Photo by Robbie Martin

Greenwood Vacation Rentals

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Vacation Rentals in Greenwood

Exquisite Rustic Modern Ski Haus Right on MT Abram Bike Park

10.0 out of 10, Exceptional, (18)
"We loved this property so much last year we had to come back for an another ski trip this year. The house is immaculate and fully stocked with everything you could need. We had 3 young kids 3-5 years old and they were able to make the walk from the back yard, to an ungroomed trail, where we then had to walk a few houses past before we could put skis on and go down a slight slope to the base. It is a very close location to a great, family friendly mountain! Hope to be back for a third time next...
Exquisite Rustic Modern Ski Haus Right on MT Abram Bike Park

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

10.0 out of 10, Exceptional, (44)
"There is nothing but great things to say about this place. It has everything you could imagine, clean and well located. The host is also very responsive and kind. 11/10 stay. Thank you!"
INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space

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

9.4 out of 10, Exceptional, (9)
"This was a great property for bringing together the 3 generations of the family! Plenty of open area for talking, playing, eating etc. and a great location for making the most of the Maine lakes region. My favorite thing was the very long dining table that could seat all 14 of us for meals as well as facilitate multiple board games at once."
Expansive Retreat - All-Season Contemporary Farmhouse [Lakes & Mountains]

The Mansion- Exclusive Private Estate on 5 Pristine Acres

10.0 out of 10, Exceptional, (33)
"The house was AMAZING! Had a wonderful time We had a pretty big group and the house was comfortable enough for all of us including kids and a dog. Did not feel crowded at all. Hosts were wonderful, very accommodating with late check out and asking if we need anything. The views from the house are spectacular, you dont need to go out at all honestly, you would have a good time just enjoying the house amenities and the views, def worth the drive from NY"
The Mansion- Exclusive Private Estate on 5 Pristine Acres

PRIVATE & PEACEFUL CABIN w/ HOT TUB and MTN VIEWS

9.6 out of 10, Exceptional, (66)
"Overall we had a great stay at this house. We got to check in early which was great. The fireplace is so cozy and the main room is an awesome place to hangout. If we had one thing that could have been better, the upstairs bedrooms need new mattresses. Ours sunk down in the middle and needed to be replaced. My brother in-law said theirs needed replacing too. Otherwise it was great! "
PRIVATE & PEACEFUL CABIN w/ HOT TUB and MTN VIEWS

Two-story dog-friendly cabin with a wood stove, pool, tennis, beach, W/D

9.6 out of 10, Exceptional, (11)
"Overall cute house and it’s great it’s dog friendly. I expected dog hairs etc but found human hairs in bathroom and dirty towel hanging. Husband found floss stick on ground too. They offered to come clean it for us which was really nice, and we didn’t feel we needed. Bed and couches really comfy. Shower loud noise. Great they have laundry. Overall good stay but very much like a rustic cabin and probably needs a different cleaner"
Two-story dog-friendly cabin with a wood stove, pool, tennis, beach, W/D

Mtn View, Sleeps 20, Hot Tub, Firepit, Wood Stove, Theater, Workspace, Bar, Gym

9.8 out of 10, Exceptional, (9)
"We had an amazing time, the place is awesome. We will definitively be looking to return"
Mtn View, Sleeps 20, Hot Tub, Firepit, Wood Stove, Theater, Workspace, Bar, Gym

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

10.0 out of 10, Exceptional, (6)
"Excellent stay in the quaint town of Bridgton"
The price is ¥22,391
¥27,660 total
includes taxes & fees
Feb 24 - Feb 25
Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES

Lakefront House with Private Sandy Beach

9.8 out of 10, Exceptional, (26)
"I would have given this property 5 stars except for the sketchy kitchen equipment. When traveling with pets it is often difficult to go out to eat. Therefore we made three meals a day and wished for 1)a toaster oven 2)electric kettle and 3) more hot pads, kitchen towels, and spatulas"
Lakefront House with Private Sandy Beach

Pet Friendly/Mt. Home/Beau Views/ 3 or more nights 20% DISC!

10.0 out of 10, Exceptional, (39)
"Everything was perfect."
The price is ¥32,747
¥90,807 total
includes taxes & fees
Mar 24 - Mar 25
Pet Friendly/Mt. Home/Beau Views/ 3 or more nights 20% DISC!

Rediker Retreat- Authentic Riverfront Luxury Log Home

10.0 out of 10, Exceptional, (84)
"Lovely mountain home, house had everything you could need and LOTS of activities for kids and teens. Hot tub and sauna were a huge hit after skiing! Owners/managers answered questions within a few minutes, very helpful. Super convenient if you are skiing at Sunday River!"
Rediker Retreat- Authentic Riverfront Luxury Log Home

Njoy Luxury - MUST experience this exclusive and stunning lakeview home

9.6 out of 10, Exceptional, (15)
"This beautiful home was perfect for our family for six adults and four small children. We live in three different states, so coming to your house allowed us to spend extended time together. One of our favorite activities was flying paper airplanes from the balcony of the top floor to the living room. Thank you for leaving two small foam airplanes to inspire us. The living room was a great place to gather to read a pile of children’s books intermittently throughout our days with our little ones....
Njoy Luxury - MUST experience this exclusive and stunning lakeview home

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

10.0 out of 10, Exceptional, (19)
"Our family stayed for 3 nights and had a great time. The place was adorable, well stocked, super cozy, and VERY clean. Would definitely recommend to others and hope to stay again ourselves! Thank you :-) "
Welcome to The Bear's Den! Dog friendly and 5 minutes to Pleasant Mountain!

