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Greenwood Holiday Rentals

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Holiday Rentals in Greenwood

Lakefront Log Home 12 feet Away from Lake

10.0 out of 10, Exceptional, (57)
"Incredible night away on a quiet Maine pond. Highly recommended, Todd was great and the place was perfect! We will be back for sure."
The price is AU$936
includes taxes & fees
7 Sept - 8 Sept
Lakefront Log Home 12 feet Away from Lake

INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space

10.0 out of 10, Exceptional, (56)
"This house was a blast - would def stay again"
INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space

Expansive Retreat - All-Season Contemporary Farmhouse [Lakes & Mountains]

9.6 out of 10, Exceptional, (15)
"Would stay here again. Loved the location and the size of the rooms! Perfect for a group and very pet friendly."
Expansive Retreat - All-Season Contemporary Farmhouse [Lakes & Mountains]

Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES

10.0 out of 10, Exceptional, (13)
"Our stay was amazing.. close to town, very comfortable and met all of our needs.. would definitely stay there again!"
The price is AU$288
includes taxes & fees
14 Sept - 15 Sept
Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES

Rediker Retreat- Authentic Riverfront Luxury Log Home

10.0 out of 10, Exceptional, (90)
"Had a wonderful stay Rediker retreat. Truly a retreat. The property had everything we needed for our holiday week. Thanks for having us. "
Rediker Retreat- Authentic Riverfront Luxury Log Home

9 Bedroom Estate, Sleeps 24, Heated Pool, Hot Tub, Movie Theater, Game Room

10.0 out of 10, Exceptional, (28)
"Great place, great location, great amenities, thanks for the great stay!"
9 Bedroom Estate, Sleeps 24, Heated Pool, Hot Tub, Movie Theater, Game Room

Lovely, Lake Front 2-Bedroom Cabin with Porch and Dock on Saturday Pond

10.0 out of 10, Exceptional, (3)
"My stay in this cute cabin was very relaxing. The view of the water was peaceful and the sound of the loons was lovely. The owners were very nice, friendly, and helpful. I enjoyed my stay."
Lovely, Lake Front 2-Bedroom Cabin with Porch and Dock on Saturday Pond

Cozy log cabin home. 5 minutes to the beach, pet and family friendly home.

2.0 out of 10, (1)
Cozy log cabin home. 5 minutes to the beach, pet and family friendly home.

Cozy 3BR home for outdoor enthusiasts, deck, pool, tennis, w/d, trails & BBQ

2.5 star property
7.2 out of 10, Good, (5)
"Friends and family gathering pre wedding party! It was pleasant!"
Cozy 3BR home for outdoor enthusiasts, deck, pool, tennis, w/d, trails & BBQ

Panoramic Water and Mountains Views with Nature appearing daily. Relax on

10.0 out of 10, Exceptional, (55)
"My kids loved the beach a short walk away, and the shallow water was crystal clear. Because of the location, there really is a view from every window. Kind of small cabin and lot though"
Panoramic Water and Mountains Views with Nature appearing daily. Relax on

Lakefront Cottage: Boat Dock, Patio & Kayaks!

3.0 star property
Lakefront Cottage: Boat Dock, Patio & Kayaks!

Maine Woods Treehouse-The Birdie

10.0 out of 10, Exceptional, (2)
"Fabulous stay. Took my adult daughter and her two dogs out for a quick overnight adventure. Loved staying in the treehouse (birdie). Perfect size, location on property was good (away from other structures) and had picnic table, potbelly stove, grill, and out house right near the treehouse. They supplied bedding,camp chairs, and even a small battery powered fan. They also offered and we accepted ATV transport of our things from our parking spot to the treehouse. Did a local mountain hike...
The price is AU$281
includes taxes & fees
28 Aug - 29 Aug
Maine Woods Treehouse-The Birdie

Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views

10.0 out of 10, Exceptional, (8)
"We loved the house. It was very clean and the view was incredible! Can’t wait to go back!"
Waterfront, dog-friendly home on 12+ acres with dock, hot tub & sunset views

Secluded dog-friendly getaway with hot tub, game room, firepit, mountain views

8.8 out of 10, Excellent, (39)
"Great views and location if you are looking for a part of Maine not super coastal and touristy."
Secluded dog-friendly getaway with hot tub, game room, firepit, mountain views

The Artist's Cabin at Powder Ridge Overlooking Sunday River SKI PARKING PASS

10.0 out of 10, Exceptional, (323)
"Great place!"
The Artist's Cabin at Powder Ridge Overlooking Sunday River SKI PARKING PASS

Lakefront home with lovely lake views - one mile from the casino

9.8 out of 10, Exceptional, (46)
"Really enjoyed the location and charm of the place. It has the rustic feel of a cabin with all the modern amenities for a comfortable stay."
Lakefront home with lovely lake views - one mile from the casino

Welcome to The Bear's Den! Dog friendly and 5 minutes to Pleasant Mountain!

10.0 out of 10, Exceptional, (31)
"Sindi and Doug were excellent hosts! The property was extremely clean, welcoming and full stocked with everything needed for a ski weekend!"
Welcome to The Bear's Den! Dog friendly and 5 minutes to Pleasant Mountain!

Unique lodging in the wilderness. Off the grid location great place to disconnect and enjoy nature. Access via foot or other in wintertime.

9.4 out of 10, Exceptional, (26)
"Also fun to stay here!"
The price is AU$210
includes taxes & fees
28 Aug - 29 Aug
Unique lodging in the wilderness. Off the grid location great place to disconnect and enjoy nature. Access via foot or other in wintertime.

Hike, fish, bike, float the river, explore or just relax...

9.4 out of 10, Exceptional, (23)
"The house is exactly as pictured. It's clean, airy, great view of the slopes from the huge windows in the living room! Kitchen has the core things you need. Kids really enjoyed the basement couch area. Host was super responsive and accommodating. Highly recommend!!"
Hike, fish, bike, float the river, explore or just relax...

Riverfront Ski Chalet Cabin only minutes to Sunday River Resort & Trails Galore!

10.0 out of 10, Exceptional, (120)
"Nice comfortable stay near Sunday River. Worked great for two families staying for the weekend. "
Riverfront Ski Chalet Cabin only minutes to Sunday River Resort & Trails Galore!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Greenwood Hotel Reviews

Frequently asked questions

Can I find a holiday rental in Greenwood?

Yes, there are holiday rentals close to the most popular sights in Greenwood, or you can select a more secluded option if you're looking for a relaxing stay. Greenwood is known for its ski areas.

What are some of the best holiday rentals that Greenwood has to offer?

INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space: This holiday home rental outside of Greenwood is located on a river, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Greenwood?

With 21 Expedia holiday rentals, you're guaranteed to find just the right place for your Greenwood stay.

What’s there to see and do in Greenwood?

While exploring the area, visit family-friendly sights like Mineral Collector, or get outside and enjoy nature at Papoose Pond. While here, Mt. Abram and Tucker's Tumble Glades are other places worth a visit.

What’s a holiday rental in Greenwood like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Greenwood. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a small group gathering.