Winchester Hotels
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Go beyond your typical stay in Winchester
Cabin
Family friendly
Apartment
Cottage
Pet friendly
Condo
Waterpark
Check prices for these dates
Tonight
7 Aug - 8 AugTomorrow
8 Aug - 9 AugThis weekend
7 Aug - 9 AugNext weekend
14 Aug - 16 AugOur top choices for Winchester hotels
1. Windmill Motel Restaurant
Windmill Motel RestaurantBernardston
Robert
€118
includes taxes & fees
9 Aug - 10 Aug
2. Keene Elm City Hotel, an Ascend Collection Hotel
Keene Elm City Hotel, an Ascend Collection HotelKeene
Ramica
€107
includes taxes & fees
1 Sept - 2 Sept
3. The Burrell House
The Burrell HouseKeene
Justin
€112
includes taxes & fees
10 Aug - 11 Aug
4. Colonial Motel
Colonial MotelBrattleboro
James
€71
includes taxes & fees
9 Aug - 10 Aug
5. Hampton Inn Brattleboro
Hampton Inn BrattleboroBrattleboro
Kyle
€117
includes taxes & fees
16 Aug - 17 Aug
6. The Covered Bridge Inn
The Covered Bridge InnBrattleboro
VINCENT JOEL
€74
includes taxes & fees
28 Aug - 29 Aug
7. Days Inn by Wyndham Keene NH
Days Inn by Wyndham Keene NHKeene
Michael
€82
includes taxes & fees
2 Sept - 3 Sept
8. Best Western Plus Keene Hotel
Best Western Plus Keene HotelKeene
Helen
€140
includes taxes & fees
9 Aug - 10 Aug
10. Hampton Inn & Suites Keene
Hampton Inn & Suites KeeneKeene
Debra
€140
includes taxes & fees
1 Sept - 2 Sept
11. Comfort Inn & Suites Brattleboro I-91
Comfort Inn & Suites Brattleboro I-91Brattleboro
Bonnie
€124
includes taxes & fees
31 Aug - 1 Sept
12. Riverside Hotel, an Ascend Collection Hotel
Riverside Hotel, an Ascend Collection HotelWest Chesterfield
Pauline
€135
includes taxes & fees
6 Sept - 7 Sept
13. The Inn At Crumpin Fox
The Inn At Crumpin FoxBernardston
allisha
€157
includes taxes & fees
9 Aug - 10 Aug
14. Vikings Villages Resort
Vikings Villages ResortGuilford
Otgonzaya
€173
includes taxes & fees
20 Aug - 21 Aug
15. Fairfield Inn & Suites by Marriott Keene Downtown
Fairfield Inn & Suites by Marriott Keene DowntownKeene
Brian
€151
includes taxes & fees
30 Aug - 31 Aug
16. Travelodge by Wyndham Brattleboro VT
Travelodge by Wyndham Brattleboro VTBrattleboro
Brian
€64
includes taxes & fees
17 Aug - 18 Aug
17. The Carriage Barn Inn
The Carriage Barn InnKeene
Jonathan
€138
includes taxes & fees
9 Aug - 10 Aug
18. Holiday Inn Express Hotel & Suites Brattleboro by IHG
Holiday Inn Express Hotel & Suites Brattleboro by IHGBrattleboro
Marnie
€156
includes taxes & fees
6 Sept - 7 Sept
19. Econo Lodge Brattleboro South
Econo Lodge Brattleboro SouthBrattleboro
Aigul
€85
includes taxes & fees
13 Aug - 14 Aug
20. The Putney Inn
The Putney InnPutney
Robert
€107
includes taxes & fees
11 Aug - 12 Aug
Stay near popular Winchester attractions
Cass Pond
This serene 54-acre pond in Richmond offers peaceful fishing for bass, pickerel, and perch. Bring your own gear and a valid New Hampshire fishing licence to fully enjoy this tranquil natural retreat.
