Windsor Holiday Rentals

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Check prices for these dates

Tonight
6 Dec - 7 Dec
Tomorrow
7 Dec - 8 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Holiday Rentals in Windsor

Fridge, oven, stovetop, dishwasher
Classy AF Home Steps from Colby and Trails

Classy AF Home Steps from Colby and Trails

Oakland
10.0 out of 10, Exceptional, (49)
"Clean, comfortable and incredibly close to campus for a college visit."
United States
Patricia R.
Classy AF Home Steps from Colby and Trails
TV
Spacious Country Home w/ Hot Tub, near Colby/Thomas

Spacious Country Home w/ Hot Tub, near Colby/Thomas

Sidney
9.8 out of 10, Exceptional, (35)
"Very nice hot tub, quite and beautiful area! Air quality amazing and AC works fantasticly!"
United States
Nathan
The price is HK$1,697
HK$3,673 total
includes taxes & fees
28 Dec - 29 Dec
Spacious Country Home w/ Hot Tub, near Colby/Thomas
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)
"Check in was a breeze. Right on the lake. House was just the right size for me and my 3 adult sons. Was lovely to paddle, canoe or swim just walking down the porch stairs"
United States
Heather A.
The price is HK$1,016
HK$2,481 total
includes taxes & fees
9 Dec - 10 Dec
Cozy Cottage on water's edge of Lake Cobbosseecontee
Property grounds
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !

Maine Cabin Masters Camp completely redone waiting for a Lake loving family !

2.0 star property
Readfield
10.0 out of 10, Exceptional, (7)
"It was a wonderful week. The cabin is very well appointed. We lacked for nothing! Thank you "
United States
Gigi A.
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !
Fridge, microwave, oven, stovetop
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.
The price is HK$1,086
HK$2,515 total
includes taxes & fees
9 Dec - 10 Dec
Waterfront 2br/2ba cottage
TV, fireplace
Peaceful home with forest views & great yard - minutes to town

Peaceful home with forest views & great yard - minutes to town

Wiscasset
7.8 out of 10, Good, (9)
"Fit our needs perfectly!"
United States
Aimee K.
Peaceful home with forest views & great yard - minutes to town
Interior
Maine Waterfront Cottage: Nestled on an acre of land, with 500ft of shore front

Maine Waterfront Cottage: Nestled on an acre of land, with 500ft of shore front

Newcastle
10.0 out of 10, Exceptional, (65)
"Fabulous we will definitely be going back."
United States
Peggy B.
Maine Waterfront Cottage: Nestled on an acre of land, with 500ft of shore front
Front of property
My Valhalla Farm

My Valhalla Farm

3.5 star property
Oakland
The price is HK$1,751
HK$2,687 total
includes taxes & fees
7 Dec - 8 Dec
My Valhalla Farm
Outdoor spa tub
Spectacular Cobbossee Lakefront with Hot Tub & Dog Friendly

Spectacular Cobbossee Lakefront with Hot Tub & Dog Friendly

Manchester
10.0 out of 10, Exceptional, (255)
"We had a fantastic time! The lake is beautiful and the house has everything you need to enjoy it. "
United States
Dave S.
Spectacular Cobbossee Lakefront with Hot Tub & Dog Friendly
Exterior
Dome 1 - Luxury Dome at Come Spring Farm

Dome 1 - Luxury Dome at Come Spring Farm

Union
9.6 out of 10, Exceptional, (17)
"We had never stayed in a yurt before and this one had everything you need. We ate breakfast out on the deck and enjoyed the scenery. We had a really nice time!"
United States
Karen I.
Dome 1 - Luxury Dome at Come Spring Farm
Interior
NEW! Long Pond Lake View Getaway w/HOT TUB, ME

NEW! Long Pond Lake View Getaway w/HOT TUB, ME

Mount Vernon
10.0 out of 10, Exceptional, (2)
"This house was absolutely stunning! Had absolutely everything that you needed the house offered everything that one would need and plenty of space for everybody! The game room was so fun! The hot tub was a great bonus! Everyone had an amazing time while staying."
United States
Rachael L.
NEW! Long Pond Lake View Getaway w/HOT TUB, ME
Exterior
Sunfish Cove is the perfect year round getaway.

Sunfish Cove is the perfect year round getaway.

Monmouth
10.0 out of 10, Exceptional, (51)
"Awesome property for an extended family stay"
United States
shannon p.
Sunfish Cove is the perfect year round getaway.
Marina
Spacious 1 Bedroom Cottage Close to Everything 5

Spacious 1 Bedroom Cottage Close to Everything 5

Edgecomb
10.0 out of 10, Exceptional, (10)
"This place was an awesome weekend staycation soot"
United States
William B.
Spacious 1 Bedroom Cottage Close to Everything 5
5 bedrooms, iron/ironing board, Internet, bed sheets
Idyllic lakeside house with outdoor sauna, patio and firepit

Idyllic lakeside house with outdoor sauna, patio and firepit

Hope
10.0 out of 10, Exceptional, (2)
"The house was so beautiful and relaxing and right on the lake. The dock + provided boats/SUP were amazing. Sauna was also an excellent perk, even in summer. It’s close to lots of cute towns (everything closes early so plan ahead). There are lots of bugs (mosquitoes + spiders+ black flys) and can get a little hot because there is no A/C. But none of that ultimately is a deal breaker because it is so lovely."
United States
Miranda R.
Idyllic lakeside house with outdoor sauna, patio and firepit
Exterior
Beautiful 13 acre Property on Sheepscot River w/ 2 Bedroom Cottage & Air Stream

Beautiful 13 acre Property on Sheepscot River w/ 2 Bedroom Cottage & Air Stream

Wiscasset
10.0 out of 10, Exceptional, (74)
"Lovely little cottage, gorgeous grounds. And we loved Wiscasset!"
United States
barbara l.
Beautiful 13 acre Property on Sheepscot River w/ 2 Bedroom Cottage & Air Stream
Interior
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.
The price is HK$3,852
HK$4,801 total
includes taxes & fees
15 Dec - 16 Dec
Camp Lintonia on Tacoma Lakes
Fridge, microwave, oven, stovetop
Lakefront Cabin

Lakefront Cabin

China
10.0 out of 10, Exceptional, (27)
"Very clean, great view, quiet, serene location right on the lake."
United States
katherine b.
Lakefront Cabin
Outdoor dining
Lighthouse Lane

Lighthouse Lane

Manchester
10.0 out of 10, Exceptional, (70)
"The house location on the lake is perfect! So beautiful and quiet:) The house was overall very nice to live in."
United States
Nathalie N.
The price is HK$2,802
HK$3,715 total
includes taxes & fees
15 Dec - 16 Dec
Lighthouse Lane
Outdoor dining
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.
The price is HK$1,040
HK$2,211 total
includes taxes & fees
9 Dec - 10 Dec
Ice Fishing, Dog Friendly, Lake Great Pond
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

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.
The price is HK$1,167
HK$1,747 total
includes taxes & fees
12 Dec - 13 Dec
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards
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
"Very nice stay, friendly"
Jill 1-night trip
Posted 4 days ago
Cod Cove Inn, BW Signature Collection

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

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Look no further and take a look at our great range of rental properties in Windsor!

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?

Classy AF Home Steps from Colby and Trails: This holiday home rental outside of Windsor offers a private garden, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 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 Kennebec River Rail Trail. In the wider area, you’ll find Capitol Park 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.