A calm lake surrounded by autumn-colored trees and houses in the background.

Greenwood Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Greenwood holiday rentals

A spacious living room with a high ceiling, large windows, and a fireplace.

1. Lakefront Family Retreat: Skiing & Mountain Biking

Lakefront Family Retreat: Skiing & Mountain Biking
3.0 star property
Greenwood
Lakefront Family Retreat: Skiing & Mountain Biking
A room with a large window, a sofa with patterned cushions, a small table with a vase of flowers, and a radiator.

2. Evergreen Valley Inn by Coolvacay

Evergreen Valley Inn by Coolvacay
3.0 star property
Stoneham
8.2 out of 10, Very good, (194 reviews)
"Very secluded and quiet If your looking for a little pice of Heaven look no further then here It was lovely Very friendly and very welcoming . I can’t wait to visit again"
United States
Terry
The price is HK$872
HK$951 total
includes taxes & fees
13 Oct - 14 Oct
Evergreen Valley Inn by Coolvacay
A person sitting on a bed in a room with wooden walls and a ceiling, reading a book.

3. Nature Retreat, Sauna, Hot Tub, Gameroom, Fire Pit

Nature Retreat, Sauna, Hot Tub, Gameroom, Fire Pit
Woodstock
The price is HK$1,260
HK$4,991 total
includes taxes & fees
25 Oct - 26 Oct
Nature Retreat, Sauna, Hot Tub, Gameroom, Fire Pit
A wooden interior with a dining area, a sofa, and large windows offering a view of the outdoors.

4. Sleeps 10, Lake View Retreat, with Hot tub & Barrel Sauna

Sleeps 10, Lake View Retreat, with Hot tub & Barrel Sauna
Woodstock
The price is HK$2,655
HK$5,190 total
includes taxes & fees
12 Oct - 13 Oct
Sleeps 10, Lake View Retreat, with Hot tub & Barrel Sauna
A bedroom with a bed, a wooden staircase leading to a bathtub, and a wall-mounted heater.

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

Adult Themed get-a-way! Centrally located to ski mountains, Oxford Casino, OPS.
South Paris
8.8 out of 10, Excellent, (38 reviews)
"Great place to stay"
United States
Hannah G.
The price is HK$883
HK$1,347 total
includes taxes & fees
6 Oct - 7 Oct
Adult Themed get-a-way! Centrally located to ski mountains, Oxford Casino, OPS.
A modern kitchen with dark cabinetry, a central island, pendant lighting, and a large window.

6. NEW Luxury Retreat Hot Tub+Swim Lake+Firepits

NEW Luxury Retreat Hot Tub+Swim Lake+Firepits
Woodstock
8.0 out of 10, Very good, (1 review)
The price is HK$2,558
HK$6,038 total
includes taxes & fees
5 Oct - 6 Oct
NEW Luxury Retreat Hot Tub+Swim Lake+Firepits
A bedroom with a large bed, a fireplace, a hanging chair, and a view of a forest and stream.

7. Ultra Private, Crooked Reflections, Riverside Retreat, Hot Tub, Waterfront Glass

Ultra Private, Crooked Reflections, Riverside Retreat, Hot Tub, Waterfront Glass
Norway
9.8 out of 10, Exceptional, (10 reviews)
"Such a great and cozy few days away from reality, highly recommend this warm, home away from home kind of place!"
United States
Elizabeth S.
The price is HK$3,923
HK$6,354 total
includes taxes & fees
15 Oct - 16 Oct
Ultra Private, Crooked Reflections, Riverside Retreat, Hot Tub, Waterfront Glass
A hot tub in a forested area with outdoor seating and a grill.

