Search Vacation Homes in Windsor

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 151 Vacation Homes in Windsor with updated reviews, rates, and availability.

Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
View of house from lake

Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly

10.0 out of 10, Exceptional, (238)
"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
Cozy House in the heart of Waterville Maine.
Living area

Cozy House in the heart of Waterville Maine.

9.6 out of 10, Exceptional, (38)
"Everything was good. Would stay there again."
Cozy House in the heart of Waterville Maine.
Luxurious lakefront home with 750' of spectacular frontage on Great Pond
Property grounds

Luxurious lakefront home with 750' of spectacular frontage on Great Pond

10.0 out of 10, Exceptional, (3)
"Property was exactly as listed - view of the lake from the deck and living rooms was beautiful. Host was very available and responsive. We had a wonderful time - there were 3 generations of our family with up to 14 members staying at the home. We also hosted a larger family get-together with an additional 10 people for an afternoon with permission from the host. Everyone was impressed with the house, property, lake views, deck and dock. Four of our young adult cousins stayed in the log cabin...
Luxurious lakefront home with 750' of spectacular frontage on Great Pond
Spacious Country Home w/ Hot Tub, near Colby/Thomas
Spacious dining room for your meals, game night, or remote office. (1)

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

9.8 out of 10, Exceptional, (17)
"This house has everything for a weekend family vacay; you can spend the whole weekend enjoying the house & amenities such as the hot tub!"
Spacious Country Home w/ Hot Tub, near Colby/Thomas
3 Bedroom year round lakefront home on Three Mile Pond in South China, ME

3 Bedroom year round lakefront home on Three Mile Pond in South China, ME

9.8 out of 10, Exceptional, (81)
"Great property, third tine here, excellent stocked kitchen"
3 Bedroom year round lakefront home on Three Mile Pond in South China, ME
Welcome to Alva’s Retreat located in the heart of Mid-Coast Maine
Property grounds

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

10.0 out of 10, Exceptional, (3)
"The house is new, absolutely immaculate and filled with light. The fully equipped kitchen was a joy to work in. The proximity to both Belfast and Camden was a huge plus. Our 2 dogs loved the open grassy field! A very friendly neighborhood too."
Welcome to Alva’s Retreat located in the heart of Mid-Coast Maine
Cozy Long Pond Cottage: private mooring & shared dock
Come enjoy this warm cottage!

Cozy Long Pond Cottage: private mooring & shared dock

9.8 out of 10, Exceptional, (11)
"Very good stay."
Cozy Long Pond Cottage: private mooring & shared dock
Camp Lintonia on Tacoma Lakes
Exterior

Camp Lintonia on Tacoma Lakes

10.0 out of 10, Exceptional, (5)
"Comfortable, clean, good amenities. Fun home layout for family gathering."
The price is AED 1,561
AED 1,918 total
includes taxes & fees
18 Feb - 19 Feb
Camp Lintonia on Tacoma Lakes
Big Pines Cabin: A Waterfront Retreat Open 4 Seasons, with Private Dock
Beautiful view of Belgrade Stream from the private dock.

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

2.0 star property
10.0 out of 10, Exceptional, (4)
"Very nice property that is clean and well managed "
Big Pines Cabin: A Waterfront Retreat Open 4 Seasons, with Private Dock
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Exterior

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

10.0 out of 10, Exceptional, (20)
"We usually rent right near our relatives closer to Newcastle, but there was a problem with heat in property so we needed a new rental to move into and “Otterly getaway” was willing to rent to us the day before they technically were available which was good for us. The kitchen of the getaway is just perfect for cooking side dishes for our large family Thanksgiving that was just about 20 minutes a way. We slept in the king bed and it was excellent sleeping. The heating system kept us also very...
The price is AED 694
AED 1,305 total
includes taxes & fees
18 Feb - 19 Feb
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Private and Calming Waterfront to the Rescue!
40 foot dock for boating, fishing and swimming

Private and Calming Waterfront to the Rescue!

9.6 out of 10, Exceptional, (76)
"We stayed at the property for a trade show with our team and enjoyed a comfortable clean and amazing overall stay. The house was clean kept and the owner was easy to deal with would highly recommend "
Private and Calming Waterfront to the Rescue!
Wildewood Haven - Charming 3-bedroom home located on Long Pond, Rome, ME
Exterior

Wildewood Haven - Charming 3-bedroom home located on Long Pond, Rome, ME

2.0 star property
10.0 out of 10, Exceptional, (2)
"We were just there for the weekend but if I could have stayed longer I would have . The house was clean and had plenty of space for everyone it was just my husband and me and our two grandkids but we had so much room and we did not even use the one room or the loft . The kitchen had everything you needed and then some I enjoyed the mint tea the owner had left for everyone. . They have soaps, bags,, spices, it all the little touches that make this place special. Can’t wait to go back."
Wildewood Haven - Charming 3-bedroom home located on Long Pond, Rome, ME
Spacious 5-bedroom waterfront house in lovely Sidney with WiFi, AC
Property grounds

Spacious 5-bedroom waterfront house in lovely Sidney with WiFi, AC

Spacious 5-bedroom waterfront house in lovely Sidney with WiFi, AC
Cozy Keyes Cottage- Rare Lakefront Getaway

Cozy Keyes Cottage- Rare Lakefront Getaway

10.0 out of 10, Exceptional, (9)
"A perfect 5 weeks! Owner was always available and very quick to respond to all requests.a perfect experience in all ways!"
The price is AED 1,983
AED 3,615 total
includes taxes & fees
18 Feb - 19 Feb
Cozy Keyes Cottage- Rare Lakefront Getaway
Lake Front with Amazing Sunsets on McGrath Pond
Enjoy beautiful sunsets every night.

