4 bedrooms
•
8 beds
•
4 bathrooms
•
12 guests
•
3500 sq. ft.

Saved to wishlist
Living Room
1 full sofa
Bedroom 1
1 king bed
Bedroom 2
1 king bed
Bedroom 3
1 king bed
Bedroom 4
4 twin bunk beds
Living Room
1 full sofa
Bedroom 1
1 king bed
Bedroom 2
1 king bed
Bedroom 3
1 king bed
Bedroom 4
4 twin bunk beds
Monterey, Massachusetts 1245, United States
Monterey, Massachusetts, United StatesNestled in the Berkshires countryside, Cantina 229 delivers playful farm-to-table cuisine blending global flavors like smoked pork tacos and kimchi pancakes with hyper-local ingredients from their own farm. Enjoy casual fine dining in a modern space with floor-to-ceiling windows, an open kitchen buzz, and a scenic deck perfect for craft cocktails.[1][2][6]
Nestled in the Berkshires, Roadside Store & Café serves farm-fresh American breakfasts and lunches from its own garden and bakery, fostering community connections through Gould Farm's empowering social enterprise.[1][2]
Nestled at the base of Otis Ridge ski area, Grouse House offers slopeside dining with outstanding smoked BBQ, ribs, and seasonal specials in a cozy, casual country inn atmosphere. Perfect for post-ski relaxation or a quiet lunch watching the action.
Nestled in a magnificent converted barn, Gedney Farm serves chef-crafted, locally sourced seasonal dishes from a wood-fired Argentinian grill, blending inventive New England flavors with cozy, welcoming vibes.[1][2][4][6]
Step back in time at The Old Inn on the Green, a 1760 stagecoach stop glowing with candlelight and cozy fireplaces, where Chef Peter Platt crafts innovative, farm-fresh American cuisine like lobster pasta and butter-braised cod in an intimate historic setting.
Discover Beartown State Forest's serene Benedict Pond loops and lookout trails, where wildlife sightings like bears add thrill amid uncrowded Berkshires beauty—ideal for solo hikers, nature lovers, and winter snowshoers seeking peaceful adventure.[1][2][6]
A peaceful, family-friendly loop around a scenic freshwater pond with easy trails, occasional rocky ledges and a short Appalachian Trail spur—perfect for casual hikers, picnickers, and photographers.
Step back in time at the Bidwell House Museum, an authentically restored 1760s Georgian saltbox amid 194 acres of heritage gardens, trails, and woods in the Berkshire Hills. History buffs and nature lovers will relish guided tours of 18th-century life plus self-guided Native American paths.
Hike the thrilling 2-mile loop at Tyringham Cobble, summiting twin knobs via the Appalachian Trail for panoramic Berkshire views and spotting the whimsical Rabbit Rock formation. Nature lovers, families, and moderate hikers will love this rewarding adventure through meadows, forests, and orchards.[1][2][3][5]
Discover the enchanting Ashintully Gardens, where elegant formal landscapes blend with historic mansion ruins, sculpture, and a babbling stream amid the Berkshires' forested hills. History buffs, gardeners, and serenity seekers will love this free, intimate woodland escape.[1][2]
Perfect for families and beginners, Otis Ridge offers friendly instruction, gentle terrain, and low‑key lift lines so kids and new skiers can learn, progress, and have fun together.
Park the car at Main Road and step onto a peaceful stretch of the Appalachian Trail where rolling fields, woodlands, and easy day-hike options make it perfect for families, casual hikers, and anyone craving a quick nature escape.
Spend a weekend unplugged in the Berkshires at Hume Christian Camp & Retreat Center — energizing worship, cozy campfires, and outdoor activities on 425 acres make it perfect for youth groups, church retreats, and anyone seeking faith, fellowship, and fresh‑air fun.
Cancel within 24 hours for a full refund.
