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$411 per night from 15 Dec to 16 Dec
AU$411
15 Dec - 16 Dec
includes taxes & fees
Harbour House Inn: Bed & breakfast with free breakfast and free WiFi. Located near skiing.
The owner Brandi was outstanding, friendly, she made us fresh homemade breakfast each morning, which the best. Will differently stay there again. Wonderful place and people.

Reviewed on 12 Sept 2025

Opens in a new windowHarbour 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$185 per night from 15 Nov to 16 Nov
AU$185
15 Nov - 16 Nov
includes taxes & fees
Vacation Village in the Berkshires: Family-friendly condo with free WiFi and free parking. Located near skiing.
We loved almost everything, but they need to replace sofa, armchair and the bed in this unit. Too old. The sofa and armchair have bad smell of very old furniture.

Reviewed on 7 Nov 2025

Opens in a new windowVacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St, North Adams, MA
Fully refundable
The price is AU$247 per night from 15 Dec to 16 Dec
AU$247
15 Dec - 16 Dec
includes taxes & fees
Hotel Downstreet, an Ascend Collection Hotel: Pet-friendly hotel with free WiFi and free parking. Located near skiing.
Very clean and inviting Hotel located in downtown area. Very walkable area. Parking was free. Front desk very friendly and helpful. Would stay again.

Reviewed on 3 Nov 2025

Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
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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.