Lake Front with Amazing Sunsets on McGrath Pond

10.0 out of 10, Exceptional, (17)
"Very clean, cute lake house. Owner responsive, everything you need for a rental home. Lake and lake toys were so great! We really enjoyed our stay. Thank you!!! "
Lake Front with Amazing Sunsets on McGrath Pond
Relaxing Log Cabin on Quantabacook Lake House<br>*** 11+ years of renting ***
Screened in porch

Relaxing Log Cabin on Quantabacook Lake House<br>*** 11+ years of renting ***

9.6 out of 10, Exceptional, (7)
"Great place for a relaxing quiet vacation. Plenty of amenities inside the cabin. There was no mention in the listing of no AC but most cabins don’t have them anyway. Plenty of fans available and the evenings were cool. We would definitely recommend this place to others."
Relaxing Log Cabin on Quantabacook Lake House<br>*** 11+ years of renting ***
4-bedroom Waterfront LAKEHOUSE in Maine. Hot tub, firepit, deck & private dock.
View of the lake from our dock.

4-bedroom Waterfront LAKEHOUSE in Maine. Hot tub, firepit, deck & private dock.

2.0 star property
9.0 out of 10, Wonderful, (4)
"We enjoyed this house with plenty of comfortable spaces for our family! It had all the essentials and a nice Hot Tub to enjoy the cooler weather in. The beds were comfortable, plenty of pillows and extra blankets. The space in the basement was lovely. We did have to be mindful of the water pressure so someone could shower 1 at a time. But overall, this was a beautiful home away from home"
4-bedroom Waterfront LAKEHOUSE in Maine. Hot tub, firepit, deck & private dock.
Lakefront Midcoast Maine retreat-Damariscotta Lake
Lake facing view

Lakefront Midcoast Maine retreat-Damariscotta Lake

10.0 out of 10, Exceptional, (22)
"We had a fantastic four day stay to celebrate my Dad's 80th birthday and my parent's 61st wedding anniversary! Damariscotta Lake holds a special place in our family's hearts as we had a cabin nearby for nearly 30 years. The quiet location on the cove is spectacular and the cabin itself is adorable! Plenty of room for three couples and a teenager! The cabin was well stocked with basic supplies, sheets/towels, cookware, smart tv and internet to make everyone feel at home. We enjoyed the fire pit...
Lakefront Midcoast Maine retreat-Damariscotta Lake
Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK

Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK

8.8 out of 10, Excellent, (19)
"Comfortable, quiet location. Appreciated the many nightlights. Both showers need grab bars. Basement shower drain not attached to shower floor."
Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

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

8.0 out of 10, Very Good, (15)
"This house has a beautiful location. My husband and I stayed for a weekend getaway and enjoyed our stay. One issue that we had was the water pressure. It was hard to shower because the water kept going in and out. As others have stated, the inside of the house could use some TLC. Some of the decorations are falling apart on the wall. The paint on the walls in some rooms look incomplete. Overall it was a good stay. "
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
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

High End Apartment in Downtown Hallowell

High End Apartment in Downtown Hallowell

10.0 out of 10, Exceptional, (74)
"Property was very clean. Great location between Augustus and Gardner. Will definitely be staying there again when I go back."
The price is AED 386
AED 721 total
includes taxes & fees
23 Feb - 24 Feb
High End Apartment in Downtown Hallowell
A Charming Waterfront Cottage with Touches of Elegance
This 44 foot porch runs the width of the house with panoramic views of the water

A Charming Waterfront Cottage with Touches of Elegance

10.0 out of 10, Exceptional, (99)
"We loved our stay in this beautiful home. Very comfortable, clean and so much attention to detail. The view was both serene and lovely."
A Charming Waterfront Cottage with Touches of Elegance
March Special, Ice Fishing, Dog Friendly
Outdoor entertaining

March Special, Ice Fishing, Dog Friendly

10.0 out of 10, Exceptional, (31)
"Good space for 3 adults and two kids to stay, 25 min commute to Colby college and Quarry Road trails. Couch was comfy and nice for gathering. Beds also comfy and the double bunks were helpful for our group. Plow came quickly after snowstorm. We didn’t get out on the lake due to cold but nice to have it close by. "
The price is AED 501
AED 1,054 total
includes taxes & fees
20 Feb - 21 Feb
March Special, Ice Fishing, 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.