Cheshire Holiday Packages

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Don't waste your hard-earned cash! Be a sensible spender with Wotif.

Our fantastic packages combine your hotels and flights to make life simpler.

This way, you'll have extra finances for your Cheshire holiday.

Many travellers save up to . Also, you have the flexibility to pick and choose from more than 550 airlines and 665,000 properties.

Some of the most competitive prices available can be found on Wotif. So pack your luggage, pull out your passport and get moving!

Cheshire Accommodation

Wotif's got your back when it comes to locking in the best place to stay. You'd best get cracking though. There are only 3 accommodations in Cheshire.

You've earned this getaway, right? Then it's fitting you should stay in a place with great facilities and excellent reviews. Our recommendations are the Topia Inn - An Organic Oasis and The Spring's Inn.

Holidays to Cheshire

Booked those plane tickets, packed your fave thongs but don't know a thing about Cheshire? Listen up. We'll let you in on this awesome destination.

Cheshire is just down the road from a few major cities that'll help you get your bearings. Just 8 kilometres to the north is Adams. The town isn't far from Pittsfield either. You only need to travel southwest for 15 kilometres before you hit it.

With so many awesome things on offer in the area, it's not hard to see why approximately 500 people call this area of The Berkshires home.

Top Cheshire hotels

Harbour House Inn

Harbour House Inn

3.5 out of 5
725 North State Road, Cheshire, MA
The price is AU$387 per night from 13 Aug to 14 Aug
AU$387
13 Aug - 14 Aug
includes taxes & fees
Harbour House Inn: Bed & breakfast with free breakfast and free WiFi. Located in the mountains.
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!!"

Reviewed on 4 Jul. 2025

Harbour House Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is AU$168 per night from 25 Aug to 26 Aug
AU$168
25 Aug - 26 Aug
includes taxes & fees
Vacation Village in the Berkshires: Family-friendly condo with free WiFi and free parking. Located near theme parks.
"The staff was very friendly. The room and property were fairly clean. There were used pillow cases left on our bed and a safety pin and toothpick left on the dresser when we arrived. Comfortable but out dated. Definitely could use a renovation."

Reviewed on 28 Jul. 2025

Vacation Village in the Berkshires
Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is AU$295 per night from 3 Aug to 4 Aug
AU$295
3 Aug - 4 Aug
includes taxes & fees
Hotel Downstreet, Ascend Hotel Collection: Pet-friendly hotel with free WiFi and free parking. Located in the entertainment district.
"Loved the staff and art centric area."

Reviewed on 27 Jul. 2025

Hotel Downstreet, Ascend Hotel Collection
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.