rating
Greenwood stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with a patio Greenwood
- Rentals with a hot tub Greenwood
- Rentals with a fire pit Greenwood
- Family-friendly rentals Greenwood
- House rentals Greenwood
- Rentals with lake access Greenwood
- Rentals with a kayak Oxford County
- Rentals with a kayak Maine
- Rentals with a kayak United States
- White Mountain National Forest
- Sebago Lake
- Sunday River Resort
- Story Land
- Mount Washington Cog Railway
- Saddleback Ski Mountain Maine
- Cranmore Mountain Resort
- King Pine Ski Area
- East End Beach
- Omni Mount Washington Resort
- Diana's Baths
- Waterville Valley Resort
- Pleasant Mountain Ski Area
- Wolfe's Neck Woods State Park
- Conway Scenic Railroad
- Wildcat Mountain
- Portland Museum of Art
- Bradbury Mountain State Park
- Mt. Abram
- Santa's Village
- Echo Lake State Park
- Jackson Xc
- Maine Mineral & Gem Museum
- Grafton Notch State Park




