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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Windsor vacation rentals

TV

1. 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, (92 reviews)
"House and community was amazing love the vibe of house experience was far and above expectations "
United States
Mike W.
The price is AED 459
AED 881 total
includes taxes & fees
3 Sep - 4 Sep
Two bedroom Mid Century Modern apartment in Downtown Hallowell
Terrace/patio

2. Get in touch with nature.

Get in touch with nature.
Richmond
10.0 out of 10, Exceptional, (45 reviews)
"Wonderful place very peaceful very friendly Aaron was spectacular couldn't ask for a more wonderful enjoyable spot"
United States
Keith R
The price is AED 331
AED 561 total
includes taxes & fees
31 Aug - 1 Sep
Get in touch with nature.
Cottage (2 Bedrooms) | Interior

3. Rustic Retreat Across From Lake; Family Friendly!

Rustic Retreat Across From Lake; Family Friendly!
3.0 star property
Union
8.0 out of 10, Very Good, (3 reviews)
"The cottage is cute with a great view of the lake. Quiet and peaceful yet convenient to town. Plenty to see and do in the area. We had a wonderful time and I highly recommend staying here!"
United States
Lorraine
The price is AED 485
AED 1,435 total
includes taxes & fees
30 Aug - 31 Aug
Rustic Retreat Across From Lake; Family Friendly!
Exterior

4. Perfectly Located 1 Bedroom, newly remodeled

Perfectly Located 1 Bedroom, newly remodeled
Augusta
10.0 out of 10, Exceptional, (4 reviews)
"I’ve stayed in many rental properties and this one is by far the cleanest and nicest. Everything was exactly as described and there was even a second ac unit in the bedroom. It’s on a nice quiet street and convenient to many things. You truly can’t go wrong choosing to stay here."
United States
Lisa G.
The price is AED 588
AED 1,029 total
includes taxes & fees
27 Aug - 28 Aug
Perfectly Located 1 Bedroom, newly remodeled
TV, fireplace, books

5. Private Dock on Messalonskee Lake: Cozy Cottage!

Private Dock on Messalonskee Lake: Cozy Cottage!
Sidney
9.0 out of 10, Wonderful, (12 reviews)
"Great place to stay for our annual fishing weekend in the Belgrade Lakes region! "
United States
Shawn H.
The price is AED 283
AED 1,221 total
includes taxes & fees
16 Sep - 17 Sep
Private Dock on Messalonskee Lake: Cozy Cottage!
Interior

6. River View Retreat, Hot Tub, Balcony, Kayaks & Bikes

River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
Hallowell
10.0 out of 10, Exceptional, (2 reviews)
"Great place and great host. Right in the water and close to New York and Canada"
United States
Anthony R.
The price is AED 512
AED 639 total
includes taxes & fees
31 Aug - 1 Sep
River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
Exterior

7. Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (10 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is AED 443
AED 963 total
includes taxes & fees
28 Aug - 29 Aug
Sister A-Frame in Woods B
Interior

8. Fabulous 3-bedroom RV with direct access to the Sebasticook River!

Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Benton
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful camper and property! We loved it!"
United States
Tracy D.
The price is AED 331
AED 520 total
includes taxes & fees
30 Aug - 31 Aug
Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Terrace/patio

9. Cozy cottage in the Winthrop Lakes Area

Cozy cottage in the Winthrop Lakes Area
Winthrop
9.8 out of 10, Exceptional, (7 reviews)
"My only regret is that we were only there for one night & didn’t have time to enjoy the surroundings."
United States
Nicole B.
The price is AED 382
AED 685 total
includes taxes & fees
7 Sep - 8 Sep
Cozy cottage in the Winthrop Lakes Area
Property grounds

10. Glamping at Maine Water Buffalo Farm

Glamping at Maine Water Buffalo Farm
Appleton
8.8 out of 10, Excellent, (6 reviews)
"Very quite and private and beautiful surroundings"
United States
Gary
The price is AED 474
AED 597 total
includes taxes & fees
31 Aug - 1 Sep
Glamping at Maine Water Buffalo Farm
Property grounds

11. Glamping Lakefront Island Retreat w/ Kayak & Pet-Friendly

Glamping Lakefront Island Retreat w/ Kayak & Pet-Friendly
Monmouth
10.0 out of 10, Exceptional, (4 reviews)
"The island is great from the walking trails, amenities and great fishing. "
United States
Jeremy F.
The price is AED 213
AED 737 total
includes taxes & fees
17 Sep - 18 Sep
Glamping Lakefront Island Retreat w/ Kayak & Pet-Friendly
Interior

