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60 reviews
Operated by a Wander partner
Trusted operators, vetted by Wander
Wander Hillsdale Valley is a majestic retreat nestled in the picturesque landscape of the Catskill Mountains and the Berkshires, offering unparalleled luxury and breathtaking views. One of the highlights of this property is its unique layout: two beautifully designed homes—a spacious Main House and a charming Cottage—are included with every reservation. That means more room to relax, more privacy, and the perfect setup for families or groups traveling together. Wake up to sweeping views of rolling hills and lush forests, all visible right from your bedroom window. Step outside to your private outdoor dining area and enjoy unforgettable meals surrounded by the beauty of the mountains.
Bedroom 1
1 king bed
Bedroom 2
1 queen bed
Bedroom 3
2 twin bunk beds, 1 twin trundle bed
Bedroom 4
1 queen bed
Bedroom 1
1 king bed
Bedroom 2
1 queen bed
Bedroom 3
2 twin bunk beds, 1 twin trundle bed
Bedroom 4
1 queen bed
Jodie
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June 2026
Theresa
•
May 2026
Gili
•
May 2026
Hillsdale, New York 12529, United States
Hillsdale, New York, United StatesHeirloom Lodge is a seasonal, wine-focused restaurant in the Berkshires, offering a changing menu rich in local produce. Its ambiance combines rustic charm with a sophisticated dining experience.
The Circle Museum offers a unique experience with whimsical metal sculptures set amidst nature. It's perfect for art enthusiasts and those seeking an offbeat adventure.
Lake Mansfield offers a serene escape with its beach, playground, and trails, perfect for families and nature lovers. Enjoy swimming, picnicking, and exploring the forest's diverse wildlife.
Experience the thrill of Catamount Aerial Adventure Park, featuring nine tree-top courses with ziplines and obstacles perfect for adventure-seekers. This park is ideal for families and groups seeking an exciting outdoor challenge.
Catamount Mountain Resort offers thrilling summer activities, perfect for adventure-seekers and families. Enjoy ziplining, aerial adventures, and scenic chairlift rides amidst beautiful mountain scenery.
Beebe Hill State Forest offers a scenic hike to a historic fire tower with breathtaking views, perfect for nature lovers and families seeking adventure. The picturesque trail and stunning vistas make it an ideal outing for those who appreciate the outdoors.
The Guthrie Center offers a unique blend of cultural preservation and community engagement, perfect for those interested in music, spirituality, and social issues. It's ideal for anyone seeking a welcoming space for cultural exchange and community connection.
Roeliff Jansen Park offers a serene escape with trails, picnic areas, and a farmers market, perfect for families and nature lovers. Its unique blend of recreation and community events makes it a special spot for those seeking outdoor fun and local charm.
French Park offers a fun, family-friendly atmosphere with basketball, tennis, and volleyball courts, plus a playground and barbecue area. It's perfect for families and outdoor enthusiasts looking for a lively community setting.
Explore Harvey Mountain State Forest, a haven for nature lovers, offering easy and scenic hikes perfect for families and outdoor enthusiasts. Its trails provide a tranquil escape amidst Columbia County's beautiful landscapes.
Fox Hill Camping Area offers a serene escape with its spacious sites and family-friendly activities like disc golf and playgrounds, perfect for families seeking a relaxing outdoor adventure. It's ideal for those who want to enjoy nature without the hustle of nearby Wisconsin Dells.
Free cancellation up to 30 days before check-in. 50% refund up to 7 days before. No refund after that.
