Photo by Robbie Martin

Book a Greenwood Cottage

    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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

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

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

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

9.2 out of 10, Wonderful, (71)
"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!
Panoramic Water and Mountains Views with Nature appearing daily. Relax on
Exterior

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

10.0 out of 10, Exceptional, (55)
"My kids loved the beach a short walk away, and the shallow water was crystal clear. Because of the location, there really is a view from every window. Kind of small cabin and lot though"
Panoramic Water and Mountains Views with Nature appearing daily. Relax on
Newly renovated 4-bedroom cottage, directly on Highland Lake
Property grounds

Newly renovated 4-bedroom cottage, directly on Highland Lake

2.0 star property
10.0 out of 10, Exceptional, (3)
"House was beautiful! We loved the location in Bridgton, close to shops, restaurants, church. The proximity to the water was amazing, so nice to sit out on the docks with coffee or a glass of wine and watch the boats go by. The house itself was lovely, plenty of room for our group of 6 with stocked updated kitchen and lots of bedroom space for all. We were fortunate to have fantastic weather as well; definitely one of our best vacation weeks ever!"
Newly renovated 4-bedroom cottage, directly on Highland Lake
Quiet Long Lake Cottage in Bridgton with dock for boat. Canoe/Kayaks/PaddleBoard
Property grounds

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

10.0 out of 10, Exceptional, (43)
"Beautiful property on the lake. Well stocked and clean. We had a great stay!"
The price is NZ$953
includes taxes & fees
25 Aug - 26 Aug
Quiet Long Lake Cottage in Bridgton with dock for boat. Canoe/Kayaks/PaddleBoard
Two-story dog-friendly cabin with a wood stove, pool, tennis, beach, W/D
Outdoor dining

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

9.2 out of 10, Wonderful, (15)
"Kitchen table big enough for large family"
Two-story dog-friendly cabin with a wood stove, pool, tennis, beach, W/D
The Wee White Cottage on Tripp Lake in Poland, Maine.
Exterior

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

9.8 out of 10, Exceptional, (70)
"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.
Kezar Lake Lovell ME, Discount promotion Wk of Aug 23 Beach, Dock, Watercraft AC
Property grounds

Kezar Lake Lovell ME, Discount promotion Wk of Aug 23 Beach, Dock, Watercraft AC

10.0 out of 10, Exceptional, (23)
"We love Clover Cottage! It’s lovely, well appointed and in a great location. The host has thought of everything. This was our second stay and it did not disappoint."
Kezar Lake Lovell ME, Discount promotion Wk of Aug 23 Beach, Dock, Watercraft AC
Charming Lovell Cabin - 7 Mi to Kezar Lake!
House (2 Bedrooms) | 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!
Cozy lake house with private beach
Property grounds

Cozy lake house with private beach

9.0 out of 10, Wonderful, (10)
"Totally enjoyed this comfortable and lovely home on the pond. The porch and view made for very wonderful lounging. Day trips were easy from this destination. Everything that I needed during my stay was right there for it to be a home away from home for me."
Cozy lake house with private beach
SLEEPS 15 WITH A PRIVATE SANDY BEACH ON LONG LAKE.
Outdoor dining

SLEEPS 15 WITH A PRIVATE SANDY BEACH ON LONG LAKE.

10.0 out of 10, Exceptional, (2)
"Beautiful spot, great swimming, spacious and comfortable. Great indoor and outdoor space. Close to town and groceries. Perfect for a large family gathering!"
SLEEPS 15 WITH A PRIVATE SANDY BEACH ON LONG LAKE.
Cozy Cottage w/ Lil' Pond, Fenced Yard & Firepit (Dog friendly!)
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (19)
"This was a great spot for my family and I to relax. Appreciated the fenced in yard."
Cozy Cottage w/ Lil' Pond, Fenced Yard & Firepit (Dog friendly!)
Water Front Cape Style Cottage
Exterior

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
Charming cottage just 12' from the water's edge with gorgeous sunrise views!
Terrace/patio

Charming cottage just 12' from the water's edge with gorgeous sunrise views!

9.0 out of 10, Wonderful, (2)
"Spent a lovely week in Bridgton. House was just what we were looking for. Simple and quaint. Plenty of good restaurants close by and enough to do. Would definitely pick this place again. "
Charming cottage just 12' from the water's edge with gorgeous sunrise views!
Inviting Countryside Home: 4 Mi to Long Lake!
House (3 Bedrooms) | Interior

Inviting Countryside Home: 4 Mi to Long Lake!

3.0 star property
Inviting Countryside Home: 4 Mi to Long Lake!
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!
Charming 1-bedroom cottage in fabulous Bridgton with WiFi, AC, private dock
Outdoor dining

Charming 1-bedroom cottage in fabulous Bridgton with WiFi, AC, private dock

10.0 out of 10, Exceptional, (1)
"From start to finish, the Violas have been welcoming and have shown us the best in hospitality. We are honored to be the first renters of this brand new property. I think Peggy and Bob are naturals when it comes to being accommodating and providing for their guests' comfort. The setting is serene and just far enough off the beaten path to be secluded, even though amenities are less than ten minutes from the cottage, including a rare drive-in movie theater. If you stay here you will be well taken...
Charming 1-bedroom cottage in fabulous Bridgton with WiFi, AC, private dock
40min from Portland- Sandy Ridge Family Cottage
Property grounds

40min from Portland- Sandy Ridge Family Cottage

10.0 out of 10, Exceptional, (8)
"This cottage stay was everything we'd hoped for and more. The pond and grounds are beautiful. Our two girls (3 and 7) enjoyed the stay as much as we did. The cottage itself is cozy, clean and well maintained. It provided our family of 4 with the perfect amount of space. Our host went above and beyond to make us feel welcome and provided us with information about the local area in advance. I wish we could have stayed for longer. I thoroughly recommend and hope we can return one day!"
40min from Portland- Sandy Ridge Family Cottage
Lakefront cabin with spectacular sunsets included
Property grounds

Lakefront cabin with spectacular sunsets included

10.0 out of 10, Exceptional, (14)
"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
Kezar Lake Waterfront Cottage Fully Booked. See our Other Listing, # 305700.
Dining

Kezar Lake Waterfront Cottage Fully Booked. See our Other Listing, # 305700.

10.0 out of 10, Exceptional, (39)
"This property, location and owner were all excellent. Very quiet area, yet reasonably close to shopping and other amenities. Owner was excellent to work with. Highly recommend this property for anyone looking for a quiet getaway."
Kezar Lake Waterfront Cottage Fully Booked. See our Other Listing, # 305700.
Peaceful Highland Lake Home w/ Kayaks, Dock Access
House (3 Bedrooms) | 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
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
Sign in
Sign up, it's free

Top Greenwood Hotel Reviews

Best Western Plus Rumford Falls

Best Western Plus Rumford Falls

10/10 Excellent
"Nice, clean and convenient location hotel. Nice and helpful front desk staff. good breakfast."
Kazimierz 1-night trip
Posted 2 days ago
Best Western Plus Rumford Falls

Frequently asked questions

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.