House vacation rentals in Greenwood

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Quick stats about house rentals in Greenwood

  • Total vacation rentals

    Explore 70 vacation rentals in Greenwood

  • Nightly prices starting at

    Greenwood vacation rentals start at G$23,040 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,170 verified reviews to help you choose

  • Family-friendly vacation rentals

    70 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    70 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!

Top-rated house rentals in Greenwood

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

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Guest favorite
The A-frame cabin features a striking green metal roof and large triangular windows. A spacious deck, supported by wooden beams, provides outdoor seating. Surrounding greenery complements the cabin's rustic charm, while a picnic table is situated in the yard, offering a serene spot for meals.
Home in Harrison
4.9 out of 5 average rating, 360 reviews

Privacy, River, Pond, A frame Hot Tub EPIC Views,

14 Acres Secluded A-frame nestled along Clean Crooked River, Hot tub with breathtaking VIEWS and world-class fishing. Swim in the river, private pond or explore hiking trails right from your door. Central AC - Gas Fireplace - Modern Kitchen. Just minutes from pristine lakes, primo golf courses, and thrilling ski slopes, this charming private oasis offers an ideal mix of tranquil relaxation and outdoor adventure. Invite a private chef, florist or yoga teacher to fully unwind. Heated bath floors.

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Top guest favorite
A private hot tub is situated outdoors, surrounded by greenery and offering views of the lake and mountains in the background. Two glasses of sparkling wine are placed on the tub's edge, reflecting the natural scenery under a clear blue sky.
Home in Woodstock
4.99 out of 5 average rating, 153 reviews

Sunset & Lake View, Theater, HTub, Xbox, Mini Golf

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!

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Top guest favorite
Home in West Paris
4.99 out of 5 average rating, 142 reviews

Four Season Western Maine Adventure Base

Make some memories at this family-friendly property. Enjoy panoramic views of Maine's western foothills. Owned by an outdoor-loving family, complete with hounds and chickens, this is a perfect spot to launch your Maine adventures. On the doorstep of skiing, hiking, biking, hunting, fishing, kayaking,canoeing. Enjoy beautiful sunrises and sunsets, sightings of eagles, moose, deer, sounds of peepers, woodcock, wild turkey gobbles and whip-o-wills. Enjoy the lifestyle that makes this Vacationland.

ValueFamilySkiing

Guest favorite
A spacious lakefront home is depicted against a backdrop of lush greenery. A large deck with seating is visible, complemented by colorful landscaping. The yard, featuring well-kept grass, offers ample space, while the sun casts gentle shadows across the scene, inviting outdoor relaxation.
Home in Woodstock
4.88 out of 5 average rating, 135 reviews

One of a kind Lakefront home near Sunday river

Amazing large lakefront home right on the water near Sunday river ski resort. Sleeps upwards of 25 people. There is a small surcharge per person for groups larger than 20. At certain times of year we rent to smaller than average groups at an other than listed price. Great for family reunions, weddings etc. Largest yard on the lake! And our hot tub is very invigorating after a day of skiing or hiking! Hot tub is charged separately. NOTE: From late June to late August we only rent by the week.

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Top guest favorite
The open-concept living area showcases natural wood walls and a ceiling, with large windows allowing ample light. A soft sofa and a daybed are arranged around a round coffee table on a striped area rug. A staircase leads to the upper level, visible in the background.
Home in Farmington
4.97 out of 5 average rating, 323 reviews

Carriage House

Renovated circa 1920 carriage house in a quaint New England college town. Eight-minute walk to busy downtown with restaurants, bars, shops, and grocery store. Elegant contemporary style. Open concept downstairs with sofa, daybed (napping in the sun!), and chef-designed kitchen. Second level with two queen beds and small balcony. Adjoins miles of walking trails and forest, full of wildlife. Less than 5-minute drive to a 1.5 mile running trail along the Sandy River, with refreshing swimming.

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Top guest favorite
A hot tub is positioned on a spacious deck, offering a stunning view of a mountain during sunset. The scenery features a blend of warm hues in the sky, with gentle slopes visible in the background. Steps lead up to the hot tub, enhancing accessibility.
Home in Bridgton
4.95 out of 5 average rating, 170 reviews

*1MMview*Bar,Hot Tub,3mins2Pleasant Mnt, Pool tab.

This special, completely renovated place can host your family gathering or group of friends in an inviting setting. This unique house with a private bar, spa, and a pool table will satisfy all your vacation needs! Located close to everything, but absolutely quite and private 20 acres property! It is situated on a ridge with a spectacular mountain view. Our house offers comfort & entertainment. The property will give you the full vacation in the woods experience. This is just what you need!

