Greenwood Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Greenwood vacation rentals

Lakefront Family Retreat: Skiing & Mountain Biking

Lakefront Family Retreat: Skiing & Mountain Biking
Greenwood
9.8 out of 10, Exceptional, (10 reviews)
"We so enjoyed our week long stay. The house was lovely and very comfortable for 8 adults. Any questions we had were answered really quickly. Great experience all round."
United States
RM
The price is ¥73,413
¥170,162 total
includes taxes & fees
Jun 22 - Jun 23
Lakefront Family Retreat: Skiing & Mountain Biking

5br/2ba Lake & Ski House w/ Waterfront & Hot Tub

5br/2ba Lake & Ski House w/ Waterfront & Hot Tub
Greenwood
10.0 out of 10, Exceptional, (1 review)
"Great stay! "
United States
Brooks K.
5br/2ba Lake & Ski House w/ Waterfront & Hot Tub

Lakefront Family Retreat: Skiing & Mountain Biking

Lakefront Family Retreat: Skiing & Mountain Biking
3.0 star property
Greenwood
The price is ¥82,389
¥169,418 total
includes taxes & fees
Jun 22 - Jun 23
Lakefront Family Retreat: Skiing & Mountain Biking

Cabin in Maine Woods-The Bogey

Cabin in Maine Woods-The Bogey
Stoneham
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property, beautiful cabin, just a perfect couple days of quiet, will definitely be back "
United States
Scott C.
The price is ¥12,022
¥22,208 total
includes taxes & fees
Jun 22 - Jun 23
Cabin in Maine Woods-The Bogey

An Authentic Clean & Cozy Maine Homestay

An Authentic Clean & Cozy Maine Homestay
Buckfield
9.8 out of 10, Exceptional, (66 reviews)
"My tenants said the accommodations were lovely "
United States
Nathan
The price is ¥19,908
¥32,882 total
includes taxes & fees
Jun 9 - Jun 10
An Authentic Clean & Cozy Maine Homestay

1 bedroom cottage with queen bed and 2 person whirlpool tub.

1 bedroom cottage with queen bed and 2 person whirlpool tub.
Norway
The price is ¥24,524
¥30,575 total
includes taxes & fees
Jun 9 - Jun 10
1 bedroom cottage with queen bed and 2 person whirlpool tub.

Cabin in Maine Woods-The Beech

Cabin in Maine Woods-The Beech
Stoneham
10.0 out of 10, Exceptional, (2 reviews)
"I planned this trip for my birthday, and it was absolutely what I was hoping for. The people running the place were beyond kind and helpful, and went out of their way to make sure we were comfortable/happy. The cabin was exactly as portrayed, if not better. "
United States
joss r.
The price is ¥12,022
¥22,208 total
includes taxes & fees
Jun 21 - Jun 22
Cabin in Maine Woods-The Beech

Manor Suite,cozy newly renovated,downtown & beach

Manor Suite,cozy newly renovated,downtown & beach
Bridgton
10.0 out of 10, Exceptional, (1 review)
"Property was very clean! it had everything you needed right there! "
United States
Lisa
The price is ¥11,214
¥23,580 total
includes taxes & fees
Jun 10 - Jun 11
Manor Suite,cozy newly renovated,downtown & beach

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
8.6 out of 10, Excellent, (27 reviews)
"Dunkin near by peaceful and nice good value"
United States
Brian G.
The price is ¥18,033
¥27,519 total
includes taxes & fees
Jun 11 - Jun 12
Adult Themed get-a-way! Centrally located to ski mountains, Oxford Casino, OPS.

