Find hotels in Windsor, VA from $53

Top reasons to visit Windsor

• Outdoor Adventures: Enjoy scenic boardwalks and family-friendly activities in Windsor's beautiful outdoor spaces.
• Local Attractions: Explore historic houses, arts centers, and amusement parks that cater to all ages.
• Topgolf Experience: Visit nearby Virginia Beach for a fun, competitive outing at Topgolf.
• Southern Hospitality: Experience the warm, welcoming atmosphere that Windsor is known for.
• Diverse Accommodations: Choose from a variety of hotels, including pet-friendly and LGBTQIA-friendly options.

Find great hotels near Windsor

Discover the charm of Windsor, Virginia, where a variety of lodging options await to ensure a comfortable stay. Whether you're looking for pet-friendly hotels, convenient motels, or accommodations that embrace LGBTQIA travelers, Windsor has something for everyone. With a focus on business travel amenities, you'll find the perfect place to unwind after a day of exploring this delightful area. Start your vacation by choosing from the best hotels in Windsor for an unforgettable experience.

• Comfort Suites Suffolk - Chesapeake: This budget-friendly hotel caters to families and business travelers alike, providing a comfortable and convenient stay just 17 miles from Windsor. Known for its spacious suites, Comfort Suites offers amenities such as free cribs for children, making it an excellent choice for families. Guests appreciate the welcoming atmosphere and the hotel's commitment to service, which includes a complimentary breakfast to start your day right. With easy access to local attractions and business centers, it's an ideal base for both leisure and work-related trips.
• Extended Stay America Select Suites - Chesapeake - Churchland Blvd: Perfect for those traveling with pets, this budget-friendly hotel is located 19 miles from Windsor. Extended Stay America allows pets on the property, making it a great option for travelers who don’t want to leave their furry companions behind. The hotel features essential amenities for long-term stays, including kitchen facilities in each suite, allowing guests to prepare their own meals. With a pet-friendly policy that includes restrictions and waived fees for service animals, this hotel combines comfort with convenience for both you and your pet.
• Sleep Inn & Suites Chesapeake - Portsmouth: This budget-friendly hotel, situated 19 miles from Windsor, is designed with business travelers in mind. Sleep Inn & Suites offers modern accommodations that make it easy to unwind after a long day of meetings. Guests can enjoy features like a well-equipped business center and complimentary Wi-Fi, along with a hearty breakfast to fuel your day. The hotel’s convenient location means that you're close to major business hubs and local attractions, making it an excellent choice for work-related trips and leisurely exploration.

Where to stay in and around Windsor

Windsor, Virginia, offers a delightful blend of outdoor adventures and Southern hospitality, making it perfect for family, romantic, or relaxing getaways. Explore scenic spots that showcase the heart of Virginia, all while enjoying the friendly atmosphere of this charming city. Nearby neighborhoods beckon with family-friendly excursions and unique experiences, ensuring your visit is filled with memorable moments and friendly faces. Discover the best Windsor has to offer during your vacation.

• Suffolk: Located 11 miles away from Windsor, Suffolk is a vibrant city known for its family-friendly atmosphere and outdoor activities. Visitors can enjoy a variety of experiences, from leisurely strolls along the picturesque boardwalk to shopping at local centers and malls. The city’s peak tourist seasons in April and June to July bring a lively ambiance, making it an ideal time to explore its urban attractions. Don’t miss the local landmarks such as the scenic esplanade and nearby beaches, perfect for a romantic getaway or a fun family outing.
• Isle of Wight: Nestled in the vicinity of Windsor, the village of Isle of Wight offers a charming escape with its beautiful scenery and outdoor adventures. The peak visiting months from June to August attract those seeking beach experiences and leisurely days in urban parks. Whether you want to play a round of golf or enjoy a peaceful day by the lake, Isle of Wight provides ample opportunities for relaxation and enjoyment. Its close-knit community and laid-back vibe make it a perfect spot for travelers looking to soak in the natural beauty of the area.
• Zuni: Just 6 miles from Windsor, Zuni is a quaint village that beckons outdoor enthusiasts and families alike. With its peak visitor numbers from June to August, Zuni is a hub for recreational activities. Golfing, shopping, and exploring local parks are popular among visitors. Nature lovers will appreciate the nearby nature reserves, which offer a serene escape into the great outdoors. Zuni's friendly atmosphere and city-themed experiences make it an inviting destination for a day trip or a relaxing weekend getaway.