12. High End Apartment in Downtown Hallowell

High End Apartment in Downtown Hallowell
Hallowell
10.0 out of 10, Exceptional, (106 reviews)
"Lovely stay in Hallowell."
United States
Lori D.
The price is AED 437
AED 797 total
includes taxes & fees
13 Sep - 14 Sep
High End Apartment in Downtown Hallowell
House (3 Bedrooms) | Front of property

13. Near Lakes, Bay & Trails! Historic Waldoboro Gem

Near Lakes, Bay & Trails! Historic Waldoboro Gem
3.0 star property
Waldoboro
10.0 out of 10, Exceptional, (2 reviews)
"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!"
United States
Deborah
The price is AED 665
AED 1,802 total
includes taxes & fees
9 Sep - 10 Sep
Near Lakes, Bay & Trails! Historic Waldoboro Gem
Interior

14. Quiet & Lovely Lakefront Cottage for Families!

Quiet & Lovely Lakefront Cottage for Families!
Union
9.8 out of 10, Exceptional, (16 reviews)
"Evocative of my youth and going to the family lake camp in the summer. We had great weather and a great time. The cabin is a ‘Mainer’s’ memories wrapped in eclectic reminders. What a joy!"
United States
Venise B.
The price is AED 503
AED 1,882 total
includes taxes & fees
27 Aug - 28 Aug
Quiet & Lovely Lakefront Cottage for Families!
Interior

15. Island Tree House Glamping

Island Tree House Glamping
Monmouth
9.8 out of 10, Exceptional, (10 reviews)
"Sunset/rise were so perfect, and we got a special appearance of a double rainbow during our stay!"
United States
Desiree L.
The price is AED 275
AED 1,117 total
includes taxes & fees
17 Sep - 18 Sep
Island Tree House Glamping
Coffee/tea maker, fridge, microwave, stovetop

16. Near Lakes, Bay & Trails! Historic Waldoboro Gem

Near Lakes, Bay & Trails! Historic Waldoboro Gem
Waldoboro
9.8 out of 10, Exceptional, (27 reviews)
"It was a wonderful stay at this home. The home was incredibly clean, the beds were very comfortable and had great bedding on them. It was a great location to all the nearby places we wanted to go to. Loved the historic charm. We would love to come and stay again!"
United States
Tina S.
Near Lakes, Bay & Trails! Historic Waldoboro Gem
2 bedrooms, WiFi, bed sheets

17. The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.0 out of 10, Wonderful, (10 reviews)
"Host was very accommodating "
United States
Maureen
The price is AED 422
AED 853 total
includes taxes & fees
29 Aug - 30 Aug
The heart of the Belgrade Lakes
Property grounds

18. Floating Island Cabin

Floating Island Cabin
Monmouth
10.0 out of 10, Exceptional, (9 reviews)
"What an absolute pleasure it was staying in the floating home on the island. It was everything we wanted it to be. We will make this an annual trip. "
United States
Carissa P.
The price is AED 309
AED 861 total
includes taxes & fees
17 Sep - 18 Sep
Floating Island Cabin
Interior

19. “Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Nobleboro
9.8 out of 10, Exceptional, (46 reviews)
"We loved our cozy stay everything was clean and tidy, and we had everything that we needed"
United States
Betty Jo O.
The price is AED 823
AED 1,486 total
includes taxes & fees
27 Aug - 28 Aug
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Property grounds

20. Rustic Retreat Across from Lake; Family Friendly!

Rustic Retreat Across from Lake; Family Friendly!
Union
8.8 out of 10, Excellent, (22 reviews)
"Great location for visiting the coast."
United States
Sallie S.
The price is AED 364
AED 1,473 total
includes taxes & fees
30 Aug - 31 Aug
Rustic Retreat Across from Lake; Family 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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Top Windsor Hotel Reviews

Hampton Inn Waterville

Hampton Inn Waterville

10/10 Excellent
"Clean room"
Sandra 2-night trip
Posted 6 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?

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting: This vacation home rental outside of Windsor is located on a lake and has a fireplace, a patio, and a barbecue grill 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. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 Threemile Pond. In the larger area, you’ll find China Lake and Old Fort Western.

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.