1/88

Hillsdale, New York

Wander Hillsdale Valley

4 bedrooms6 beds4 baths10 guests

4.91 (62)

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.

Property License: License: N/A

Availability & Pricing

For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.

Date	Price (excl. fees and taxes)	Availability	Min Stay (nights)
Nov 5, 2026	$579	Not Available	3
Nov 6, 2026	$579	Not Available	3
Nov 7, 2026	$589.50	Not Available	3
Nov 8, 2026	$552.33	Not Available	3
Nov 9, 2026	$518	Not Available	3
Nov 10, 2026	$468.80	Not Available	3
Nov 11, 2026	$459.83	Not Available	3
Nov 12, 2026	$458.50	Not Available	3
Nov 13, 2026	$465	Not Available	3
Nov 14, 2026	$468	Not Available	3
Nov 15, 2026	$465	Not Available	3
Nov 16, 2026	$432.25	Not Available	3
Nov 17, 2026	$409.50	Available	3
Nov 18, 2026	$424.20	Available	3
Nov 19, 2026	$453.50	Available	3
Nov 20, 2026	$504	Not Available	3
Nov 21, 2026	$533.80	Not Available	3
Nov 22, 2026	$539.17	Not Available	3
Nov 23, 2026	$557.60	Available	2
Nov 24, 2026	$582.50	Not Available	3
Nov 25, 2026	$601.50	Not Available	3
Nov 26, 2026	$625	Not Available	3
Nov 27, 2026	$626.67	Not Available	3
Nov 28, 2026	$625	Not Available	3
Nov 29, 2026	$589.50	Available	3
Nov 30, 2026	$562.40	Available	3
Dec 1, 2026	$509.86	Available	3
Dec 2, 2026	$451.43	Available	3
Dec 3, 2026	$422.57	Available	3
Dec 4, 2026	$421	Available	3
Dec 5, 2026	$421	Available	3
Dec 6, 2026	$420	Available	3
Dec 7, 2026	$393.33	Available	3
Dec 8, 2026	$391.50	Available	3
Dec 9, 2026	$387	Available	3
Dec 10, 2026	$394	Available	3
Dec 11, 2026	$423.67	Available	3
Dec 12, 2026	$429	Available	3
Dec 13, 2026	$423.67	Available	3
Dec 14, 2026	$395.25	Available	3
Dec 15, 2026	$387	Available	3
Dec 16, 2026	$394.50	Available	3
Dec 17, 2026	$412.75	Available	3
Dec 18, 2026	$438	Available	3
Dec 19, 2026	$467.50	Available	3
Dec 20, 2026	$489.57	Available	3
Dec 21, 2026	$491	Available	3
Dec 22, 2026	$497	Available	3
Dec 23, 2026	$525.25	Available	3
Dec 24, 2026	$551.50	Not Available	3
Dec 25, 2026	$569.67	Not Available	3
Dec 26, 2026	$577	Not Available	3
Dec 27, 2026	$551.50	Not Available	3
Dec 28, 2026	$519.60	Not Available	3
Dec 29, 2026	$491.67	Not Available	3
Dec 30, 2026	$485.14	Not Available	3
Dec 31, 2026	$513	Not Available	3
Jan 1, 2027	$517.67	Not Available	3
Jan 2, 2027	$517.67	Not Available	3
Jan 3, 2027	$501	Not Available	3
Jan 4, 2027	$487.67	Not Available	3
Jan 5, 2027	$468	Not Available	3
Jan 6, 2027	$462	Not Available	3
Jan 7, 2027	$462	Not Available	3
Jan 8, 2027	$492	Not Available	3
Jan 9, 2027	$493.67	Not Available	3
Jan 10, 2027	$492	Not Available	3
Jan 11, 2027	$470.71	Not Available	3
Jan 12, 2027	$471.83	Not Available	3
Jan 13, 2027	$490	Not Available	3
Jan 14, 2027	$522.20	Available	2
Jan 15, 2027	$550.33	Not Available	3
Jan 16, 2027	$563	Not Available	3
Jan 17, 2027	$568	Not Available	3
Jan 18, 2027	$563	Not Available	3
Jan 19, 2027	$541.50	Available	3
Jan 20, 2027	$514.83	Available	3
Jan 21, 2027	$486.20	Available	3
