Trips to Windsor

Plan Your Next Trip to Windsor and explore unforgettable sights, local flavors, and exciting experiences.

Property Image From $87
         

|
7.3 (57 Reviews)
House
  • Parking
  • Balcony/Terrace
  • Child Friendly
Property Image From $174
         

|
10.0 (10 Reviews)
Cabin
  • 592 ft² Cabin
  • Parking
  • TV
  • View
Property Image From $758
         

10.0 (1 Review)
House
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
Property Image From $343
         

10.0 (2 Reviews)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
Property Image From $183
         

|
8.6 (76 Reviews)
House
  • Parking
  • Pet Friendly
  • Balcony/Terrace
Property Image From $329
         

8.6 (10 Reviews)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible

Luxury Places to Stay in Windsor

Over 754+ Luxury Places to Stay in or Near Windsor
Property Image From $1,896
         

10.0 (2 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
Property Image From $1,499
         

|
New
House
  • Parking
  • Pet Friendly
  • Security/Safety
Property Image From $1,229
         

10.0 (3 Reviews)
House
  • Parking
  • TV
  • Balcony/Terrace
Property Image From $982
         

8.0 (6 Reviews)
House
  • Parking
  • View
  • Security/Safety

Top-Rated Vacation Rentals with a Pool in Windsor

Over 9+ Top-Rated Vacation Rentals with a Pool in or Near Windsor
Property Image From $157
         

|
9.0
Hotel
  • 301 ft² Hotel
  • Parking
  • Pool
  • Accessibility
Property Image From $181
         

|
8.2 (182 Reviews)
Hotel
  • Parking
  • Pool
  • TV
Property Image From $415
         

|
7.9 (496 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Property Image From $154
         

|
7.8 (4534 Reviews)
Hotel
  • Parking
  • Pet Friendly
  • Pool
Property Image From $145
         

|
7.8 (1005 Reviews)
Hotel
  • Parking
  • Pool
  • TV

Pet-Friendly Vacation Rentals in Windsor

Over 95+ Pet-Friendly Vacation Rentals in or Near Windsor
Property Image From $732
         

Property Image From $166
         

|
10.0 (4 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Accessibility
Property Image From $101
         

|
2.0 (1 Review)
Apartment
  • Pet Friendly
  • Balcony/Terrace
  • Bedding/Linens
Property Image From $191
         

Property Image From $518
         

Property Image From $463
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $220
         

See More Pet-Friendly Vacation Rentals in Windsor on PetFriendly.io

Large Vacation Homes & Villas in Windsor

Over 48+ Large Vacation Homes & Villas in or Near Windsor
Property Image From $636
         

Property Image From $441
         

|
9.8 (19 Reviews)
Villa
  • Parking
  • View
  • Balcony/Terrace
Property Image From $319
         

|
8.0 (4 Reviews)
Ski Chalet
  • 1076 ft² Ski Chalet
  • Parking
  • TV
  • Security/Safety
Property Image From $256
         

10.0 (1 Review)
Cottage
  • Parking
  • TV
  • Security/Safety
Property Image From $125
         

|
9.8 (6 Reviews)
Apartment
  • Parking
  • Security/Safety
  • Sports/Activities
Property Image From $272
         

|
9.7 (55 Reviews)
Apartment
  • Security/Safety
  • Fireplace/Heating
  • Child Friendly

Wheelchair Accessible Vacation Homes in Windsor

Over 45+ Wheelchair Accessible Vacation Homes in or Near Windsor
Property Image From $163
         

10.0 (2 Reviews)
Apartment
  • TV
  • Wheelchair Accessible
  • Accessibility
Property Image From $386
         

|
8.9 (86 Reviews)
House
  • Parking
  • Pet Friendly
  • View
Property Image From $320
         

|
9.6 (67 Reviews)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
Property Image From $301
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
Property Image From $320
         

|
8.9 (12 Reviews)
House
  • Parking
  • View
  • Wheelchair Accessible
Property Image From $183
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
Property Image From $130
         

|
7.0 (1566 Reviews)
Apartment
  • Parking
  • Wheelchair Accessible
  • Accessibility
Property Image From $353
         

9.8 (10 Reviews)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible

Windsor Varoom and Airbnb Places to Stay Under $200

Over 208+ Windsor Varoom and Airbnb Places to Stay Under $200
Property Image From $176
         

10.0 (1 Review)
Cabin
  • Parking
  • TV
  • Balcony/Terrace
Property Image From $129
         

|
10.0 (2 Reviews)
Apartment
  • Parking
  • Security/Safety
  • Sports/Activities
Property Image From $180
         

10.0
Apartment
  • 624 ft² Apartment
  • TV
  • Security/Safety
  • Bedding/Linens
Property Image From $158
         

|
9.8 (184 Reviews)
Bed & Breakfast
  • Parking
  • TV
  • Accessibility
Property Image From $151
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Security/Safety
Property Image From $156
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
Property Image From $136
         

|
10.0 (1 Review)
Apartment
  • View
  • Security/Safety
  • Sports/Activities

Instantly Bookable Vacation Homes in Windsor

Over 252+ Instantly Bookable Vacation Homes in or Near Windsor
Property Image From $462
         

10.0 (14 Reviews)
House
  • Parking
  • TV
  • Security/Safety
Property Image From $701
         

New
Apartment
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
Property Image From $499
         

10.0 (11 Reviews)
House
  • Parking
  • TV
  • Balcony/Terrace
Property Image From $334
         

10.0 (5 Reviews)
Apartment
  • Parking
  • TV
  • Balcony/Terrace
Property Image From $329
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Property Image From $277
         

Property Image From $236
         

10.0 (5 Reviews)
House
  • Parking
  • TV
  • Security/Safety
Property Image From $214
         

10.0 (5 Reviews)
Apartment
  • Parking
  • TV
  • Accessibility

About Windsor Vacation Rentals

With more than 763 Windsor vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Smartours 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 Smartours 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 595.13 ft² on average, with prices averaging $303 a night.

Smartours 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
Holiday Apartments 409
Vacation Homes 265
Hotels with Suites 33
Cottages 21
B&B 9
Cabin Rentals 7
Ski Chalet Rentals 5
Villas 4
Others 2

Use these Quick Filters to Find a Vacation Rental in Windsor

Pro Tip: Smartours makes it easy to compare the best listings on Smartours homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Smartours 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 43°F       Low 32°F
March - May
High 61°F       Low 36°F
June - August
High 63°F       Low 48°F
September - November
High 58°F       Low 35°F