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Greenwood Holiday Rentals

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Holiday Rentals in Greenwood

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

9.4 out of 10, Exceptional, (13)
"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, (10)
"Our stay was amazing.. close to town, very comfortable and met all of our needs.. would definitely stay there again!"
The price is AU$287
includes taxes & fees
12 Aug - 13 Aug
Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES

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

10.0 out of 10, Exceptional, (2)
"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

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$1,523
includes taxes & fees
30 July - 31 July
Lakefront Log Home 12 feet Away from Lake

Rediker Retreat- Authentic Riverfront Luxury Log Home

10.0 out of 10, Exceptional, (89)
"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

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

Sleeps 20 | Hot Tub | Game Room | Fire Pit |4500SF

10.0 out of 10, Exceptional, (7)
"We stayed over there for three night over Xmas holidays. The property is very organized and beautiful. The kitchen is equipped very well. The beds are very nice and comfy. Great location, it’s right near Sunday River ski resort."
Sleeps 20 | Hot Tub | Game Room | Fire Pit |4500SF

Dog-friendly riverfront retreat with two decks, washer/dryer, Ping-Pong, & AC

10.0 out of 10, Exceptional, (2)
"My in-laws are from Miami & Colombia … it was the first time they saw snow!! Truly a dream house in the wilderness!! Complete luxury!! We will definitely be back!! "
Dog-friendly riverfront retreat with two decks, washer/dryer, Ping-Pong, & AC

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.

Lakefront Cottage: Boat Dock, Patio & Kayaks!

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

Adult Themed get-a-way! Centrally located to ski mountains, Oxford Casino, OPS.

8.0 out of 10, Very good, (16)
"We had an amazing stay here. Very clean property with all the necessities. We tried a Jamaican restaurant close by- delicious! Stayed here for our anniversary weekend and had an amazing time. "
The price is AU$297
includes taxes & fees
11 Aug - 12 Aug
Adult Themed get-a-way! Centrally located to ski mountains, Oxford Casino, OPS.

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

10.0 out of 10, Exceptional, (52)
"This house was a blast - would def stay again"
INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space

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

10.0 out of 10, Exceptional, (28)
"We had a great time for new years with a group of 24. There was plenty of room to spread out. Location of the home is fantastic for skiing at Sunday River. We were also very pleased with the cleanliness of the home and the snow removal service. A few upgrades to pots/pans and sleeper sofa are recommended but overall a fantastic stay."
9 Bedroom Estate, Sleeps 24, Heated Pool, Hot Tub, Movie Theater, Game Room

Million-Dollar View: Waterfront Cabin in Bridgton!

Million-Dollar View: Waterfront Cabin in Bridgton!

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

9.8 out of 10, Exceptional, (45)
"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

Newly renovated 4-bedroom cottage, directly on Highland Lake

2.0 star property
10.0 out of 10, Exceptional, (2)
"Private, beautiful, everything we wanted for a peaceful family getaway. All the rooms had a spectacular view of the lake, and we looked forward to getting up every single day to enjoy the water. Thank you again!! "
Newly renovated 4-bedroom cottage, directly on Highland Lake

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

9.6 out of 10, Exceptional, (21)
"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...

90 Second, Traffic-Free Drive to Sunday River

10.0 out of 10, Exceptional, (20)
"This house if perfect for two couples with two kids in tow. Super clean and organized - comfortable and charming to spend time in after days of skiing. Would highly recommend and will definitely book again."
90 Second, Traffic-Free Drive to Sunday River

Brand new 2BR, 1.5BA-close to amenities yet feels secluded. 2 story, AC, wifi!

10.0 out of 10, Exceptional, (1)
"A quiet but newly constructed home with all the amenities is a perfect place for a vacation. We especially loved the free range chickens that visited our home daily. And we arrived to find a dozen of their different color eggs ready to scramble for a nice breakfast. The beds were comfortable and the 1.5 bathrooms were good. The expansive backyard with trees made some great bird watching in the mornings with our coffee. Shopping at Renny’s and access to a the public beach in Brighton for...
Brand new 2BR, 1.5BA-close to amenities yet feels secluded. 2 story, AC, wifi!

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$280
includes taxes & fees
30 July - 31 July
Maine Woods Treehouse-The Birdie
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?

Rediker Retreat- Authentic Riverfront Luxury Log Home: This holiday home rental outside of Greenwood is located on the waterfront, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. It has 5 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, an arcade/games room 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 Snow Falls. 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.