Saved to wishlist
Book with confidence. Read more.
Restaurant Matilda offers a vibrant blend of fresh, locally sourced dishes inspired by Mexican and Tuscan flavors, all served in a cozy, family-owned setting that brings warmth and authenticity to every meal. Its unique fusion and inviting ambiance make it a memorable dining spot.
Windham Mountain Club offers an exclusive dining experience with diverse options from signature roasts and seafood to Michelin-quality Italian dishes, all set against stunning mountain views and a refined, members-only ambiance.
Main Street Market specializes in natural, organic, and specialty foods sourced locally and globally, featuring chef-crafted grab-and-go dishes alongside artisan groceries, specialty wines, and cheeses for a unique shopping experience.
Hickory Hill Market offers a unique blend of upscale convenience with fresh produce, artisan cheeses, a full-service deli, and brick-oven pizzas baked in an 800-degree oven. Their extensive selection of craft beers and welcoming atmosphere make it a must-visit for locals and visitors alike.
The Henson offers a refined dining experience with a menu celebrating fresh, local produce and seasonal vegetables, set in an elegant yet comfortable Catskill retreat perfect for relaxing and savoring natural wines, craft beers, and creative cocktails.
Paracasa is a modern Catskills general store offering unique global delicacies like Spanish tinned seafood, French Comté cheese, and New Mexican wagyu beef, alongside local farm-fresh produce and a popular self-serve olive oil station. It’s a cozy community hub with curated home goods and specialty flavors.
The Windham Local Public House offers fresh, homemade comfort food made with local ingredients in a bright, welcoming space. Enjoy specialty coffee, local craft beer, and live music on weekends for a true community vibe.
Chicken Run Family Restaurant and Steak House offers hearty, homemade comfort food with a focus on fresh-cut steaks, chicken, and ribs in a warm, rustic family-friendly atmosphere complete with live weekend music and private dining options.
Catskill Mountain Country Store & Restaurant in Windham offers a cozy, family-friendly atmosphere with hearty breakfast and lunch made from local recipes, alongside a charming country store featuring homemade jams, baked goods, and unique gifts. Enjoy garden walks and friendly farm animals for a true Catskills experience.
Alpine Garden Convenience offers a charming selection of unique plants, garden pots, and delightful trinkets that bring joy to any home or garden. Visitors love exploring its friendly atmosphere and discovering unexpected treasures around every corner.
Taphouse Grille Windham offers an inviting atmosphere centered around a striking reclaimed barn wood bar, serving elevated pub-style fare with specialty sandwiches, farm-fresh salads, and regional dishes paired with a wide selection of craft beers, wines, and cocktails. It's the perfect spot to enjoy great food and drinks while catching major sports events.
Windham Diner offers a warm, family-friendly atmosphere with an extensive menu featuring classic American diner favorites served all day, making it a beloved spot for breakfast, lunch, and dinner in the heart of Windham. Cash only and open daily for a welcoming local experience.
Day June Luncheonette in Hensonville offers a cozy, homey atmosphere with a fresh take on classic American breakfast and lunch, featuring locally sourced ingredients and whimsical dishes like omelets stuffed with French fries. It’s a charming spot to enjoy coffee, sandwiches, and desserts in the heart of the Catskills.
Millrock Restaurant & Bar Room offers intimate Italian fare featuring brick oven pizzas, hearty pastas, and fresh seafood in a warm, welcoming setting with stunning views of Windham Mountain and a lively open kitchen. Their new bar room and outdoor deck add to the inviting ambiance.
The Vineyard at Windham offers a unique blend of wine tasting experiences, from casual flights to guided tours of the vineyard and winery, perfect for wine lovers and anyone looking to savor local flavors in a relaxed, scenic setting. It's ideal for those who appreciate good wine and a welcoming atmosphere.
The Windham Path is a scenic, family-friendly 1.5-mile loop perfect for leisurely walks, biking, or winter sports, offering peaceful views of meadows, woodlands, and the picturesque covered bridge over Batavia Kill Stream—ideal for nature lovers and all ages seeking easy outdoor fun.
C D Lane Park in Maplecrest offers a perfect blend of outdoor fun and natural beauty, featuring a beach, playground, sports courts, walking trails, and kayak rentals. It’s ideal for families, sports enthusiasts, and nature lovers seeking a vibrant day out in the Catskills.
The Escarpment Trailhead offers hikers a captivating journey through lush forests and dramatic cliffs, culminating in breathtaking panoramic views of the Catskills. It's perfect for outdoor enthusiasts seeking both adventure and stunning natural scenery.
2K Trail Rides at Mountain Brook Farm offers scenic backcountry horseback adventures through the beautiful Northern Catskill Mountains, perfect for riders of all ages and experience levels who enjoy nature and friendly farm hospitality. Families and outdoor lovers will especially appreciate the welcoming atmosphere and chance to connect with horses and other farm animals.
Elm Ridge Wild Forest offers over 25 miles of scenic trails perfect for hikers, mountain bikers, and nature lovers seeking stunning Catskills views and year-round outdoor adventure. It’s ideal for both beginners and seasoned explorers looking to immerse themselves in a peaceful forest escape.
The Windham Path offers a scenic, easy-to-access trail loop perfect for casual hikers and outdoor lovers, with convenient parking right off Route 296. It's ideal for those seeking a peaceful nature walk close to town with well-marked paths and beautiful surroundings.
Phoenix Web Free Store, Maker's Space, & Artist Shop is a vibrant community hub where creativity meets sustainability through free sharing, skill-building workshops, and art. It’s perfect for makers, artists, and anyone eager to connect and contribute to a supportive, eco-conscious space.
