Winchester Holidays

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Top hotels in Winchester

The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road Gardner MA
Fully refundableReserve now, pay when you stay
The price is S$204 per night from 13 May to 14 May
S$204
13 May - 14 May
includes taxes & fees
8.8/10 Excellent! (1,012 reviews)
Excellent wedding venue

Reviewed on 8 May, 2026

The Colonial Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is S$177 per night from 7 Jun to 8 Jun
S$177
7 Jun - 8 Jun
includes taxes & fees
8.2/10 Very Good! (972 reviews)
Great experience

Reviewed on 8 May, 2026

Hampton Inn Brattleboro
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is S$154 per night from 12 May to 13 May
S$154
12 May - 13 May
includes taxes & fees
8.6/10 Excellent! (877 reviews)
Really great place to stay in Brattleboro. Clean room, friendly and helpful staff, free coffee in the lobby and a great little bar/restaurant is attached. I'll definitely be back.

Reviewed on 8 May, 2026

Latchis Hotel
See all 468 properties in Winchester
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.

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