Photo by Robbie Martin

Greenwood Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Browse Select Greenwood Vacation Homes

River House Rumford Point. 14 mins to Sunday River

9.6 out of 10, Exceptional, (4)
"We were staying near my mother’s hometown with extended family, and the extensive space worked great. We had a lot of fun with the game room and movie room, and the grill got a lot of use for family meals."
River House Rumford Point. 14 mins to Sunday River

Stunning views, luxurious home, heated pool, hot tub, games

10.0 out of 10, Exceptional, (88)
"This the fourth year my family has stayed at this property and we are always happy to come back."
Stunning views, luxurious home, heated pool, hot tub, games

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

10.0 out of 10, Exceptional, (56)
"This house was a blast - would def stay again"
INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space

Fully renovated home with lake view, dock & mooring access, kayaks, & deck

9.8 out of 10, Exceptional, (41)
"Very clean, comfortable."
Fully renovated home with lake view, dock & mooring access, kayaks, & deck

Luxurious, 4 Season Waterfront Home On Long Lake, Sebago Lake Regions In Maine

10.0 out of 10, Exceptional, (45)
"Our third stay at this property."
Luxurious, 4 Season Waterfront Home On Long Lake, Sebago Lake Regions In Maine

An Authentic Clean & Cozy Maine Homestay

9.8 out of 10, Exceptional, (60)
"The host provided excellent information and was very easy to communicate with. The property was very comfortable and clean. "
The price is CA $159
CA $260 total
includes taxes & fees
Aug 27 - Aug 28
An Authentic Clean & Cozy Maine Homestay

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

10.0 out of 10, Exceptional, (16)
"We stayed here as a group of 9 friends for a ski weekend and this place was absolutely perfect for us. The house was extremely clean and a great size for our group. We loved the hot tub, living room setup and games in the house. Sunday River is only a 12 minute drive from the house. Trevor, the host, was wonderfully communicative and our check-in and check-out processes were very easy. We would absolutely stay here again."
The price is CA $309
CA $816 total
includes taxes & fees
Aug 26 - Aug 27
Ursa Major House - Quiet family getaway, minutes from skiing, hiking, biking.

Sauna, Hot Tub, Game Room & Mountain Views

10.0 out of 10, Exceptional, (3)
"Amazing place"
Sauna, Hot Tub, Game Room & Mountain Views

White Cap B-113 | 1 Bed, 1 Bath

9.0 out of 10, Wonderful, (4)
"Responsive owner and a great stay"
White Cap B-113 | 1 Bed, 1 Bath

Rediker Retreat- Authentic Riverfront Luxury Log Home

10.0 out of 10, Exceptional, (91)
"Had a wonderful stay Rediker retreat. Truly a retreat. The property had everything we needed for our holiday week. Thanks for having us. "
Rediker Retreat- Authentic Riverfront Luxury Log Home

The Artist's Cabin at Powder Ridge Overlooking Sunday River SKI PARKING PASS

10.0 out of 10, Exceptional, (323)
"Great place!"
The Artist's Cabin at Powder Ridge Overlooking Sunday River SKI PARKING PASS

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

10.0 out of 10, Exceptional, (24)
"Great location , plenty of room for a large family or group."
The price is CA $830
CA $1,549 total
includes taxes & fees
Sep 14 - Sep 15
Highland Dream: Summer Paradise! 5BR/2BA W Sandy Beach, Stay and Play. 4 Seasons

Secluded dog-friendly getaway with hot tub, game room, firepit, mountain views

8.8 out of 10, Excellent, (40)
"Great views and location if you are looking for a part of Maine not super coastal and touristy."
Secluded dog-friendly getaway with hot tub, game room, firepit, mountain views

Safety Certified luxury private, dog-friendly new home, 3 miles to Sunday River.

10.0 out of 10, Exceptional, (13)
"Cozy , fresh air , perfect place for the family and the kid Highly recommend,"
The price is CA $553
CA $1,206 total
includes taxes & fees
Sep 2 - Sep 3
Safety Certified luxury private, dog-friendly new home, 3 miles to Sunday River.

Long Lake, Harrison, Naples, Bridgton, Windham, Sebago Lake

9.4 out of 10, Exceptional, (17)
"Our family thoroughly enjoyed our stay at this wonderful lake house. The sunsets were absolutely stunning, the location on the lake is perfect. We rented a pontoon boat and 2 jet skis and they fit nicely on the dock. We spent time swimming, boating, kayaking and sunsets at the fire pit. The property manager Jill is very responsive and made sure we had everything we needed. We will be back!"
Long Lake, Harrison, Naples, Bridgton, Windham, Sebago Lake

Private Beach - Indoor/Outdoor Living - 8 Kayaks/Canoes - Multi-Family Getaway

10.0 out of 10, Exceptional, (132)
"Perfect for multigenerational family vacation"
Private Beach - Indoor/Outdoor Living - 8 Kayaks/Canoes - Multi-Family Getaway

Lakefront haven near Pleasant Mt-central location-25 mi. to N.Conway

10.0 out of 10, Exceptional, (51)
"It was a quick weekend trip, but the house was very comfortable and close to the town of Bridgton. Check in/out was extremely easy and communication with the host was seamless. The house isn't right on the water, but there are still nice lake-views and a short walk down to the shared beach access."
The price is CA $198
CA $494 total
includes taxes & fees
Sep 17 - Sep 18
Lakefront haven near Pleasant Mt-central location-25 mi. to N.Conway

Lakeside house with a separate bunkhouse

8.2 out of 10, Very good, (10)
"We enjoyed our stay here. Clean and comfortable house in a great location."
Lakeside house with a separate bunkhouse

Brookside II B-305 | 1 Bed, 1 Bath

9.6 out of 10, Exceptional, (5)
"Great location, great condo"
Brookside II B-305 | 1 Bed, 1 Bath

Brookside I B-306 | 2 Bed, 1 Bath

9.6 out of 10, Exceptional, (4)
"This property fit our needs, was clean and great location! "
Brookside I B-306 | 2 Bed, 1 Bath
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