Holiday rentals near Charles H. Baldwin & Sons
We found 1,132 holiday rentals — enter your dates for availability
If you are looking to stay near Charles H. Baldwin & Sons, scroll through and discover holiday rentals to find the perfect one for your trip. Whether you're staying in a holiday rental with a group or just with your pet, you'll find the amenities that you need and want, which might include parking and a hot tub. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Charles H. Baldwin & Sons
Showing deals for:31 Oct - 7 Nov
Image gallery for Berkshires Summer Chalet w/ Pool + Private Hiking Trails
1010 out of 10 rating
Exceptional
(7 reviews)
Berkshires Summer Chalet w/ Pool + Private Hiking Trails
Great Barrington, MA
15% off
Price is AU$6,494
AU$6,494
AU$928 per night
includes taxes & fees
Image gallery for Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
1010 out of 10 rating
Exceptional
(6 reviews)
Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
Stockbridge, MA
8% off
Price is AU$13,283
AU$13,283
AU$1,898 per night
includes taxes & fees
Image gallery for Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
1010 out of 10 rating
Exceptional
(26 reviews)
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Great Barrington, MA
8% off
Price is AU$9,090
AU$9,090
AU$1,299 per night
includes taxes & fees
Image gallery for Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
1010 out of 10 rating
Exceptional
(15 reviews)
Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
Sheffield, MA
8% off
Price is AU$6,637
AU$6,637
AU$948 per night
includes taxes & fees
Image gallery for 1500 sqft private entrance with beautiful views of the Berkshire Mountains
1010 out of 10 rating
Exceptional
(44 reviews)
1500 sqft private entrance with beautiful views of the Berkshire Mountains
Lee, MA
8% off
Price is AU$3,842
AU$3,842
AU$549 per night
includes taxes & fees
Image gallery for Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
1010 out of 10 rating
Exceptional
(13 reviews)
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
West Stockbridge, Massachusetts
17% off
Price is AU$12,029
AU$12,029
AU$1,718 per night
includes taxes & fees
Image gallery for Peaceful Retreat Compound 10 Minutes to Great Barrington!
1010 out of 10 rating
Exceptional
(26 reviews)
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Great Barrington, MA
8% off
Price is AU$12,278
AU$12,278
AU$1,754 per night
includes taxes & fees
Image gallery for Beautiful Home in AMAZING Berkshire Location
1010 out of 10 rating
Exceptional
(17 reviews)
Beautiful Home in AMAZING Berkshire Location
Lee, MA
8% off
Price is AU$6,841
AU$6,841
AU$977 per night
includes taxes & fees
Image gallery for Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
9.89.8 out of 10 rating
Exceptional
(13 reviews)
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Great Barrington, MA
6% off
Price is AU$7,091
AU$7,091
AU$1,013 per night
includes taxes & fees
Image gallery for Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Hinsdale, MA
8% off
Price is AU$2,096
AU$2,096
AU$299 per night
includes taxes & fees
Image gallery for BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS
9.69.6 out of 10 rating
Exceptional
(88 reviews)
BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS
Old Chatham, NY
8% off
Price is AU$17,867
AU$17,867
AU$2,552 per night
includes taxes & fees
Image gallery for Charming Columbia County Farm House
9.49.4 out of 10 rating
Exceptional
(25 reviews)
Charming Columbia County Farm House
Hillsdale, NY
8% off
Price is AU$2,471
AU$2,471
AU$353 per night
includes taxes & fees
Image gallery for Mountain Luxury Retreat-Amazing Views/Saltwater Pool/Family Friendly/Berkshires
1010 out of 10 rating
Exceptional
(46 reviews)
Mountain Luxury Retreat-Amazing Views/Saltwater Pool/Family Friendly/Berkshires
Copake Falls, NY
8% off
Price is AU$12,027
AU$12,027
AU$1,718 per night
includes taxes & fees
Image gallery for Private Berkshire Cabin on 27acres near Jiminy Peak.
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Private Berkshire Cabin on 27acres near Jiminy Peak.
Williamstown, MA
13% off
Price is AU$3,643
AU$3,643
AU$520 per night
includes taxes & fees
Image gallery for Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
1010 out of 10 rating
Exceptional
(11 reviews)
Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
Lee, MA
8% off
Price is AU$6,882
AU$6,882
AU$983 per night
includes taxes & fees
Image gallery for Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
1010 out of 10 rating
Exceptional
(126 reviews)
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
West Stockbridge, MA
8% off
Price is AU$4,884
AU$4,884
AU$698 per night
includes taxes & fees
Image gallery for Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.89.8 out of 10 rating
Exceptional
(29 reviews)
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale, MA
12% off
Price is AU$3,670
AU$3,670
AU$524 per night
includes taxes & fees
Image gallery for Best of the Berkshires & Hudson Valley
1010 out of 10 rating
Exceptional
(12 reviews)
Best of the Berkshires & Hudson Valley
Canaan, NY
8% off
Price is AU$5,813
AU$5,813
AU$830 per night
includes taxes & fees
Image gallery for Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
1010 out of 10 rating
Exceptional
(5 reviews)
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
Lanesborough, MA
12% off
Price is AU$4,742
AU$4,742
AU$677 per night
includes taxes & fees
Image gallery for Forget-Me-Not by AvantStay | Bold Lakefront Escape
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Forget-Me-Not by AvantStay | Bold Lakefront Escape
Monterey, Massachusetts
9% off
Price is AU$10,771
AU$10,771
AU$1,539 per night
includes taxes & fees
Image gallery for Amore Estate - beautiful room with many places to explore and relax in.
9.09.0 out of 10 rating
Wonderful
(25 reviews)
Amore Estate - beautiful room with many places to explore and relax in.
Lenox, MA
8% off
Price is AU$11,557
AU$11,557
AU$1,651 per night
includes taxes & fees
Image gallery for Modern Victorian Walk to Main Street
1010 out of 10 rating
Exceptional
(25 reviews)
Modern Victorian Walk to Main Street
Great Barrington, MA
15% off
Price is AU$5,371
AU$5,371
AU$767 per night
includes taxes & fees
Image gallery for Hudson Valley Chalet
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Hudson Valley Chalet
East Chatham, NY
26% off
Price is AU$7,080
AU$7,080
AU$1,011 per night
includes taxes & fees
Image gallery for Little Longbow Lakefront Chalet
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Little Longbow Lakefront Chalet
Becket, MA
8% off
Price is AU$5,546
AU$5,546
AU$792 per night
includes taxes & fees
Find spaces that suit your style
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Villa
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Find the best place to stay - Charles H. Baldwin & Sons
COZY LOFT w/ PRIVATE BEACH ON GORGEOUS MOUNTAIN LAKE IN THE BERKSHIRES
Sleeps 5 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
164 reviews(164 reviews)
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Sleeps 10 · 4 bedrooms · 2 bathrooms
7.27.2 out of 10
Goodgood
45 reviews(45 reviews)
The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History
Sleeps 20 · 6 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
235 reviews(235 reviews)
Villa with Access to Amazing Amenities!
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
127 reviews(127 reviews)
Private Island - Largest Fresh Water Reservoir in Mass....
Sleeps 6 · 2 bedrooms · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
7 reviews(7 reviews)
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sleeps 10 · 4 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
43 reviews(43 reviews)
Top rated rentals - Charles H. Baldwin & Sons
Lakeside in the Berkshires
1010 out of 10
Exceptionalexceptional
61 reviews(61 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value