8. Cedar🏡 Waterfront💦 Hot tub🔥 Pool🎱 Privacy 🕵️

Cedar🏡 Waterfront💦 Hot tub🔥 Pool🎱 Privacy 🕵️
Norway
9.6 out of 10, Exceptional, (24 reviews)
"The cabin was very clean and cozy and relaxing, we had a wonderful time there!"
United States
Colby S.
The price is HK$3,766
HK$6,158 total
includes taxes & fees
15 Oct - 16 Oct
Cedar🏡 Waterfront💦 Hot tub🔥 Pool🎱 Privacy 🕵️
A cozy log cabin interior with a stone fireplace, a comfortable sofa, and a large window offering a view of the outdoors.

9. Ursa Major House - Quiet family getaway, minutes from skiing, hiking, biking.

Ursa Major House - Quiet family getaway, minutes from skiing, hiking, biking.
Bethel
10.0 out of 10, Exceptional, (26 reviews)
"We had a wonderful stay! The communication was super easy. The house was clean and had plenty of room. The living-room was so cozy and loved the hot tub at the end of a long day. Close to beautiful hikes and great restaurants. Definitely would book again! "
United States
Tanya M.
The price is HK$2,097
HK$5,545 total
includes taxes & fees
5 Oct - 6 Oct
Ursa Major House - Quiet family getaway, minutes from skiing, hiking, biking.
A cozy interior with a stone fireplace, a seating area with sofas and chairs, a dining table, and a view of the outdoors through large windows.

10. Hot Tub, Sauna, Game Room, Fire Pit, BBQ, Karaoke, Dogs OK

Hot Tub, Sauna, Game Room, Fire Pit, BBQ, Karaoke, Dogs OK
Bethel
9.8 out of 10, Exceptional, (12 reviews)
"It was amazing everything was just as it was shown perfect place to book for family "
United States
Leslie D.
The price is HK$2,753
HK$6,978 total
includes taxes & fees
14 Oct - 15 Oct
Hot Tub, Sauna, Game Room, Fire Pit, BBQ, Karaoke, Dogs OK
A log cabin with a balcony, a stone chimney, and a large window.

11. Bethel Chalet- Hot Tub + Sauna- 3 kings & bunk room

Bethel Chalet- Hot Tub + Sauna- 3 kings & bunk room
Bethel
10.0 out of 10, Exceptional, (6 reviews)
"Great house for families! Super clean. Host was very nice. The finished basement w/ ping pong was a huge hit. We will for sure be staying there again."
United States
Gioia B.
The price is HK$4,061
HK$7,496 total
includes taxes & fees
12 Oct - 13 Oct
Bethel Chalet- Hot Tub + Sauna- 3 kings & bunk room
A spacious living area with a sofa, coffee table, and dining table. There is a kitchen in the background with modern appliances.

12. Cozy Retreat w/ Fireplace, EV Charger, King Bed

Cozy Retreat w/ Fireplace, EV Charger, King Bed
Bethel
9.4 out of 10, Exceptional, (12 reviews)
"Place was clean, comfy, and in a great location - just as described. Host was responsive and left clear instructions for everything. "
United States
Kevin S.
The price is HK$1,211
HK$2,295 total
includes taxes & fees
6 Oct - 7 Oct
Cozy Retreat w/ Fireplace, EV Charger, King Bed
A cozy living room with a wooden ceiling, a sofa, a coffee table, and a dining area with a table and chairs.

13. Sunday River Condo Near Ski Lifts, Breweries & Downtown Bethel

Sunday River Condo Near Ski Lifts, Breweries & Downtown Bethel
Bethel
10.0 out of 10, Exceptional, (13 reviews)
"Clean, comfortable and great location near the mountain. "
United States
Matthew B.
The price is HK$1,860
HK$3,183 total
includes taxes & fees
9 Oct - 10 Oct
Sunday River Condo Near Ski Lifts, Breweries & Downtown Bethel
A spacious living room with a brown leather sofa, a flat-screen TV, and a wooden ceiling.

