Estia Villas - Vacation Rentals in Windsor
Cottage
10.0
(
31 Reviews
)
3 Bedrooms
1 Bathroom
7 Guests
-
Parking -
Balcony/Terrace -
Kitchen -
Internet
US $579
/Night
7 Nights - $4,055
House
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
4 Guests
645.83 ft²
-
Parking
-
Air Conditioner -
Internet
-
Child Friendly
US $247
/Night
7 Nights - $1,731
Cottage
10.0
(
29 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $278
/Night
7 Nights - $1,948
Cottage
10.0
(
13 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
560 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $336
/Night
7 Nights - $2,350
Cabin
10.0
(
13 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
144 ft²
-
Hot Tub -
Parking
-
Balcony/Terrace
-
Kitchen
US $227
/Night
7 Nights - $1,591
Apartment
10.0
(
8 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $266
/Night
7 Nights - $1,862
Cabin
10.0
(
7 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $183
/Night
7 Nights - $1,282
House
10.0
(
5 Reviews
)
4 Bedrooms
2 Bathrooms
10 Guests
2332 ft²
-
Parking
-
Skiing -
Ocean View -
Balcony/Terrace
US $458
/Night
7 Nights - $3,205
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Luxury Places to Stay in Windsor
Over 54+
Luxury Places to Stay in or Near Windsor
House
9.0
(
17 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
1320 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $587
/Night
7 Nights - $4,106
House
8.5
(
2 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
1323.96 ft²
-
Breakfast -
Parking
-
View -
Air Conditioner
US $511
/Night
7 Nights - $3,574
Cottage
10.0
(
1 Review
)
2 Bedrooms
1 Bathroom
8 Guests
1200 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $475
/Night
7 Nights - $3,327
House
9.8
(
103 Reviews
)
4 Bedrooms
1 Bathroom
8 Guests
1550 ft²
-
Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
US $425
/Night
7 Nights - $2,978
House
9.0
(
14 Reviews
)
3 Bedrooms
2 Bathrooms
16 Guests
2500 ft²
-
Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
US $415
/Night
7 Nights - $2,907
House
10.0
(
6 Reviews
)
2 Bedrooms
1 Bathroom
7 Guests
1000 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $409
/Night
7 Nights - $2,862
House
9.8
(
89 Reviews
)
4 Bedrooms
2 Bathrooms
14 Guests
2067 ft²
-
Parking
-
Balcony/Terrace
-
View
-
Kitchen
US $405
/Night
7 Nights - $2,833
New
Cabin
2 Bedrooms
2 Bathrooms
4 Guests
1100 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $396
/Night
7 Nights - $2,773
See More Windsor Luxury Vacation Rentals
Find More Windsor Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Windsor
Over 2+
Top-Rated Vacation Rentals with a Pool in or Near Windsor
House
9.2
(
6 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
979.52 ft²
-
Oceanfront -
Parking
-
Pool -
Ocean View
US $292
/Night
7 Nights - $2,044
House
10.0
(
1 Review
)
1 Bedroom
2 Bathrooms
2 Guests
-
Breakfast
-
Parking
-
Pool
-
Ocean View
US $114
/Night
7 Nights - $798
See More Windsor Vacation Rentals with a Pool
Pet-Friendly Vacation Rentals in Windsor
Over 22+
Pet-Friendly Vacation Rentals in or Near Windsor
Cabin
9.8
(
31 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
100 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $215
/Night
7 Nights - $1,503
House
8.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
602.78 ft²
-
Breakfast
-
Parking
-
Air Conditioner
-
Internet
US $164
/Night
7 Nights - $1,146
Cabin
9.2
(
26 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
1250 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $359
/Night
7 Nights - $2,515
Apartment
8.0
(
7 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $225
/Night
7 Nights - $1,576
New
Cottage
1 Bedroom
1 Bathroom
2 Guests
600 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $285
/Night
7 Nights - $1,992
New
Cabin
10.0
(
3 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $356
/Night
7 Nights - $2,491
Cabin
10.0
(
13 Reviews
)
2 Bedrooms
1 Bathroom
7 Guests
893 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $367
/Night
7 Nights - $2,571
House
9.4
(
3 Reviews
)
2 Bedrooms
1 Bathroom
8 Guests
1000 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $206
/Night
7 Nights - $1,439
See More Pet-Friendly Vacation Rentals in Windsor on PetFriendly.io
Large Vacation Homes & Villas in Windsor
Over 3+
Large Vacation Homes & Villas in or Near Windsor
House
6.8
(
3 Reviews
)
4 Bedrooms
2 Bathrooms
10 Guests
2000 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $421
/Night
7 Nights - $2,944
House
4.0
(
2 Reviews
)
6 Bedrooms
