Vacation rentals in Greenwood

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Top-rated vacation rentals in Greenwood

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite
The exterior of the log cabin features a large covered porch with wooden railings, complemented by stacked stone accents on the chimney. Surrounded by a grassy landscape, the cabin sits amidst tall trees, showcasing its rustic charm in a serene natural setting.
Cabin in Greenwood
4.92 out of 5 average rating, 156 reviews

Mt Abram ski in ski out Log Home

This cozy 15 year old log cabin sleeps 6 comfortable and has that log cabin and log furniture feeling and look. Situated on the slopes of Mt Abrams with very easy ski in and out. With a outdoor fireplace on large deck. This is truly your log cabin experience and sking adventure. The cabin has great views of the mountain range for viewing in Fall and Winter. it has 2 King beds, 2 Queen beds, 4 Twin beds, and 1 Full size bunk bed. This log cabin sits half way up Mount Abrams so you ski in and out.

Top guest favourite
A charming chalet is surrounded by a winter landscape, featuring a wooden exterior and large glass windows. The deck offers outdoor seating options, and a fire pit is visible in the snowy yard. Leafless trees create a serene, rustic atmosphere.
Cabin in Stoneham
4.99 out of 5 average rating, 206 reviews

Mad Moose Lodge• Secluded Cabin w/ Mountain View’s

Welcome to the Mad Moose Lodge! Year-round adventures begin at this 2-bed, 2.5-bath Stoneham chalet. This vacation rental provides incredible fall foliage views and easy access to mountains and lakes! Close by to cross-country skiing and snowshoeing in the winter and hiking, mountain biking, boating and swimming in the summer there are endless options of outdoor enjoyment. Enjoy stunning sunsets over the mountains from the comfort of the couch, or while enjoying a game of pool in the game room!

Guest favourite
A charming wooden chalet is surrounded by vibrant fall foliage, showcasing a welcoming deck with red Adirondack chairs. An American flag gently flutters outside, while the natural landscape offers a serene backdrop to the cozy exterior.
Cabin in Greenwood
4.92 out of 5 average rating, 159 reviews

Cozy Cabin w/ Hot Tub & Fire Pit-Walk to Ski Lift!

Whether you want to relax by the fire pit or chill in the hot tub under the stars, grill out on deck w/ mountain views, get cozy by the fireplace playing board games, hike local trails & waterfalls, swim/boat/fish at the beach, or walk to Mt Abram 2 min from cabin to hike/mountain bike/ski/snowmobile &enjoy live music, dinner & drinks at the outdoor beer garden-The Mountain House truly has it all! Explore surrounding area with a quick drive to downtown Bethel,Sunday River,& The White Mountains!

Guest favourite
A private hot tub is surrounded by trees displaying vibrant autumn leaves, with a gentle stream flowing nearby. A fire pit sits beside the hot tub, offering a cozy gathering space. The cabin's exterior features wooden siding and large windows that invite natural light.
Tiny homes in Norway
4.93 out of 5 average rating, 240 reviews

Glass Wall Waterfront Hot Tub Fireplace Tiny Home

Wake up to rushing waterfalls right outside your glass wall in this romantic waterfront tiny home in Norway, Maine! Private hot tub with river views, see-through gas fireplace, cozy raised queen bed overlooking the water, outdoor shower, hammocks, and direct access to hiking trails. Total privacy—no neighbors in sight. Modern kitchen, heated floors, fast WiFi, and thoughtful touches for couples or solo escapes. Romantic getaway near Sunday River skiing, golf & Maine adventures. Nature's oasis

Top guest favourite
A cozy cabin is nestled among snow-covered trees, showcasing a wooden exterior in warm tones. The entrance features a welcoming pathway lined with snow, while the nearby deck offers a glimpse into the winter landscape, creating a serene atmosphere in the snowy environment.
Cabin in Hanover
4.99 out of 5 average rating, 517 reviews

Cabin retreat just steps from adventure

Nestled on 80 acres in the woods alongside a stream, this cabin is the perfect retreat. Whether you are looking for a romantic getaway, a family vacation, or a gathering of your closest friends-this cabin is ideal. It is located on a private road and close to Howard Pond, Androscoggin River, and Sunday River skiing. No matter the season, opportunities await, whether you decide to stay close or venture out. There are plenty of trails nearby to explore, canoe rentals, skiing and so much more.

