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10 guests
6 beds
4 bathrooms
10 guests
4 bedrooms
6 beds
4 bathrooms
2500 sq. ft.
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.

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Check-in after 4:00pm • Check-out before 10:00am • Pets allowed
Cancel within 24 hours for a full refund.
Arrive to five star cleaning • No chores at checkout • Just lock up and go
Wander is the best of both worlds. The quality of a luxury hotel with the comfort of a private vacation home just for you and your guests.
Bedroom 1
1 king bed
Bedroom 2
1 queen bed
Bedroom 3
2 twin bunk beds, 1 twin trundle bed
Office 1
1 full sofa
Bedroom 4
1 queen bed
Nestled in the heart of the Hudson Valley, this location offers easy access to a wide range of outdoor and cultural activities. Enjoy scenic hikes and nature walks at Taconic State Park or Bash Bish Falls, just a short drive away.
Heirloom 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.
Choose your check-in & check-out dates

based on 41 reviews
Guests love the home for its stunning wrap around windows, spacious deck with BBQ and outdoor dining that showcase mountain and forest views. They praise the peaceful yet convenient Berkshires location, spotless cleanliness and the hosts' fast responsive and flexible service.
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Here are some things which you should know before booking Wander Hillsdale Valley
Check-in: after 4:00 pm
Check-out: before 10:00 am
10 guests maximum
Pets allowed
No smoking - fees will apply
Events require approval
Cancel within 24 hours for a full refund.
Check-in: after 4:00 pm
Check-out: before 10:00 am
10 guests maximum
Pets allowed
No smoking - fees will apply
Events require approval
Quiet hours are from 10 PM to 8 AM. We kindly ask that you refrain from hosting parties or creating excessive noise during your stay, as we strive to maintain a peaceful environment for both our guests and neighbors. Amplified outdoor sounds are strictly prohibited.
This home contains features that may be difficult for mobility-challenged guests, including climbing stairs to navigate the property.
This home follows a strict maximum occupancy rule. Please make sure that the total number of guests accompanying you (including both children and adults) doesn’t exceed the indicated maximum occupancy above to avoid cancellation of your stay and additional fees.
This Wander is located off of a private road. In accordance with local regulations, please do not trespass on other properties off the main road and be on the lookout for any Private Property signage.
Parties & Events
Parties and events are not allowed without permission. Events that invite outside guests not part of the booking are strictly prohibited, but you may host family reunions and other intimate events in this Wander. Please reach out to Concierge with your request in advance.
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Jan 11, 2026 | $632 | Not Available |
| Jan 12, 2026 | $632 | Not Available |
| Jan 13, 2026 | $632 | Not Available |
| Jan 14, 2026 | $656 | Not Available |
| Jan 15, 2026 | $656 | Not Available |
| Jan 16, 2026 | $656 | Not Available |
| Jan 17, 2026 | $750 | Not Available |
| Jan 18, 2026 | $750 | Not Available |
| Jan 19, 2026 | $713 | Not Available |
| Jan 20, 2026 | $713 | Not Available |
| Jan 21, 2026 | $713 | Not Available |
| Jan 22, 2026 | $750 | Not Available |
| Jan 23, 2026 | $750 | Not Available |
| Jan 24, 2026 | $750 | Not Available |
| Jan 25, 2026 | $612 | Not Available |
| Jan 26, 2026 | $612 | Available |
| Jan 27, 2026 | $612 | Available |
| Jan 28, 2026 | $602 | Available |
| Jan 29, 2026 | $602 | Available |
| Jan 30, 2026 | $602 | Not Available |
| Jan 31, 2026 | $750 | Not Available |
| Feb 1, 2026 | $615 | Not Available |
| Feb 2, 2026 | $615 | Available |
| Feb 3, 2026 | $615 | Available |
| Feb 4, 2026 | $568 | Not Available |
| Feb 5, 2026 | $750 | Not Available |
| Feb 6, 2026 | $750 | Not Available |
| Feb 7, 2026 | $750 | Not Available |
| Feb 8, 2026 | $617 | Available |
| Feb 9, 2026 | $617 | Available |
| Feb 10, 2026 | $617 | Available |
| Feb 11, 2026 | $651 | Available |
| Feb 12, 2026 | $651 | Available |
| Feb 13, 2026 | $651 | Not Available |
| Feb 14, 2026 | $750 | Not Available |
| Feb 15, 2026 | $750 | Not Available |
| Feb 16, 2026 | $841 | Not Available |
| Feb 17, 2026 | $841 | Available |
| Feb 18, 2026 | $841 | Available |
| Feb 19, 2026 | $749 | Available |
| Feb 20, 2026 | $688 | Not Available |
| Feb 21, 2026 | $750 | Not Available |
| Feb 22, 2026 | $636 | Not Available |
| Feb 23, 2026 | $587 | Available |
| Feb 24, 2026 | $587 | Available |
| Feb 25, 2026 | $586 | Available |
| Feb 26, 2026 | $622 | Available |
| Feb 27, 2026 | $635 | Available |
| Feb 28, 2026 | $642 | Available |
| Mar 1, 2026 | $635 | Available |
| Mar 2, 2026 | $588 | Available |
| Mar 3, 2026 | $583 | Available |
| Mar 4, 2026 | $573 | Available |
| Mar 5, 2026 | $620 | Available |
| Mar 6, 2026 | $631 | Available |
| Mar 7, 2026 | $638 | Available |
| Mar 8, 2026 | $631 | Available |
| Mar 9, 2026 | $585 | Available |
| Mar 10, 2026 | $581 | Available |
| Mar 11, 2026 | $572 | Available |
| Mar 12, 2026 | $581 | Available |
| Mar 13, 2026 | $618 | Available |
| Mar 14, 2026 | $622 | Available |
| Mar 15, 2026 | $622 | Available |
| Mar 16, 2026 | $613 | Available |
| Mar 17, 2026 | $582 | Available |
| Mar 18, 2026 | $575 | Available |
| Mar 19, 2026 | $582 | Available |
| Mar 20, 2026 | $634 | Available |
| Mar 21, 2026 | $643 | Available |
| Mar 22, 2026 | $635 | Available |
| Mar 23, 2026 | $591 | Available |
| Mar 24, 2026 | $587 | Available |
| Mar 25, 2026 | $587 | Available |
| Mar 26, 2026 | $624 | Available |
| Mar 27, 2026 | $653 | Available |
| Mar 28, 2026 | $730 | Available |
| Mar 29, 2026 | $721 | Available |
| Mar 30, 2026 | $653 | Available |
| Mar 31, 2026 | $627 | Available |
| Apr 1, 2026 | $624 | Available |
| Apr 2, 2026 | $630 | Available |
| Apr 3, 2026 | $631 | Available |
| Apr 4, 2026 | $631 | Available |
| Apr 5, 2026 | $631 | Available |
| Apr 6, 2026 | $631 | Available |
| Apr 7, 2026 | $629 | Available |
| Apr 8, 2026 | $571 | Available |
| Apr 9, 2026 | $615 | Available |
| Apr 10, 2026 | $631 | Available |
| Apr 11, 2026 | $638 | Available |