Winchester, NH

Travel Guide

The Ashuelot Covered Bridge is a historic wooden covered bridge over the Ashuelot River on Bolton Road, just south of its intersection with NH 119 in Ashuelot, New Hampshire, an unincorporated village of Winchester.
The Ashuelot Covered Bridge is a historic wooden covered bridge over the Ashuelot River on Bolton Road, just south of its intersection with NH 119 in Ashuelot, New Hampshire, an unincorporated village of Winchester.
The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road Gardner MA
Book a stay at this business-friendly hotel in Gardner. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
8.8/10 Excellent! (1,002 reviews)
Amazing hotel and outstanding staff. Would absolutely stay here again.

Reviewed on 17 January 2026

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The Colonial Hotel
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
The price is SAR 500 per night from Jan 29 to Jan 30
SAR 500
SAR 550 total
29 Jan - 30 Jan
includes taxes & fees
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.4/10 Very Good! (758 reviews)
Great staff

Reviewed on 5 January 2026

Comfort Inn & Suites Brattleboro I-91
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
The price is SAR 550 per night from Jan 30 to Jan 31
SAR 550
SAR 605 total
30 Jan - 31 Jan
includes taxes & fees
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the ...
8.2/10 Very Good! (936 reviews)
As always, Hampton Inn are great. I think I’m reliable, super comfortable, good breakfast. What makes this location stand out was the really outstanding customer service. Everyone was so helpful and engaging and funny! Which always helps. So, we’ll definitely be back.

Reviewed on 17 January 2026

Hampton Inn Brattleboro
See all 456 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.
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Townshend VT
Book a stay at this family-friendly vacation home in Townshend. Enjoy free WiFi, private pools, and a garden. Popular attractions Townshend State Park and Townshend ...
10/10 Exceptional! (62 reviews)
The home was as pictured. Great space to host larger groups of people

Reviewed on 17 November 2025

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Beautiful, private log cabin with huge, relaxing screened porch

Beautiful, private log cabin with huge, relaxing screened porch

Townshend VT
Book a stay at this family-friendly vacation home in Townshend. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Townshend State Park and ...
10/10 Exceptional! (43 reviews)
This was a great little place for our family to stay while we enjoyed the local ski resorts. The kitchen was well appointed and there was plenty of room. Everything was clean as well.

Reviewed on 15 January 2026

Beautiful, private log cabin with huge, relaxing screened porch
Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment

Greenfield MA
Book a stay at this family-friendly vacation home in Greenfield. Enjoy a garden, an in-room coffeemaker, and housekeeping. Popular attractions Poet's Seat Tower ...
10/10 Exceptional! (46 reviews)
Beautifully appointed and comfortable.

Reviewed on 4 January 2026

Lovely 2nd Floor Apartment
See all 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.

Popular places to visit

New England Sweetwater Farm & Distillery

You can take time to visit New England Sweetwater Farm & Distillery during your travels to Winchester. While you're in the area, stroll along the lakeside.

New England Sweetwater Farm & Distillery

Bennett Gorge

You can take time to visit Bennett Gorge during your travels to Richmond.

Bennett Gorge

Cass Pond

Commune with nature and explore the great outdoors at Cass Pond during your travels in Richmond.

Cass Pond

Richmond Town Hall

After visiting Richmond Town Hall, make a plan to see the other sights and activities in Richmond.

Richmond Town Hall

Barden State Wildlife Management Area

Explore the great outdoors at Barden State Wildlife Management Area, a lovely green space in Richmond.

Barden State Wildlife Management Area

Richmond Wildlife Manangement Area

Explore the great outdoors at Richmond Wildlife Manangement Area, a lovely green space in Richmond.

Richmond Wildlife Manangement Area

Reviews of Winchester

4
Top Destination
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4 - Good 100%
3 - Okay
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4/5 - Good

Verified traveler

We found a great diner, the food was delicious and the staff was wonderful. The only drawback was it being so far away from any major stores.