3 Bathrooms
14 Guests
2600 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $544
/Night
7 Nights - $3,805
House
3 Bedrooms
2 Bathrooms
10 Guests
-
Hot Tub
-
Parking
-
Kitchen
-
Air Conditioner
US $645
/Night
7 Nights - $4,514
See More Family Vacation Rentals in Windsor on FVR
Windsor Vacation Rentals and Airbnb Places to Stay Under $200
Over 6+
Windsor Vacation Rentals and Airbnb Places to Stay Under $200
New
Apartment
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
3 Guests
-
Internet
-
Bedding/Linens -
Security/Safety
US $180
/Night
7 Nights - $1,259
Apartment
6.8
(
3 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
-
Internet
-
Bedding/Linens
-
Wellness Facilities -
Security/Safety
US $179
/Night
7 Nights - $1,251
House
8.4
(
12 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
1000 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $193
/Night
7 Nights - $1,353
Apartment
7.0
(
8 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
300 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $158
/Night
7 Nights - $1,104
Cottage
6.4
(
7 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
1100 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $199
/Night
7 Nights - $1,395
Apartment
10.0
(
2 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
1050 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Pet Friendly
US $135
/Night
7 Nights - $944
See More Windsor Vacation Rental Deals
Instantly Bookable Vacation Homes in Windsor
Over 16+
Instantly Bookable Vacation Homes in or Near Windsor
House
9.8
(
43 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $280
/Night
7 Nights - $1,961
Cottage
9.8
(
24 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
980 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $373
/Night
7 Nights - $2,608
House
9.4
(
11 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1440 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $372
/Night
7 Nights - $2,602
New
Cabin
1 Bedroom
1 Bathroom
-
Hot Tub
-
Air Conditioner
-
Internet
-
Child Friendly
US $306
/Night
7 Nights - $2,144
New
House
2 Bedrooms
1 Bathroom
4 Guests
1280 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $304
/Night
7 Nights - $2,126
New
Cottage
2 Bedrooms
1 Bathroom
8 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $250
/Night
7 Nights - $1,750
House
10.0
(
11 Reviews
)
2 Bedrooms
1 Bathroom
3 Guests
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $267
/Night
7 Nights - $1,869
House
9.2
(
9 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1440 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $333
/Night
7 Nights - $2,330
See More Windsor Short-Term Vacation Rentals
About Windsor Vacation Rentals
With more than 63 Windsor vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Windsor.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Windsor, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Windsor. Places to stay near Windsor are 828.66 ft² on average, with prices averaging US $313 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Windsor with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Windsor
| Type | Count |
|---|---|
| Vacation Homes | 36 |
| Cabin Rentals | 12 |
| Cottages | 9 |
| Holiday Apartments | 6 |
Use these Quick Filters to Find a Vacation Rental in Windsor
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Windsor.
Weather in Windsor
View the weather forecast for Windsor before booking your Windsor Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Windsor, ME
Estiavillas offers a large selection of top attractions around Windsor. Research things to do on your vacation before you visit Windsor.
Augusta Civic Center
Colby College
Maine State House
Waterville Opera House
University of Maine at Augusta
Old Fort Western
Maine State Museum
Belgrade Lakes Golf
Capitol Park
Belgrade Lakes Chain
Augusta Country Club
Kennebec Ice Arena
Midcoast Kayak
Frances Perkins Center
Liberty Tool Company
Old Western Fort
Androscoggin River
Savage Oakes Vineyard and Winery
Morse's Sauerkraut
Dodge Point Public Reserved Land
Windsor Vacation Rental Frequently Asked Questions
Which vacation homes in Windsor are best for families?
If you are looking for a family-friendly vacation home in Windsor, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windsor:
How many vacation rentals are available in Windsor?
Currently, the total number of properties listed in 2026 is over 63 in the Windsor area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Windsor.