Jan 22, 2027	$482	Available	3
Jan 23, 2027	$482	Available	3
Jan 24, 2027	$480.57	Available	3
Jan 25, 2027	$447	Available	3
Jan 26, 2027	$419.20	Available	3
Jan 27, 2027	$422.60	Available	3
Jan 28, 2027	$439	Available	3
Jan 29, 2027	$475.67	Available	3
Jan 30, 2027	$487	Available	3
Jan 31, 2027	$475.67	Available	3
Feb 1, 2027	$453.67	Available	3
Feb 2, 2027	$435	Available	3
Feb 3, 2027	$435	Available	3
Feb 4, 2027	$452.75	Available	3
Feb 5, 2027	$480.67	Not Available	3
Feb 6, 2027	$488	Not Available	3
Feb 7, 2027	$480.67	Not Available	3
Feb 8, 2027	$452.75	Available	3
Feb 9, 2027	$446	Available	3
Feb 10, 2027	$455.20	Available	3
Feb 11, 2027	$489	Available	3
Feb 12, 2027	$512	Available	3
Feb 13, 2027	$516	Available	3
Feb 14, 2027	$516	Available	3
Feb 15, 2027	$516	Available	3
Feb 16, 2027	$492.75	Not Available	3
Feb 17, 2027	$480	Not Available	3
Feb 18, 2027	$481.50	Not Available	3
Feb 19, 2027	$514.33	Not Available	3
Feb 20, 2027	$514.67	Not Available	3
Feb 21, 2027	$514.33	Available	3
Feb 22, 2027	$481.50	Available	3
Feb 23, 2027	$452	Available	3
Feb 24, 2027	$434	Available	3
Feb 25, 2027	$438.50	Not Available	3
Feb 26, 2027	$469.33	Not Available	3
Feb 27, 2027	$472.67	Not Available	3
Feb 28, 2027	$469.33	Not Available	3
Mar 1, 2027	$437.33	Not Available	3
Mar 2, 2027	$409.60	Not Available	3
Mar 3, 2027	$398	Not Available	3
Mar 4, 2027	$402.50	Not Available	3
Mar 5, 2027	$425.33	Not Available	3
Mar 6, 2027	$426.67	Not Available	3
Mar 7, 2027	$425.33	Not Available	3
Mar 8, 2027	$400.33	Not Available	3
Mar 9, 2027	$387	Not Available	3
Mar 10, 2027	$384	Not Available	3
Mar 11, 2027	$387.75	Not Available	3
Mar 12, 2027	$415.67	Not Available	3
Mar 13, 2027	$417.33	Not Available	3
Mar 14, 2027	$415.67	Not Available	3
Mar 15, 2027	$389.67	Not Available	3
Mar 16, 2027	$383.50	Not Available	3
Mar 17, 2027	$383.50	Not Available	3
Mar 18, 2027	$387.25	Not Available	3
Mar 19, 2027	$414	Not Available	3
Mar 20, 2027	$417.33	Not Available	3
Mar 21, 2027	$417.33	Not Available	3
Mar 22, 2027	$409.50	Not Available	3
Mar 23, 2027	$391	Not Available	3
Mar 24, 2027	$382.50	Not Available	3
Mar 25, 2027	$387.50	Not Available	3
Mar 26, 2027	$413.33	Not Available	3
Mar 27, 2027	$419.33	Not Available	3
Mar 28, 2027	$419.33	Not Available	3
Mar 29, 2027	$409	Not Available	3
Mar 30, 2027	$393	Not Available	3
Mar 31, 2027	$408.33	Not Available	3
Apr 1, 2027	$414.50	Not Available	3
Apr 2, 2027	$456.67	Not Available	3
Apr 3, 2027	$462.67	Not Available	3
Apr 4, 2027	$456.67	Not Available	3
Apr 5, 2027	$422.33	Not Available	3
Apr 6, 2027	$401.50	Not Available	3
Apr 7, 2027	$398	Not Available	3
Apr 8, 2027	$401.50	Not Available	3
Apr 9, 2027	$424.33	Not Available	3
Apr 10, 2027	$428	Not Available	3
Apr 11, 2027	$428	Not Available	3
Apr 12, 2027	$405	Not Available	3
Apr 13, 2027	$404	Not Available	3
Apr 14, 2027	$405	Not Available	3
Apr 15, 2027	$431.67	Not Available	3
Apr 16, 2027	$451.50	Not Available	3
Apr 17, 2027	$458.67	Not Available	3
