Windsor Vacation Rentals

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Check prices for these dates

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Aug 10 - Aug 11
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Aug 15 - Aug 17
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Aug 22 - Aug 24

Vacation Rentals in Windsor

Lighthouse Lane
Outdoor dining

Lighthouse Lane

10.0 out of 10, Exceptional, (59)
"Check in and check out was super easy. Photos are super accurate and the property is beautiful. Thank you for sharing your beautiful with us!"
The price is ￥66,483
￥85,671 total
includes taxes & fees
Sep 7 - Sep 8
Lighthouse Lane
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !
Property grounds

Maine Cabin Masters Camp completely redone waiting for a Lake loving family !

2.0 star property
10.0 out of 10, Exceptional, (5)
"Wonderful hosts, they thought of everything we might need including many nice extra touches! Beautiful quiet spot with the opportunity to paddle boat, kayak, canoe, swim, fish, enjoy campfires, outdoor grilling, observe wildlife (Osprey, Bald Eagle, Deer)"
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !
Cozy Cottage on water's edge of Lake Cobbosseecontee
Property grounds

Cozy Cottage on water's edge of Lake Cobbosseecontee

8.8 out of 10, Excellent, (12)
"Great little getaway, sitting right by the water. We loved our time there. Alarice is a great hot and responded quickly to any needs or questions."
The price is ￥19,280
￥47,104 total
includes taxes & fees
Aug 17 - Aug 18
Cozy Cottage on water's edge of Lake Cobbosseecontee
A Charming Waterfront Cottage with Touches of Elegance
Dining

A Charming Waterfront Cottage with Touches of Elegance

10.0 out of 10, Exceptional, (111)
"My husband and our 1 year old daughter had a wonderful stay. The home is close to everything and has everything you may need. Would love to stay again. "
A Charming Waterfront Cottage with Touches of Elegance
Peaceful.... Lakefront Cottage... Kayakers Paradise....
Exterior

Peaceful.... Lakefront Cottage... Kayakers Paradise....

10.0 out of 10, Exceptional, (55)
"Beautiful, peaceful location. Great fishing. Comfortable, immaculate cabin."
Peaceful.... Lakefront Cottage... Kayakers Paradise....
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Property grounds

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

10.0 out of 10, Exceptional, (27)
"The owners were ver accommodating and the place is a quiet, pretty location "
The price is ￥27,923
￥52,015 total
includes taxes & fees
Sep 9 - Sep 10
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Peaceful home with forest views & great yard - minutes to town
TV, fireplace

Peaceful home with forest views & great yard - minutes to town

8.8 out of 10, Excellent, (5)
"Your home is beautiful!! Love all the windows, very comfortable!!"
Peaceful home with forest views & great yard - minutes to town
Charming 3-bedroom waterfront cottage with AC, WiFi and spectacular sunset views
3 bedrooms, WiFi, bed sheets

Charming 3-bedroom waterfront cottage with AC, WiFi and spectacular sunset views

9.0 out of 10, Wonderful, (2)
"Cozy cottage by the lake. Great scenery and wildlife. Great communication with host. "
Charming 3-bedroom waterfront cottage with AC, WiFi and spectacular sunset views
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Exterior

Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

9.4 out of 10, Exceptional, (56)
"Very pretty spot. Nice lake, good for kayaking.we enjoyed the fire pit. "
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Newly Restored Waterfront Cottage with Private Dock, Fireplace, & Farm - Dogs OK
Exterior

Newly Restored Waterfront Cottage with Private Dock, Fireplace, & Farm - Dogs OK

2.0 star property
9.0 out of 10, Wonderful, (102)
"The place was very clean. Right on the water. Spectacular views. Sunrise in the morning. A great experience. A lovely get away. Want to go back again"
Newly Restored Waterfront Cottage with Private Dock, Fireplace, & Farm - Dogs OK
Beautiful 13 acre Property on Sheepscot River w/ 2 Bedroom Cottage & Air Stream
Exterior

