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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Windsor vacation rentals

A living room with a fireplace, a glass of white wine, a cutting board with cheese, and a remote control.

1. High End Apartment in Downtown Hallowell

High End Apartment in Downtown Hallowell
Hallowell
10.0 out of 10, Exceptional, (113 reviews)
"Bigger than I expected and one of the homier properties I have been to in a while. Great location to walk around town and minutes to Augusta. Will book again"
United States
Shawn
The price is AED 437
AED 789 total
includes taxes & fees
2 Nov - 3 Nov
High End Apartment in Downtown Hallowell
A bathroom with a white sink, wooden paneling, a mirror with a bead trim, and a view of a house through a window.

2. 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 519
AED 646 total
includes taxes & fees
13 Oct - 14 Oct
River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
A two-story house with a front porch, a small tree, and a brick pathway.

3. Perfectly Located 1 Bedroom, newly remodeled

Perfectly Located 1 Bedroom, newly remodeled
Augusta
10.0 out of 10, Exceptional, (6 reviews)
"The area is so convenient for any business you have in the Augusta area- right off the main thoroughfare yet far enough away to be private. Check in was as simple as getting the lock code from vrbo check in emails. The apartment is even more lovely than the pictures- almost too clean and comfortable to be real! Bedtime was silent so I got a great night sleep. I only wish we would have had more time to enjoy :) Highly recommend!! "
United States
w c.
The price is AED 591
AED 1,029 total
includes taxes & fees
12 Oct - 13 Oct
Perfectly Located 1 Bedroom, newly remodeled
A modern living room with a flat-screen TV, a yellow armchair, a beige sofa, and a coffee table.

4. 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, (94 reviews)
"We keep coming back!!! The location is perfect! Walk to everything, eating, walking and watching sturgeonsThe apartment is so welcoming. Coffee options, bottled water…Looking forward to our next stay :)"
United States
Eileen S.
The price is AED 459
AED 881 total
includes taxes & fees
1 Nov - 2 Nov
Two bedroom Mid Century Modern apartment in Downtown Hallowell
A wooden cabin with a porch, a door, and a green chair.

5. Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (13 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is AED 367
AED 865 total
includes taxes & fees
3 Nov - 4 Nov
Sister A-Frame in Woods B
A tent with a bed, two chairs, and a table.

6. Get in touch with nature.

Get in touch with nature.
Richmond
10.0 out of 10, Exceptional, (50 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
13 Oct - 14 Oct
Get in touch with nature.
A single-story house with a gray siding exterior, a white front door, and two flower planters on either side of the entrance.

7. Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (20 reviews)
"Great communication. The location was excellent for a few day trips. Very clean and well maintained. Would definitely stay here again if in the area."
United States
Patricia
Discover Oakland charm near Colby College 10 min
A bedroom with a bed, a bedside table, a lamp, and a window with curtains.

8. The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.2 out of 10, Wonderful, (11 reviews)
"Host was very accommodating "
United States
Maureen
The price is AED 422
AED 861 total
includes taxes & fees
12 Oct - 13 Oct
The heart of the Belgrade Lakes
A covered porch with wicker furniture, a white door, and a welcome mat.

9. Cozy cottage in the Winthrop Lakes Area

Cozy cottage in the Winthrop Lakes Area
Winthrop
9.8 out of 10, Exceptional, (9 reviews)
"The property was lovely, and the host was wonderful!"
United States
Treseanne A.
The price is AED 382
AED 677 total
includes taxes & fees
1 Nov - 2 Nov
Cozy cottage in the Winthrop Lakes Area
Property grounds

10. Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.
Oakland
10.0 out of 10, Exceptional, (50 reviews)
"Apartment was comfortable and as described. I had a nice stay."
United States
kathy e.
The price is AED 382
AED 909 total
includes taxes & fees
1 Nov - 2 Nov
Central Maine Apartment offering 4 Seasons of Fun.
A floating house with a glass door, a deck, and a table and chairs.