Apr 18, 2027	$442.67	Not Available	3
Apr 19, 2027	$422.75	Not Available	3
Apr 20, 2027	$398	Not Available	3
Apr 21, 2027	$392	Not Available	3
Apr 22, 2027	$395	Not Available	3
Apr 23, 2027	$419.33	Not Available	3
Apr 24, 2027	$424	Not Available	3
Apr 25, 2027	$423.50	Not Available	3
Apr 26, 2027	$398.67	Not Available	3
Apr 27, 2027	$394	Not Available	3
Apr 28, 2027	$390.67	Not Available	3
Apr 29, 2027	$394	Not Available	3
Apr 30, 2027	$414	Not Available	3
May 1, 2027	$414	Not Available	3
May 2, 2027	$412.50	Not Available	3
May 3, 2027	$387.67	Not Available	3
May 4, 2027	$387	Not Available	3
May 5, 2027	$387	Not Available	3
May 6, 2027	$395.67	Not Available	3
May 7, 2027	$423.67	Not Available	3
May 8, 2027	$425.33	Not Available	3
May 9, 2027	$423.67	Not Available	3
May 10, 2027	$392.75	Not Available	3
May 11, 2027	$388	Not Available	3
May 12, 2027	$416.20	Not Available	3
May 13, 2027	$436	Not Available	3
May 14, 2027	$482.33	Not Available	3
May 15, 2027	$491.67	Not Available	3
May 16, 2027	$482.33	Not Available	3
May 17, 2027	$453.50	Not Available	3
May 18, 2027	$417.80	Not Available	3
May 19, 2027	$401	Not Available	3
May 20, 2027	$410.25	Not Available	3
May 21, 2027	$435	Not Available	3
May 22, 2027	$456	Not Available	3
May 23, 2027	$462.33	Not Available	3
May 24, 2027	$483.33	Not Available	3
May 25, 2027	$486.33	Not Available	3
May 26, 2027	$486.33	Not Available	3
May 27, 2027	$486.33	Not Available	3
May 28, 2027	$486.33	Not Available	3
May 29, 2027	$486	Not Available	3
May 30, 2027	$489.67	Not Available	3
May 31, 2027	$489.67	Not Available	3
Jun 1, 2027	$489.67	Not Available	3
Jun 2, 2027	$465.25	Not Available	3
Jun 3, 2027	$462.50	Not Available	3
Jun 4, 2027	$475.33	Not Available	3
Jun 5, 2027	$480.33	Not Available	3
Jun 6, 2027	$475.33	Not Available	3
Jun 7, 2027	$457	Not Available	3
Jun 8, 2027	$448	Not Available	3
Jun 9, 2027	$443	Not Available	3
Jun 10, 2027	$448.50	Not Available	3
Jun 11, 2027	$471.67	Not Available	3
Jun 12, 2027	$476.67	Not Available	3
Jun 13, 2027	$476.67	Not Available	3
Jun 14, 2027	$457.50	Not Available	3
Jun 15, 2027	$453.67	Not Available	3
Jun 16, 2027	$457.50	Not Available	3
Jun 17, 2027	$465	Not Available	3
Jun 18, 2027	$491.33	Not Available	3
Jun 19, 2027	$498.33	Not Available	3
Jun 20, 2027	$498.33	Not Available	3
Jun 21, 2027	$484	Not Available	3
Jun 22, 2027	$478.40	Not Available	3
Jun 23, 2027	$500.20	Not Available	3
Jun 24, 2027	$511	Not Available	3
Jun 25, 2027	$559.67	Not Available	3
Jun 26, 2027	$570.50	Not Available	3
Jun 27, 2027	$559.67	Not Available	3
Jun 28, 2027	$550.33	Not Available	3
Jun 29, 2027	$523	Not Available	3
Jun 30, 2027	$544.80	Not Available	3
Jul 1, 2027	$582.25	Not Available	3
Jul 2, 2027	$602.33	Not Available	3
Jul 3, 2027	$606.33	Not Available	3
Jul 4, 2027	$606.33	Not Available	3
Jul 5, 2027	$582.25	Not Available	3
Jul 6, 2027	$550.80	Not Available	3
Jul 7, 2027	$545	Not Available	3
Jul 8, 2027	$553	Not Available	3
Jul 9, 2027	$582	Not Available	3
