Windsor holiday rentals

We found 153 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Windsor to find one that's perfect for your trip. Holiday homes offer the best amenities for your stay with friends, family or just your pet, such as a hot tub and a washer and dryer. No matter what you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Windsor

Showing deals for:18 Dec - 25 Dec

Living area
Interior
Dining
Interior
Exceptional
(23 reviews)

Sunny Chalet Nestled in the Woods of Ashfield

Ashfield

16% off
AU$4,442
for 7 nights, 1 chalet
AU$635 per night
includes taxes & fees
Sunny Chalet Nestled in the Woods of Ashfield
View of the lower deck from the sunroom
view from the 2nd bedroom
Open plan dining area with water views and access to the sunroom
Workstation with a view!
Exceptional
(65 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
AU$8,017
for 7 nights, 1 home
AU$1,145 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Interior
Living area
Interior
Exterior detail
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
AU$6,358
for 7 nights, 1 home
AU$908 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
Night skiing view from living room
Spring at Jiminy Peak 2019
Country Inn heated pool & outdoor hot tub is open all year. Towels are provided
Interior
Exceptional
(46 reviews)

Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.

Hancock

13% off
AU$12,746
for 7 nights, 1 home
AU$1,821 per night
includes taxes & fees
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
Large Smart HDTV with electric fireplace in living room, showing dining room
View from 2nd floor balcony (after leaves have fallen)
Entrance into house with wood burning stove to right and staircase
Smart TV in Downstairs room with view of entrance to house and doors to room
Exceptional
(73 reviews)

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

Williamstown

12% off
AU$3,569
for 7 nights, 1 home
AU$510 per night
includes taxes & fees
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
another view of same bedroom as well as makeup table
new backyard table
Beaver Pond Pool/clubhouse
kitchen and laundry room area
Exceptional
(17 reviews)

3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

Lanesborough

23% off
AU$5,050
for 7 nights, 1 apartment
AU$721 per night
includes taxes & fees
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Property grounds
Interior
Interior
Bathroom
Exceptional
(6 reviews)

Historic Stone Church in The Berkshires

Lanesborough

8% off
AU$3,838
for 7 nights, 1 home
AU$548 per night
includes taxes & fees
Historic Stone Church in The Berkshires

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    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Windsor getaway

Learn about the unique charm of Windsor with a stay in a holiday home rental. This city is well-known for its restaurants and shopping. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Windsor

Are you looking for attractions to visit during your stay? Venture out of your holiday home and experience everything that Windsor has to offer. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Berkshire East Ski Resort (11.5 mi / 18.5 km)
  • Jiminy Peak Mountain Resort (12.9 mi / 20.8 km)
  • Bousquet Ski Area (13.6 mi / 21.8 km)
  • Waubeeka Golf Links (14.2 mi / 22.9 km)
  • Wyndhurst Golf & Club (16.1 mi / 25.9 km)
  • Kennedy Park (14.8 mi / 23.8 km)

Exploring the natural landscape of Windsor

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Windsor is a great place to spend some time outside. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Wahconah Falls State Park (3.8 mi / 6.1 km)
  • Mount Greylock State Reservation Visitor Center (9.1 mi / 14.6 km)
  • Pontoosuc Lake (10.4 mi / 16.7 km)
  • Swift River (10.8 mi / 17.4 km)
  • Mount Greylock (10.8 mi / 17.4 km)
  • Mount Greylock State Reservation (11.5 mi / 18.5 km)

Transport to and around Windsor

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 13.8 mi (22.2 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Westfield, MA (BAF-Barnes Municipal), which is 28.9 mi (46.5 km) away.

