Photo by Robbie Martin

Greenwood Holiday Rentals

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Holiday Rentals in Greenwood

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]

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

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

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 AU$1,125
includes taxes & fees
24 Feb - 25 Feb
Pet Friendly/Mt. Home/Beau Views/ 3 or more nights 20% DISC!

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!

The Farmhouse at Bryant Pond

10.0 out of 10, Exceptional, (44)
"Close to skiing/hiking/ice fishing/skating. Well appointed modernized, old farmhouse - plenty of bedrooms, bathrooms, big kitchen, laundry. Evenings by the fire. Hard to imagine a better place for our family, (ages 7 months to 86 years old), getaway."
The Farmhouse at Bryant Pond

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

Highland Dream: Summer Paradise! 5BR/2BA W Sandy Beach, Stay and Play. 4 Seasons

10.0 out of 10, Exceptional, (20)
"We had a great time during our week at Highland Lake. The property was just what we were looking for. The host was great to work with, quickly answering all our questions. The lake and area are beautiful."
Highland Dream: Summer Paradise! 5BR/2BA W Sandy Beach, Stay and Play. 4 Seasons

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

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 AU$297
includes taxes & fees
24 Feb - 25 Feb
Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES

Unwind at Our Beautiful Sanctuary | Scenic Views by RedAwning

2.0 star property
10.0 out of 10, Exceptional, (2)
"Very nice property. Clean. Comfortable. Convenient to Moose Pond, Pleasant Mountain, Bridgeton Center, and Fryburg Center. Only about 35 mins to North Conway. Owners were very nice and helpful. We recommend this property. "
Unwind at Our Beautiful Sanctuary | Scenic Views by RedAwning

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 AU$217
includes taxes & fees
18 Feb - 19 Feb
Unique lodging in the wilderness. Off the grid location great place to disconnect and enjoy nature. Access via foot or other in wintertime.

Cozy Studio with Slopeside Access, Pool, Sauna, and Mountain Views

6.0 out of 10, (1)
"The unit matched the description and photos, with great natural light and convenient ski-in/ski-out access. However, there were a few issues:No parking pass was provided at arrival, and Vacasa's management status with the property caused confusion. The building manager, though helpful, had to intervene to prevent towing. We weren’t given access to the ski lockers, leaving us without proper gear storage despite signs prohibiting skis/boots in the unit. This is disappointing for a ski-in/ski-out...
Cozy Studio with Slopeside Access, Pool, Sauna, and Mountain Views

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!"
The price is AU$3,717
includes taxes & fees
18 Feb - 19 Feb
Sleeps 20 | Hot Tub | Game Room | Fire Pit |4500SF

2 miles within Sunday river, mountain side house

9.6 out of 10, Exceptional, (29)
"We had family and friends staying for a ski weekend and the house was perfect! 6 adults and 5 children and we had plenty of space and the house is gorgeous with the most incredible view of Sunday River! We were so close to the mountain which made the drive to and from a breeze! "
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 AU$299
includes taxes & fees
18 Feb - 19 Feb
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

Snow Cap Inn

2.5 star property
8.8 out of 10, Excellent, (285)
"Great option for affordable lodging close to resort. Shuttle service was excellent. "
The price is AU$250
includes taxes & fees
4 Mar - 5 Mar
Snow Cap Inn

Jordan Hotel

3.0 star property
8.6 out of 10, Excellent, (304)
"Renovation made the hotel even more inviting. Very attentive and friendly employees. Beds are very comfortable. A little way to improve - the heater is very loud."
The price is AU$388
includes taxes & fees
9 Mar - 10 Mar
Jordan Hotel

Grand Summit Hotel

3.0 star property
8.2 out of 10, Very good, (239)
"classic lodge feeling"
The price is AU$477
includes taxes & fees
25 Feb - 26 Feb
Grand Summit 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 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?

Stunning view of Sunday River, Luxurious Home, Hot Tub, Games, Ski: This holiday home rental outside of Greenwood is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 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 20 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 Pennesseewassee lake. 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.