Jul 10, 2027	$585.67	Not Available	3
Jul 11, 2027	$582	Not Available	3
Jul 12, 2027	$557	Not Available	3
Jul 13, 2027	$542.50	Not Available	3
Jul 14, 2027	$553.83	Not Available	3
Jul 15, 2027	$581.80	Not Available	3
Jul 16, 2027	$616.50	Not Available	3
Jul 17, 2027	$654.33	Not Available	3
Jul 18, 2027	$655.50	Not Available	3
Jul 19, 2027	$654.33	Not Available	3
Jul 20, 2027	$592.75	Not Available	3
Jul 21, 2027	$571.33	Not Available	3
Jul 22, 2027	$563.50	Not Available	3
Jul 23, 2027	$605.67	Not Available	3
Jul 24, 2027	$606	Not Available	3
Jul 25, 2027	$605.67	Not Available	3
Jul 26, 2027	$578.25	Not Available	3
Jul 27, 2027	$549.20	Not Available	3
Jul 28, 2027	$545	Not Available	3
Jul 29, 2027	$561	Not Available	3
Jul 30, 2027	$595.67	Not Available	3
Jul 31, 2027	$602	Not Available	3
Aug 1, 2027	$595.67	Not Available	3
Aug 2, 2027	$573.50	Not Available	3
Aug 3, 2027	$551	Not Available	3
Aug 4, 2027	$551	Not Available	3
Aug 5, 2027	$571.50	Not Available	3
Aug 6, 2027	$598.33	Not Available	3
Aug 7, 2027	$613.33	Not Available	3
Aug 8, 2027	$598.33	Not Available	3
Aug 9, 2027	$578.33	Not Available	3
Aug 10, 2027	$549.50	Not Available	3
Aug 11, 2027	$547	Not Available	3
Aug 12, 2027	$567	Not Available	3
Aug 13, 2027	$590	Not Available	3
Aug 14, 2027	$608	Not Available	3
Aug 15, 2027	$599	Not Available	3
Aug 16, 2027	$579.33	Not Available	3
Aug 17, 2027	$555	Not Available	3
Aug 18, 2027	$551.50	Not Available	3
Aug 19, 2027	$569.50	Not Available	3
Aug 20, 2027	$595.67	Not Available	3
Aug 21, 2027	$612	Not Available	3
Aug 22, 2027	$595.67	Not Available	3
Aug 23, 2027	$572.50	Not Available	3
Aug 24, 2027	$546	Not Available	3
Aug 25, 2027	$543.33	Not Available	3
Aug 26, 2027	$557.50	Not Available	3
Aug 27, 2027	$580	Not Available	3
Aug 28, 2027	$595	Not Available	3
Aug 29, 2027	$581	Not Available	3
Aug 30, 2027	$562.67	Not Available	3
Aug 31, 2027	$536.50	Not Available	3
Sep 1, 2027	$532.67	Not Available	3
Sep 2, 2027	$533	Not Available	3
Sep 3, 2027	$556.33	Not Available	3
Sep 4, 2027	$556.33	Not Available	3
Sep 5, 2027	$556.33	Not Available	3
Sep 6, 2027	$553	Not Available	3
Sep 7, 2027	$522.67	Not Available	3
Sep 8, 2027	$509.50	Not Available	3
Sep 9, 2027	$489.33	Not Available	3
Sep 10, 2027	$496	Not Available	3
Sep 11, 2027	$496.33	Not Available	3
Sep 12, 2027	$496.33	Not Available	3
Sep 13, 2027	$494.71	Not Available	3
Sep 14, 2027	$494.71	Not Available	3
Sep 15, 2027	$505.20	Not Available	3
Sep 16, 2027	$543	Not Available	3
Sep 17, 2027	$584	Not Available	3
Sep 18, 2027	$592.67	Not Available	3
Sep 19, 2027	$584	Not Available	3
Sep 20, 2027	$528	Not Available	3
Sep 21, 2027	$497.60	Not Available	3
Sep 22, 2027	$486	Not Available	3
Sep 23, 2027	$483.67	Not Available	3
Sep 24, 2027	$485.43	Not Available	3
Sep 25, 2027	$497.67	Not Available	3
Sep 26, 2027	$497.67	Not Available	3
Sep 27, 2027	$474.67	Not Available	3
Sep 28, 2027	$463	Not Available	3
Sep 29, 2027	$474.80	Not Available	3
Sep 30, 2027	$510.50	Not Available	3
