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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Windsor vacation rentals

Terrace/patio

Get in touch with nature.

Get in touch with nature.
Richmond
10.0 out of 10, Exceptional, (43 reviews)
"Wonderful place very peaceful very friendly Aaron was spectacular couldn't ask for a more wonderful enjoyable spot"
United States
Keith R
$140 nightly
The price is $153
Jul 20 - Jul 21
Total with taxes and fees
Get in touch with nature.
Cottage (2 Bedrooms) | Front of property

Private Dock on Messalonskee Lake: Cozy Cottage!

Private Dock on Messalonskee Lake: Cozy Cottage!
3.0 star property
Augusta
10.0 out of 10, Exceptional, (1 review)
"Great little lake cabin. Had everything we needed. Clean, comfortable, quite. Beautiful area and views. We had a wonderful stay and would stay again."
United States
John
$298 nightly
The price is $324
Jul 29 - Jul 30
Total with taxes and fees
Private Dock on Messalonskee Lake: Cozy Cottage!
Exterior

Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (9 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
$240 nightly
The price is $261
Jul 20 - Jul 21
Total with taxes and fees
Sister A-Frame in Woods B
Property grounds

Rustic Retreat Across from Lake; Family Friendly!

Rustic Retreat Across from Lake; Family Friendly!
Union
8.8 out of 10, Excellent, (19 reviews)
"Great location for visiting the coast."
United States
Sallie S.
$379 nightly
The price is $413
Aug 16 - Aug 17
Total with taxes and fees
Rustic Retreat Across from Lake; Family Friendly!
Smart TV

Charming cabin in the birches right on the atv trail!

Charming cabin in the birches right on the atv trail!
Fairfield
8.6 out of 10, Excellent, (9 reviews)
"The Host was great, I highly recommend this spot, everything was super smooth and the cabin was beautiful. "
United States
Jason B.
$158 nightly
The price is $172
Jul 21 - Jul 22
Total with taxes and fees
Charming cabin in the birches right on the atv trail!
Exterior

Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (14 reviews)
"Place was very clean. Host was wonderful and easy to communicate with. "
United States
Tammy W.
$184 nightly
The price is $200
Jul 29 - Jul 30
Total with taxes and fees
Discover Oakland charm near Colby College 10 min
Coffee/tea maker, fridge, microwave, stovetop

Spacious 1 Bedroom Cottage Close to Everything 5

Spacious 1 Bedroom Cottage Close to Everything 5
Edgecomb
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful, clean, small cottage close to the coast, shopping and dining."
United States
Theresa
$243 nightly
The price is $256
Jul 21 - Jul 22
Total with taxes and fees
Spacious 1 Bedroom Cottage Close to Everything 5
2 bedrooms, iron/ironing board, bed sheets

Cheerful Cottage with Loft 9

Cheerful Cottage with Loft 9
Edgecomb
10.0 out of 10, Exceptional, (4 reviews)
"Immaculate, very cute - “tiny cottage”We loved it!"
United States
Daniel B.
$248 nightly
The price is $262
Jul 22 - Jul 23
Total with taxes and fees
Cheerful Cottage with Loft 9
Spa

Floating Island Dome - Pet-Friendly Lake Retreat

Floating Island Dome - Pet-Friendly Lake Retreat
Monmouth
$206 nightly
The price is $224
Jul 20 - Jul 21
Total with taxes and fees
Floating Island Dome - Pet-Friendly Lake Retreat
2 bedrooms, WiFi, bed sheets

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
$212 nightly
The price is $231
Jul 24 - Jul 25
Total with taxes and fees
The heart of the Belgrade Lakes
Outdoor dining

Happy Cottage Near Everything 11

Happy Cottage Near Everything 11
Edgecomb
6.8 out of 10, (3 reviews)
"Great quit little place, great accommodations with even better help and information about the local area."
United States
George
$209 nightly
The price is $211
Jul 20 - Jul 21
Total with taxes and fees
Happy Cottage Near Everything 11
Interior

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Nobleboro
9.8 out of 10, Exceptional, (44 reviews)
"We loved our cozy stay everything was clean and tidy, and we had everything that we needed"
United States
Betty Jo O.
$371 nightly
The price is $405
Jul 25 - Jul 26
Total with taxes and fees
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Property grounds

Glamping at Maine Water Buffalo Farm

Glamping at Maine Water Buffalo Farm
Appleton
10.0 out of 10, Exceptional, (3 reviews)
"Really great place….very thoughtful set up for us to enjoy."
United States
Peter P.
$149 nightly
The price is $162
Jul 21 - Jul 22
Total with taxes and fees
Glamping at Maine Water Buffalo Farm
Exterior

Spacious 1 Bedroom Cottage Close to Everything 3

Spacious 1 Bedroom Cottage Close to Everything 3
Edgecomb
9.8 out of 10, Exceptional, (17 reviews)
"Great central location"
United States
Bruce O.
$285 nightly
The price is $302
Jul 20 - Jul 21
Total with taxes and fees
Spacious 1 Bedroom Cottage Close to Everything 3
Property grounds

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.
$261 nightly
The price is $284
Jul 26 - Jul 27
Total with taxes and fees
Floating Island Cabin
Dining

Peaceful Intown Studio ~ Walk to Shops & Dining

Peaceful Intown Studio ~ Walk to Shops & Dining
Newcastle
8.6 out of 10, Excellent, (4 reviews)
"Location was perfect and Lynn was so helpful. We’d definitely stay here again!"
United States
Caycee A.
$206 nightly
The price is $225
Jul 28 - Jul 29
Total with taxes and fees
Peaceful Intown Studio ~ Walk to Shops & Dining
House (3 Bedrooms) | Front of property

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
$450 nightly
The price is $491
Aug 9 - Aug 10
Total with taxes and fees
Near Lakes, Bay & Trails! Historic Waldoboro Gem
Interior

Island Tree House Glamping

Island Tree House Glamping
Monmouth
10.0 out of 10, Exceptional, (9 reviews)
"Sunset/rise were so perfect, and we got a special appearance of a double rainbow during our stay!"
United States
Desiree L.
$310 nightly
The price is $338
Jul 22 - Jul 23
Total with taxes and fees
Island Tree House Glamping
Interior

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
10.0 out of 10, Exceptional, (1 review)
"This is an adorable newly constructed unit. Lots of day light, cute decor and lake views. The one confusing part was the use of the docks which was uncomfortable at the beginning but worked out in the end. We used the dock and swam every day. The location is also convenient and has plenty of parking. Jill is a great host. We would stay here again."
United States
Katie D.
$290 nightly
The price is $316
Jul 22 - Jul 23
Total with taxes and fees
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
Outdoor dining

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, (19 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.
$464 nightly
The price is $506
Jul 29 - Jul 30
Total with taxes and fees
Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!
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

Cod Cove Inn, BW Signature Collection

Cod Cove Inn, BW Signature Collection

10/10 Excellent
"Extremely nice location. Very quiet and clean. One thing they could improve on was the Continental breakfast hours. 7:30 to 9:30 is way too late if you want to get an early start to your day."
Lynn 2-night trip
Posted 1 day ago
Cod Cove Inn, BW Signature Collection

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 $153 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.

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?

Nestled in Nobleboro: This vacation home rental outside of Windsor is located next to a golf course and has a patio, a garden, and laundry facilities to put you at ease in your new surroundings.

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 Old Fort Western and Capitol 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.