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Guest favorite
Home in Norway
4.98 out of 5 average rating, 101 reviews

Open concept 4 bedroom Lakehouse

Experience Stunning Sunsets at This Private Lakefront Retreat Escape to this 4-bedroom lakefront home on Pennesseewassee Lake (Norway Lake). Perched on a scenic hillside, it offers breathtaking water views and year-round relaxation. Ideal for families and groups, this spacious retreat sleeps 12 guests with direct lake access. Enjoy snowmobiling, skiing, and ice fishing in winter, boating, swimming, and fishing in summer, or leaf-peeping in fall—a perfect getaway for any season.

LocationValueCleanliness

Guest favorite
A modern exterior of the eco-friendly retreat is displayed, showcasing a sloped roof and large windows. The deck features comfortable seating and steps leading to the welcoming entryway. Surrounding greenery adds a natural backdrop, enhancing the serene atmosphere of the waterfront sanctuary.
Home in Sweden
4.97 out of 5 average rating, 143 reviews

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

LocationFamilyLayout

Top guest favorite
An open-concept living area features a spacious sectional sofa, a coffee table, and a large smart TV mounted on the wall. High ceilings with wooden beams enhance the room, while large windows allow natural light to fill the space, creating a welcoming atmosphere.
Home in Rumford
4.98 out of 5 average rating, 113 reviews

River Valley Sunset Retreat Bethel & Newry Skiing

Your adventure begins at River Valley Sunset Retreat. Nestled on 8.75 private acres in Rumford with stunning mountain and sunset views, this spacious rental is your gateway to Western Maine's best. A skier's dream, it's approximately 20 minutes from Sunday River, Black Mountain, and other premier resorts. Step directly onto the property to cast a line into the adjacent Androscoggin River. Discover the ultimate four-season escape tailored for families and outdoor enthusiasts.

LocationFamilyWalkability

Top guest favorite
Home in Greenwood
4.95 out of 5 average rating, 176 reviews

Bright, Vintage Maine Home, Awaiting Adventure!

Spring has SPRUNG in the mountains! Hike, bike, explore and take it all in before the hustle & bustle of summertime. Classic 3 bedroom, 1 bath centrally located Western Maine home, with hot tub! Much of the vintage charm remains in this early 1900's home, with modern comforts added throughout. This area offers four seasons of fun and you won't have to go far to find it! A mile to skiing & biking at Mt. Abram/15 minutes to Sunday River and five minutes to Bethel Village.

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Top guest favorite
A lofted bedroom features a spacious bed adorned with a vibrant striped blanket. Light filters through a window, highlighting the sloped whitewashed ceilings and simple artwork on the walls. Warm wood accents complement the soft, neutral tones throughout the room.
Home in Bridgton
4.98 out of 5 average rating, 188 reviews

Wren Cabin + Wood fired Sauna

We built the Wren Cabin to be a serene space filled with light and art and with lots of cozy details. Lofted ceilings, a spiral staircase and large open concept with lofted bedroom. The cabin also has a gorgeous wood-fired sauna for those colder days. Wren cabin has a large wraparound deck for relaxing and an outdoor fire pit, as well as shared access to Adams Pond. The space is modern Scandinavian, light and aery, and filled with thoughtful details.

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Guest favorite
The open living area features a vaulted pine ceiling and large windows that offer seasonal mountain views. A modern kitchen with a gas stove and granite countertops seamlessly connects to the sitting area, which includes a comfortable gray sofa and a 55" smart TV.
Home in Sumner
4.94 out of 5 average rating, 165 reviews

Family Getaway in Oxford Hills!

Experience this 2BR/2BA retreat, perfect for couples and small families. Nestled among nature, this hillside getaway offers privacy, modern comforts, and a peaceful ambiance. Unwind by the fireplace, fire pit, relax on the deck, or explore the great outdoors. Whether you're seeking outdoor adventure or relaxation, this hideaway is the perfect home base for your next getaway. Families of 5 or 6 can be accommodated with the queen size pull out sofa.

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Popular amenities for Greenwood house rentals

When is the best time to visit Greenwood?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$78,547 GYDG$78,547 GYDG$68,703 GYDG$63,885 GYDG$62,838 GYDG$73,311 GYDG$72,892 GYDG$72,682 GYDG$62,838 GYDG$62,838 GYDG$62,838 GYDG$76,871 GYD
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