Oct 1, 2027	$528.50	Not Available	3
Oct 2, 2027	$535.67	Not Available	3
Oct 3, 2027	$528.50	Not Available	3
Oct 4, 2027	$510.50	Not Available	3
Oct 5, 2027	$488.60	Not Available	3
Oct 6, 2027	$516.67	Not Available	3
Oct 7, 2027	$550.40	Not Available	3
Oct 8, 2027	$583.67	Not Available	3
Oct 9, 2027	$616	Not Available	3
Oct 10, 2027	$616.67	Not Available	3
Oct 11, 2027	$616	Not Available	3
Oct 12, 2027	$577.50	Not Available	3
Oct 13, 2027	$553	Not Available	3
Oct 14, 2027	$543.50	Not Available	3
Oct 15, 2027	$565.25	Not Available	3
Oct 16, 2027	$597.67	Not Available	3
Oct 17, 2027	$597.67	Not Available	3
Oct 18, 2027	$597.50	Not Available	3
Oct 19, 2027	$537.50	Not Available	3
Oct 20, 2027	$505	Not Available	3
Oct 21, 2027	$499.20	Not Available	3
Oct 22, 2027	$530.67	Not Available	3
Oct 23, 2027	$539.50	Not Available	3
Oct 24, 2027	$539.50	Not Available	3
Oct 25, 2027	$530.67	Not Available	3
Oct 26, 2027	$481	Not Available	3
Oct 27, 2027	$462.67	Not Available	3
Oct 28, 2027	$440.80	Not Available	3
Oct 29, 2027	$455.33	Not Available	3
Oct 30, 2027	$455.33	Not Available	3
Oct 31, 2027	$453.67	Not Available	3
Nov 1, 2027	$426	Not Available	3
Nov 2, 2027	$410.50	Not Available	3
Nov 3, 2027	$400.33	Not Available	3
Nov 4, 2027	$416	Not Available	3
Nov 5, 2027	$438.33	Not Available	3
Nov 6, 2027	$452.33	Not Available	3
Nov 7, 2027	$445.50	Not Available	3
Nov 8, 2027	$427.33	Not Available	3
Nov 9, 2027	$408.25	Not Available	3
Nov 10, 2027	$411	Not Available	3
Nov 11, 2027	$424.67	Not Available	3
Nov 12, 2027	$445	Not Available	3
Nov 13, 2027	$445	Not Available	3
Nov 14, 2027	$439	Not Available	3
Nov 15, 2027	$415.33	Not Available	3
Nov 16, 2027	$410.50	Not Available	3
Nov 17, 2027	$410.50	Not Available	3
Nov 18, 2027	$417.50	Not Available	3
Nov 19, 2027	$450.33	Not Available	3
Nov 20, 2027	$476.83	Not Available	3
Nov 21, 2027	$506	Not Available	3
Nov 22, 2027	$549.29	Not Available	3
Nov 23, 2027	$609	Not Available	3
Nov 24, 2027	$679.20	Not Available	3
Nov 25, 2027	$732	Not Available	3
Nov 26, 2027	$737.67	Not Available	3
Nov 27, 2027	$737.67	Not Available	3
Nov 28, 2027	$732	Not Available	3
Nov 29, 2027	$679.20	Not Available	3
Nov 30, 2027	$607.33	Not Available	3
Dec 1, 2027	$541	Not Available	3
Dec 2, 2027	$479.20	Not Available	3
Dec 3, 2027	$452.50	Not Available	3
Dec 4, 2027	$430.33	Not Available	3
Dec 5, 2027	$427.33	Not Available	3
Dec 6, 2027	$400	Not Available	3
Dec 7, 2027	$391.50	Not Available	3
Dec 8, 2027	$389.67	Not Available	3
Dec 9, 2027	$393.50	Not Available	3
Dec 10, 2027	$421.67	Not Available	3
Dec 11, 2027	$424	Not Available	3
Dec 12, 2027	$421.67	Not Available	3
Dec 13, 2027	$395.67	Not Available	3
Dec 14, 2027	$391.50	Not Available	3
Dec 15, 2027	$391.50	Not Available	3
Dec 16, 2027	$398.75	Not Available	3
Dec 17, 2027	$427.67	Not Available	3
Dec 18, 2027	$430.33	Not Available	3
Dec 19, 2027	$430.33	Not Available	3
Dec 20, 2027	$445.80	Not Available	3
Dec 21, 2027	$475.50	Not Available	3
Dec 22, 2027	$524	Not Available	3
