Search Vacation Homes in Windsor

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 184 Vacation Homes in Windsor with updated reviews, rates, and availability.

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Fridge, microwave, oven, dishwasher

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Private and Calming Waterfront to the Rescue!
Property grounds

Private and Calming Waterfront to the Rescue!

9.6 out of 10, Exceptional, (77)
"This is a very nice home and was clean upon arrival. Very responsive owner as well."
Private and Calming Waterfront to the Rescue!
Idyllic Washington Retreat w/ Fire Pit & Yard
TV, fireplace

Idyllic Washington Retreat w/ Fire Pit & Yard

9.2 out of 10, Wonderful, (12)
"We stayed here because it was outside of Augusta and centered between the coast line, Moosehead Lake, and the scenic NatIonal Park."
Idyllic Washington Retreat w/ Fire Pit & Yard
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Property grounds

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

10.0 out of 10, Exceptional, (21)
"The owners were ver accommodating and the place is a quiet, pretty location "
The price is AED 551
AED 1,145 total
includes taxes & fees
26 May - 27 May
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
Outdoor spa tub

Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly

10.0 out of 10, Exceptional, (240)
"We loved this place very much. Everything was so easy and the home/location were beautiful. We definitely plan on another trip in the future. "
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
The Modern Maine Retreat
Outdoor dining

The Modern Maine Retreat

9.0 out of 10, Wonderful, (4)
"Worked out perfectly for our needs. Owner responded immediately to assist us with minor issue. We would, and most likely will, rent this home again. Location was great for our purpose. Plenty of room."
The Modern Maine Retreat
Brand New Waterfront Lake House (completed July 2021)
Miscellaneous

Brand New Waterfront Lake House (completed July 2021)

10.0 out of 10, Exceptional, (22)
"We love this place, it's the perfect Lake House and we intend on staying every year!"
Brand New Waterfront Lake House (completed July 2021)
Charming 4-bedroom log home with WiFi and AC in pleasant Liberty
Interior

Charming 4-bedroom log home with WiFi and AC in pleasant Liberty

Charming 4-bedroom log home with WiFi and AC in pleasant Liberty
Dome 4 at Come Spring Farm
Interior

Dome 4 at Come Spring Farm

The price is AED 643
AED 909 total
includes taxes & fees
6 May - 7 May
Dome 4 at Come Spring Farm
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
Fridge, microwave, stovetop, dishwasher

Peaceful Fisherman's Paradise w/ Deck + Fire Pit!

10.0 out of 10, Exceptional, (26)
"Wife, dog, and I had a great week away from home. House had everything we needed, quiet, and comfortable. Lot of great kayaking and fishing."
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
Cozy House in the heart of Waterville Maine.
TV

Cozy House in the heart of Waterville Maine.

9.6 out of 10, Exceptional, (39)
"Everything was good. Would stay there again."
Cozy House in the heart of Waterville Maine.
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Living area

Dome 3 at Come Spring Farm Glamping - Alpaca Farm

The price is AED 643
AED 931 total
includes taxes & fees
4 May - 5 May
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Spectacular Location Reasonably Priced
Exterior

Spectacular Location Reasonably Priced

9.6 out of 10, Exceptional, (29)
"Peaceful and scenic location"
Spectacular Location Reasonably Priced
Welcome to Alva’s Retreat located in the heart of Mid-Coast Maine
Outdoor dining

Welcome to Alva’s Retreat located in the heart of Mid-Coast Maine

10.0 out of 10, Exceptional, (3)
"It is very tranquil and clean. Also a great place for walking dogs. The owner provided a binder with a lot of helpful recommendations for various things to do or places to eat. Overall, a great place to stay."
Welcome to Alva’s Retreat located in the heart of Mid-Coast Maine
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Fridge, microwave, oven, stovetop

Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

8.2 out of 10, Very Good, (16)
"Great place to stay for a few days to collect the beautiful Togus Pond Beautiful view."
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Cozy Long Pond Cottage: private mooring & shared dock
Property grounds

Cozy Long Pond Cottage: private mooring & shared dock

9.8 out of 10, Exceptional, (13)
"Very good stay."
Cozy Long Pond Cottage: private mooring & shared dock
Spacious Country Home w/ Hot Tub, near Colby/Thomas
Outdoor spa tub

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

9.8 out of 10, Exceptional, (18)
"This house has everything for a weekend family vacay; you can spend the whole weekend enjoying the house & amenities such as the hot tub!"
The price is AED 893
AED 1,973 total
includes taxes & fees
3 Jun - 4 Jun
Spacious Country Home w/ Hot Tub, near Colby/Thomas
Big Pines Cabin: A Waterfront Retreat Open 4 Seasons, with Private Dock
Terrace/patio

Big Pines Cabin: A Waterfront Retreat Open 4 Seasons, with Private Dock

2.0 star property
10.0 out of 10, Exceptional, (5)
"Very quiet with a nice view of the stream. House was very nice with everything you need."
Big Pines Cabin: A Waterfront Retreat Open 4 Seasons, with Private Dock
Riverfront Sanctuary
Interior

Riverfront Sanctuary

10.0 out of 10, Exceptional, (3)
"Home was perfect for cooking and relaxing out doors. Property owners are very responsive and helpful. No issues and we really enjoyed our stay!"
Riverfront Sanctuary
Perfect Maine Getaway in a Recently Renovated Cabin!
Fridge, stovetop, dishwasher, coffee/tea maker

Perfect Maine Getaway in a Recently Renovated Cabin!

9.6 out of 10, Exceptional, (14)
"Had a great time at the cabin, just steps from town. Would recommend if you want to close to everything."
Perfect Maine Getaway in a Recently Renovated Cabin!
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.
Don't see what you're looking for?
See all available properties in Windsor
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Windsor

Downtown! Views! Dining! King & Queen beds!
Fridge, microwave, oven, stovetop

Downtown! Views! Dining! King & Queen beds!

2.0 star property
10.0 out of 10, Exceptional, (9)
"My daughter and I came to Maine for my birthday. The VRBO rental located on Water Street was flawless and exceeded our expectations. Beautifully appointed, Spotlessly clean, cozy and wonderful beds, bedding and pillows. Fun being right on the main street and walkable to most everything. The hosts were so accommodating, wish they had places all over the world. One recommendation is a tv on the kitchen level, I like tv. But the tv area upstairs is simply wonderful, so cozy. Views are delightful...
Downtown! Views! Dining! King & Queen beds!
April Special, Lake Great Pond, Dog Friendly
Outdoor dining

April Special, Lake Great Pond, Dog Friendly

10.0 out of 10, Exceptional, (36)
"Really enjoyed our stay, will come back. "
The price is AED 560
AED 1,155 total
includes taxes & fees
5 May - 6 May
April Special, Lake Great Pond, Dog Friendly
Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop
Fridge, microwave, oven, stovetop

Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop

Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop
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.