Apartment
10.0(7 Reviews)
1 Bedroom
2 Guests
Kitchen
Air Conditioner
Internet
Child Friendly
US $187/Night
7 Nights - US $1,312
Sheffield, MA Holiday Rentals
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Compare Villas, Resorts, & Rentals in Sheffield
10.0
Bed & Breakfast
9.5(50 Reviews)
5 Bedrooms
11 Guests
Parking
Balcony/Terrace
View- Air Conditioner
US $235/Night
7 Nights - US $1,645
Bed & Breakfast
9.8(70 Reviews)
1 Bedroom
Breakfast- Parking
- Balcony/Terrace
- Kitchen
US $231/Night
7 Nights - US $1,614
House
8.8(9 Reviews)
4 Bedrooms
12 Guests
Pool- Balcony/Terrace
- Kitchen
- Air Conditioner
US $484/Night
7 Nights - US $3,386
House
9.0(3 Reviews)
3 Bedrooms
6 Guests
- Parking
- Internet
Sports/Activities
Security/Safety
US $383/Night
7 Nights - US $2,679
House
8.0(1 Review)
4 Bedrooms
8 Guests
Private Pool- Parking
- Pool
Skiing
US $1,520/Night
7 Nights - US $10,640
Apartment
10.0(9 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $260/Night
7 Nights - US $1,822
Apartment
9.8(8 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $186/Night
7 Nights - US $1,299
House
10.0(11 Reviews)
3 Bedrooms
5 Guests
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
US $459/Night
7 Nights - US $3,214
Luxury Holiday Rentals in Sheffield
Over 38+ Luxury Holiday Rentals in or Near Sheffield
House
10.0(122 Reviews)
4 Bedrooms
9 Guests
- Parking
- Skiing
- Balcony/Terrace
- Kitchen
US $1,180/Night
7 Nights - US $8,262
New
House
10.0(1 Review)
4 Bedrooms
7 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $764/Night
7 Nights - US $5,348
House
10.0(15 Reviews)
3 Bedrooms
7 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $731/Night
7 Nights - US $5,114
New
House
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $673/Night
7 Nights - US $4,710
House
10.0(7 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Kitchen
US $661/Night
7 Nights - US $4,629
House
10.0(65 Reviews)
4 Bedrooms
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $654/Night
7 Nights - US $4,578
House
8.8(18 Reviews)
5 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $628/Night
7 Nights - US $4,396
House
10.0(5 Reviews)
4 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $573/Night
7 Nights - US $4,009
US $551/Night
7 Nights - US $3,857
Top-Rated Holiday Rentals with a Pool in Sheffield
Over 2+ The Best Private Villas and Holiday Rentals in Sheffield with a Pool
New
House
4 Bedrooms
10 Guests
- Private Pool
- Parking
- Pool
- Kitchen
US $458/Night
7 Nights - US $3,205
US $190/Night
7 Nights - US $1,329
Pet-Friendly Holiday Rentals in Sheffield
Over 9+ Pet-Friendly Holiday Rentals in or Near Sheffield
House
4 Bedrooms
11 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $484/Night
7 Nights - US $3,388
House
9.0(1 Review)
5 Bedrooms
10 Guests
- Parking
- Kitchen
- Internet
Pet Friendly
US $217/Night
7 Nights - US $1,519
House
8.0(1 Review)
3 Bedrooms
5 Guests
- Hot Tub
- Parking
- Skiing
- Balcony/Terrace
US $271/Night
7 Nights - US $1,897
House
10.0(194 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $348/Night
7 Nights - US $2,436
House
9.8(36 Reviews)
3 Bedrooms
9 Guests
- Parking
Ocean View- Balcony/Terrace
- View
US $489/Night
7 Nights - US $3,423
House
8 Bedrooms
18 Guests
Spa- Balcony/Terrace
- Internet
- Pet Friendly
US $1,315/Night
7 Nights - US $9,204
House
10.0(6 Reviews)
4 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $796/Night
7 Nights - US $5,575
House
3 Bedrooms
6 Guests
- Breakfast
- Spa
- Air Conditioner
- Internet
US $82/Night
7 Nights - US $572
House
10.0(34 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $644/Night
7 Nights - US $4,506
Large Holiday Rentals and Private Villas in Sheffield
Over 5+ Large Holiday Rentals and Private Villas in or Near Sheffield
House
4 Bedrooms
10 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
US $362/Night
7 Nights - US $2,535
House
4 Bedrooms
14 Guests
US $612/Night
7 Nights - US $4,283
House
10.0(34 Reviews)
4 Bedrooms
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $486/Night
7 Nights - US $3,401
House
10.0(52 Reviews)
5 Bedrooms
15 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $756/Night
7 Nights - US $5,293
House
4.8(17 Reviews)
5 Bedrooms
10 Guests
- Balcony/Terrace
- View
- Kitchen
- Air Conditioner
US $275/Night
7 Nights - US $1,925
Sheffield Private Villas and Holiday Homes Under $200
Over 4+ Sheffield Private Villas and Holiday Homes Under $200
House
10.0(1 Review)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $157/Night
7 Nights - US $1,101
Cottage
4.9(29 Reviews)
1 Bedroom
5 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $160/Night
7 Nights - US $1,120
US $188/Night
7 Nights - US $1,316
House
2 Bedrooms
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Child Friendly
US $100/Night
7 Nights - US $700
Instantly Bookable Holiday Homes in Sheffield
Over 3+ Instantly Bookable Holiday Homes in or Near Sheffield
House
9.6(26 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $500/Night
7 Nights - US $3,499
House
10.0(45 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $427/Night
7 Nights - US $2,989
House
9.8(22 Reviews)
3 Bedrooms
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $356/Night
7 Nights - US $2,492
Book a Last Minute Place to Stay in Sheffield
About Casai's Private Villas and Holiday Rentals in Sheffield
Discover more than 47 vacation rentals available in Sheffield. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Sheffield.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Sheffield, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Sheffield. On average, places to stay near Sheffield offer 1588.7 ft², with nightly prices averaging US $478.
With Casai, finding and comparing holiday rentals in Sheffield is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other places to stay near the Sheffield, MA
There are 47 Sheffield, MA Holiday Rentals
- Prices for a holiday home in Sheffield start at US $186
- Top rated vacation home in Sheffield is Spectacular 88-acre Berkshires Retreat w/Tennis Court - Family Friendly
- Most popular short term in Sheffield is Spectacular 88-acre Berkshires Retreat w/Tennis Court - Family Friendly
- Cheapest place to stay in Sheffield is Remodeled Unit #2, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
- Most expensive holiday rental in Sheffield is Historic (updated)1812 Federal brick house well situated in Berkshires with pool
Recently Booked Holiday Rentals in Sheffield
Frequently Asked Questions About Sheffield?
What are the top holiday rentals in Sheffield?
With numerous options available in Sheffield, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Sheffield:
- Spectacular 88-acre Berkshires Retreat w/Tennis Court - Family Friendly
- Family Friendly in Sheffield, private yet close to everything!
- Cheerful 3-bedroom cottage with woodstove
- 12 minutes to Butternut Skiing, Good For 3 Families with Hot Tub & Game Room
- Serene Berkshire Artist's House
- Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
- Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.
- Berkshires Getaway Walk to Distillery - No Pet Fee!
- Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts
- Peaceful and Private Setting
Which holiday homes in Sheffield are best for families?
If you're searching for a family-friendly holiday home in Sheffield, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Sheffield:
How many Casai.com holiday rentals are available in Sheffield?
As of 2026, Casai boasts over 47 properties listed in the Sheffield area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Sheffield.
