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Compare 93 Cottages in Greenwood with updated reviews, rates, and availability.

Two-story dog-friendly cabin with a wood stove, pool, tennis, beach, W/D

9.6 out of 10, Exceptional, (12)
"Kitchen table big enough for large family"
Two-story dog-friendly cabin with a wood stove, pool, tennis, beach, W/D

Hartford Cottage w/ Private Beach on Bear Pond!

8.4 out of 10, Very Good, (27)
"Just what a camp should be, all necessary amenities, charming interior. Nice sandy beach, and warm clear water."
Hartford Cottage w/ Private Beach on Bear Pond!

Water Front Cape Style Cottage

9.4 out of 10, Exceptional, (19)
"Excellent stay at this property, clean quiet area and the lake is absolutely stunning and clean "
Water Front Cape Style Cottage

Newly renovated 4-bedroom cottage, directly on Highland Lake

2.0 star property
Newly renovated 4-bedroom cottage, directly on Highland Lake

Winter on North Pond! Ski Sunday River/Mt Abram

9.8 out of 10, Exceptional, (10)
"The property was accommodating and comfortable with a homey vibe… we had a great time "
Winter on North Pond! Ski Sunday River/Mt Abram

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!

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

Lakeside cottage with boats, grill, firepit, pet and Kid Friendly

9.6 out of 10, Exceptional, (20)
"Our stay at the cabin was wonderful quiet and great weather too host was wonderful and always responded quickly place was perfect and had everything needed to make our stay awesome thank you for a very memorable vacation "
Lakeside cottage with boats, grill, firepit, pet and Kid Friendly

Cozy lake house with private beach

9.0 out of 10, Wonderful, (8)
"The house is lovely and comfortable, very nice kitchen, great room and sun porch. The lake was wonderful with warm water for swimming, good fishing and easy access to kayak/paddle with the small beach entry and dock."
Cozy lake house with private beach

Quiet Long Lake Cottage in Bridgton with dock for boat. Canoe/Kayaks/PaddleBoard

10.0 out of 10, Exceptional, (39)
"Beautiful property on the lake. Well stocked and clean. We had a great stay!"
Quiet Long Lake Cottage in Bridgton with dock for boat. Canoe/Kayaks/PaddleBoard

Cozy Cottage w/ Lil' Pond, Fenced Yard & Firepit (Dog friendly!)

10.0 out of 10, Exceptional, (18)
"Perfect spot for seeing the area Located a short distance to awesome restaurants and town"
Cozy Cottage w/ Lil' Pond, Fenced Yard & Firepit (Dog friendly!)

Kezar Lake Waterfront Cottage + Guesthouse Sandy Beach Dog OK Full AC Boats Dock

10.0 out of 10, Exceptional, (38)
"Beautiful location. Well-equipped house. Low boat traffic. We hope to return!"
Kezar Lake Waterfront Cottage + Guesthouse Sandy Beach Dog OK Full AC Boats Dock

Private Island w/ 2 Cottages on Kezar Lake!

10.0 out of 10, Exceptional, (5)
"Main Cabin is redone to perfection. Second cabin has a rustic but still with tons of charm. We had a stormy week so second cabin was a "
Private Island w/ 2 Cottages on Kezar Lake!

Lakefront cabin with spectacular sunsets included

9.8 out of 10, Exceptional, (10)
"Quintessential lake cabin with upgraded amenities. Clean lake with beautiful views. We enjoyed the fire pit by the lake each evening and fell asleep to the loons. I didn't want to leave! We hope to rent again."
Lakefront cabin with spectacular sunsets included

Panoramic Water and Mountains Views with Nature appearing daily. Relax on

10.0 out of 10, Exceptional, (55)
"Great place, and in a unique location on the tip of a small peninsula."
Panoramic Water and Mountains Views with Nature appearing daily. Relax on

Sweet waterfront cottage, stunning sunsets, private, sleeps 4-8

10.0 out of 10, Exceptional, (16)
"Beautiful place very clean very relaxing super helpful owners"
Sweet waterfront cottage, stunning sunsets, private, sleeps 4-8

SLEEPS 15 WITH A PRIVATE SANDY BEACH ON LONG LAKE.

SLEEPS 15 WITH A PRIVATE SANDY BEACH ON LONG LAKE.

The Wee White Cottage on Tripp Lake in Poland, Maine.

9.8 out of 10, Exceptional, (68)
"We were looking for a quiet getaway and found the perfect spot. The wee white cottage was cozy and so charming. It provided us the perfect vacation Loved watching the ducks and having our coffee outside every morning."
The Wee White Cottage on Tripp Lake in Poland, Maine.

Pet-friendly cottage on Tripp Lake with spectacular sunset views!

Pet-friendly cottage on Tripp Lake with spectacular sunset views!

Vintage Rustic Cottage on Brettun’s Pond, boat accessible, PET FRIENDLY!

9.2 out of 10, Wonderful, (65)
"We had an awesome week with our family very comfy and a great spot on Brettuns pond"
Vintage Rustic Cottage on Brettun’s Pond, boat accessible, PET FRIENDLY!
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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Other property types in Greenwood

Rediker Retreat- Authentic Riverfront Luxury Log Home

10.0 out of 10, Exceptional, (86)
"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

Pet Friendly/Mt. Home/Beau Views/ 3 or more nights 20% DISC!

10.0 out of 10, Exceptional, (43)
"Highly recommended "
The price is SAR 634
SAR 2,087 total
includes taxes & fees
7 May - 8 May
Pet Friendly/Mt. Home/Beau Views/ 3 or more nights 20% DISC!

*NEW* Luxury A-Frame by Sunday River w/ hot tub

10.0 out of 10, Exceptional, (13)
"Amazing property and great location!"
*NEW* Luxury A-Frame by Sunday River w/ hot tub
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.