11. Floating Island Cabin

Floating Island Cabin
Monmouth
10.0 out of 10, Exceptional, (13 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 857 total
includes taxes & fees
12 Oct - 13 Oct
Floating Island Cabin
A wooden deck with picnic tables overlooking a calm lake, surrounded by dense greenery.

12. Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!

Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!
West Gardiner
9.8 out of 10, Exceptional, (22 reviews)
"This was the ideal Maine spot."
United States
Lisa W.
The price is AED 698
AED 1,601 total
includes taxes & fees
20 Oct - 21 Oct
Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!
A living room with a sectional sofa, a coffee table, and a patterned rug. There are two paintings on the walls, a lamp, and a potted plant.

13. Cozy House in the heart of Waterville Maine.

Cozy House in the heart of Waterville Maine.
Waterville
9.6 out of 10, Exceptional, (64 reviews)
"Less than 5 minutes to Colby. We were there for a camp. AC in both bedrooms. Nice artwork and decor."
United States
Leslie G.
The price is AED 544
AED 933 total
includes taxes & fees
2 Nov - 3 Nov
Cozy House in the heart of Waterville Maine.
Outdoor dining

14. Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.

Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.
Waldoboro
The price is AED 533
AED 665 total
includes taxes & fees
17 Oct - 18 Oct
Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.
A spacious wooden cabin with a cozy living area featuring a sofa, a coffee table, and a fireplace.

15. Rustic Mountainside Cabin: “Liberty Lodge”

Rustic Mountainside Cabin: “Liberty Lodge”
Liberty
9.6 out of 10, Exceptional, (5 reviews)
"Place was great. Beautiful area and host was great about communicating so any questions we had were answered immediately"
United States
Brenda S.
The price is AED 515
AED 1,987 total
includes taxes & fees
12 Oct - 13 Oct
Rustic Mountainside Cabin: “Liberty Lodge”
A wooden deck with a glass door leading to a room.

16. Tiny Cottage Near Everything 10

Tiny Cottage Near Everything 10
Edgecomb
9.0 out of 10, Wonderful, (6 reviews)
"Great location awesome place to take it easy for a few"
United States
Gene
The price is AED 342
AED 799 total
includes taxes & fees
10 Nov - 11 Nov
Tiny Cottage Near Everything 10
A room with a hexagonal glass ceiling, a bed with a plaid blanket, and a view of greenery outside.

17. Floating Island Dome - Pet-Friendly Lake Retreat

Floating Island Dome - Pet-Friendly Lake Retreat
Monmouth
The price is AED 334
AED 865 total
includes taxes & fees
12 Oct - 13 Oct
Floating Island Dome - Pet-Friendly Lake Retreat
A modern living room with a large window, a wooden ceiling, and a view of a green landscape.

18. Come Spring Farm Airstream , Lake & farm animals

Come Spring Farm Airstream , Lake & farm animals
Union
8.4 out of 10, Very good, (5 reviews)
"Pet Friendly, Great surroundings, close to popular tourist towns in Maine"
United States
Thomas W.
The price is AED 606
AED 941 total
includes taxes & fees
28 Oct - 29 Oct
Come Spring Farm Airstream , Lake & farm animals
A spacious room with a wooden floor, a striped rug, a black chair, and a dining table.

19. Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters

Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
Winthrop
9.0 out of 10, Wonderful, (4 reviews)
"Very nice property, great location, nice decor, pet friendly, and good kitchen area."
United States
Laura M.
The price is AED 643
AED 1,137 total
includes taxes & fees
19 Oct - 20 Oct
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
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

The Elmwood

The Elmwood

10/10 Excellent
"Large double room. Nice shower. Fridge and microwave. Comfortable bed. Clean."
Marion 5-night trip
Posted 8 hours ago
The Elmwood

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 Wiscasset, Waterville and Farmington Railway Museum, or get outside and enjoy nature at Threemile Pond. In the larger area, you’ll find Capitol Park 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.