Title: Visit Winchester: 2026 Travel Guide for Winchester, New Hampshire | Expedia.com

[Hotels in Winchester](https://expedia.com/Winchester-Hotels.d3000447144.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.com/Winchester-Vacation-Rentals.d3000447144.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.com/Cheap-Flights-To-Winchester.d3000447144.Travel-Guide-Flights)[Car Rentals in Winchester](https://expedia.com/Car-Rentals-In-Winchester.d3000447144.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.com/Winchester.d3000447144.Destination-Travel-Guides)

# Winchester, NH

## Travel Guide

![Winchester, New Hampshire in winter ](https://images.trvl-media.com/place/3000447144/3e6a6279-072b-4adb-98ce-884d4d6659f9.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Winchester, New Hampshire in winter ](https://images.trvl-media.com/place/3000447144/3e6a6279-072b-4adb-98ce-884d4d6659f9.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![covered bridge in winter 
-Ashuelot Covered Bridge, Winchester, New Hampshire ](https://images.trvl-media.com/place/3000447144/a4923834-5259-4cab-a093-d05a4fb5d95d.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Black and white Lattice work detail on The Ashuelot Covered Bridge crosses the Ashuelot River and Bolton Road in Winchester New Hampshire](https://images.trvl-media.com/place/3000447144/e01c36c6-26e4-4e34-acfd-f05d6b9e1aec.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![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.](https://images.trvl-media.com/place/3000447144/529ffd18-db0c-4d9e-8844-fe610e44574f.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

## Visit Winchester

Things to do

Reviews

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

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- Winchester Hotel Deals
- Vacation Rentals in Winchester

![The Colonial Hotel](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/93940b92_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Colonial Hotel

625 Betty Spring Road Gardner MA

$160 nightly

$179 total

Mar 11 - Mar 12

Total with taxes and fees

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! (1,010 reviews)

This property needs a serious update. The property looks tired. Attempted to use the fitness room and it was dirty and much of the equipment was unusable. The pool and jacuzzi were closed and looked disgusting. The common areas and room felt unclean

Reviewed on Mar 2, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F11%2F2026&endDate=3%2F12%2F2026&selected=40458&PinnedHotelID=40458&HadPinnedHotel=true&regionId=3000447144)

![Colonial Motel And Spa](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/05f7e3bc_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Colonial Motel And Spa

889 Putney Rd Brattleboro VT

$100 nightly

$110 total

Mar 11 - Mar 12

Total with taxes and 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 (1,006 reviews)

There are two sections to the property. We asked to switch rooms because it smelled moldy on the one side. The other was in much better conditions, no smell, rooms very large, and clean. The pool is run by another company and they are strict about pool hours.

Reviewed on Mar 2, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F11%2F2026&endDate=3%2F12%2F2026&selected=1070729&PinnedHotelID=1070729&HadPinnedHotel=true&regionId=3000447144)

![Hampton Inn Brattleboro](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/44065a1d_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT

$106 nightly

$116 total

Mar 16 - Mar 17

Total with taxes and 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! (950 reviews)

I wish I could have stayed longer. Very nice hotel

Reviewed on Mar 10, 2026

[](https://expedia.com/Hotel-Search?startDate=3%2F16%2F2026&endDate=3%2F17%2F2026&selected=1158047&PinnedHotelID=1158047&HadPinnedHotel=true&regionId=3000447144)

[See all 466 properties in Winchester](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=3%2F11%2F2026&endDate=3%2F12%2F2026&regionId=3000447144)

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](https://images.trvl-media.com/lodging/92000000/91080000/91076100/91076053/9fe7ea33_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

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 Feb 19, 2026

[](https://expedia.com/Wilmington-Hotels-Cottage-In-The-Woods-With-A-Firepit.h91076053.Hotel-Information)

![Lovely 2nd Floor Apartment](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/01ff54d0_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

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 Feb 26, 2026

[](https://expedia.com/Greenfield-Hotels-Lovely-2nd-Floor-Apartment.h102386531.Hotel-Information)

![Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns](https://images.trvl-media.com/lodging/72000000/71940000/71933600/71933561/ce0724c0_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

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 Feb 5, 2026

[](https://expedia.com/Townshend-Hotels-Modern-Private-Home-30-Acres-W-Pool.h71933561.Hotel-Information)

[See all properties in Winchester](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&regionId=3000447144&sort=VACATION_RENTAL)

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.