Top guest favourite
An outdoor deck is illuminated by string lights, featuring a hot tub and a fire pit. A dining table made of wood is positioned nearby, surrounded by comfortable chairs. The sunset casts a warm glow over the scene, enhancing the greenery of the surrounding trees.
Yurt in Woodstock
5 out of 5 average rating, 268 reviews

Luxury Romantic Yurt •Hot Tub •Mt Views •AC •WiFi

Escape to Birdsong Yurt, a romantic and luxurious retreat nestled in the mountains of Maine. Enjoy beautiful mountain views, serene privacy on 2 acres, and a cozy yurt experience you won’t forget. Perfect for couples, friends, or small families seeking a magical getaway. Whether sipping wine under the stars, relaxing sunsets in the hot tub, or cozying up by the fireplace, Birdsong Yurt is your perfect mountain escape. Book your unforgettable experience today! •Full Kitchen/Bathroom •WiFi/AC

Guest favourite
Two Adirondack chairs are positioned on the snowy shore, facing a serene lake framed by tall trees. The still water reflects the surrounding landscape, including snow-capped mountains under a partly cloudy sky. A peaceful winter scene is captured in this outdoor setting.
Cabin in Greenwood
4.94 out of 5 average rating, 270 reviews

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*

Guest favourite
The glamping Geodome is nestled among snow-covered trees, showcasing a warm glow from its interior. The dome's transparent roof allows for views of the sky, while snow blankets the ground, creating a serene winter landscape.
Dome in Buckfield
4.84 out of 5 average rating, 248 reviews

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!

Top guest favourite
A cozy interior features natural wood paneling and beams. Two upholstered chairs are positioned near a large window, allowing light to fill the space. A small bookshelf holds several books, while kitchenware is organized on a nearby shelf. A white stove complements the rustic setting.
Cabin in Bridgton
4.95 out of 5 average rating, 175 reviews

Writers Cabin in the Woods with Sauna!

Nestled in the woods and on Adams Pond with new wood fired sauna! The cabin feels totally hidden away but is less than 10 minutes to Bridgton and Naples, hiking, beaches and restaurants. The woods are beautiful and peaceful and the pond is just down a mossy path. Great for couples or a weekend away. Large deck with grill and outdoor shower, firepit. There is a shared dock on the pond for swimming, fishing, or just enjoying the view as well as a canoe and 2 kayaks, and a paddle board.

Guest favourite
A wooden dock extends into a calm lake, flanked by lush greenery and colorful foliage. Two Adirondack chairs are positioned invitingly at the end of the dock, with a brightly colored blanket draped over one. Reflections of clouds and trees are visible on the water's surface.
Cabin in Woodstock
4.96 out of 5 average rating, 163 reviews

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.

Top guest favourite
Treehouse in Woodstock
4.98 out of 5 average rating, 298 reviews

Treehouse With Hot Tub Close to Sunday River!

This authentic, luxury treehouse was designed by B'Fer Roth, DIY Network TV host of The Treehouse Guys and built by the Treehouse Guys. Nestled in the woods on a quiet, private rd with no neighbors in sight, the treehouse is just 15 minutes to Sunday River Ski Resort, 5 minutes to Mt. Abram and 10 minutes to downtown Bethel. The treehouse is abutted by 626 acres of Bucks Ledge Community Forest (7 miles of hiking/snowshoeing trails accessible from the treehouse).

Top guest favourite
A scenic view showcases the vivid colors of autumn foliage across rolling hills under a blue sky. Pine trees frame the foreground, while distant mountains provide a tranquil backdrop.
Apartment in Woodstock
4.96 out of 5 average rating, 276 reviews

Ski, Swim, Hike, Bike, Repeat!

Come to a cozy mtn getaway (private separate entrance apt within the host's home) nestled in the foothills of the Mahoosuc Range with a view of the White Mtns. In winter, enjoy the hot tub aprés ski, and in warm months enjoy the shaded patio or the apt's naturally cool interior. Outdoor & dining destinations are within as few as ten minutes. Since there is no traditional oven or stove, guests are welcome to safely use their own portable grill on the patio.

Popular amenities for Greenwood vacation rentals

When is the best time to visit Greenwood?

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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Greenwood?

    Greenwood has more than 120 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in cabin rentals in Greenwood?

    Experience the best of Greenwood with our cabin rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Greenwood?

    Four-legged friends are welcome in Greenwood. Choose from more than 70 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Greenwood?

    Yes! Work meets play with ease at over 50 vacation rentals in Greenwood featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do chalet rentals in Greenwood have air conditioning?

    Absolutely! We offer over 10 chalet rentals with air conditioning in Greenwood. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Greenwood have a kitchen?

    Absolutely! We offer over 60 house rentals with a kitchen in Greenwood. Enjoy a tailored experience with all the comforts you desire.

  • Do chalet rentals in Greenwood have wifi?

    Absolutely! We offer over 10 chalet rentals with wifi in Greenwood. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Greenwood have free parking?

    Absolutely! We offer over 60 house rentals with free parking in Greenwood. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Greenwood

  • Total vacation rentals

    Explore 140 vacation rentals in Greenwood

  • Nightly prices starting at

    Greenwood vacation rentals start at $139 CAD per night before taxes and fees

  • Verified guest reviews

    Over 5,540 verified reviews to help you choose

  • Family-friendly vacation rentals

    120 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 70 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    130 of Greenwood vacation rentals include wifi 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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