Sheffield Vacation Home Rentals(22)
Berkshire Home w Tennis Court; great for Weddings, close to skiing
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 9
$2,900
per week
3 - 56 night minimum stay
- 4 BR,
- 3 BA,
- Sleeps 9
Berkshire Monarch Hill Retreat , Pool, Views, Secluded Setting
- 4 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 8
- 4 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 8
Antique Farmhouse Totally Restored & Crafted
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 16
$350 -
$600
per night
2 night minimum stay
- 4 BR,
- 3 BA,
- Sleeps 16
Beautiful Berkshire Country House, Views-Winter Specials!!!
- 2 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 8
$2,195
per week
7 night minimum stay
- 2 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 8
Special Offer
Selected High Season Summer Week Special (July 6 - August 30)
Ford Hill Farm
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 6
- 2 BR,
- 2 BA,
- Sleeps 6
Family Friendly Berkshires Rental
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
$175
per night
5 night minimum stay
- 3 BR,
- 2 BA,
- Sleeps 6
3 Bedroom, 2.5 Bathroom Berkshire Get Away!
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 6
$1,302
per week
7 night minimum stay
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 6
Fantastic views of Bartholemews Cobble on 12 Acres
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 8
$500
per night
2 - 30 night minimum stay
- 2 BR,
- 2 BA,
- Sleeps 8
Lovely 3BR Home on 2 Secluded Acres with Private Hot Tub
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 8
- 3 BR,
- 2 BA,
- Sleeps 8
Luxury home with pool, unique privacy and amazing views
- 5 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 9
$500
per night
2 night minimum stay
- 5 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 9
Gateway To The Berkshires
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 8
- 3 BR,
- 2 BA,
- Sleeps 8
Spectacularly Renovated 5 bedroom Barn with Pool, Pond, and Tennis!
- 5 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 12
- 5 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 12
Beautiful House, Featured in 'Country Living' Magazine
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 6
$400 -
$450
per night
2 night minimum stay
- 3 BR,
- 2 BA,
- Sleeps 6
Completely private home set on 4 acres along the banks of the Housatonic River.
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 8
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 8
Berkshires--Sheffield--Mini Estate--Luxurious
- 4 Bedrooms, Sleeps 10
- 4 BR,
- Sleeps 10
7 More choices from HomeAway International Websites
Elterwater--Sought after and rare private idyllic Berkshire lakefront
- 3 Bedrooms,
- 2 Bathrooms, Sleeps 4
$150 -
$250
per night
2 - 3 night minimum stay
- 3 BR,
- 2 BA,
- Sleeps 4
Berkshires House August Rental
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 8
$8,100
per month
30 night minimum stay
- 4 BR,
- 3 BA,
- Sleeps 8
Adorable Sheffield Cottage!! Country Feel But Close to All!!!
- 2 Bedrooms,
- 1 Bathroom,
- 1 Half Bath, Sleeps 4
$375
per night
2 night minimum stay
- 2 BR,
- 1 BA,
- 1 HF BA,
- Sleeps 4
Berkshire Country Home--Sleeps 12
- 5 Bedrooms,
- 3 Bathrooms, Sleeps 12
- 5 BR,
- 3 BA,
- Sleeps 12
Mountainside Home in the Berkshires
- 2 Bedrooms, Sleeps 10
$1,505
per week
7 night minimum stay
- 2 BR,
- Sleeps 10
Completely Private Home Set on 4 Acres
- 3 Bedrooms, Sleeps 8
- 3 BR,
- Sleeps 8
Bright, Spacious Country Home on 4.5 Acres
- 4 Bedrooms, Sleeps 6
- 4 BR,
- Sleeps 6
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