Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Windsor

Fridge, oven, stovetop, dishwasher
No bookings after 8/15/2024. Property sold. VRBO Thank you.

No bookings after 8/15/2024. Property sold. VRBO Thank you.

Searsmont
10.0 out of 10, Exceptional, (5)
"Perfect fit for our trip. Everything we needed in this cute little home."
United States
Carol F.
The price is ￥15,300
￥21,731 total
includes taxes & fees
Nov 18 - Nov 19
No bookings after 8/15/2024. Property sold. VRBO Thank you.
Exterior
Island Aframe Adventure in Maine

Island Aframe Adventure in Maine

Monmouth
10.0 out of 10, Exceptional, (6)
"We had two adults, two teens and one very active dog. Guess who was NOT thrilled with the no-plumbing no-electricity situation?!? But that’s the point- reconnect with nature and slow down. We even got them off their phones for a while. (Although internet is strong! Totally remote workable) The island is beautiful and serene and clean. A great escape from the hustle and bustle of DC (where we live). We fished in the canoe, wandered around in the kayaks….. Our dog Archie roamed the island (he is...
United States
Carolyn F.
Island Aframe Adventure in Maine
Exterior
Sister A-Frame in Woods B

Sister A-Frame in Woods B

Oakland
10.0 out of 10, Exceptional, (8)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is ￥18,639
￥35,309 total
includes taxes & fees
Nov 18 - Nov 19
Sister A-Frame in Woods B
Fridge, microwave, oven, stovetop
Waterfront 2br/2ba cottage

Waterfront 2br/2ba cottage

West Gardiner
9.8 out of 10, Exceptional, (15)
"Very nice and clean place. We used this rental as a hub to go around and see lots that Maine had to offer. Hosts were very nice and kept a very clean place."
United States
Bruce J.
The price is ￥17,387
￥44,558 total
includes taxes & fees
Nov 18 - Nov 19
Waterfront 2br/2ba cottage
Living area
The heart of the Belgrade Lakes

The heart of the Belgrade Lakes

Oakland
9.0 out of 10, Wonderful, (9)
"your attention to details and the care you've put into the space - it really stood out to us!!! 5 stars it is not enough. "
United States
Anna D.
The price is ￥12,441
￥29,565 total
includes taxes & fees
Nov 18 - Nov 19
The heart of the Belgrade Lakes
TV
Two bedroom Mid Century Modern apartment in Downtown Hallowell

Two bedroom Mid Century Modern apartment in Downtown Hallowell

Hallowell
10.0 out of 10, Exceptional, (80)
"We had a lovely stay at this apartment. Very clean, accommodating and inviting. Comfortable beds and available hosts! Pam suggested The Liberal Cup for dinner when we asked and it was a perfect way to wrap up our evening in lovely Hallowell! Highly recommend this rental!"
United States
carlin o.
The price is ￥19,319
￥36,556 total
includes taxes & fees
Nov 30 - Dec 1
Two bedroom Mid Century Modern apartment in Downtown Hallowell
Fridge, microwave, oven, stovetop
Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min

2.0 star property
Oakland
10.0 out of 10, Exceptional, (6)
"I would highly recommend this beautiful rental to anyone. Brand new, super clean , all necessities ( down to complimentary shampoo/ conditioner)A lot of bang for your buck! Host was absolutely amazing to work with . "
United States
Mary G.
The price is ￥15,300
￥41,609 total
includes taxes & fees
Dec 1 - Dec 2
Discover Oakland charm near Colby College 10 min
Property grounds
Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.

Oakland
10.0 out of 10, Exceptional, (43)
"Amazing stay loved how clean everything was"
United States
Britney A.
The price is ￥16,228
￥38,072 total
includes taxes & fees
Nov 18 - Nov 19
Central Maine Apartment offering 4 Seasons of Fun.
Outdoor dining
Minutes to Colby

Minutes to Colby

Waterville
8.8 out of 10, Excellent, (22)
"This was such a wonderful option. Location, clean, and adorable. "
United States
Laurie L.
The price is ￥17,001
￥29,481 total
includes taxes & fees
Nov 18 - Nov 19
Minutes to Colby
Property grounds
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards

Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards

Whitefield
9.8 out of 10, Exceptional, (29)
"Great maintained property, plenty of fun things to do. Very secluded in in the woods but not too far from town. Loved staying here and would love to visit again!"
United States
Annabelle N.
The price is ￥23,183
￥34,535 total
includes taxes & fees
Nov 18 - Nov 19
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards
Property grounds
Cozy Cottage on water's edge of Lake Cobbosseecontee