Dec 23, 2027	$551	Not Available	3
Dec 24, 2027	$594	Not Available	3
Dec 25, 2027	$594.33	Not Available	3
Dec 26, 2027	$594	Not Available	3
Dec 27, 2027	$562.25	Not Available	3
Dec 28, 2027	$547	Not Available	3
Dec 29, 2027	$547	Not Available	3
Dec 30, 2027	$576.50	Not Available	3
Dec 31, 2027	$577.33	Not Available	3
Jan 1, 2028	$577.33	Not Available	3
Jan 2, 2028	$568.33	Not Available	3
Jan 3, 2028	$524.60	Not Available	3
Jan 4, 2028	$497.80	Not Available	3
Jan 5, 2028	$458.50	Not Available	3
Jan 6, 2028	$447	Not Available	3
Jan 7, 2028	$465.67	Not Available	3
Jan 8, 2028	$465.67	Not Available	3
Jan 9, 2028	$464	Not Available	3
Jan 10, 2028	$436	Not Available	3
Jan 11, 2028	$426	Not Available	3
Jan 12, 2028	$429	Not Available	3
Jan 13, 2028	$448	Not Available	3
Jan 14, 2028	$485.67	Not Available	3
Jan 15, 2028	$504.67	Not Available	3
Jan 16, 2028	$503.50	Not Available	3
Jan 17, 2028	$489	Not Available	3
Jan 18, 2028	$481	Not Available	3
Jan 19, 2028	$455.33	Not Available	3
Jan 20, 2028	$450	Not Available	3
Jan 21, 2028	$451.67	Not Available	3
Jan 22, 2028	$484.50	Not Available	3
Jan 23, 2028	$451.67	Not Available	3
Jan 24, 2028	$451.67	Not Available	3
Jan 25, 2028	$424	Not Available	3
Jan 26, 2028	$418	Not Available	3
Jan 27, 2028	$592.67	Not Available	3
Jan 28, 2028	$592.67	Not Available	3
Jan 29, 2028	$592.67	Not Available	3
Jan 30, 2028	$592.67	Not Available	3
Jan 31, 2028	$592.67	Not Available	3
Feb 1, 2028	$592.67	Not Available	3
Feb 2, 2028	$592.67	Not Available	3
Feb 3, 2028	$592.67	Not Available	3
Feb 4, 2028	$592.67	Not Available	3
Feb 5, 2028	$592.67	Not Available	3
Feb 6, 2028	$592.67	Not Available	3
Feb 7, 2028	$592.67	Not Available	3
Feb 8, 2028	$592.67	Not Available	3
Feb 9, 2028	$592.67	Not Available	3
Feb 10, 2028	$592.67	Not Available	3
Feb 11, 2028	$592.67	Not Available	3
Feb 12, 2028	$592.67	Not Available	3
Feb 13, 2028	$592.67	Not Available	3
Feb 14, 2028	$592.67	Not Available	3
Feb 15, 2028	$592.67	Not Available	3
Feb 16, 2028	$592.67	Not Available	3
Feb 17, 2028	$592.67	Not Available	3
Feb 18, 2028	$592.67	Not Available	3
Feb 19, 2028	$592.67	Not Available	3
Feb 20, 2028	$592.67	Not Available	3
Feb 21, 2028	$592.67	Not Available	3
Feb 22, 2028	$592.67	Not Available	3
Feb 23, 2028	$592.67	Not Available	3
Feb 24, 2028	$592.67	Not Available	3
Feb 25, 2028	$592.67	Not Available	3
Feb 26, 2028	$592.67	Not Available	3
Feb 27, 2028	$592.67	Not Available	3
Feb 28, 2028	$592.67	Not Available	3
Feb 29, 2028	$592.67	Not Available	3
Mar 1, 2028	$592.67	Not Available	3
Mar 2, 2028	$592.67	Not Available	3
Mar 3, 2028	$592.67	Not Available	3
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Apr 30, 2028	$592.67	Not Available	3
May 1, 2028	$592.67	Not Available	3
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May 3, 2028	$407.05	Not Available	3
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May 6, 2028	$415.45	Not Available	3
May 7, 2028	$444.85	Not Available	3
May 8, 2028	$446.59	Not Available	3

