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Stay in Windsor | Hotels, Inns & Vacation Rentals
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Experience a stay unlike any other in a one-of-a-kind Halloween-themed bed and breakfast. This B&B combines cozy accommodations with playful décor, themed guest rooms, and homemade breakfasts featuring locally sourced ingredients. All Hallows Inn offers a memorable getaway where every day feels like Halloween.

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Nestled at the base of Mount Ascutney in nearby Brownsville, Holiday Inn Club Vacations Mount Ascutney Resort offers spacious villas and family-friendly amenities. Enjoy indoor and outdoor pools, hiking and mountain biking trails, tennis and pickleball courts, a fitness center, and seasonal activities.

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Located just across the Connecticut River in Cornish, New Hampshire, The Chase House Inn is a beautifully restored historic property offering elegant accommodations with sweeping views of Mount Ascutney and the surrounding Vermont countryside. It's an ideal nearby retreat for visitors looking to stay just minutes from Windsor.

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Named Vermont's Best Farm Stay by Yankee Magazine! A memorable getaway on a 60-acre working farm, guests can enjoy cozy private cabins with sweeping views of rolling fields and distant hills. Meet friendly farm animals, enjoy lawn games, gather around the fire pit for spectacular sunsets, or simply relax in the peaceful countryside.

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One of Vermont's oldest state parks with 38 tent/RV campsites, 10 lean-to sites, and five rustic cabins nestled along the parkway. Spend your days hiking more than 12 miles of trails, taking in panoramic summit views of Mount Ascutney, and watching hang gliders and paragliders soar overhead.

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Perched on a hill overlooking Mount Ascutney, Lake Runnemede, and the Connecticut River Valley, Windsor Mansion Inn blends historic elegance with modern comfort. This beautifully restored 1902 Colonial Revival mansion features 16 uniquely appointed guest rooms and suites on a 15-acre estate. In addition to luxury accommodations, the inn is a popular wedding and special event venue, offering breathtaking views, beautifully landscaped grounds, inviting outdoor terraces, and a custom fire pit. 

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Choose from fully outfitted glamping tents, traditional tent campsites, or multi-day paddle-and-camp adventures along the scenic Connecticut River. Nestled within the tranquil Path of Life Sculpture Garden, campers enjoy peaceful surroundings, private river access, campfires, and easy access to kayaking, canoeing, tubing, and paddle boarding. 

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Running Bear Camping Area features 95 spacious tent and RV campsites in a peaceful natural setting. Guests can enjoy fishing, kayaking, canoeing, swimming, hiking, a heated saltwater pool, playground, basketball court, horseshoe pits, summer live music, and on-site camp store next to the Epic Deli. 

Other Nearby Lodging Resources

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In addition to traditional lodging options, there are a selection of privately hosted vacation rentals through platforms such as Airbnb or VRBO. While availability and amenities vary widely, they can be a useful alternative when inns, hotels, or campgrounds are fully booked.

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