Cozy Cottage on water's edge of Lake Cobbosseecontee

Manchester
8.8 out of 10, Excellent, (17)
"Perfect old fashion Maine cottage! Great sunsets!"
United States
Anita W.
The price is ￥20,169
￥49,275 total
includes taxes & fees
Nov 18 - Nov 19
Cozy Cottage on water's edge of Lake Cobbosseecontee
Outdoor dining
Ice Fishing, Dog Friendly, Lake Great Pond

Ice Fishing, Dog Friendly, Lake Great Pond

Belgrade
10.0 out of 10, Exceptional, (47)
"Perfect for our family to come into town for a graduation celebration. Loved the little extras that we did not have to buy while in town!"
United States
Jerilyn H.
The price is ￥24,023
￥49,264 total
includes taxes & fees
Nov 24 - Nov 25
Ice Fishing, Dog Friendly, Lake Great Pond
Property grounds
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

Nobleboro
10.0 out of 10, Exceptional, (42)
"This a gem of a place. Quiet, cozy spots, beautiful proximity to the lake. We really enjoyed our night, and were sorry we did not have a longer stay."
United States
Sarah H.
The price is ￥23,028
￥48,011 total
includes taxes & fees
Dec 9 - Dec 10
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Living area
Peaceful Intown Studio ~ Walk to Shops & Dining

Peaceful Intown Studio ~ Walk to Shops & Dining

2.0 star property
Newcastle
The price is ￥20,524
￥25,740 total
includes taxes & fees
Nov 18 - Nov 19
Peaceful Intown Studio ~ Walk to Shops & Dining
Exterior
Naughty Dog Private Island Log Cabin

Naughty Dog Private Island Log Cabin

Monmouth
10.0 out of 10, Exceptional, (11)
"My family stayed on the little island for four nights and had an absolutely perfect vacation. This is our 2nd trip to the islands and it was just as good as the first trip last summer. We kayaked, canoed over the big island, played games, explored the island, cooked amazing meals, learned new card games, wrote in our journals, swam and most importantly fished (my older son caught 200 fish!!). This is now going to be a yearly family tradition that we hope to share with our friends in coming...
United States
IsabelV
Naughty Dog Private Island Log Cabin
Interior
Island Tree House Glamping

Island Tree House Glamping

Monmouth
10.0 out of 10, Exceptional, (9)
"We stayed at the Octagon it was a beautiful place. The scenery was just beautifu. Fishing was great. Kent and Heather were amazing hosts. They have you set up for everything. Can't wait to go back. "
United States
Jennifer S.
Island Tree House Glamping
Property grounds
3350 Middle Road

3350 Middle Road

Sidney
8.0 out of 10, Very Good, (3)
"The house was clean a nice place to stay. We were there in September, and the pool was not heated, so be aware of that. That didn't matter to my group. My only comment is that they had several plug in scent units around the first floor, and that smell was a bit too much for some of us, so we unplugged them while we were there. Problem solved. "
United States
Donald A.
The price is ￥41,729
￥52,054 total
includes taxes & fees
Nov 18 - Nov 19
3350 Middle Road
Outdoor spa tub
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP

Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP

Whitefield
10.0 out of 10, Exceptional, (6)
"Great getaway! We loved all of the discoveries to be made both in the cabin and on the property. We stayed in Stella. It was adorable, functional, and very welcoming. We also enjoyed an outing to Kennebec Maine Cabin Masters only 20 min away! "
United States
Sandra L.
The price is ￥28,592
￥45,990 total
includes taxes & fees
Nov 18 - Nov 19
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Outdoor dining
Lighthouse Lane

Lighthouse Lane

Manchester
10.0 out of 10, Exceptional, (70)
"Excellent, beautiful location next to the lake."
United States
Sten K.
The price is ￥55,638
￥74,122 total
includes taxes & fees
Nov 18 - Nov 19
Lighthouse Lane
Exterior
Island Glamping in a Secluded A-Frame Cabin on a Lake in Monmouth, Maine

Island Glamping in a Secluded A-Frame Cabin on a Lake in Monmouth, Maine

Monmouth
Island Glamping in a Secluded A-Frame Cabin on a Lake in Monmouth, Maine
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

Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

10/10 Excellent
"Room was clean and tidy"
Scott 1-night trip
Posted 2 days ago
Fireside Inn & Suites Waterville

Find out more about Windsor

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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?

Spacious Country Home w/ Hot Tub, near Colby/Thomas: This vacation home rental outside of Windsor is located in a rural location and has a hot tub, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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 Capitol Park. In the larger area, you’ll find Old Fort Western and Maine State House.

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.