Cottage
10.0(8 Reviews)
1 Bedroom
10 Guests
Parking
Kitchen
Air Conditioner
Internet
US $356/Night
7 Nights - US $2,493
Windsor Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Windsor
10.0
House
10.0(1 Review)
3 Bedrooms
6 Guests
- Parking
Spa
Balcony/Terrace
View
US $496/Night
7 Nights - US $3,472
Cabin
9.8(61 Reviews)
2 Bedrooms
4 Guests
Oceanfront- Parking
Ocean View- Balcony/Terrace
US $309/Night
7 Nights - US $2,166
House
9.8(4 Reviews)
4 Bedrooms
8 Guests
- Parking
- View
- Internet
Pet Friendly
US $567/Night
7 Nights - US $3,967
Apartment
9.8(31 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $323/Night
7 Nights - US $2,264
House
9.6(23 Reviews)
1 Bedroom
2 Guests
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
US $240/Night
7 Nights - US $1,677
House
9.2(81 Reviews)
2 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $332/Night
7 Nights - US $2,322
House
10.0(63 Reviews)
4 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $294/Night
7 Nights - US $2,056
House
10.0(19 Reviews)
3 Bedrooms
6 Guests
- Balcony/Terrace
- Kitchen
- Internet
Child Friendly
US $556/Night
7 Nights - US $3,894
Luxury Holiday Rentals in Windsor
Over 23+ Luxury Holiday Rentals in or Near Windsor
House
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Internet
Sports/Activities
US $596/Night
7 Nights - US $4,172
Cabin
9.8(39 Reviews)
3 Bedrooms
8 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $543/Night
7 Nights - US $3,801
New
House
4 Bedrooms
10 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $540/Night
7 Nights - US $3,780
House
9.8(47 Reviews)
5 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $510/Night
7 Nights - US $3,571
House
3 Bedrooms
5 Guests
Private Beach- Oceanfront
- Parking
- Ocean View
US $491/Night
7 Nights - US $3,437
House
10.0(11 Reviews)
5 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $483/Night
7 Nights - US $3,382
House
6.0(1 Review)
3 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $443/Night
7 Nights - US $3,102
House
9.8(91 Reviews)
3 Bedrooms
10 Guests
- Parking
Skiing- Ocean View
- Balcony/Terrace
US $340/Night
7 Nights - US $2,381
Other
4 Bedrooms
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $268/Night
7 Nights - US $1,878
Top-Rated Holiday Rentals with a Pool in Windsor
Over 4+ The Best Private Villas and Holiday Rentals in Windsor with a Pool
Cabin
10.0(1 Review)
1 Bedroom
2 Guests
Pool- Internet
- Child Friendly
Restaurant
US $142/Night
7 Nights - US $991
Cabin
9.8(6 Reviews)
1 Bedroom
2 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $142/Night
7 Nights - US $991
New
Cabin
1 Bedroom
2 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Internet
US $137/Night
7 Nights - US $962
Cabin
10.0(1 Review)
1 Bedroom
2 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $136/Night
7 Nights - US $954
Pet-Friendly Holiday Rentals in Windsor
Over 1+ Pet-Friendly Holiday Rentals in or Near Windsor
House
10.0(2 Reviews)
1 Bedroom
2 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Pet Friendly
US $136/Night
7 Nights - US $954
Windsor Private Villas and Holiday Homes Under $200
Over 1+ Windsor Private Villas and Holiday Homes Under $200
US $180/Night
7 Nights - US $1,260
Instantly Bookable Holiday Homes in Windsor
Over 6+ Instantly Bookable Holiday Homes in or Near Windsor
House
10.0(22 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $436/Night
7 Nights - US $3,051
US $325/Night
7 Nights - US $2,275
House
3 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $464/Night
7 Nights - US $3,246
US $216/Night
7 Nights - US $1,511
House
9.8(24 Reviews)
4 Bedrooms
6 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $307/Night
7 Nights - US $2,150
House
9.6(40 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $327/Night
7 Nights - US $2,289
Book a Last Minute Place to Stay in Windsor
About Casai's Private Villas and Holiday Rentals in Windsor
Discover more than 32 vacation rentals available in Windsor. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Windsor.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Windsor, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Windsor. On average, places to stay near Windsor offer 1213.62 ft², with nightly prices averaging US $367.
With Casai, finding and comparing holiday rentals in Windsor is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
There are 32 Windsor, MA Holiday Rentals
- Prices for a holiday home in Windsor start at US $137
- Top rated vacation home in Windsor is Berkshire Lake access
- Most popular short term in Windsor is Secluded house with fireplace, indoor parking, pond near Berkshire East Skiing
- Cheapest place to stay in Windsor is Historic, Waterfront Suite Rental close to Boston, Massachusetts
- Most expensive holiday rental in Windsor is Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!
Recently Booked Holiday Rentals in Windsor
- Charming 1-bedroom cottage on the border of Plainfield, Savoy, on Windsor Pond!
- Hot Tub, Lake Views! All-Season Hinsdale Haven
- Ashmere Lake Log Cabin with privacy/2 Bedrooms/3 night minimum
- Berkshire Hills Nature Lovers' Log Home Retreat
- Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Frequently Asked Questions About Windsor?
What are the top holiday rentals in Windsor?
With numerous options available in Windsor, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Windsor:
- Berkshire Lake access
- Hot Tub, Lake Views! All-Season Hinsdale Haven
- Hummingbird Haven is a woodland retreat surrounded by Nature and Local Charm.
- Charming 1-bedroom cottage on the border of Plainfield, Savoy, on Windsor Pond!
- Hot Tub, Lake Views! All-Season Hinsdale Haven
- Romantic Weekend Retreat in the Quiet Town of Cummington, Massachusetts
- Secluded house with fireplace, indoor parking, pond near Berkshire East Skiing
- Ashmere Lake Log Cabin with privacy/2 Bedrooms/3 night minimum
- Brooksong, the perfect Berkshires getaway
- Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Which holiday homes in Windsor are best for families?
If you're searching for a family-friendly holiday home in Windsor, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Windsor:
How many Casai.nz holiday rentals are available in Windsor?
As of 2026, Casai boasts over 32 properties listed in the Windsor area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Windsor.
