Holiday Homes in Windsor

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Holiday Homes in Windsor

Our top choices for Windsor holiday homes

Cozy Cottage on water's edge of Lake Cobbosseecontee
Property grounds

Cozy Cottage on water's edge of Lake Cobbosseecontee

8.8 out of 10, Excellent, (12)
"Great little getaway, sitting right by the water. We loved our time there. Alarice is a great hot and responded quickly to any needs or questions."
The price is AU$501
includes taxes & fees
25 Aug - 26 Aug
Cozy Cottage on water's edge of Lake Cobbosseecontee
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Property grounds

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

10.0 out of 10, Exceptional, (30)
"The owners were ver accommodating and the place is a quiet, pretty location "
The price is AU$537
includes taxes & fees
26 Aug - 27 Aug
“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage
Come Spring Farm Glamping Dome 2
WiFi

Come Spring Farm Glamping Dome 2

The price is AU$446
includes taxes & fees
25 Aug - 26 Aug
Come Spring Farm Glamping Dome 2
Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly
Fridge, microwave, oven, stovetop

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

9.2 out of 10, Wonderful, (20)
"The house & deck were very nice with beautiful view of the lake. It could use some typical amenities like tissues, hair dryer, etc. The main problem is getting to the house. It’s a 3/4 mile drive down a narrow stone road riddled with potholes and bumps. I was afraid I was going to do damage to the rental car and that’s driving at or lower than the 15mph speed limit! "
Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly
New Waterfront Lake House - completed 2021
Outdoor dining

New Waterfront Lake House - completed 2021

10.0 out of 10, Exceptional, (25)
"We love this place, it's the perfect Lake House and we intend on staying every year!"
New Waterfront Lake House - completed 2021
Peaceful home with forest views & great yard - minutes to town
TV, fireplace

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

7.8 out of 10, Good, (6)
"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
Terrace/patio

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

9.8 out of 10, Exceptional, (27)
"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 with private dock
Exterior

3 Bedroom year round lakefront home on Three Mile Pond with private dock

9.8 out of 10, Exceptional, (90)
"Great location. Very peaceful with beautiful view too. Would stay here again!"
3 Bedroom year round lakefront home on Three Mile Pond with private dock
Discover Oakland charm near Colby College 10 min
Fridge, microwave, oven, stovetop

Discover Oakland charm near Colby College 10 min

2.0 star property
10.0 out of 10, Exceptional, (3)
"New, clean and had everything we needed. "
Discover Oakland charm near Colby College 10 min
Spectacular Location Reasonably Priced
Exterior

Spectacular Location Reasonably Priced

9.6 out of 10, Exceptional, (30)
"Peaceful and scenic location"
Spectacular Location Reasonably Priced
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (11)
"Nice time"
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
Living area

Dome 3 at Come Spring Farm Glamping - Alpaca Farm

8.4 out of 10, Very good, (5)
The price is AU$446
includes taxes & fees
31 Aug - 1 Sept
Dome 3 at Come Spring Farm Glamping - Alpaca Farm
The Modern Maine Retreat
Dining

The Modern Maine Retreat

8.6 out of 10, Excellent, (10)
"Multi generation family in town to visit other family. Kitchen adequate for meal prep, "
The Modern Maine Retreat
3 Bedroom Happy Cottage 15
Fridge, microwave, oven, stovetop

3 Bedroom Happy Cottage 15

3 Bedroom Happy Cottage 15
NEW! Long Pond Lake View Getaway w/HOT TUB, ME
Interior

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

NEW! Long Pond Lake View Getaway w/HOT TUB, ME
Sunfish Cove is the perfect year round getaway.
Exterior

Sunfish Cove is the perfect year round getaway.

10.0 out of 10, Exceptional, (49)
"We had a wonderful stay. Everything was clean and the amenities were perfect. The kids had fun with all the games. The hosts responded quickly to all questions and had great suggestions for activities in the area. When we return we will be sure to stay again. "
Sunfish Cove is the perfect year round getaway.
Damariscotta Lakefront 3BR+
Property grounds

Damariscotta Lakefront 3BR+

7.0 out of 10, Good, (2)
"The house has good size rooms. The house is hot on hot days - definitely needs more ceiling fans or some AC units and/or box fans for air circulation. Screened in porch is very nice. Not our definition of lake front (would call it lake house) and the water at dock very shallow so not boat friendly other than kayaks/canoes. Lots of lily pads and water weeds. Quiet cove except when nearby camp going on but happy noises with that but louder. "
Damariscotta Lakefront 3BR+
Camp Lintonia on Tacoma Lakes
Interior

Camp Lintonia on Tacoma Lakes

10.0 out of 10, Exceptional, (8)
"Comfortable, clean, good amenities. Fun home layout for family gathering."
The price is AU$970
includes taxes & fees
4 Sept - 5 Sept
Camp Lintonia on Tacoma Lakes
Historic Home w/ Gas Fireplace, Fast WiFi, & Private W/D - Snowbird-Friendly
Exterior

Historic Home w/ Gas Fireplace, Fast WiFi, & Private W/D - Snowbird-Friendly

9.0 out of 10, Wonderful, (19)
"Very roomy has everything you need for a vacation"
Historic Home w/ Gas Fireplace, Fast WiFi, & Private W/D - Snowbird-Friendly
“STEP BACK IN TIME” 1880’ charmer.<br>Riverside Cottage<br>
Outdoor dining

“STEP BACK IN TIME” 1880’ charmer.<br>Riverside Cottage<br>

9.6 out of 10, Exceptional, (44)
"The house was lovely, beautifully situated and everything was clean and comfortable !"
“STEP BACK IN TIME” 1880’ charmer.<br>Riverside Cottage<br>
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

Days Inn by Wyndham Augusta

Days Inn by Wyndham Augusta

10/10 Excellent
"An excellent property, clean and well kept. The night I stayed the Expedia was literally 1/3 of the major chain across the street where I usually stay. There was a little computer glitch which threatened to delay the checkins of myself and another guest. But when the other guest mentioned he needed sleep for an early morning job, the host managed a work around to check us in expeditiously, even though it meant extra work for him to follow up with our paper work. I will definitely choose this property on my next trip!"
Evelyn 1-night trip
Posted 2 days ago
Days Inn by Wyndham Augusta