Things to do in Windsor

Windsor, Virginia, offers a delightful mix of outdoor activities perfect for family, romantic getaways, and fun outings. Visitors can enjoy the scenic boardwalk, explore a local amusement park, and shop at nearby stores. For a unique experience, consider a visit to Topgolf in Virginia Beach, which is great for family outings and friendly competition.

Shopping

In Windsor, browse local shops for unique gifts and souvenirs. If you're up for a drive, head to the nearby Chesapeake Square Mall, about 12 miles away, featuring a range of stores from popular brands to local boutiques, perfect for finding that special memento from your trip.

Recreation

In Windsor, the Windsor Wellness Retreat offers serene yoga sessions and holistic therapies to rejuvenate your mind and body. Nearby, the tranquil Lake Windsor provides opportunities for kayaking and leisurely walks, allowing you to connect with nature while enjoying peaceful surroundings.

Adventure

In Windsor, explore the scenic trails of the Windsor Castle Park for hiking and birdwatching. Experience kayaking on the Blackwater River, where you can paddle through tranquil waters surrounded by nature. Don’t miss the chance to visit local farms for fresh produce and unique adventures.

Nightlife

Experience the cozy vibe at The Corner Bar on Main Street, where you can enjoy classic cocktails and friendly chatter. For a lively night, check out the local bands at Windsor Live Music Venue, showcasing emerging talent with a fun atmosphere and great drinks.

Booking tips and Expedia advantages for Windsor

• The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Windsor are December to February, where the prices are slightly lower. This is in comparison to May to July, where prices are slightly higher.
• The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Windsor is Tuesday. The most expensive day to stay in Windsor is Saturday.
• Find cheap hotels on Expedia: Utilize Expedia’s search tool to customize your options based on your budget, desired location, and preferred hotel type. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels that are currently available. To find the best prices and deals, arrange the price filter from lowest to highest.
• Consider bundling your trip: You can save money by combining your Windsor hotel reservation with your flights and activities through an Expedia package.

Find the best attractions in and around Windsor

Windsor, Virginia, offers a delightful mix of outdoor adventures and family-friendly activities, making it perfect for romantic getaways as well. Visitors can explore a variety of attractions, including historic houses, arts centers, and local landmarks. Whether you're seeking cultural experiences or outdoor fun, Windsor has something to cater to every traveler's interest.

• Lake Prince: Located 7 miles from Windsor, Lake Prince offers a serene escape with its picturesque scenery. Enjoy outdoor activities like fishing, kayaking, or simply relaxing on the beach. It's a perfect spot for romantic picnics or peaceful walks along the shore, surrounded by nature's beauty.
• Suffolk Center for Cultural Arts: Situated 11 miles away, this arts center is a cultural gem. It hosts a variety of performances, exhibitions, and workshops, making it a vibrant hub for local artists and art lovers alike. Immerse yourself in the rich cultural experiences it offers.
• Boykin's Tavern: Nestled in Windsor, Boykin's Tavern is a historic building that reflects the town's heritage. Step back in time and explore its unique architecture and exhibits that showcase the local history and culture, making it a must-visit for history enthusiasts.

Best time to go to Windsor

The best time to visit Windsor can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Windsor falls in July, when visitor numbers are high and weather is mostly sunny with light rain. The coolest average temperature in Windsor falls in January, visitor numbers are low and weather is mostly sunny with light rain.

The nearest major airports for your trip to Windsor

If you're planning a trip to Windsor, Virginia, you have several airport options. RIChmond International Airport (RIC) is 58 miles away, with nearby hotels like The Jefferson Hotel and Omni Richmond Hotel, both about 7 miles from the airport. NORFolk International Airport (ORF) is closer at 31 miles, featuring hotels such as Doubletree by Hilton Hotel Norfolk Airport, just 2 miles away. Lastly, Newport News-Williamsburg International Airport (PHF) is 26 miles from Windsor, with options including Kingsmill Resort and DoubleTree by Hilton Williamsburg, both 12 miles from the airport. Each airport offers convenient access to local accommodations for a comfortable stay.