14. NEW! Modern Getaway - Hot Tub/Fire Pit/Pool table

NEW! Modern Getaway - Hot Tub/Fire Pit/Pool table
Norway
10.0 out of 10, Exceptional, (2 reviews)
"We had a great couple of nights here, plenty of space for 6 adults and 3 kids. Everything was clean, worked well, and easy to find what we needed. Great location to drive back to after skiing and we'd definitely stay again if in the area. We all loved the hot tub!"
United States
Irene S.
The price is HK$2,511
HK$6,551 total
includes taxes & fees
14 Oct - 15 Oct
NEW! Modern Getaway - Hot Tub/Fire Pit/Pool table
A dining table set with plates, cutlery, and a charcuterie board with various cheeses, fruits, and meats.

15. NEW Chalet 6 minutes from Sunday River! Hot tub, Sauna, Sleeps 12, Dog Friendly!

NEW Chalet 6 minutes from Sunday River! Hot tub, Sauna, Sleeps 12, Dog Friendly!
Bethel
10.0 out of 10, Exceptional, (12 reviews)
"Great place! Clean, pictures lived up to expectations, owner was responsive and location was great. Would definitely go back!!!"
United States
Brian D.
The price is HK$2,291
HK$6,030 total
includes taxes & fees
4 Oct - 5 Oct
NEW Chalet 6 minutes from Sunday River! Hot tub, Sauna, Sleeps 12, Dog Friendly!
A hot tub on a deck with a view of a sunset over a valley.

16. EPIC VIEWS - Pond - Crooked River 14 ACRES - SECLUDED

EPIC VIEWS - Pond - Crooked River 14 ACRES - SECLUDED
Harrison
9.0 out of 10, Wonderful, (6 reviews)
"We wanted a few days to disconnect from work and our busy lives, and this cabin was perfect. The hot tub on the deck was so lovely, especially around sunrise and sunset, and the living room was so cozy that each night was pure relaxation."
United States
Thomas D.
The price is HK$3,845
HK$6,252 total
includes taxes & fees
1 Nov - 2 Nov
EPIC VIEWS - Pond - Crooked River 14 ACRES - SECLUDED
A room with a large window, a leather armchair, a wooden table, and a small wooden chest.

17. Sunday River Getaway | Sleeps 6 | Pet-Friendly

Sunday River Getaway | Sleeps 6 | Pet-Friendly
Bethel
The price is HK$1,080
HK$3,298 total
includes taxes & fees
5 Oct - 6 Oct
Sunday River Getaway | Sleeps 6 | Pet-Friendly
A bedroom with a bed, wooden ceiling, a window with blinds, a nightstand, and a framed picture on the wall.

18. An Authentic Clean & Cozy Maine Homestay

An Authentic Clean & Cozy Maine Homestay
Buckfield
9.8 out of 10, Exceptional, (69 reviews)
"This place is amazing! Quintessential Maine home experience!"
United States
Meagan D.
The price is HK$975
HK$1,610 total
includes taxes & fees
8 Oct - 9 Oct
An Authentic Clean & Cozy Maine Homestay
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

Jordan Hotel

Jordan Hotel

8/10 Good
"It was beyond what I expected, I even got to see the northern lights after I hiked. The room was beautiful. Everything about the place was wonderful."
John 2-night trip
Posted 12 hours ago
Jordan Hotel

Find out more about Greenwood

Search for holiday rentals in Greenwood on Expedia! You can easily find your home rentals, villas, holiday apartments in Greenwood using one of the methods below:

  • View our selection of featured holiday rentals in Greenwood
  • Use the map to find apartments and other holiday homes in the Greenwood neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Greenwood while they last

Look no further and take a look at our great range of rental properties in Greenwood!

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?

Luxury Lakefront Estate on 138 Acres - Pickleball, Reunions & Weddings: This holiday home rental outside of Greenwood is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a library and 1 hot tub.

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?

Uncle Tom Mountain and Bryant Pond are a couple of lovely local spots to get outside and enjoy nature. 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.