Winchester accommodation from AU$125

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The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road, Gardner, MA
The price is AU$240 per night
AU$240
includes taxes & fees
25 Nov - 26 Nov
42.31 km from city centre
The Colonial Hotel: Pet-friendly hotel with free WiFi and free parking. Located near skiing.
Pool
Hot tub
Free cancellation
Reserve now, pay when you stay
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
The price is AU$178 per night
AU$178
includes taxes & fees
3 Dec - 4 Dec
18.53 km from city centre
Colonial Motel And Spa: Pet-friendly motel with free WiFi and free parking. Located near skiing.
Free cancellation
Reserve now, pay when you stay
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road, Brattleboro, VT
The price is AU$125 per night
AU$125
includes taxes & fees
29 Nov - 30 Nov
18.68 km from city centre
The Covered Bridge Inn: Business-friendly hotel with free breakfast and free WiFi. Located near skiing.
Free cancellation
Reserve now, pay when you stay
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
The price is AU$164 per night
AU$164
includes taxes & fees
22 Dec - 23 Dec
19.03 km from city centre
Hampton Inn Brattleboro: Pet-friendly hotel with free breakfast and free WiFi. Located near skiing.
Pool
Hot tub
Free cancellation
Reserve now, pay when you stay
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

3 out of 5
75 Railroad St, Keene, NH
The price is AU$197 per night
AU$197
includes taxes & fees
23 Dec - 24 Dec
19.73 km from city centre
Courtyard by Marriott Keene Downtown: Pet-friendly hotel with free WiFi and free parking. Located in the city centre.
Free cancellation
Reserve now, pay when you stay
The Putney Inn

The Putney Inn

2.5 out of 5
57 Putney Landing Rd, Putney, VT
The price is AU$155 per night
AU$155
includes taxes & fees
25 Nov - 26 Nov
23.92 km from city centre
The Putney Inn: Pet-friendly motel with free breakfast and free WiFi. Guests love the helpful staff!
Free cancellation
Reserve now, pay when you stay
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road, Brattleboro, VT
The price is AU$175 per night
AU$175
includes taxes & fees
25 Nov - 26 Nov
18.95 km from city centre
Comfort Inn & Suites Brattleboro I-91: Business-friendly hotel with free breakfast and free WiFi. Located near ski lifts.
Free cancellation
Reserve now, pay when you stay
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

2.5 out of 5
184 Shelburne Rd, Greenfield, MA
The price is AU$232 per night
AU$232
includes taxes & fees
8 Dec - 9 Dec
28.52 km from city centre
Hampton Inn & Suites Greenfield: Pet-friendly hotel with free breakfast and free WiFi. Located near skiing.
Pool
Breakfast included
Free cancellation
Reserve now, pay when you stay
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

2.5 out of 5
126 Key Rd, Keene, NH
The price is AU$224 per night
AU$224
includes taxes & fees
19 Dec - 20 Dec
18.21 km from city centre
Hampton Inn & Suites Keene: Pet-friendly hotel with free WiFi and free parking. Guests love the helpful staff!
Free cancellation
Reserve now, pay when you stay
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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.

Accommodation in Winchester

You'll struggle to find accommodation in the centre of Winchester. There's only 1 hotel within 10 kilometres, so you must hurry!

The Centennial House may be your only choice if you are keen on staying close to the action.

If you don't have any issues with staying 20 kilometres outside of the city's core, consider the neighbourhood of Keene. It's got 5 accommodation options available, such as Fairfield Inn & Suites by Marriott Keene Downtown and Courtyard by Marriott Keene Downtown.

If you find yourself in need of more accommodation options in Winchester, try the 1868 Crosby House and the Hampton Inn & Suites Greenfield. They are located 18 kilometres and 30 kilometres away from the center. Further alternatives are the Chesterfield Inn, 18 kilometres away, and the Riverside Hotel, an Ascend Hotel Collection Member, 18 kilometres.

Attractions and Hotels Near Winchester

Why not stay an extra couple of nights and enjoy all New Hampshire offers? You could tour regional places of interest, enjoy snowboarding and skiing, or simply lose yourself in the area's forests and lakes.

If you want to check out some nearby cities, check out Keene and Bennington. Travel 20 kilometres to the northeast from Winchester and you'll discover Keene. That said, Bennington is 45 kilometres to the northeast. Keene hotels and apartments include the Holiday Inn Express Keene and Best Western Plus Keene Hotel. Bennington choices include the Crotched Mountain Resort and Maplehurst Inn.

Mad about sport? Enjoy your obsession by visiting Mullins Center, which is situated to the south of Winchester. Those wanting to sleep nearby can select from The Lord Jeffery Inn and the Courtyard by Marriott Hadley Amherst.

Manchester-Boston Regional Airport is the nearest preferred airport for flying into Winchester and is 80 kilometres from the heart of town. If you would like to stay nearby, try the Homewood Suites by Hilton Manchester/Airport or the Holiday Inn Manchester Airport.

Winchester hotels essential information

Accommodation
394 hotels
Lowest Price
AU$125
Highest Price
AU$240
Popular hotels
The Colonial Hotel, Colonial Motel And Spa, The Covered Bridge Inn, Hampton Inn Brattleboro, Courtyard by Marriott Keene Downtown, The Putney Inn, Comfort Inn & Suites Brattleboro I-91, Hampton Inn & Suites Greenfield, Hampton Inn & Suites Keene

Frequently asked questions

How many days should I spend in Winchester?
There’s a whole bunch of things you’ll want to consider before you book that Winchester hotel, starting with exactly what you want to do and see. Think about whether you prefer a fast-paced or more leisurely experience. Also work out how your budget aligns with the cost of accommodation, any tours you book and daily expenses.
Where should a first-time tourist stay in Winchester?
If you’ve never visited Winchester before, make your trip as easy as possible. Stay someplace central so you’ll be near the top sights, public transport and things like restaurants or cafés. Look for Winchester hotels that are in good locations and come highly recommended by other first-time travellers.
How much does a Winchester hotel cost?
Winchester hotel prices vary depending on when you travel and just how swish you want your digs to be. To lock in AU$125 cheap accommodation in Winchester, enter your details, click search, then filter your results by budget, property class, amenities and more. Want another cost-saving tip? Avoid booking in the busiest months of June, July and August, when rates are generally higher. Because the only thing better than going on holiday is getting it for a steal!
How do I get a cheap hotel in Winchester?
Crack the code to finding cheap hotels in Winchester with some of these tips and tricks:

  • Choose midweek stays: Rates are nearly always cheaper between Monday and Thursday.
  • Unlock a treasure trove of savings: Sign up for a Wotif account and join those in the know who enjoy Mates Rates, including discounts of 10% or more.
  • Go off-peak: October, November and December are Winchester’s slower months. Flights, accommodation and sightseeing activities are more affordable during these times.
  • Refine your search using our handy filter tool: Then simply sort by the lowest price to score a sweet deal.

What is the best area to stay in Winchester?
Have a squiz at the vibrant East Swanzey neighbourhood. Or, for other Winchester accommodation options nearby, click “View map” at the top of the page. Wherever you decide to kick back here, Wotif will help you find the perfect spot for your Winchester hotel.

New reviews! Best hotels in Winchester

The Covered Bridge Inn
Wotif Verified Review
5 / 5
The housekeeping services were excellent and the staff was friendly The facility is a bit old but incredibly clean
A verified traveller stayed at The Covered Bridge Inn
Posted 3 days ago
The Covered Bridge Inn

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