We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Search results; Over 1,000 homes in Sheffield

Photo 1 of 27

Top Guest favourite

Apartment in Sheffield

Hideaway with Spectacular Berkshire Views

1 bedroom, 2 beds, 1 private bath

24–29 Oct

$1,606 AUD total

,

5.0 out of 5 average rating, 416 reviews

Photo 1 of 29

Superhost

Home in Sheffield

Timber Frame • Big Deck • Game Room | Near Trails

4 bedrooms, 6 beds, 4 baths

4–9 Oct

$2,352 AUD total

New place to stay

Photo 1 of 29

Cottage in Sheffield

Charming Handcrafted Cottage in the Berkshires!

3 bedrooms, 5 beds, 2 baths

12–17 Oct

$2,255 AUD total

4.78 out of 5 average rating, 101 reviews

Photo 1 of 27

Guest favourite

Home in Sheffield

Bull Hill Bungalow

3 bedrooms, 3 beds, 2 baths

25–30 Oct

$2,042 AUD total

Free cancellation

4.98 out of 5 average rating, 55 reviews

Photo 1 of 29

Cabin in Sheffield

Log Cabin - playroom, fireplace, skiing - $0 fees

4 bedrooms, 8 beds, 3 baths

1–6 Oct

$2,611 AUD total

4.77 out of 5 average rating, 353 reviews

Photo 1 of 24

Guest favourite

Home in Sheffield

Berkshires Retreat w/ Pickleball – for Big Groups!

7 bedrooms, 8 beds, 3.5 baths

1–6 Oct

5.0 out of 5 average rating, 10 reviews

Photo 1 of 29

Top Guest favourite

Home in Sheffield

Family friendly house with fenced yard & fire pit

3 bedrooms, 3 beds, 2 baths

26–31 Oct

$2,636 AUD total

Free cancellation

4.97 out of 5 average rating, 33 reviews

Photo 1 of 29

Home in Sheffield

Berkshire Lake Hideaway

3 bedrooms, 5 beds, 3 baths

4–9 Oct

$2,911 AUD total

New place to stay

Photo 1 of 29

Guest favourite

Home in Sheffield

Berkshire Getaway~ No Pet Fee! Walk to Distillery

3 bedrooms, 3 beds, 2 baths

26–31 Oct

4.9 out of 5 average rating, 103 reviews

Photo 1 of 29

Superhost

Home in Sheffield

Pool Open Through Columbus Day - Sleeps 10!

3 bedrooms, 7 beds, 3 baths

1–6 Oct

$6,358 AUD total

New place to stay

Photo 1 of 16

Guest favourite

Barn in Sheffield

Modern Dairy Barn

4 bedrooms, 5 beds, 3 baths

25–30 Oct

$3,745 AUD total

5.0 out of 5 average rating, 27 reviews

Photo 1 of 29

Top Guest favourite

Home in Sheffield

Belle Meade

2 bedrooms, 2 beds, 2 baths

8–13 Dec

$3,432 AUD total

4.99 out of 5 average rating, 134 reviews

Photo 1 of 29

Guest favourite

Home in Sheffield

Serene Berkshire Artist's House

3 bedrooms, 3 beds, 2.5 baths

4–9 Oct

$3,572 AUD total

4.99 out of 5 average rating, 69 reviews

Photo 1 of 29

Top Guest favourite

Home in Sheffield

Beautiful Berkshires Home | Perfect For 3 Families

4 bedrooms, 9 beds, 2 baths

12–17 Oct

$4,762 AUD total

4.97 out of 5 average rating, 29 reviews

Photo 1 of 28

Guest favourite

Home in Sheffield

Ashley Falls Home w/ Fire Pit: Hike & Ski!

5 bedrooms, 6 beds, 3 baths

26–31 Oct

$2,331 AUD total

4.9 out of 5 average rating, 52 reviews

Photo 1 of 29

Top Guest favourite

Home in Sheffield

52-Acre Berkshires Farmhouse • Fire Pit + Trails

4 bedrooms, 9 beds, 2.5 baths

1–6 Oct

5.0 out of 5 average rating, 15 reviews

Photo 1 of 29

Top Guest favourite

Home in Sheffield

The Kellogg House in the Heart of The Berkshires

2 bedrooms, 2 queen beds, 1 bath

1–6 Oct

$2,656 AUD total

4.99 out of 5 average rating, 73 reviews

Photo 1 of 29

Home in Sheffield

Water-View Home in the Berkshires

3 bedrooms, 4 beds, 2 baths

17–22 Oct

$2,574 AUD total

4.95 out of 5 average rating, 39 reviews

Photo 1 of 29

Guest favourite

Cottage in Sheffield

Cheerful 3-bedroom cottage with woodstove.

3 bedrooms, 3 beds, 2.5 baths

25–30 Oct

$1,721 AUD total

4.92 out of 5 average rating, 196 reviews

Enter dates and number of guests to show the total trip price including additional fees (but excluding any taxes).