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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Cottages in Greenwood

Charming Lovell Cabin - 7 Mi to Kezar Lake!
Interior

Charming Lovell Cabin - 7 Mi to Kezar Lake!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The cabin is charming in a quintessential Maine setting. Thank you for your hospitality! "
Charming Lovell Cabin - 7 Mi to Kezar Lake!
Inviting Countryside Home: 4 Mi to Long Lake!
Interior

Inviting Countryside Home: 4 Mi to Long Lake!

3.0 star property
Inviting Countryside Home: 4 Mi to Long Lake!
Peaceful Highland Lake Home w/ Kayaks, Dock Access
Interior

Peaceful Highland Lake Home w/ Kayaks, Dock Access

3.0 star property
10.0 out of 10, Exceptional, (2)
"We went to this area for the annual fair and enjoyed staying at this property. We got a good taste of Maine for a few days. The owners were quick to reply if we had questions. The kitchen is well stocked and great for a family visiting. We would stay there again. "
Peaceful Highland Lake Home w/ Kayaks, Dock Access
Mountain-view Home in Stoneham w/ Hot Yoga Studio!
Interior

Mountain-view Home in Stoneham w/ Hot Yoga Studio!

3.0 star property
Mountain-view Home in Stoneham w/ Hot Yoga Studio!
Spacious Harrison Cabin ~ 1 Mi to Long Lake!
Property grounds

Spacious Harrison Cabin ~ 1 Mi to Long Lake!

3.0 star property
8.0 out of 10, Very good, (1)
"Would recommend this stay for anybody - great communication with the host. Easily accessible area as well. "
Spacious Harrison Cabin ~ 1 Mi to Long Lake!
Cozy Thompson Lake Cabin w/ Boat Dock & Launch
Interior

Cozy Thompson Lake Cabin w/ Boat Dock & Launch

3.0 star property
10.0 out of 10, Exceptional, (1)
"We loved this property My grandson didn’t want to leave kayaks fishing ABoys dream!!!"
Cozy Thompson Lake Cabin w/ Boat Dock & Launch
Ski, Hike & Boat: Modern Bridgton Retreat
Interior

Ski, Hike & Boat: Modern Bridgton Retreat

3.0 star property
Ski, Hike & Boat: Modern Bridgton Retreat
Charming Lovell Farmhouse - 17 Acres w/ Mtn Views!
Interior

Charming Lovell Farmhouse - 17 Acres w/ Mtn Views!

3.0 star property
Charming Lovell Farmhouse - 17 Acres w/ Mtn Views!
Gorgeous Sunday River Cabin w/ Saltwater Hot Tub!
Terrace/patio

Gorgeous Sunday River Cabin w/ Saltwater Hot Tub!

3.0 star property
Gorgeous Sunday River Cabin w/ Saltwater Hot Tub!
Bethel Chalet w/ Hot Tub: 3 Miles to Sunday River!
Outdoor spa tub

Bethel Chalet w/ Hot Tub: 3 Miles to Sunday River!

3.0 star property
10.0 out of 10, Exceptional, (1)
"WONDERFUL!! Kimberly was excellent about contacts and very accomodating (we asked for an early check in). House was perfect for our family (lots of bedrooms!) and the hot tub was a big hit especially with the grandkids. Ample supplies for the kitchen too! Quiet spot but close to Bethel etc. Thank you!! "
Bethel Chalet w/ Hot Tub: 3 Miles to Sunday River!
Spacious Cabin: 10 Mi to Sunday River Skiing!
Interior

Spacious Cabin: 10 Mi to Sunday River Skiing!

3.0 star property
Spacious Cabin: 10 Mi to Sunday River Skiing!
Hartford Cottage w/ Private Beach on Bear Pond!
Exterior

Hartford Cottage w/ Private Beach on Bear Pond!

2.0 star property
8.8 out of 10, Excellent, (3)
"This was such a nice retreat. Beautiful views. Quiet comfortable getaway. It felt homey and inviting. I grew up going to a cottage like this and it was a blissful nostalgic weekend getaway right on the water. "
Hartford Cottage w/ Private Beach on Bear Pond!
Andover House w/ Private Yard & ATV Trail Access!
Exterior

Andover House w/ Private Yard & ATV Trail Access!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Huge improvement over a hotel. Susan and Brian are super nice and serve up some tasty ice cream treats right next door. They seem more set up for winter guests as there was only one horribly undersized ac for the whole house. Thankfully, it wasn't ridiculously hot so we did ok with fans. Church tower rings on the hour, every hour, all night long. Not great for us old people who sleep lightly. There's a small grocery/diner/liquor store just a couple steps away as well. We did a short hike up to...
Andover House w/ Private Yard & ATV Trail Access!
Lakefront Cottage: Boat Dock, Patio & Kayaks!
Front of property

Lakefront Cottage: Boat Dock, Patio & Kayaks!

3.0 star property
Lakefront Cottage: Boat Dock, Patio & Kayaks!
Million-dollar View: Waterfront Cabin in Bridgton!
Interior

Million-dollar View: Waterfront Cabin in Bridgton!

3.0 star property
Million-dollar View: Waterfront Cabin in Bridgton!
Spacious Cabin w/ Private Dock on Thompson Lake
Interior

Spacious Cabin w/ Private Dock on Thompson Lake

3.0 star property
Spacious Cabin w/ Private Dock on Thompson Lake
Near Skiing: Serene Harrison Retreat w/ Fire Pit
Interior

Near Skiing: Serene Harrison Retreat w/ Fire Pit

2.5 star property
Near Skiing: Serene Harrison Retreat w/ Fire Pit
Elegant & Quiet Maine Escape w/ Sauna & Deck!
Exterior

Elegant & Quiet Maine Escape w/ Sauna & Deck!

3.0 star property
Elegant & Quiet Maine Escape w/ Sauna & Deck!
Lakefront Hartford Cabin w/ Canoe & Boat Ramp
Exterior

Lakefront Hartford Cabin w/ Canoe & Boat Ramp

3.0 star property
Lakefront Hartford Cabin w/ Canoe & Boat Ramp
Private Hot Tub & Sauna: Bryant Pond Retreat!
Interior

Private Hot Tub & Sauna: Bryant Pond Retreat!

3.0 star property
Private Hot Tub & Sauna: Bryant Pond Retreat!
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

Grand Summit Hotel

Grand Summit Hotel

10/10 Excellent
"Love this hotel; fitness center is wonderful: coffee in the lobby is hot. Staff is incredibly friendly."
Fred 1-night trip
Posted 4 days ago
Grand Summit Hotel

Frequently asked questions

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What is there to do in Greenwood near my cottage?
Once you've unpacked and settled in, get out and discover the cool things Greenwood has on offer. Zephyr's Glades is a great attraction to add to your to-do list.