Winchester Speedpark
Winchester Speedpark thrills with professionally designed motocross tracks featuring challenging jumps and turns. Experience heart-pounding night races or watch competitors tackle the New England racing circuit.
Richmond Wildlife Manangement Area
This protected wilderness features diverse New Hampshire ecosystems across forests, wetlands, and meadows. Explore marked trails for wildlife viewing, especially during spring migration or autumn's foliage display.
New England Sweetwater Farm & Distillery
This rustic distillery crafts award-winning spirits using locally sourced ingredients. Sample their unique vodkas and whiskies while learning about the distillation process in a warm space adorned with reclaimed wood.
Barden State Wildlife Management Area
This serene wildlife reserve in New Hampshire offers undisturbed natural landscapes for wildlife observation. Bring binoculars for spotting native species while exploring the peaceful trails during spring through fall.
Bennett Gorge
This secluded woodland trail winds alongside a brook to the remnants of an historic mill. Explore Richmond's industrial past while enjoying the tranquil sounds of flowing water and forest solitude.
Conant Public Library
This historic 1892 library houses Winchester's heritage collection, including one of New England's earliest pipe organs. Browse artefacts or research local history with help from knowledgeable staff.
Richmond Town Hall
This 1780 New England meeting house showcases traditional white weatherboard architecture and historic timber framing. Explore one of New Hampshire's oldest civic buildings, listed on the National Register.
Learn more about Winchester
Hike the scenic trails of Pisgah State Park where rangers know which routes offer the best wildlife viewing. Explore the historic city centre district with its charming 19th-century architecture and local shops selling New Hampshire maple products.
See all hotels in Winchester
Top Winchester Hotel Reviews
Keene Elm City Hotel, an Ascend Collection Hotel
10/10 Excellent
"Breakfast offered a lot of good choices from eggs to cereal to fresh fruit. The room was clean throughout and the AC quiet and efficient. The staff was excellent in providing information and Dillan's recommendation for dinner was "spot on". The room price was very reasonable, and the indoor heated pool provide a relaxing afternoon."
Hampton Inn Brattleboro
10/10 Excellent
"Amazing service! Perfect"
Holiday Inn Express Hotel & Suites Brattleboro by IHG
10/10 Excellent
"Great hotel. Lovely pool."
Hampton Inn & Suites Greenfield
10/10 Excellent
"Visiting family in Greenfield and really only needed a spot with a clean bed. I was pleasantly surprised by the Hampton Inn. Room was clean and staff was friendly and helpful. We didn't eat breakfast there, but did enjoy the free coffee in the lobby. Only odd thing about this hotel is its location. The entrance to the hotel is from the back of the parking lot of the 99 restaurant. Next time I visit, I'm staying here."
The Inn At Crumpin Fox
10/10 Excellent
"Rustic and very clean my only complaint would be the tiny pillows."
Vikings Villages Resort
10/10 Excellent
"Absolute gem of a stay. Every little detail was thought of ! Easy check in and out ! Close to a small general store and great ice cream shop! Worth a visit !! So unique ! Cabin was immaculate and decorated so tasteful !"
Gardner Inn
10/10 Excellent
"great place"
Riverside Hotel, an Ascend Collection Hotel
10/10 Excellent
"We have stayed here twice in the last week - each end of a trip. This is a hidden gem. Incredibly clean, quiet, and comfy. River is beautiful- balconies and porch are lovely both morning and evening."
Comfort Inn & Suites Brattleboro I-91
10/10 Excellent
"Clean room, quiet, very nice breakfast choices. Did not interact much with staff, just at checkin and checkout. Friendly."