Whispering Waters Farmhouse/Barn

Whispering Waters Farmhouse/Barn

Sunday River Rental

9.6 out of 10, Exceptional, (34)
"We had an issue with access instructions but once we heard back from the owner that was resolved. The property was a good size for our group, clean and well-equipped. The location was close enough to Sunday River for skiing and we watched the NYE fireworks there as well! The location was also good for access to restaurants in Bethel - and the bowling alley! "
Sunday River Rental

Luxurious Slope side Ski-in Ski-out Locke Mountain Townhouse Sunday River

10.0 out of 10, Exceptional, (67)
"We had a fantastic time at the Locke Mountain Townhouse! Chet went above and beyond to ensure we could enjoy the full weekend which was much appreciated. Highly recommend!"
Luxurious Slope side Ski-in Ski-out Locke Mountain Townhouse Sunday River

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, (25)
"Me and a group of friends rented this Yurt for a little hiking weekend trip! The yurt was really nice and the property was beautiful. Justin provided a sled to us to help trek our stuff up and it was really helpful! The only issue we had during the trip was with parking. We parked about 100ft from the no parking sign but then received a text when we got back down in the morning that parking authorities didn’t like us parking there. Justin handled the situation great! The wood stove was super...
The price is ¥13,434
¥20,245 total
includes taxes & fees
Feb 23 - Feb 24
Unique lodging in the wilderness. Off the grid location great place to disconnect and enjoy nature. Access via foot or other in wintertime.

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

10.0 out of 10, Exceptional, (6)
"House was beautiful. Enough group spaces for all to watch movies and football together or aprt. Kitchens had everything we needed. Beds were comfortable. Hot to was a blessing after a day on the slopes. Less than 10 minutes to the slopes. Would recommend to all. The use of the garage was a great bonus to unload . Recommend this house for a big group!!! wHadapart!"
Sleeps 20 | Hot Tub | Game Room | Fire Pit |4500SF

2 miles within Sunday river, mountain side house

9.6 out of 10, Exceptional, (29)
"Nice home, very convenient to Sunday River. House is well stocked and the hot tub was a hit with our group that included 3 families and 6 children ages 5-8. There were a few minor issues that arose during our stay, but overall found the host to be responsive and helpful. "
2 miles within Sunday river, mountain side house

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

7.8 out of 10, Good, (14)
"This is my second time staying here and the home is amazing and super cozy. Very clean and easy access. The kitchen is full of appliances which allows for cooking very easy and convenient "
The price is ¥18,659
¥27,985 total
includes taxes & fees
Feb 23 - Feb 24
Adult Themed get-a-way! Centrally located to ski mountains, Oxford Casino, OPS.
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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Other types of properties in Greenwood you may be interested in

Exquisite Rustic Modern Ski Haus Right on MT Abram Bike Park

10.0 out of 10, Exceptional, (18)
"We loved this property so much last year we had to come back for an another ski trip this year. The house is immaculate and fully stocked with everything you could need. We had 3 young kids 3-5 years old and they were able to make the walk from the back yard, to an ungroomed trail, where we then had to walk a few houses past before we could put skis on and go down a slight slope to the base. It is a very close location to a great, family friendly mountain! Hope to be back for a third time next...
Exquisite Rustic Modern Ski Haus Right on MT Abram Bike Park

Snow Cap Inn

2.5 star property
8.8 out of 10, Excellent, (292)
"Great place to stay at Sunday River on somewhat of a budget. Close to everything. Cookies were a great idea but school break was tough time to get one"
The price is ¥19,480
¥23,731 total
includes taxes & fees
Mar 4 - Mar 5
Snow Cap Inn

Jordan Hotel

3.0 star property
8.6 out of 10, Excellent, (306)
"The food is so expensive. It looks great after the last renovations. Outdoor pool and hot tubs are awesome. "
The price is ¥30,227
¥36,822 total
includes taxes & fees
Mar 9 - Mar 10
Jordan Hotel
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.

Frequently asked questions

Can I find a vacation rental in Greenwood?

Yes, you can find vacation rentals close to the most popular points of interest in Greenwood, or you can go with a secluded option if you want a relaxing place to stay. Greenwood is known for its ski areas.

What's the top vacation rental in Greenwood?

INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space: Visitors like this Greenwood vacation home rental. It is located on a river and has an outdoor pool, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Greenwood?

With 20 Expedia vacation rentals, you're sure 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 Pennesseewassee lake. While here, Mt. Abram and Tucker's Tumble Glades are other places worth a visit.

What’s a vacation rental in Greenwood like?

Vacation rentals are private properties you can stay in for several days or longer in Greenwood. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a small group gathering.