Windsor holiday rentals

Why visit Windsor

• Historic charm: Wander through the Windsor Historic District, admiring beautifully preserved homes and significant landmarks.
• Iconic bridge: Cross the Windsor Bridge, a quintessential emblem of the town's rich heritage.
• Urban parks: Enjoy scenic strolls and picnics in the town's well-kept green spaces.
• Local exploration: Meander along Windsor Street and Windsor Road for a taste of local shops and eateries.
• Family-friendly fun: Revel in diverse outdoor activities and cultural experiences that suit every traveller.

Popular types of accommodation in Windsor

Discover Windsor, Connecticut – a charming city offering a variety of holiday accommodation options including private holiday homes, cosy cottages and modern apartments. Enjoy a rooftop terrace, spacious bathroom house, family home or comfortable bedroom houses, perfect for a fantastic rental opportunity. With a rich blend of local attractions and landmarks, Windsor invites you to explore its unique experiences and welcoming community.

• Private Holiday Homes: The top choice among visitors, offering exclusive and cosy retreats for a memorable stay in Windsor.
• Cottages: A charming option, these quaint abodes provide a picturesque setting for a delightful holiday experience.
• Apartments: Modern and well-appointed, these units offer comfort and convenience for a relaxing break.
• Cabins: Ideal for those seeking a rustic escape, these cosy lodgings blend simplicity with scenic charm.
• Condos: Stylish and contemporary, these properties provide a refined base for exploring Windsor.**

Top attractions near Windsor

Windsor, Connecticut offers a delightful mix of attractions for families, couples, and outdoor enthusiasts. Explore its urban parks, historic houses, and nature reserves, which provide an ideal backdrop for a cultural and relaxing holiday. A visit to the iconic Windsor Bridge adds to the charm, ensuring a memorable experience within this quaint American town.

• Mark Twain House & Museum: A historic house imbued with cultural ambience, offering insight into literary history, located 11km from Windsor.
• Elizabeth Park: An urban park with a city, family, outdoor atmosphere, perfect for leisurely strolls, located 11km from Windsor.
• Connecticut State Capital: A historic civic government building exuding cultural charm, situated 10km from Windsor.

Things to do recommended for couples

Windsor offers a delightful escape for couples. Take a leisurely stroll along the scenic banks of the Connecticut River or enjoy a picnic at the picturesque Northwest Park. For an intimate evening, dine at a charming local restaurant, savouring exquisite cuisine together.

Things to do recommended for families

Families visiting Windsor can explore the charming Windsor Historical Society to learn about local heritage and enjoy interactive exhibits. A scenic walk along the Farmington River adds to the delightful experience for all ages.

Things to do recommended for groups

Groups visiting Windsor, Connecticut, can experience the thrill of motor racing at Stafford Motor Speedway, located 29km away. This venue offers an exciting atmosphere perfect for adventure seekers, making it an ideal spot for a memorable group outing.

What do I need to keep in mind when booking a vacation in Windsor

Whether you're journeying with a group, travelling as a family, accompanied by your pets, or seeking extended stays, ensure you prioritise the right filters. Here are some Stayz booking tips for you.

• Traveling to Windsor with a group: Consider how many bedrooms will be required, along with facilities like a fully-equipped kitchen or an outdoor area for group gatherings. Fortunately, on Stayz you can filter for all of these features and more.
• Traveling to Windsor with young kids: Traveling with young children can be challenging. You must prioritise their comfort and safety, ensuring access to age-appropriate facilities, such as a private swimming pool. It is also advisable to consider your closeness to family-friendly attractions.
• Taking your pets with you to Windsor: For many, a family holiday simply isn’t complete without their furry companion. If that resonates with you, consider browsing Stayz properties that welcome pets. Numerous pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels right at home.
• Planning for a long term stay visiting Windsor: If you are seeking holiday lets offering discounts for stays of a month or more, you have come to the right place. With the appropriate filter, you can effortlessly discover and save on monthly lets. You might also consider including a parking space, a well-equipped kitchen or a private pool in your search.

Where to stay near Windsor

Windsor, Connecticut, offers a delightful blend of family-friendly activities and romantic spots for every traveller. Explore the charming Windsor Historic District, featuring beautifully preserved homes and historical landmarks. Enjoy the scenic parks perfect for outdoor adventures and picnics. Stroll along Windsor Street to experience local shops and eateries, while the serene atmosphere of Windsor Road invites leisurely walks. Whether you're seeking history or outdoor fun, Windsor promises a memorable holiday experience.

• Hartford: Hartford, a vibrant city located 11km away from Windsor, offers a diverse travel experience. Visitors can enjoy a blend of family, romantic, and city-themed adventures. The city is renowned for its rich cultural scene, featuring activities such as educational visits, theatre performances, and live music concerts. Notable nearby landmarks include an event conference venue, a convention centre, and a historic college university, providing a unique mix of heritage and modernity.
• West Hartford: West Hartford is a lively city situated 13km from Windsor, celebrated for its city-themed, family-friendly, and outdoor attractions. The area boasts a range of engaging activities, from exploring educational and shopping areas to enjoying a round of golf at a local course. Among the highlighted attractions are a historic college university, an event conference venue, and an urban park, each adding to the region's diverse appeal and inviting ambiance.
• South Windsor: South Windsor, only 6km away from Windsor, promises a dynamic blend of city-themed, family-oriented, and business-themed experiences. This vibrant locale offers activities such as educational tours, music concerts, and visits to resort areas. Key attractions in the vicinity include an event conference venue, a historic college university, and a convention centre, creating a well-rounded destination that caters to varied interests and tastes.

Best time to go to Windsor

If you're planning a trip to Windsor, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	27.9°F (-2.3°C)	Light Rain	Mostly Sunny	Average	Slightly Low
February	29.3°F (-1.5°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	37.0°F (2.8°C)	Light Rain	Mostly Sunny	Average	Slightly Low
April	48.4°F (9.1°C)	Light Rain	Mostly Sunny	Slightly High	Average
May	59.2°F (15.1°C)	Light Rain	Mostly Sunny	Average	Slightly High
June	67.3°F (19.6°C)	Light Rain	Mostly Sunny	Average	Average
July	73.9°F (23.3°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	72.1°F (22.3°C)	Light Rain	Mostly Sunny	Average	Slightly High
September	65.1°F (18.4°C)	Light Rain	Mostly Sunny	Slightly High	Average
October	54.0°F (12.2°C)	Light Rain	Mostly Sunny	Slightly Low	Average
November	42.3°F (5.7°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	34.2°F (1.2°C)	Light Rain	Mostly Sunny	Slightly Low	Average

Booking with Stayz is a breeze

Looking to stretch your travel budget further? Consider remaining flexible with your travel dates, as prices can vary. Additionally, booking a longer stay often results in significant savings. To find the ideal Stayz property suited to your budget, use our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning made easy

Stayz’s Trip Board provides an organised platform for you to plan new journeys, manage your existing arrangements, or review your bookings. Your saved or reserved properties are conveniently categorised into Potential, Upcoming, or Current Trips. To discover the features of Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.