Windham High Peak via Peck Road Trailhead offers a scenic 6.4-mile round-trip hike with rewarding summit views, perfect for outdoor enthusiasts seeking a moderate challenge in the Catskills. Nature lovers and adventure seekers will enjoy its peaceful forest paths and panoramic vistas.
The Knitting Room in Windham offers a cozy, welcoming space where beginners and fiber enthusiasts can learn to knit a stylish pompom hat while enjoying scenic Catskills views—perfect for friends, families, or anyone looking for a creative and relaxing experience.
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Oct 28, 2025 | $642 | Not Available |
| Oct 29, 2025 | $515 | Available |
| Oct 30, 2025 | $684 | Available |
| Oct 31, 2025 | $1077 | Not Available |
| Nov 1, 2025 | $1064 | Not Available |
| Nov 2, 2025 | $594 | Available |
| Nov 3, 2025 | $510 | Available |
| Nov 4, 2025 | $510 | Available |
| Nov 5, 2025 | $510 | Available |
| Nov 6, 2025 | $719 | Not Available |
| Nov 7, 2025 | $1064 | Not Available |
| Nov 8, 2025 | $1064 | Not Available |
| Nov 9, 2025 | $594 | Available |
| Nov 10, 2025 | $510 | Available |
| Nov 11, 2025 | $510 | Available |
| Nov 12, 2025 | $510 | Available |
| Nov 13, 2025 | $727 | Not Available |
| Nov 14, 2025 | $1148 | Not Available |
| Nov 15, 2025 | $1148 | Not Available |
| Nov 16, 2025 | $644 | Available |
| Nov 17, 2025 | $560 | Available |
| Nov 18, 2025 | $569 | Available |
| Nov 19, 2025 | $569 | Available |
| Nov 20, 2025 | $652 | Available |
| Nov 21, 2025 | $1596 | Available |
| Nov 22, 2025 | $1596 | Available |
| Nov 23, 2025 | $1610 | Available |
| Nov 24, 2025 | $1470 | Available |
| Nov 25, 2025 | $1624 | Available |
| Nov 26, 2025 | $1708 | Not Available |
| Nov 27, 2025 | $1848 | Not Available |
| Nov 28, 2025 | $1722 | Not Available |
| Nov 29, 2025 | $1596 | Available |
| Nov 30, 2025 | $1610 | Available |
| Dec 1, 2025 | $1000 | Available |
| Dec 2, 2025 | $1000 | Available |
| Dec 3, 2025 | $1000 | Available |
| Dec 4, 2025 | $1139 | Not Available |
| Dec 5, 2025 | $1440 | Not Available |
| Dec 6, 2025 | $1440 | Not Available |
| Dec 7, 2025 | $1000 | Available |
| Dec 8, 2025 | $1000 | Available |
| Dec 9, 2025 | $1000 | Available |
| Dec 10, 2025 | $1000 | Available |
| Dec 11, 2025 | $1093 | Not Available |
| Dec 12, 2025 | $1520 | Not Available |
| Dec 13, 2025 | $1536 | Not Available |
| Dec 14, 2025 | $1047 | Available |
| Dec 15, 2025 | $1058 | Available |
| Dec 16, 2025 | $1058 | Available |
| Dec 17, 2025 | $1127 | Not Available |
| Dec 18, 2025 | $1242 | Not Available |
| Dec 19, 2025 | $1568 | Not Available |
| Dec 20, 2025 | $2464 | Not Available |
| Dec 21, 2025 | $2464 | Not Available |
| Dec 22, 2025 | $2464 | Not Available |
| Dec 23, 2025 | $2464 | Not Available |
| Dec 24, 2025 | $2464 | Not Available |
| Dec 25, 2025 | $2640 | Not Available |
| Dec 26, 2025 | $2480 | Not Available |
| Dec 27, 2025 | $2480 | Not Available |
| Dec 28, 2025 | $2480 | Not Available |
| Dec 29, 2025 | $2480 | Not Available |
| Dec 30, 2025 | $2480 | Not Available |
| Dec 31, 2025 | $2480 | Not Available |
| Jan 1, 2026 | $3630 | Not Available |
| Jan 2, 2026 | $3410 | Not Available |
| Jan 3, 2026 | $3300 | Not Available |
| Jan 4, 2026 | $1235 | Not Available |
| Jan 5, 2026 | $1235 | Not Available |
| Jan 6, 2026 | $1235 | Available |
| Jan 7, 2026 | $1235 | Available |
| Jan 8, 2026 | $1430 | Not Available |
| Jan 9, 2026 | $2200 | Not Available |
| Jan 10, 2026 | $2200 | Not Available |
| Jan 11, 2026 | $1235 | Available |
| Jan 12, 2026 | $1235 | Available |
| Jan 13, 2026 | $1235 | Available |
| Jan 14, 2026 | $1235 | Available |
| Jan 15, 2026 | $1430 | Not Available |
| Jan 16, 2026 | $2750 | Not Available |
| Jan 17, 2026 | $2750 | Not Available |
| Jan 18, 2026 | $2750 | Not Available |
| Jan 19, 2026 | $2640 | Available |
| Jan 20, 2026 | $1235 | Available |
| Jan 21, 2026 | $1300 | Not Available |
| Jan 22, 2026 | $1430 | Not Available |
| Jan 23, 2026 | $2200 | Not Available |
| Jan 24, 2026 | $2200 | Not Available |
| Jan 25, 2026 | $1235 | Available |
| Jan 26, 2026 | $1235 | Available |