Holiday Rentals in Windsor

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Our top choices for Windsor holiday rentals

9.2 out of 10, Wonderful, (7 reviews)
"Very neat cabin. Spacious all utilities and a fire pit"
United States
Lisa O.
The price is €152
includes taxes & fees
15 Mar - 16 Mar
Charming cabin in the birches right on the atv trail!
10.0 out of 10, Exceptional, (83 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.
The price is €205
includes taxes & fees
10 Mar - 11 Mar
Two bedroom Mid Century Modern apartment in Downtown Hallowell
10.0 out of 10, Exceptional, (9 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
Sister A-Frame in Woods B

Cottage in West Gardiner

Waterfront 2br/2ba cottage
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.
The price is €305
includes taxes & fees
9 Mar - 10 Mar
Waterfront 2br/2ba cottage
8.0 out of 10, Very good, (3 reviews)
"Location was perfect and Lynn was so helpful. We’d definitely stay here again!"
United States
Caycee A.
The price is €159
includes taxes & fees
17 Mar - 18 Mar
Peaceful Intown Studio ~ Walk to Shops & Dining

Cottage in Manchester

Lighthouse Lane
10.0 out of 10, Exceptional, (72 reviews)
"Very nice stay Beautiful lake views "
United States
Karen G.
The price is €262
includes taxes & fees
10 Mar - 11 Mar
Lighthouse Lane
8.6 out of 10, Excellent, (20 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.
The price is €286
includes taxes & fees
8 Mar - 9 Mar
Cozy Cottage on water's edge of Lake Cobbosseecontee
9.8 out of 10, Exceptional, (9 reviews)
"We enjoyed our stay."
United States
Tyson W.
The price is €696
includes taxes & fees
9 Mar - 10 Mar
Family's Paradise: 3BR/2BA,Game Room & Lake Access
9.0 out of 10, Wonderful, (8 reviews)
"Beautiful location and a unique stay."
United States
Sabrina D.
The price is €243
includes taxes & fees
5 Apr - 6 Apr
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
10.0 out of 10, Exceptional, (51 reviews)
"Great location!"
United States
Gail D.
The price is €292
includes taxes & fees
11 Mar - 12 Mar
Ice Fishing, Dog Friendly, Lake Great Pond
10.0 out of 10, Exceptional, (43 reviews)
"Great hiking - nice views."
United States
Norbert A.
The price is €220
includes taxes & fees
10 Mar - 11 Mar
Central Maine Apartment offering 4 Seasons of Fun.
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.
The price is €239
includes taxes & fees
9 Mar - 10 Mar
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
10.0 out of 10, Exceptional, (6 reviews)
"Very clean and comfy. A pleasure to stay there. "
United States
Vicki W.
The price is €220
includes taxes & fees
19 Mar - 20 Mar
Discover Oakland charm near Colby College 10 min
10.0 out of 10, Exceptional, (1 review)
"Pet Friendly, Great surroundings, close to popular tourist towns in Maine"
United States
Thomas W.
Come Spring Farm Airstream , Lake & farm animals
9.0 out of 10, Wonderful, (9 reviews)
"Host was very accommodating "
United States
Maureen
The price is €204
includes taxes & fees
5 Apr - 6 Apr
The heart of the Belgrade Lakes
10.0 out of 10, Exceptional, (10 reviews)
"It was that was said to be The host was very nice and helpful . I enjoyed my stay "
United States
Andrea C.
The price is €329
includes taxes & fees
15 Mar - 16 Mar
Cozy getaway: farmhouse with wood stove & jacuzzi tub

Holiday Home in Sidney

Peaceful Home in Central Maine
8.4 out of 10, Very good, (5 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.
The price is €369
includes taxes & fees
10 Mar - 11 Mar
Peaceful Home in Central Maine

Apartment in Waterville

Minutes to Colby
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.
The price is €168
includes taxes & fees
9 Mar - 10 Mar
Minutes to Colby
6.8 out of 10, (3 reviews)
"My friends and I had a great time at Come Spring Farm! We got hit with a lot of rain as soon as we arrived and it was really cool to watch the storm through the windows in the dome. We were impressed with the bathroom/shower facilities and the Coop hang out space, and I was thrilled to help feed the animals in the morning. We hope to return soon!"
United States
Healy C.
The price is €216
includes taxes & fees
5 Apr - 6 Apr
Come Spring Farm Glamping Dome 2

Holiday Home in Litchfield

Camp Lintonia on Tacoma Lakes
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.
The price is €236
includes taxes & fees
9 Mar - 10 Mar
Camp Lintonia on Tacoma Lakes
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

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windsor holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as €236 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday 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 holiday.

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 holiday rentals in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select 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 holiday rentals that Windsor has to offer?

Spacious Country Home w/ Hot Tub, near Colby/Thomas: This holiday home rental outside of Windsor is located in a rural location, and has 1 hot tub, a BBQ 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 that 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 wider area, you’ll find Old Fort Western and Maine State House.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for small groups.