## Check Winchester hotel availability

[Tonight

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=3000447144&startDate=2026-03-10&endDate=2026-03-11)[Mar 10 - Mar 11](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=3000447144&startDate=2026-03-10&endDate=2026-03-11)

[Tomorrow night

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=3000447144&startDate=2026-03-11&endDate=2026-03-12)[Mar 11 - Mar 12](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=3000447144&startDate=2026-03-11&endDate=2026-03-12)

[This weekend

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=3000447144&startDate=3%2F13%2F2026&endDate=3%2F15%2F2026)[Mar 13 - Mar 15](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=3000447144&startDate=3%2F13%2F2026&endDate=3%2F15%2F2026)

[Next weekend

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=3000447144&startDate=3%2F20%2F2026&endDate=3%2F22%2F2026)[Mar 20 - Mar 22](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=3000447144&startDate=3%2F20%2F2026&endDate=3%2F22%2F2026)

### Popular places to visit

#### 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. 

[](https://expedia.com/Winchester-Speedpark-Winchester.d934550877316976640.Vacation-Attraction)

#### Barden State Wildlife Management Area

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

[](https://expedia.com/Barden-State-Wildlife-Management-Area-Winchester.d934551042299895808.Vacation-Attraction)

#### 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. 

[](https://expedia.com/New-England-Sweetwater-Farm-Distillery-Winchester.d934551452230144000.Vacation-Attraction)

#### Cass Pond

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

[](https://expedia.com/Cass-Pond-Winchester.d934550841938022400.Vacation-Attraction)

#### Richmond Town Hall

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

[](https://expedia.com/Richmond-Town-Hall-Winchester.d934551059299713024.Vacation-Attraction)

#### 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. 

[](https://expedia.com/Loring-Field-Winchester.d934551530481532928.Vacation-Attraction)

## Reviews of Winchester

4

Top Destination

5 - Excellent

0

4 - Good

1

3 - Okay

0

2 - Disappointing

0

1 - Terrible

0

### 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.

## Cities near Winchester

![Aerial winter view of Fitzwilliam, New Hampshire ](https://images.trvl-media.com/place/104340/6fa042d8-f5d2-4551-a4e1-8b2736cb31e3.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Fitzwilliam

![A hidden oasis from a forgotten era. A small pool of crystal clear water forms just outside the stone tunnel. An absolutely breath-taking find. The exact location couldn't be remembered, but I do remember its along this river and under the rail line. ](https://images.trvl-media.com/place/6025729/436902cc-a7f3-4edc-b09f-8b1c08f61297.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Northfield

![Chesterfield showing autumn leaves, tranquil scenes and forest scenes](https://images.trvl-media.com/place/6052872/fc91b262-156e-463c-9b9c-bb779209c85d.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Chesterfield

![Aerial view of West Swanzey New Hampshire in early fall  ](https://images.trvl-media.com/place/6348108/1856e823-b9c5-4cc3-880a-1fd676222faf.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Swanzey

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- [Visit Ashuelot ](https://www.expedia.com/Ashuelot.dx3000421398)
- [Visit Hinsdale ](https://www.expedia.com/Hinsdale.dx3000447021)
- [Visit Spofford ](https://www.expedia.com/Spofford.dx6267420)
- [Visit Swanzey ](https://www.expedia.com/Swanzey.dx6348108)
- [Visit Chesterfield ](https://www.expedia.com/Chesterfield.dx6052872)
- [Madame Sherri Forest ](https://www.expedia.com/Madame-Sherri-Forest-West-Chesterfield.d553248621587477429.Vacation-Attraction)
- [Madame Sherris Castle Ruins ](https://www.expedia.com/Madame-Sherris-Castle-Ruins-West-Chesterfield.d6273836.Vacation-Attraction)
- [Rhododendron State Park ](https://www.expedia.com/Rhododendron-State-Park-New-Hampshire.d553248621532667357.Vacation-Attraction)
- [Spofford Lake ](https://www.expedia.com/Spofford-Lake-Spofford.d6265753.Vacation-Attraction)
- [Visit West Chesterfield ](https://www.expedia.com/West-Chesterfield.dx183592)
- [Stonewall Farm ](https://www.expedia.com/Stonewall-Farm-Keene.d553248621532666932.Vacation-Attraction)

