Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Feb 13 - Feb 15
In two months
Mar 27 - Mar 29
In three months
Apr 24 - Apr 26
In four months
May 22 - May 24

Our top choices for Windsor vacation rentals

Fridge, microwave, oven, stovetop

Waterfront 2br/2ba cottage

Waterfront 2br/2ba cottage
West Gardiner
9.8 out of 10, Exceptional, (16 reviews)
"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.
$331 nightly
The price is $361
Feb 2 - Feb 3
Total with taxes and fees
Waterfront 2br/2ba cottage
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 reviews)
"Great hiking - nice views."
United States
Norbert A.
$221 nightly
The price is $241
Feb 2 - Feb 3
Total with taxes and fees
Central Maine Apartment offering 4 Seasons of Fun.
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, (82 reviews)
"Great apartment, close to town, very clean, comfortable beds. Loved the little extras too.. coffee, creamer, etc! Will definitely stay again. "
United States
Rebekah B.
$211 nightly
The price is $230
Feb 1 - Feb 2
Total with taxes and fees
Two bedroom Mid Century Modern apartment in Downtown Hallowell
2 bedrooms, WiFi, bed sheets

The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.0 out of 10, Wonderful, (9 reviews)
"Host was very accommodating "
United States
Maureen
$215 nightly
The price is $234
Feb 16 - Feb 17
Total with taxes and fees
The heart of the Belgrade Lakes
TV

NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.

NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.
Oakland
$270 nightly
The price is $294
Jan 31 - Feb 1
Total with taxes and fees
NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.
Outdoor dining

Lighthouse Lane

Lighthouse Lane
Manchester
10.0 out of 10, Exceptional, (70 reviews)
"Very nice stay Beautiful lake views "
United States
Karen G.
$286 nightly
The price is $312
Feb 2 - Feb 3
Total with taxes and fees
Lighthouse Lane
Interior

Ice Fishing, Dog Friendly, Lake Great Pond

Ice Fishing, Dog Friendly, Lake Great Pond
Belgrade
10.0 out of 10, Exceptional, (49 reviews)
"All was exactly as we hoped it would be, perfect for a family and added benefit of pet friendly."
United States
Jonathan I.
$322 nightly
The price is $350
Feb 3 - Feb 4
Total with taxes and fees
Ice Fishing, Dog Friendly, Lake Great Pond
Property grounds

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 reviews)
"Very quiet spot right on the lake, relatively easy to get to, close to town. Cabin is small, which was perfect for the two of us. "
United States
Stephanie P.
$309 nightly
The price is $337
Jan 31 - Feb 1
Total with taxes and fees
Cozy Cottage on water's edge of Lake Cobbosseecontee
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 reviews)
"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.
$260 nightly
The price is $283
Feb 4 - Feb 5
Total with taxes and fees
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Exterior

Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
10.0 out of 10, Exceptional, (6 reviews)
"Very clean and comfy. A pleasure to stay there. "
United States
Vicki W.
$236 nightly
The price is $257
Feb 1 - Feb 2
Total with taxes and fees
Discover Oakland charm near Colby College 10 min
Terrace/patio

Family's Paradise: 3BR/2BA,Game Room & Lake Access

Family's Paradise: 3BR/2BA,Game Room & Lake Access
Belgrade
9.8 out of 10, Exceptional, (9 reviews)
"We enjoyed our stay."
United States
Tyson W.
$771 nightly
The price is $840
Feb 3 - Feb 4
Total with taxes and fees
Family's Paradise: 3BR/2BA,Game Room & Lake Access
Dining

Peaceful Intown Studio ~ Walk to Shops & Dining

Peaceful Intown Studio ~ Walk to Shops & Dining
Newcastle
6.0 out of 10, (1 review)
$166 nightly
The price is $181
Jan 31 - Feb 1
Total with taxes and fees
Peaceful Intown Studio ~ Walk to Shops & Dining
Exterior

Cozy getaway: farmhouse with wood stove & jacuzzi tub

Cozy getaway: farmhouse with wood stove & jacuzzi tub
Oakland
10.0 out of 10, Exceptional, (9 reviews)
"It was that was said to be The host was very nice and helpful . I enjoyed my stay "
United States
Andrea C.
$345 nightly
The price is $367
Jan 31 - Feb 1
Total with taxes and fees
Cozy getaway: farmhouse with wood stove & jacuzzi tub
Outdoor dining

Minutes to Colby

Minutes to Colby
Waterville
8.8 out of 10, Excellent, (22 reviews)
"Easy check in and spacious apartment. Excellent location- within minutes of Colby and downtown restaurants. Super comfy living room to relax in after a full day of Parents Weekend:"
United States
Jodie M.
$230 nightly
The price is $251
Feb 2 - Feb 3
Total with taxes and fees
Minutes to Colby
Interior

Camp Lintonia on Tacoma Lakes

Camp Lintonia on Tacoma Lakes
Litchfield
10.0 out of 10, Exceptional, (12 reviews)
"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
Feb 2 - Feb 3
Total with taxes and fees
Camp Lintonia on Tacoma Lakes
Exterior

Hilltop 3BR Getaway w/ Chef BBQ, Fire Pit, Patios & Room to Relax

Hilltop 3BR Getaway w/ Chef BBQ, Fire Pit, Patios & Room to Relax
Waldoboro
9.6 out of 10, Exceptional, (9 reviews)
"Good visit overall."
United States
Gerald S.
$571 nightly
The price is $622
Feb 1 - Feb 2
Total with taxes and fees
Hilltop 3BR Getaway w/ Chef BBQ, Fire Pit, Patios & Room to Relax
Exterior detail

Peaceful Home in Central Maine

Peaceful Home in Central Maine
Sidney
8.0 out of 10, Very Good, (3 reviews)
"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.
$382 nightly
The price is $416
Feb 23 - Feb 24
Total with taxes and fees
Peaceful Home in Central Maine
Living area

Cozy newly built 1-bedroom apartment in charming Smithfield

Cozy newly built 1-bedroom apartment in charming Smithfield
Smithfield
$256 nightly
The price is $279
Feb 1 - Feb 2
Total with taxes and fees
Cozy newly built 1-bedroom apartment in charming Smithfield
Property grounds

7BR Hilltop Retreat · 2 Kitchens & Decks

7BR Hilltop Retreat · 2 Kitchens & Decks
Waldoboro
9.6 out of 10, Exceptional, (5 reviews)
"The house and location was perfect, sitting around the fire pit to end the night was perfect "
United States
william h.
$1,164 nightly
The price is $1,269
Feb 1 - Feb 2
Total with taxes and fees
7BR Hilltop Retreat · 2 Kitchens & Decks
Interior

High End Apartment in Downtown Hallowell

High End Apartment in Downtown Hallowell
Hallowell
10.0 out of 10, Exceptional, (98 reviews)
"We will definitely try and stay there again!"
United States
scott s.
$189 nightly
The price is $206
Feb 1 - Feb 2
Total with taxes and fees
High End Apartment in Downtown Hallowell
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

Maine Evergreen Hotel, an Ascend Collection Hotel

Maine Evergreen Hotel, an Ascend Collection Hotel

10/10 Excellent
"Room clean, comfortable, and had a great reading chair!"
Terri 3-night trip
Posted 4 days ago
Maine Evergreen Hotel, an Ascend Collection Hotel

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 $277 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 Capitol Park. In the larger area, you’ll find Maine State House and Damariscotta Lake State 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.