Beautiful 13 acre Property on Sheepscot River w/ 2 Bedroom Cottage & Air Stream

10.0 out of 10, Exceptional, (68)
"The cottage was perfect for a post Christmas relaxing week of downtime."
Beautiful 13 acre Property on Sheepscot River w/ 2 Bedroom Cottage & Air Stream
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Interior

Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

9.0 out of 10, Wonderful, (22)
"Great view, clean, central a/c, even the ppl using powerboats (4th of July!) were respectful. Exactly the getaway I needed!"
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Sister A-Frame in Woods B
Exterior

Sister A-Frame in Woods B

10.0 out of 10, Exceptional, (3)
"Great stay. Would stay here again if in the area."
The price is ￥17,817
￥34,074 total
includes taxes & fees
Aug 11 - Aug 12
Sister A-Frame in Woods B
Cheerful Cottage Close to Everything 12
Marina

Cheerful Cottage Close to Everything 12

9.4 out of 10, Exceptional, (12)
"Well appointed and comfortable cabin. Loved the retro fridge and microwave and sitting on the deck with a morning coffee. We awoke to a woodsy view every morning. The location was perfect for us; convenient to Wiscasset, Damariscotta and Pemaquid Point. Our host was fabulous with his timely communication and down east hospitality. If we pass through this way again, we will be sure to stay here again."
Cheerful Cottage Close to Everything 12
Mountainside cabin "Sasquatch Haven"
Interior

Mountainside cabin "Sasquatch Haven"

9.4 out of 10, Exceptional, (20)
"Wonderful stay!"
Mountainside cabin "Sasquatch Haven"
Spacious 1 Bedroom Close to Everything 4
Marina

Spacious 1 Bedroom Close to Everything 4

10.0 out of 10, Exceptional, (17)
"This was a lovely little cabin. Everything was as described and my husband and I really enjoyed our stay."
Spacious 1 Bedroom Close to Everything 4
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
Dining

Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

9.8 out of 10, Exceptional, (31)
"This place was perfect for our 3-night stay. Inside, it hits the sweet spot between well-equipped but uncluttered. The bird-watching overlooking the water was fantastic - from huge bald eagles to petite hummingbirds. "
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Fridge, microwave, oven, stovetop

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

10.0 out of 10, Exceptional, (11)
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Fridge, microwave, oven, stovetop

Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

7.6 out of 10, Good, (21)
"We enjoyed this place and will definitely come back again."
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Sunset Chalet Lakefront Hot Tub Game Room
Dining

Sunset Chalet Lakefront Hot Tub Game Room

10.0 out of 10, Exceptional, (24)
"Very nice quiet location. Loved the game room. Relaxing stay."
The price is ￥54,221
￥113,531 total
includes taxes & fees
Aug 11 - Aug 12
Sunset Chalet Lakefront Hot Tub Game Room
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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Top Windsor Hotel Reviews

Hampton Inn Waterville

Hampton Inn Waterville

10/10 Excellent
"Clean, quiet, friendly staff!! A lot of dining options in the area. A perfect stay!"
Jean 1-night trip
Posted 17 hours ago
Hampton Inn Waterville

Frequently asked questions

Are there vacation rentals in Windsor?

Yes, we offer vacation rentals close to popular sights in Windsor, or you can go with a more secluded option if you're looking for a relaxing stay. Windsor is known for its shopping and restaurants.

What are some of the best vacation home rentals in Windsor?

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage: This vacation home rental outside of Windsor offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books in this rental home to help you unwind.

What can I see and do in Windsor?

While exploring the area, visit family-friendly sights like Maine State Museum, or get outside and enjoy nature at Kennebec River Rail Trail. In the larger area, you’ll find Old Fort Western and Capitol Park.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned accommodations you can reserve for a short or long stay in Windsor. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for small groups.