Pets not allowed
No smoking - fees will apply
Events require approval
Check-in after 4:00 pm
Check-out before 11:00 am
12 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Mar 13, 2026 | $690 | Not Available |
| Mar 14, 2026 | $709 | Not Available |
| Mar 15, 2026 | $531 | Available |
| Mar 16, 2026 | $531 | Available |
| Mar 17, 2026 | $531 | Available |
| Mar 18, 2026 | $531 | Available |
| Mar 19, 2026 | $531 | Not Available |
| Mar 20, 2026 | $670 | Not Available |
| Mar 21, 2026 | $690 | Not Available |
| Mar 22, 2026 | $531 | Not Available |
| Mar 23, 2026 | $531 | Not Available |
| Mar 24, 2026 | $531 | Available |
| Mar 25, 2026 | $531 | Available |
| Mar 26, 2026 | $531 | Available |
| Mar 27, 2026 | $973 | Not Available |
| Mar 28, 2026 | $1034 | Not Available |
| Mar 29, 2026 | $531 | Not Available |
| Mar 30, 2026 | $531 | Not Available |
| Mar 31, 2026 | $587 | Not Available |
| Apr 1, 2026 | $587 | Not Available |
| Apr 2, 2026 | $587 | Not Available |
| Apr 3, 2026 | $642 | Not Available |
| Apr 4, 2026 | $653 | Not Available |
| Apr 5, 2026 | $531 | Available |
| Apr 6, 2026 | $531 | Available |
| Apr 7, 2026 | $531 | Available |
| Apr 8, 2026 | $531 | Available |
| Apr 9, 2026 | $531 | Available |
| Apr 10, 2026 | $587 | Available |
| Apr 11, 2026 | $587 | Available |
| Apr 12, 2026 | $587 | Available |
| Apr 13, 2026 | $587 | Available |
| Apr 14, 2026 | $587 | Available |
| Apr 15, 2026 | $587 | Available |
| Apr 16, 2026 | $587 | Available |
| Apr 17, 2026 | $587 | Available |
| Apr 18, 2026 | $587 | Available |
| Apr 19, 2026 | $587 | Available |
| Apr 20, 2026 | $587 | Available |
| Apr 21, 2026 | $587 | Available |
| Apr 22, 2026 | $587 | Available |
| Apr 23, 2026 | $587 | Not Available |
| Apr 24, 2026 | $815 | Not Available |
| Apr 25, 2026 | $838 | Not Available |
| Apr 26, 2026 | $587 | Available |
| Apr 27, 2026 | $587 | Available |
| Apr 28, 2026 | $587 | Available |
| Apr 29, 2026 | $587 | Available |
| Apr 30, 2026 | $587 | Available |
| May 1, 2026 | $804 | Available |
| May 2, 2026 | $824 | Available |
| May 3, 2026 | $587 | Available |
| May 4, 2026 | $587 | Available |
| May 5, 2026 | $587 | Available |
| May 6, 2026 | $587 | Available |
| May 7, 2026 | $587 | Available |
| May 8, 2026 | $741 | Not Available |
| May 9, 2026 | $764 | Not Available |
| May 10, 2026 | $587 | Available |
| May 11, 2026 | $587 | Available |
| May 12, 2026 | $587 | Available |
| May 13, 2026 | $587 | Available |
| May 14, 2026 | $587 | Available |
| May 15, 2026 | $601 | Not Available |
| May 16, 2026 | $625 | Not Available |
| May 17, 2026 | $587 | Not Available |
| May 18, 2026 | $587 | Available |
| May 19, 2026 | $587 | Available |
| May 20, 2026 | $587 | Available |
| May 21, 2026 | $1035 | Available |
| May 22, 2026 | $1035 | Not Available |
| May 23, 2026 | $1035 | Not Available |
| May 24, 2026 | $1035 | Not Available |
| May 25, 2026 | $587 | Not Available |
| May 26, 2026 | $587 | Not Available |
| May 27, 2026 | $587 | Not Available |
| May 28, 2026 | $595 | Not Available |
| May 29, 2026 | $693 | Not Available |
| May 30, 2026 | $702 | Not Available |
| May 31, 2026 | $587 | Not Available |
| Jun 1, 2026 | $587 | Not Available |
| Jun 2, 2026 | $594 | Not Available |
| Jun 3, 2026 | $615 | Not Available |
| Jun 4, 2026 | $663 | Not Available |
| Jun 5, 2026 | $787 | Not Available |
| Jun 6, 2026 | $820 | Not Available |
| Jun 7, 2026 | $719 | Available |
| Jun 8, 2026 | $653 | Available |
| Jun 9, 2026 | $631 | Available |
| Jun 10, 2026 | $631 | Available |
| Jun 11, 2026 | $703 | Available |