Woodbury(United States) Travel 2026: Cheap Flights, Hotels & Top Attractions

In Woodbury, the top family-friendly hotel is The Woodbury Inn & Spa, located just steps from Woodbury Common Premium Outlets. This boutique property offers spacious family rooms, kid-friendly amenities like play areas and in-room games, and a seasonal outdoor pool. The hotel’s proximity to parks, hiking trails, and local farms makes it ideal for active families. Breakfast features locally sourced ingredients, including fresh eggs and homemade granola. Nearby, Holiday Inn Woodbury also provides an indoor pool, fitness center, and free shuttle service to shopping outlets, making it a reliable choice for families seeking comfort and convenience in a safe, welcoming environment.

The downtown Woodbury district is the most convenient area for tourists. It's centrally located near Woodbury Common Premium Outlets, Old Stone Church, and the Woodbury Historical Society Museum. Staying here allows easy walking access to shops, restaurants, and seasonal events like farmers' markets and summer festivals. Hotels such as The Woodbury Inn & Spa and Holiday Inn Woodbury offer excellent proximity to major sights, with secure parking and well-lit streets ensuring safety. This vibrant core combines charm, accessibility, and authentic small-town appeal—perfect for travelers who want both comfort and immersion in local culture.

Visitors to Woodbury can experience the annual Woodbury Summer Festival, a celebration of music, crafts, and local food that reflects the town’s rural heritage. Another highlight is touring the Old Stone Church, built in 1752, which stands as a testament to colonial architecture and history. During autumn, guests can join the Harvest Day event, where they pick apples and pumpkins, sample homemade cider, and enjoy warm apple pie. These hands-on activities offer a genuine connection to the community’s traditions and slow-paced lifestyle, providing memorable moments beyond typical sightseeing.

For a truly distinctive stay, book a room at The Old Mill House Bed & Breakfast, a historic 18th-century mill transformed into a charming B&B. Each room—like "The Millroom" and "The Forge"—features original stone walls, exposed beams, and custom furnishings. Guests enjoy breakfast with farm-fresh eggs and blueberry muffins made on-site. The inn hosts intimate Evening Story Nights, where owners share true tales of Woodbury’s past. With its peaceful setting, private garden, and personalized touches, this property offers an immersive, authentic experience far removed from chain hotels—ideal for travelers seeking character and soul.

The Woodbury Inn & Spa offers serene accommodations perfect for solo travelers. Its single rooms feature soundproof windows, quiet hallways, and peaceful courtyard views. The hotel includes a tranquil reading nook and a rooftop terrace ideal for stargazing or morning yoga. Complimentary personalized itinerary planning helps solo guests discover hidden gems—like local art galleries or scenic walking trails. With a low guest turnover and a focus on relaxation, this hotel fosters a calm, private atmosphere—making it an ideal sanctuary for those seeking solitude and self-reflection.

For couples seeking romance, The Old Mill House Bed & Breakfast offers the "Love Nest" suite—a secluded attic room with a fireplace, hot tub, and panoramic views of the river. The inn arranges private candlelit dinners and offers couples’ spa treatments in a dedicated wellness room. On select evenings, guests can join a sunset nature walk along forest trails, ending at a tree with a love lock. With its intimate ambiance, storytelling evenings, and personalized service, this B&B creates unforgettable moments—perfect for rekindling connections or celebrating milestones.

Holiday Inn Woodbury, located directly next to Woodbury Common Premium Outlets, is the premier choice for shoppers. The hotel provides a free shuttle service to the mall, running up to six times daily. Rooms include high-speed Wi-Fi, smart TVs, and luggage storage. Guests receive exclusive perks like early access to brand stores and a complimentary gift bag with local treats. After a day of shopping, unwind with a BBQ dinner on the outdoor patio. This seamless blend of convenience and comfort makes it ideal for travelers who want to maximize their retail experience without sacrificing rest.

The Woodbury Inn & Spa is the top choice for business travelers. It features fully equipped meeting rooms with video conferencing tools, high-speed internet throughout, and a dedicated business center. The executive floor offers priority check-in/out and a quiet work lounge. Located just minutes from I-84 Highway, the hotel provides easy access to New York City (within 30 minutes). Additional services include printing, courier dispatch, and airport transfer coordination. With its professional facilities and peaceful environment, this hotel ensures productivity and comfort—perfect for meetings, conferences, or remote work stays.

The Old Mill House Bed & Breakfast is ideal for road-trippers. It offers ample free parking, a scenic location near Housatonic River Trail, and a convenient base for exploring Litchfield Hills and surrounding countryside. The inn provides a Road Trip Kit with maps, route suggestions, and local dining tips. Guests staying two nights or more receive a free car wash and a welcome package including bottled water and energy snacks. With its friendly staff and vehicle-centric services, this B&B enhances the freedom and flexibility of driving adventures—perfect for those embracing the open road.

To savor authentic Connecticut fare, visit The Red Barn Restaurant, a century-old farm-to-table eatery using ingredients from local producers. Must-try dishes include Hartford-style Apple Butter Pork Chop and a seasonal Farmers’ Market Salad with honey-mustard dressing. Their signature Bran Muffin, baked fresh daily, pairs perfectly with house-made jam. Every Saturday, the restaurant hosts a Farm-to-Table Dinner Night, featuring live cooking demos and stories from local farmers. Take home a bottle of Woodbury Heritage Jam, crafted from regional fruit—ideal as a souvenir or gift reflecting the region’s culinary heart.