What this home offers

Guest house

BBQ Area

Balcony

Mountain view

Forest view

What our guests say

4.91

62 reviews

Deyvon

2 weeks ago

Its a very quint residence. Getting in and out cab be a challenge if its bad weather. Lots of leaves everywhere

Benjamin

September 2026

Our host Ben was outstanding! He went above and beyond every step of the way for to make our stay enjoyable. The property is extremely peaceful and clean. The master suite is perfection. I would highly recommend staying here. Hillsdale is such a cute town with plenty to do. A standout for us in town was The Little Apple Cidery, so fun. And honestly we could not ask for a better host. Thank you for sharing your beautiful home with us.

Jodie

June 2026

We had a great family get-together at Ben’s home. It is in a good location for access to both the Berkshires (and Tanglewood) along with the Hudson River Valley. Beautiful property on a quiet private road, perfect for walks. It’s great to have separate bathrooms for each of the bedrooms, along with a few different areas for gathering and relaxation. Property is a bit hilly with stone stairs, for those that may have mobility challenges.

Where you’ll be

Hillsdale, New York, 12529, United States

Our promise to you

Lower prices, every time

Direct line, real care

Not just a transaction

Things to know

Check-in & check-out

Check-in after 4:00 PM.

Check-out before 10:00 AM.

Property rules

Not suitable for children (2–12 years).

Not suitable for infants (under 2).

Maximum 10 guests.

No pets allowed.

No parties or events.

Cancellation policy

Add your trip dates to get the cancellation details for this stay.

Benjamin Lockspeiser

Benjamin Lockspeiser

Benjamin Lockspeiser

Wander Hillsdale Valley

Availability & Pricing

What this home offers

What our guests say

Where you’ll be

Our promise to you

Things to know

Check-in & check-out

Property rules

Number and age of guests

Pets

Events

Smoking

Check-in & check-out

Cancellation policy