Frequently asked questions

What is the best area to stay in Windsor when booking a holiday rental?
When considering a holiday rental in Windsor, Massachusetts, the most appealing area to stay in is the charming neighbourhood surrounding the scenic Berkshire Mountains. This area is known for its stunning natural beauty and offers a tranquil atmosphere superb for relaxation. With a variety of properties available, visitors can choose from cosy cabins to spacious homes, making it an excellent option for families and groups alike.One of the top attractions nearby is the picturesque October Mountain State Forest, which boasts an array of outdoor activities such as hiking, biking, and birdwatching. Additionally, the area is close to the renowned Tanglewood Music Centre, a cultural gem where visitors can enjoy world-class performances, particularly during the summer months.
What is the most popular type of holiday rental accomodation in Windsor?
In Windsor, cottages are the most popular type of holiday rental, with several available throughout the area. These charming properties often provide a rustic, homey atmosphere that appeals to travellers seeking a peaceful retreat. Most cottages come equipped with essential amenities such as fully stocked kitchens, comfortable living areas, and outdoor spaces for enjoying the serene surroundings. Nestled near local attractions such as the picturesque landscapes and recreational areas, these rentals offer a delightful base for exploring the natural beauty of Windsor.
Are there pet-friendly house rentals in Windsor?
In Windsor, Massachusetts, there are several pet-friendly house rentals available, making it a welcoming destination for travellers with pets. Many of these properties are set in picturesque surroundings, offering amenities such as spacious backyards, fully equipped kitchens, and cosy living areas, ideal for families or groups. Guests can expect comfortable accommodations that often include features like outdoor decks, BBQ facilities, and fireplaces, enhancing the overall stay.The area around Windsor is known for its natural beauty, with opportunities for outdoor activities such as hiking and exploring nearby parks. This makes it a great spot for pet owners looking to enjoy nature with their furry companions. The tranquil environment and scenic landscapes provide a superb backdrop for a relaxing getaway.
Are there any remote work holiday rentals in Windsor?
In Windsor, Massachusetts, there are several holiday rentals that cater to those looking for remote work amenities. These properties typically offer features such as dedicated workspaces, desks, and free Wi-Fi, both in rooms and in public areas, ensuring that guests can stay productive while enjoying their getaway.The area itself is known for its beautiful natural surroundings, making it a tranquil spot for working remotely. Guests can expect accommodations that provide a comfortable environment for both work and relaxation, often with access to scenic views and outdoor spaces. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Windsor?
In Windsor, popular rental amenities include features that enhance comfort and convenience for travellers. Many holiday rentals come equipped with fireplaces, creating a warm and inviting atmosphere, especially during the cooler months. Kitchens are a common amenity, allowing guests to prepare their own meals and enjoy home-cooked dining. Additionally, rentals often provide dedicated desk spaces or laptop workspaces, making it easier for those who may need to work during their stay. For visitors with vehicles, parking is typically available nearby at no extra cost.
When is the best time to visit Windsor for a holiday rental?
The best time to visit Windsor for a holiday rental is during the peak season from September to November. This period is particularly delightful, as the autumn months bring a spectacular display of fall foliage, transforming the landscape into a vibrant palette of reds, oranges, and yellows. The crisp air and stunning scenery create a friendly space for outdoor activities such as hiking and sightseeing, making it a prime time for nature enthusiasts and families alike.November, in particular, stands out as a popular month. Visitors can enjoy the beauty of the changing leaves while exploring local trails or simply relaxing in a charming holiday rental. Temperatures during this month typically range from 0 to around 10 degrees Celsius, providing a comfortable climate for outdoor exploration.For those looking for a more budget-friendly option, February can be an appealing time to visit Windsor. While it's considered the low season, the tranquility of winter offers a different kind of beauty, with serene landscapes and fewer crowds. This quieter time allows for reflective walks in the snow-covered surroundings and cosy evenings by the fire.Ultimately, the best time to visit Windsor depends on whether you wish to immerse yourself in the vibrant autumn colours or enjoy the peaceful allure of winter.
What are the top attractions in Windsor?
In Windsor, Massachusetts, visitors can enjoy a variety of attractions that highlight the area's natural beauty and outdoor activities. The nearby October Mountain State Forest offers extensive hiking trails, great for those looking to explore the scenic landscapes and enjoy the peaceful surroundings. This forest is a great spot for both seasoned hikers and casual walkers, with opportunities for wildlife observation and picnicking along the way.Additionally, Windsor is close to the picturesque Lake Ashmere, where guests can enjoy recreational activities such as swimming, fishing, and kayaking during the warmer months. The lake's serene environment makes it a lovely place for relaxation and enjoying nature.For those interested in local culture, the town itself features charming small-town architecture and a friendly atmosphere.
Are all fees included in the Windsor holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Windsor holiday homes with parking?
Stayz offers a wide selection of holiday homes in Windsor with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Windsor holiday homes?
You can find great discounts on holiday homes in Windsor on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Windsor holiday home booking on Stayz?
To find Windsor holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Windsor?
A long-stay holiday home in Windsor is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Windsor holiday home?
Book your Windsor holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Windsor?
Prices for holiday homes in Windsor vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Windsor to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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