More cheap stays in Winchester
Days Inn by Wyndham Keene NH
3 Ash Brook Road Keene NH
€82
2 Sept - 3 Sept
includes taxes & fees
7/10 Good! (1,002 reviews)
Gardner Inn
22 Pearson Blvd Gardner MA
€107
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (47 reviews)
Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd Keene NH
€107
1 Sept - 2 Sept
includes taxes & fees
8.6/10 Excellent! (1,009 reviews)
Hampton Inn Brattleboro
1378 Putney Road Brattleboro VT
€117
16 Aug - 17 Aug
includes taxes & fees
8.2/10 Very good! (1,002 reviews)
Comfort Inn & Suites Brattleboro I-91
1186 Putney Road Brattleboro VT
€124
31 Aug - 1 Sept
includes taxes & fees
8.6/10 Excellent! (843 reviews)
Frequently asked questions
Explore a world of travel with Expedia
- 5 Star Hotels in Wilton
- Amherst Hotels
- Antrim Hotels
- Bedford Hotels
- Bennington Hotels
- Charlestown Hotels
- Claremont Hotels
- Cabin Rentals in Dublin
- Dublin Hotels
- Fitzwilliam Hotels
- Cottages in Georges Mills
- Henniker Hotels
- Hillsboro Hotels
- Hollis Hotels
- Hotels with Restaurant in Jaffrey
- Jaffrey Hotels
- Beach Hotels in Keene
- Keene Hotels
- Apartments in Manchester
- B&B in Manchester
- Caravan Parks in Manchester
- Hyatt Hotels in Manchester
- Luxury Hotels in Manchester
- Motels in Manchester
- Mason Hotels
- Merrimack Hotels
- Hotels near Merrimack Premium Outlets
- Vail Resorts in Monadnock Region
- Ski Hotels in Mount Sunapee
- New Boston Hotels
- Newbury Hotels
- Newport Hotels
- Peterborough Hotels
- Rindge Hotels
- Sullivan Hotels
- Swanzey Hotels
- Temple Hotels
- Walpole Hotels
- Lgbt-Friendly Hotels in Warner
- Warner Hotels
- Weare Hotels
- West Chesterfield Hotels
- Westmoreland Hotels
- Historic Hotels in Winchester
- Flights to Hopkinton
- Flights to Manchester
- Flights to Merrimack
- Flights to Nashua
- Flights from Manchester-Boston Regional
- Flights from Bradford
- Flights from Winchester
- Flights from Brookline
- Flights from Cheshire County
- Flights from Manchester
- Flights from Birmingham (BHM) to Manchester (MHT)
- Flights from Cancun (CUN) to Manchester (MHT)
- Flights from Washington (DCA) to Manchester (MHT)
- Flights from New York (JFK) to Manchester (MHT)
- Flights from Kingston (KIN) to Manchester (MHT)
- Flights from Mandalay (MDL) to Nashua (ASH)
- Flights from Chicago (ORD) to Manchester (MHT)
- Flights from Raleigh (RDU) to Manchester (MHT)
- Visit Bedford
- Center of New Hampshire Expo Center
- Cornish-Windsor Covered Bridge
- Visit Cornish
- Crotched Mountain Ski and Ride Area
- Eaton's Magic Morsel
- Visit Francestown
- Greenfield Holidays
- Holy Resurrection Orthodox Church
- John Hay National Wildlife Refuge
- Keene Holidays
- Manchester Holidays
- Visit Merrimack
- Visit Nashua
- New London Barn Playhouse
- Northeast Delta Dental Stadium
- Pats Peak
- Visit Peterborough
- Saint Joseph Cathedral
- Visit Temple
- Visit Walpole
- Warner Holidays
- Budget Rental Cars in Manchester-Boston Regional
- Car hire Bow
- Car hire Dublin
- Rental cars Manchester-Boston Regional airport
- Car hire Manchester
- Car hire near New London Barn Playhouse
- Car hire Temple
- Enterprise Rental Cars in Manchester-Boston Regional
- Luxury Car Hire near Manchester-Boston Regional
- Luxury Car Hire in Manchester
- Car hire in Sixt Bahrain International Airport, Building 200 Road 2403 Blk 224
- Car hire in Sixt Port Elizabeth Int. Airport, Allister Miller Drive, Walmer
- Suv Car Hire near Manchester-Boston Regional
- Thrifty Car Rental Rental Cars in Manchester-Boston Regional
