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Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 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)
"clean place listed accordingly "
Private and Calming Waterfront to the Rescue!
Beautiful lakeside 4 bedroom retreat with private dock and walkout basement
Terrace/patio

Beautiful lakeside 4 bedroom retreat with private dock and walkout basement

2.0 star property
Beautiful lakeside 4 bedroom retreat with private dock and walkout basement
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
Fridge, microwave, oven, stovetop

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

10.0 out of 10, Exceptional, (21)
"Had a huge job nearby, needed a place for 2 employees owners of company and 3 large trucjs to stay the night. Perfection!"
The price is AED 694
AED 1,321 total
includes taxes & fees
27 Apr - 28 Apr
“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)
"Had another great fishing trip with this as our home base! Always clean and comfortable! "
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
The Modern Maine Retreat
Property grounds

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)
Fridge, microwave, oven, stovetop

Brand New Waterfront Lake House (completed July 2021)

10.0 out of 10, Exceptional, (22)
"We had an amazing week at this property. House was spacious, clean and had everything that we needed. We plan to stay here again next summer! "
Brand New Waterfront Lake House (completed July 2021)
Charming 4-bedroom log home with WiFi and AC in pleasant Liberty
Microwave, oven, stovetop, dishwasher

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
3 May - 4 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)
"The property was as advertised! For a family with little kids, this was a great place to stay. David was helpful and very responsive!"
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)
"Very clean nice home, close to restaurants and shops. The owner was easily accessible if needed. "
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 735
AED 1,043 total
includes taxes & fees
1 May - 2 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)
"This is the quintessential cabin rental which provides good modern facilities with the vintage Maine camp feel we have always looked for. We will return to our 3rd rental at this property next year. Very satisfied with our experience."
Spectacular Location Reasonably Priced
Welcome to Alva’s Retreat located in the heart of Mid-Coast Maine
Terrace/patio

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
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 location! Very nice place"
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Cozy Long Pond Cottage: private mooring & shared dock
Terrace/patio

Cozy Long Pond Cottage: private mooring & shared dock

9.8 out of 10, Exceptional, (13)
" Cute place"
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)
"We had an awesome time playing in the snow in the backyard and enjoying the relaxing hot tub. The house accommodated our large family and the host was very responsive and came quickly when we needed help. Will definitely come back "
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)
"Did not want to leave. So thankful work took me to this beautiful property. The views did not disappoint. Alyssa and Mike were such a pleasure to work with. Thank you for opening your home away from home for me. My family and I will definitely be back. "
Big Pines Cabin: A Waterfront Retreat Open 4 Seasons, with Private Dock
Riverfront Sanctuary
Smart TV, books

Riverfront Sanctuary

10.0 out of 10, Exceptional, (3)
"This was a perfect location and setting for our family stay to attend our nephews wedding. The home has so much character with antique furnishings and a beautiful country setting overlooking the river. The hosts were very accommodating, responsive and a pleasure to deal with. "
Riverfront Sanctuary
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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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, (8)
"Great location, we traveled up to Bangor and down to Portland from this central location.The apartment was beautiful and clean with a great view of the river on one side, and the main road (which was quiet) on the other.Check in and out was seamless and Drew was very communicative before and during our stay. They even cleared the balcony and steps of snow."
Downtown! Views! Dining! King & Queen beds!
April Special, Lake Great Pond, Dog Friendly
Exterior

April Special, Lake Great Pond, Dog Friendly

10.0 out of 10, Exceptional, (36)
"With one kid already in college locally and the other on their way there in August we have got to know this neck of the woods quite well in recent years. Driftwood Cottage provides a perfect base for visits to the area with great access to Augusta and Waterville while sitting in the idyllic Belgrade Lakes region.We don’t visit Maine for fancy, we want practical, comfortable, clean and convenient and this house that in spades. We also greatly appreciated the dog-friendliness!Hosts could not...
The price is AED 560
AED 1,155 total
includes taxes & fees
27 Apr - 28 Apr
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.