Windsor Vacation Rentals

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In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Windsor vacation rentals

Exterior
Cozy getaway: farmhouse with wood stove & jacuzzi tub

Cozy getaway: farmhouse with wood stove & jacuzzi tub

Cozy getaway: farmhouse with wood stove & jacuzzi tub
Oakland
10.0 out of 10, Exceptional, (7)
"It was that was said to be The host was very nice and helpful . I enjoyed my stay "
United States
Andrea C.
$380 nightly
The price is $405
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cozy getaway: farmhouse with wood stove & jacuzzi tub
Fridge, microwave, oven, stovetop
Discover Oakland charm near Colby College 10 min

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)
"New, clean and had everything we needed. "
United States
Lara B.
$235 nightly
The price is $256
Jan 11 - Jan 12, 2026
Total with taxes and fees
Discover Oakland charm near Colby College 10 min
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.

No bookings after 8/15/2024. Property sold. VRBO Thank you.
Searsmont
10.0 out of 10, Exceptional, (5)
"Love the cottage and very clean and quiet."
United States
Jeanne
$129 nightly
The price is $141
Dec 29 - Dec 30
Total with taxes and fees
No bookings after 8/15/2024. Property sold. VRBO Thank you.
Property grounds
3350 Middle Road

3350 Middle Road

3350 Middle Road
Sidney
8.0 out of 10, Very Good, (3)
"A great spot for all 7 of us. Nice house with zones for everyone. Lovely backyard. Big kitchen and dining table"
United States
Pat D.
$308 nightly
The price is $336
Jan 5 - Jan 6, 2026
Total with taxes and fees
3350 Middle Road
Living area
The heart of the Belgrade Lakes

The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.0 out of 10, Wonderful, (9)
"Host was very accommodating "
United States
Maureen
$176 nightly
The price is $191
Jan 4 - Jan 5, 2026
Total with taxes and fees
The heart of the Belgrade Lakes
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

Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards
Whitefield
9.8 out of 10, Exceptional, (30)
"We stayed in this cabin for two nights with our dog and it was very peaceful and fun! The cabin has a campfire, lots of batteries for charging, lights, battery fans, etc. There were many long walking trails with fun activities; like kayaking, axe throwing, a pizza oven… Exactly what we were looking for! Would stay again! "
United States
Ben R.
$206 nightly
The price is $225
Jan 11 - Jan 12, 2026
Total with taxes and fees
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards
Interior
High End Apartment in Downtown Hallowell

High End Apartment in Downtown Hallowell

High End Apartment in Downtown Hallowell
Hallowell
10.0 out of 10, Exceptional, (96)
"Beautiful place to stay. Having coffee with all the fixings already there along with snacks was great! Would definitely stay here again!"
United States
John H.
$189 nightly
The price is $206
Jan 2 - Jan 3, 2026
Total with taxes and fees
High End Apartment in Downtown Hallowell
Property grounds
Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.
Oakland
10.0 out of 10, Exceptional, (43)
"Great hiking - nice views."
United States
Norbert A.
$221 nightly
The price is $241
Jan 5 - Jan 6, 2026
Total with taxes and fees
Central Maine Apartment offering 4 Seasons of Fun.
1 bedroom, iron/ironing board, WiFi, bed sheets
Peaceful Intown Studio ~ Walk to Shops & Dining

Peaceful Intown Studio ~ Walk to Shops & Dining

Peaceful Intown Studio ~ Walk to Shops & Dining
2.0 star property
Newcastle
$153 nightly
The price is $167
Jan 2 - Jan 3, 2026
Total with taxes and fees
Peaceful Intown Studio ~ Walk to Shops & Dining
Outdoor dining
Lighthouse Lane

Lighthouse Lane

Lighthouse Lane
Manchester
10.0 out of 10, Exceptional, (70)
"Great location. Large comfy house and beds!! The back patio with bar seating ingenious! "
United States
Barbara C.
$286 nightly
The price is $312
Dec 29 - Dec 30
Total with taxes and fees
Lighthouse Lane
Exterior
Sister A-Frame in Woods B

Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (9)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
$210 nightly
The price is $228
Jan 1 - Jan 2, 2026
Total with taxes and fees
Sister A-Frame in Woods B
Property grounds
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Nobleboro
9.8 out of 10, Exceptional, (43)
"House was very clean and beautiful the beach and fishing are were lovely as well very nicecstay"
United States
Lori R.
$268 nightly
The price is $292
Dec 29 - Dec 30
Total with taxes and fees
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Outdoor dining
Minutes to Colby

Minutes to Colby

Minutes to Colby
Waterville
8.8 out of 10, Excellent, (22)
"Close to our event, great communication, clean, comfortable & cozy"
United States
Shelly B.
$174 nightly
The price is $190
Jan 5 - Jan 6, 2026
Total with taxes and fees
Minutes to Colby
Fridge, microwave, oven, stovetop
Waterfront 2br/2ba cottage

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.
$333 nightly
The price is $363
Dec 29 - Dec 30
Total with taxes and fees
Waterfront 2br/2ba cottage
Interior
Camp Lintonia on Tacoma Lakes

Camp Lintonia on Tacoma Lakes

Camp Lintonia on Tacoma Lakes
Litchfield
10.0 out of 10, Exceptional, (11)
"Booked this property for a girls trip and this property was stunning! Wish we would’ve booked for more days! Ample space for everyone, views were amazing, and the house was gorgeous! Already considering booking again next year! "
United States
Emma B.
$254 nightly
The price is $277
Dec 30 - Dec 31
Total with taxes and fees
Camp Lintonia on Tacoma Lakes
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

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.
$271 nightly
The price is $295
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Property grounds
Cozy Cottage on water's edge of Lake Cobbosseecontee

Cozy Cottage on water's edge of Lake Cobbosseecontee

Cozy Cottage on water's edge of Lake Cobbosseecontee
Manchester
8.6 out of 10, Excellent, (18)
"Great views of the from the screened porch! Lots to loons too, a big bonus!"
United States
Randy P.
$309 nightly
The price is $337
Dec 29 - Dec 30
Total with taxes and fees
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

Ice Fishing, Dog Friendly, Lake Great Pond
Belgrade
10.0 out of 10, Exceptional, (48)
"Great place for us to get in 2 days of golf and 2 days of fishing. House was clean and communication with host prior to arrival and during our stay was excellent. "
United States
Thomas B.
$367 nightly
The price is $400
Jan 4 - Jan 5, 2026
Total with taxes and fees
Ice Fishing, Dog Friendly, Lake Great Pond
TV
Two bedroom Mid Century Modern apartment in Downtown Hallowell

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, (81)
"Great location and excellent accommodations. Just what we needed for this quick stay. We would definitely stay here again!"
United States
J K.
$217 nightly
The price is $237
Dec 30 - Dec 31
Total with taxes and fees
Two bedroom Mid Century Modern apartment in Downtown Hallowell
Interior
The Entire Waldoboro Inn

The Entire Waldoboro Inn

The Entire Waldoboro Inn
Waldoboro
$1,194 nightly
The price is $1,301
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Entire Waldoboro Inn
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, great staff, nice breakfast"
Chrystie 1-night trip
Posted 3 days ago
Hampton Inn Waterville

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $225 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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 Kennebec River Rail Trail. 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.