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
6 Jum. II - 8 Jum. II
In two weeks
13 Jum. II - 15 Jum. II
In one month
27 Jum. II - 29 Jum. II
In two months
25 Raj. - 27 Raj.

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

Waterfront retreat with stunning views, dock access and washer/dryer
Dining

Waterfront retreat with stunning views, dock access and washer/dryer

Waterfront retreat with stunning views, dock access and washer/dryer
“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 SAR 559
SAR 1,165 total
includes taxes & fees
9 Jun - 10 Jun
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly
Miscellaneous

Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly

9.2 out of 10, Wonderful, (19)
"Location is beautiful and private"
Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Fridge, microwave, oven, dishwasher

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

10.0 out of 10, Exceptional, (1)
"Nice time"
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Peaceful home with forest views & great yard - minutes to town
TV, fireplace

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

8.0 out of 10, Very Good, (3)
"Your home is beautiful!! Love all the windows, very comfortable!!"
Peaceful home with forest views & great yard - minutes to town
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, (19)
"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 SAR 840
SAR 1,924 total
includes taxes & fees
3 Jun - 4 Jun
Spacious Country Home w/ Hot Tub, near Colby/Thomas
Dome 4 at Come Spring Farm
Interior

Dome 4 at Come Spring Farm

10.0 out of 10, Exceptional, (1)
"Great, secluded location. Hosts were very generous with us! We loved getting to see their animals and enjoy the property! There was plenty of room for our family to relax and enjoy but be disconnected from the world! We spent a wonderful afternoon kayaking and spent a lot of time playing card games at the table inside the dome! Would highly recommend time away here!"
The price is SAR 563
SAR 805 total
includes taxes & fees
29 May - 30 May
Dome 4 at Come Spring Farm
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
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Living area

Dome 3 at Come Spring Farm Glamping - Alpaca Farm

The price is SAR 563
SAR 828 total
includes taxes & fees
29 May - 30 May
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Private and Calming Waterfront to the Rescue!
Property grounds

Private and Calming Waterfront to the Rescue!

9.6 out of 10, Exceptional, (78)
"This is a very nice home and was clean upon arrival. Very responsive owner as well."
Private and Calming Waterfront to the Rescue!
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
Great Pond Waterfront: Dog-friendly Home Near Colby College
Beach towels

Great Pond Waterfront: Dog-friendly Home Near Colby College

9.6 out of 10, Exceptional, (30)
"Thanks again for sharing your cottage with us! Everything was as described and the location was perfect. We’re looking forward to returning in the future."
Great Pond Waterfront: Dog-friendly Home Near Colby College
Near Waterville: Cozy Midcoast Vacation Rental!
TV, fireplace, DVD player, books

Near Waterville: Cozy Midcoast Vacation Rental!

9.4 out of 10, Exceptional, (8)
"Nice comfortable home to stay in."
Near Waterville: Cozy Midcoast Vacation Rental!
Gorgeous Waterfront& Yard on Damariscotta Lake with an Amazing Home
Terrace/patio

Gorgeous Waterfront& Yard on Damariscotta Lake with an Amazing Home

Gorgeous Waterfront& Yard on Damariscotta Lake with an Amazing Home
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
Cozy Long Pond Cottage: private mooring & shared dock
Property grounds

Cozy Long Pond Cottage: private mooring & shared dock

9.8 out of 10, Exceptional, (14)
"Very good stay."
Cozy Long Pond Cottage: private mooring & shared dock
Lakefront Maine House ~ 4 Mi to Colby College
Microwave, stovetop, dishwasher, coffee/tea maker

Lakefront Maine House ~ 4 Mi to Colby College

8.0 out of 10, Very Good, (2)
"Convenient very clean but we were hardly there except to sleep. Thank you"
Lakefront Maine House ~ 4 Mi to Colby College
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
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, (242)
"Had another great fishing trip with this as our home base! Always clean and comfortable! "
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free