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Compare 26 Cottages in Windsor with updated reviews, rates, and availability.

Historic Waldoboro House Near Lakes, Boating, Etc!
Interior

Historic Waldoboro House Near Lakes, Boating, Etc!

3.0 star property
10.0 out of 10, Exceptional, (2)
"This home is such a gem! A historic home that is updated with many modern conveniences. We’ve been to MANY AirB&B’s and this home was probably the best equipped we’ve been in! Convenient to Boothbay and lots of downeast inlets and harbors. Very quiet, but close to groceries, food and farm stands. Our only regret was not staying longer- we would have loved to grill and use the fire pit!"
Historic Waldoboro House Near Lakes, Boating, Etc!
Springvale Farm: Freedom Home With Hiking Trail!
Interior

Springvale Farm: Freedom Home With Hiking Trail!

3.0 star property
Springvale Farm: Freedom Home With Hiking Trail!
Updated Tiny House: Walk to Wiscasset Village
Exterior

Updated Tiny House: Walk to Wiscasset Village

3.0 star property
Updated Tiny House: Walk to Wiscasset Village
Rustic Retreat Across From Lake; Family Friendly!
Cottage (2 Bedrooms) | Interior

Rustic Retreat Across From Lake; Family Friendly!

3.0 star property
8.0 out of 10, Very Good, (1)
"I liked that it was by the lake quiet and secluded. "
Rustic Retreat Across From Lake; Family Friendly!
Idyllic Washington Retreat w/ Fire Pit & Yard
TV, fireplace

Idyllic Washington Retreat w/ Fire Pit & Yard

3.0 star property
10.0 out of 10, Exceptional, (1)
"It was great. Nice property, internet connection was poor"
Idyllic Washington Retreat w/ Fire Pit & Yard
Near Waterville: Cozy Midcoast Vacation Rental!
Interior

Near Waterville: Cozy Midcoast Vacation Rental!

3.0 star property
Near Waterville: Cozy Midcoast Vacation Rental!
Lakefront Maine House ~ 4 Mi to Colby College
House (4 Bedrooms) | Interior

Lakefront Maine House ~ 4 Mi to Colby College

3.0 star property
Lakefront Maine House ~ 4 Mi to Colby College
Readfield Retreat w/ Lake Maranacook Views!
House (3 Bedrooms) | Interior

Readfield Retreat w/ Lake Maranacook Views!

3.0 star property
Readfield Retreat w/ Lake Maranacook Views!
Private Dock on Messalonskee Lake: Cozy Cottage!
Interior

Private Dock on Messalonskee Lake: Cozy Cottage!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great little lake cabin. Had everything we needed. Clean, comfortable, quite. Beautiful area and views. We had a wonderful stay and would stay again."
Private Dock on Messalonskee Lake: Cozy Cottage!
On-site Pond: Spacious Family Home in Jefferson!
Interior

On-site Pond: Spacious Family Home in Jefferson!

3.0 star property
On-site Pond: Spacious Family Home in Jefferson!
Quaint Oakland Getaway on East Pond Lake!
House (1 Bedroom) | Living area

Quaint Oakland Getaway on East Pond Lake!

2.0 star property
9.0 out of 10, Wonderful, (2)
"Lovely little cabin on a lake. No frills just quiet! Bed very comfortable. Hot water in shower. Dishes and accessories all provided. Only additions could be a coffee maker. French press was there but I was looking for a regular drip pot. Some better assortment of games might be nice too. Playing Clue with only 2 people is a little pointless!! 😂😂😂 Country Deli on the corner was great for coffee and sandwiches. Less than a mile up the road. "
Quaint Oakland Getaway on East Pond Lake!
Waterfront Dresden Cabin With Deck + Fire Pit!
Fireplace, books

Waterfront Dresden Cabin With Deck + Fire Pit!

3.0 star property
Waterfront Dresden Cabin With Deck + Fire Pit!
Unique Maine Log Cabin w/ Trout Ponds & Sauna!
Interior

Unique Maine Log Cabin w/ Trout Ponds & Sauna!

3.0 star property
Unique Maine Log Cabin w/ Trout Ponds & Sauna!
Quiet & Lovely Lakefront Cottage for Families!
Outdoor dining

Quiet & Lovely Lakefront Cottage for Families!

3.0 star property
Quiet & Lovely Lakefront Cottage for Families!
Lakefront Home With Deck, Dock, & Water Access!
Interior

Lakefront Home With Deck, Dock, & Water Access!

3.0 star property
Lakefront Home With Deck, Dock, & Water Access!
Waterville Home Rental w/ Private Yard + Deck!
Exterior

Waterville Home Rental w/ Private Yard + Deck!

3.0 star property
Waterville Home Rental w/ Private Yard + Deck!
Woodsy Pittston Retreat Near Kennebec River!
Interior

Woodsy Pittston Retreat Near Kennebec River!

3.0 star property
Woodsy Pittston Retreat Near Kennebec River!
Maine Cottage w/ Dock & Kayaks, Near Augusta!
Cottage (2 Bedrooms) | Interior

Maine Cottage w/ Dock & Kayaks, Near Augusta!

3.0 star property
Maine Cottage w/ Dock & Kayaks, Near Augusta!
Life on the Lake With Private Dock & Fire Pit!
Property grounds

Life on the Lake With Private Dock & Fire Pit!

3.0 star property
Life on the Lake With Private Dock & Fire Pit!
Waterfront Nobleboro Cottage w/ Kayaks & Boat Dock
2 bedrooms, laptop workspace, iron/ironing board, bed sheets

Waterfront Nobleboro Cottage w/ Kayaks & Boat Dock

3.0 star property
Waterfront Nobleboro Cottage w/ Kayaks & Boat Dock
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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