Photo by Robbie Martin

Holiday Homes in Greenwood

    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

Next weekend
In two weeks
In one month
In two months

Featured Holiday Homes in Greenwood

River House Rumford Point. 14 mins to Sunday River

10.0 out of 10, Exceptional, (2)
"House is very spacious and enough room for everyone to spread out. Kids enjoyed the game room and theater room the most. Located in good and quiet neighborhood. Over all had a great time."
River House Rumford Point. 14 mins to Sunday River

Expansive Retreat - All-Season Contemporary Farmhouse [Lakes & Mountains]

9.4 out of 10, Exceptional, (13)
"Would stay here again. Loved the location and the size of the rooms! Perfect for a group and very pet friendly."
Expansive Retreat - All-Season Contemporary Farmhouse [Lakes & Mountains]

"Spacious Maine Retreat near Sunday River with Hot Tub, Fire Pit & Pet-Friendly!

9.6 out of 10, Exceptional, (133)
"Plenty of room and excellent location"
"Spacious Maine Retreat near Sunday River with Hot Tub, Fire Pit & Pet-Friendly!

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, (89)
"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

Cozy 3BR home for outdoor enthusiasts, deck, pool, tennis, w/d, trails & BBQ

2.5 star property
6.6 out of 10, (4)
"This house was located in the perfect spot for our weekend away. The house was very clean, very accommodating with everything we needed and more. Looking forward to renting again in the winter for skiing."
Cozy 3BR home for outdoor enthusiasts, deck, pool, tennis, w/d, trails & BBQ

Pleasant Pine Cottage @ Moose Pond! Lake Access & Assn Pool!

10.0 out of 10, Exceptional, (8)
"We enjoyed our stay in Bridgton. The house is spacious and clean and includes all the amenities needed for a comfortable stay. The beach and pool were great and we spent many hours relaxing in the sun (and shade!). We’ll definitely be back!"
Pleasant Pine Cottage @ Moose Pond! Lake Access & Assn Pool!

Charming lakefront home with water views, dock & inviting deck, Central A/C

10.0 out of 10, Exceptional, (5)
"I have zero complaints it couldn't have been any better!!!"
Charming lakefront home with water views, dock & inviting deck, Central A/C

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

Pleasant Dutch Retreat

10.0 out of 10, Exceptional, (1)
"A great, spacious home with everything a family needs (including two WCs). Comfortable beds and clean everywhere. Lovely garden that leads into woodland.House is really charming and generally very well appointed. The decor isn't all 100% perfect but it actually puts you at ease knowing the kids won't ruin stuff just by being there!Plenty of essentials provided including S'mores kit which we didn't get to use sadly. Thanks to the host Nadine who was quick to reply to any questions. We would...
Pleasant Dutch Retreat

Private Hot Tub & Sauna: Bryant Pond Retreat!

Private Hot Tub & Sauna: Bryant Pond Retreat!

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

10.0 out of 10, Exceptional, (23)
"Great location , plenty of room for a large family or group."
Highland Dream: Summer Paradise! 5BR/2BA W Sandy Beach, Stay and Play. 4 Seasons

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

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

Cozy log cabin home. 5 minutes to the beach, pet and family friendly home.

2.0 out of 10, (1)
Cozy log cabin home. 5 minutes to the beach, pet and family friendly home.

90 Second, Traffic-Free Drive to Sunday River

10.0 out of 10, Exceptional, (20)
"Beautiful, clean, comfortable home conveniently located near Sunday River. "
The price is AU$1,068
includes taxes & fees
1 Sept - 2 Sept
90 Second, Traffic-Free Drive to Sunday River

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

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

10.0 out of 10, Exceptional, (12)
"Cozy , fresh air , perfect place for the family and the kid Highly recommend,"
The price is AU$1,284
includes taxes & fees
3 Aug - 4 Aug
Safety Certified luxury private, dog-friendly new home, 3 miles to Sunday River.
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