- [Car rentals near Hinsdale ](https://www.expedia.com/Car-Rentals-In-Hinsdale.d3000447021.Car-Rental-Guide)
- [Car rentals near East Swanzey ](https://www.expedia.com/Car-Rentals-In-East-Swanzey.d553248635976384897.Car-Rental-Guide)
- [Car rentals near Spofford ](https://www.expedia.com/Car-Rentals-In-Spofford.d6267420.Car-Rental-Guide)
- [Car rentals near Swanzey ](https://www.expedia.com/Car-Rentals-In-Swanzey.d6348108.Car-Rental-Guide)
- [Car rentals near Chesterfield ](https://www.expedia.com/Car-Rentals-In-Chesterfield.d6052872.Car-Rental-Guide)
- [Car rentals near Madame Sherris Castle Ruins ](https://www.expedia.com/Car-Rentals-In-Madame-Sherris-Castle-Ruins.d6273836.Car-Rental-Guide)
- [Car rentals near Rhododendron State Park ](https://www.expedia.com/Car-Rentals-In-Rhododendron-State-Park.d553248621532667357.Car-Rental-Guide)
- [Car rentals near Spofford Lake ](https://www.expedia.com/Car-Rentals-In-Spofford-Lake.d6265753.Car-Rental-Guide)
- [Car rental Swanzey Airport (EEN) ](https://www.expedia.com/Car-Rentals-In-Dillant-Hopkins.d6027555.Car-Rental-Guide)

- [Ashuelot Vacation Rentals ](https://www.expedia.com/Ashuelot-Vacation-Rentals.d3000421398.Travel-Guide-VacationRentals)
- [Spofford Vacation Rentals ](https://www.expedia.com/Spofford-Vacation-Rentals.d6267420.Travel-Guide-VacationRentals)

- Cities near Winchester
- Places of interest

[Fitzwilliam](https://expedia.com/Fitzwilliam.dx104340)[Northfield](https://expedia.com/Northfield.dx6025729)[Chesterfield](https://expedia.com/Chesterfield.dx6052872)[Spofford](https://expedia.com/Spofford.dx6267420)[Swanzey](https://expedia.com/Swanzey.dx6348108)[Ashuelot](https://expedia.com/Ashuelot.dx3000421398)[Hinsdale](https://expedia.com/Hinsdale.dx3000447021)

- [Green Mountain National Forest ](https://expedia.com/Green-Mountain-National-Forest-Vermont.d6115904.Vacation-Attraction)
- [Keene State College ](https://expedia.com/Keene-State-College-Keene.d553248621533117511.Vacation-Attraction)
- [Connecticut River ](https://expedia.com/Connecticut-River-United-States-of-America.d553248621555565605.Vacation-Attraction)
- [Northfield Mount Hermon School ](https://expedia.com/Northfield-Mount-Hermon-School-Massachusetts.d553248635974560180.Vacation-Attraction)
- [Landmark College ](https://expedia.com/Landmark-College-Putney.d553248635937215663.Vacation-Attraction)
- [The Stone Church ](https://expedia.com/The-Stone-Church-Brattleboro.d553248635947261535.Vacation-Attraction)
- [Historic Deerfield Village ](https://expedia.com/Historic-Deerfield-Village-Deerfield.d553248621532666737.Vacation-Attraction)
- [Spofford Lake ](https://expedia.com/Spofford-Lake-Spofford.d6265753.Vacation-Attraction)
- [Colonial Theatre ](https://expedia.com/Colonial-Theatre-Keene.d553248621532666941.Vacation-Attraction)
- [Deerfield Academy ](https://expedia.com/Deerfield-Academy-Deerfield.d553248635974587712.Vacation-Attraction)
- [Cushing Academy ](https://expedia.com/Cushing-Academy-Ashburnham.d6180070.Vacation-Attraction)
- [Eaglebrook School ](https://expedia.com/Eaglebrook-School-Deerfield.d553248635975607512.Vacation-Attraction)
- [Monadnock State Park ](https://expedia.com/Monadnock-State-Park-Jaffrey.d553248621532666842.Vacation-Attraction)
- [Brattleboro Common ](https://expedia.com/Brattleboro-Common-Brattleboro.d553248621561865132.Vacation-Attraction)
- [Historic Main Street ](https://expedia.com/Historic-Main-Street-Keene.d6337582.Vacation-Attraction)
- [Deerfield River ](https://expedia.com/Deerfield-River-United-States-of-America.d682156682122641408.Vacation-Attraction)
- [Bridge of Flowers ](https://expedia.com/Bridge-Of-Flowers-Shelburne-Falls.d553248621532666724.Vacation-Attraction)
- [Crumpin-Fox Golf Club ](https://expedia.com/Crumpin-Fox-Golf-Club-Bernardston.d553248635974587711.Vacation-Attraction)

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