Secluded A-Frame Cabin Retreat in Oxford

Secluded A-Frame Cabin Retreat in Oxford
Oxford
10.0 out of 10, Exceptional, (2 reviews)
"We had an incredible stay! Clean and every detail of the property was so well thought out. We took full advantage of the outdoor kitchen, hot tub, fire pit and canoe. Everything was great and we already want to go back!"
United States
Jamie A.
The price is ¥36,065
¥64,819 total
includes taxes & fees
Jun 10 - Jun 11
Secluded A-Frame Cabin Retreat in Oxford

12 min Sunday River! HotTub, Pet Friendly, Firepit

12 min Sunday River! HotTub, Pet Friendly, Firepit
Bethel
The price is ¥32,058
¥104,035 total
includes taxes & fees
Jun 9 - Jun 10
12 min Sunday River! HotTub, Pet Friendly, Firepit

This woods cabin is a true wilderness getaway. Get ready to commune with nature.

This woods cabin is a true wilderness getaway. Get ready to commune with nature.
Waterford
The price is ¥14,282
¥21,683 total
includes taxes & fees
Jun 9 - Jun 10
This woods cabin is a true wilderness getaway. Get ready to commune with nature.

Modern Glamping Cabin with Hot tub

Modern Glamping Cabin with Hot tub
Oxford
The price is ¥36,065
¥64,819 total
includes taxes & fees
Jun 9 - Jun 10
Modern Glamping Cabin with Hot tub

Charming Home Near Sunday River & Other Ski Areas

Charming Home Near Sunday River & Other Ski Areas
Rumford
9.8 out of 10, Exceptional, (92 reviews)
"A nice home away from home. Recommend."
United States
Preston
The price is ¥20,677
¥39,713 total
includes taxes & fees
Jun 25 - Jun 26
Charming Home Near Sunday River & Other Ski Areas

Secluded A-Frame Cabin Near Ponds Oxford

Secluded A-Frame Cabin Near Ponds Oxford
Oxford
The price is ¥36,065
¥64,819 total
includes taxes & fees
Jun 11 - Jun 12
Secluded A-Frame Cabin Near Ponds Oxford

Maine Woods Treehouse-The Birdie

Maine Woods Treehouse-The Birdie
Stoneham
9.4 out of 10, Exceptional, (6 reviews)
"Great little (big) tree house in the woods. Great spot to wake up"
United States
James D.
The price is ¥15,869
¥28,981 total
includes taxes & fees
Jun 28 - Jun 29
Maine Woods Treehouse-The Birdie

The Pleasant at Chandler Brook Village

The Pleasant at Chandler Brook Village
Bethel
9.8 out of 10, Exceptional, (7 reviews)
"This was so much fun for our family, it was our first experience staying in a Yurt. We would come back again and recommended to anyone looking for a “glamping” adventure! "
United States
Stephanie
The price is ¥28,443
¥35,545 total
includes taxes & fees
Jun 21 - Jun 22
The Pleasant at Chandler Brook Village

Little Acorn Landing

Little Acorn Landing
Norway
The price is ¥27,249
¥34,069 total
includes taxes & fees
Jun 9 - Jun 10
Little Acorn Landing

The Wild at Chandler Brook Village

The Wild at Chandler Brook Village
Bethel
10.0 out of 10, Exceptional, (8 reviews)
"This was by far my favorite place to stay! It was quiet and beautiful inside and out. We enjoyed being away from the other rentals and it really felt like a true getaway!"
United States
Allyson P.
The price is ¥26,087
¥32,628 total
includes taxes & fees
Jun 10 - Jun 11
The Wild at Chandler Brook Village

Historic, luxurious 2 bed 2 bath private suite in Lovell, 10 mins to Kezar Lake

Historic, luxurious 2 bed 2 bath private suite in Lovell, 10 mins to Kezar Lake
Lovell
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful scenery all around the area. House was quiet and conveniently located"
United States
Laura
The price is ¥24,044
¥44,903 total
includes taxes & fees
Jun 9 - Jun 10
Historic, luxurious 2 bed 2 bath private suite in Lovell, 10 mins to Kezar Lake
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Greenwood Hotel Reviews

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 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?

The Artist's Cabin at Powder Ridge Overlooking Sunday River SKI PARKING PASS: Visitors like this Greenwood vacation home rental. It is located in a rural location and has a fireplace, a patio, 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. You and your friends and family can relax into your vacation with amenities like a garden.

How many vacation rentals will I find in Greenwood?

With 19 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.