Winchester, NH

Travel Guide

Winchester, New Hampshire in winter
Winchester, New Hampshire in winter
covered bridge in winter -Ashuelot Covered Bridge, Winchester, New Hampshire
Black and white Lattice work detail on The Ashuelot Covered Bridge crosses the Ashuelot River and Bolton Road in Winchester New Hampshire
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.

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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! (1,000 reviews)
Room was large, clean; staff are always pleasant and helpful. I always enjoy my stay and take advantage of the pool and sauna.

Reviewed on 11 March 2026

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The Colonial Hotel
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd Brattleboro VT
The price is AED 349 per night from Mar 15 to Mar 16
AED 349
AED 384 total
15 Mar - 16 Mar
includes taxes & fees
Book a stay at this spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in our ...
6.8/10 (1,002 reviews)
It was good to have pool option after a ski day

Reviewed on 10 March 2026

Colonial Motel And Spa
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
The price is AED 445 per night from Mar 23 to Mar 24
AED 445
AED 490 total
23 Mar - 24 Mar
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! (951 reviews)
I wish I could have stayed longer. Very nice hotel

Reviewed on 10 March 2026

Hampton Inn Brattleboro
See all 465 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.
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Wilmington VT
Stay at this cottage in Wilmington. Enjoy a garden, laundry facilities, and an in-room coffeemaker. Popular attractions The Art of Humor Gallery and Lake Raponda ...
8.6/10 Excellent! (66 reviews)
Cozy and peaceful, just with they had turned the heat up before u got there. It was like 45-50 when I arrived and had to figure out the heating and wait for it to warm up for the first few hours.

Reviewed on 19 February 2026

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
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! (49 reviews)
Very clean, cozy and lots of nice plants!

Reviewed on 26 February 2026

Lovely 2nd Floor Apartment
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! (63 reviews)
Wonderful property. Perfect for our family trip. Plenty of room , the basement being the most used by the kids. Clean, neat with all the essentials. Large kitchen well stocked. Sledding on the property itself was priceless. Would definitely recommend and rent again. Hosts and property manager available ...

Reviewed on 5 February 2026

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

Cass Pond

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

Cass Pond

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

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

Winchester Speedpark

You can take time to visit Winchester Speedpark during your travels to Winchester. While you're in the area, stroll along the lakeside.

Winchester Speedpark

Richmond Town Hall

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

Richmond Town Hall

Loring Field

Explore the great outdoors at Loring Field, a lovely green space in Winchester. While you're in the area, stroll along the lakeside.

Loring Field

Reviews of Winchester

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Top Destination
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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.