Pets not allowed
No smoking - fees will apply
Events not allowed
Check-in after 4:00 pm
Check-out before 10:00 am
10 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Sep 11, 2026 | $615 | Not Available |
| Sep 12, 2026 | $576 | Not Available |
| Sep 13, 2026 | $576 | Not Available |
| Sep 14, 2026 | $532 | Not Available |
| Sep 15, 2026 | $509 | Not Available |
| Sep 16, 2026 | $505 | Not Available |
| Sep 17, 2026 | $528 | Not Available |
| Sep 18, 2026 | $563 | Not Available |
| Sep 19, 2026 | $574 | Not Available |
| Sep 20, 2026 | $563 | Not Available |
| Sep 21, 2026 | $560 | Not Available |
| Sep 22, 2026 | $533 | Available |
| Sep 23, 2026 | $533 | Available |
| Sep 24, 2026 | $578 | Not Available |
| Sep 25, 2026 | $648 | Not Available |
| Sep 26, 2026 | $650 | Not Available |
| Sep 27, 2026 | $650 | Not Available |
| Sep 28, 2026 | $588 | Available |
| Sep 29, 2026 | $543 | Available |
| Sep 30, 2026 | $524 | Available |
| Oct 1, 2026 | $532 | Not Available |
| Oct 2, 2026 | $580 | Not Available |
| Oct 3, 2026 | $590 | Not Available |
| Oct 4, 2026 | $580 | Not Available |
| Oct 5, 2026 | $550 | Not Available |
| Oct 6, 2026 | $550 | Not Available |
| Oct 7, 2026 | $593 | Not Available |
| Oct 8, 2026 | $643 | Not Available |
| Oct 9, 2026 | $705 | Not Available |
| Oct 10, 2026 | $732 | Not Available |
| Oct 11, 2026 | $732 | Not Available |
| Oct 12, 2026 | $687 | Not Available |
| Oct 13, 2026 | $642 | Not Available |
| Oct 14, 2026 | $636 | Not Available |
| Oct 15, 2026 | $660 | Not Available |
| Oct 16, 2026 | $744 | Not Available |
| Oct 17, 2026 | $752 | Not Available |
| Oct 18, 2026 | $744 | Not Available |
| Oct 19, 2026 | $665 | Not Available |
| Oct 20, 2026 | $633 | Not Available |
| Oct 21, 2026 | $578 | Not Available |
| Oct 22, 2026 | $608 | Not Available |
| Oct 23, 2026 | $689 | Not Available |
| Oct 24, 2026 | $695 | Not Available |
| Oct 25, 2026 | $695 | Not Available |
| Oct 26, 2026 | $612 | Not Available |
| Oct 27, 2026 | $554 | Not Available |
| Oct 28, 2026 | $516 | Not Available |
| Oct 29, 2026 | $496 | Not Available |
| Oct 30, 2026 | $496 | Not Available |
| Oct 31, 2026 | $521 | Not Available |
| Nov 1, 2026 | $487 | Available |
| Nov 2, 2026 | $452 | Available |
| Nov 3, 2026 | $455 | Available |
| Nov 4, 2026 | $463 | Available |
| Nov 5, 2026 | $497 | Available |
| Nov 6, 2026 | $551 | Not Available |
| Nov 7, 2026 | $552 | Not Available |
| Nov 8, 2026 | $551 | Not Available |
| Nov 9, 2026 | $502 | Available |
| Nov 10, 2026 | $470 | Not Available |
| Nov 11, 2026 | $467 | Not Available |
| Nov 12, 2026 | $470 | Not Available |
| Nov 13, 2026 | $477 | Not Available |
| Nov 14, 2026 | $482 | Not Available |
| Nov 15, 2026 | $477 | Not Available |
| Nov 16, 2026 | $443 | Not Available |
| Nov 17, 2026 | $429 | Available |
| Nov 18, 2026 | $429 | Available |
| Nov 19, 2026 | $454 | Available |
| Nov 20, 2026 | $504 | Not Available |
| Nov 21, 2026 | $534 | Not Available |
| Nov 22, 2026 | $540 | Not Available |
| Nov 23, 2026 | $559 | Available |
| Nov 24, 2026 | $583 | Not Available |
| Nov 25, 2026 | $602 | Not Available |
| Nov 26, 2026 | $625 | Not Available |
| Nov 27, 2026 | $627 | Not Available |
| Nov 28, 2026 | $625 | Not Available |
| Nov 29, 2026 | $583 | Available |
| Nov 30, 2026 | $562 | Available |
| Dec 1, 2026 | $514 | Available |
| Dec 2, 2026 | $451 | Available |
| Dec 3, 2026 | $441 | Available |
| Dec 4, 2026 | $443 | Available |
| Dec 5, 2026 | $444 | Available |
| Dec 6, 2026 | $443 | Available |
| Dec 7, 2026 | $414 | Available |
| Dec 8, 2026 | $406 | Available |
| Dec 9, 2026 | $406 | Available |
| Dec 10, 2026 | $416 | Available |