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18 Aug - 19 Aug
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Top hotels and accommodation in Winchester

The Putney Inn
Exterior

The Putney Inn

2.5 star property
8.4 out of 10, Very good, (1005)
"Very enjoyable stay"
The Putney Inn
Best Western Plus Keene Hotel
1 bedroom, premium bedding, individually decorated

Best Western Plus Keene Hotel

3.0 star property
8.4 out of 10, Very good, (1012)
"It was a great stay"
The price is NZ$273
includes taxes & fees
24 Aug - 25 Aug
Best Western Plus Keene Hotel
Latchis Hotel
Hiking

Latchis Hotel

2.5 star property
8.4 out of 10, Very good, (774)
"Great stay!"
The price is NZ$257
includes taxes & fees
8 Sept - 9 Sept
Latchis Hotel
Keene Elm City Hotel, Ascend Hotel Collection
Indoor pool

Keene Elm City Hotel, Ascend Hotel Collection

2.5 star property
8.4 out of 10, Very good, (880)
"Staff were friendly, room clean and comfortable "
The price is NZ$229
includes taxes & fees
24 Aug - 25 Aug
Keene Elm City Hotel, Ascend Hotel Collection
The Covered Bridge Inn
Exterior detail

The Covered Bridge Inn

2.5 star property
7.8 out of 10, Good, (1005)
"Was great for the price "
The price is NZ$270
includes taxes & fees
23 Aug - 24 Aug
The Covered Bridge Inn
Days Inn by Wyndham Keene NH
In-room safe, desk, blackout curtains, iron/ironing board

Days Inn by Wyndham Keene NH

2.0 star property
7.2 out of 10, Good, (1003)
"Would stay again"
The price is NZ$204
includes taxes & fees
1 Sept - 2 Sept
Days Inn by Wyndham Keene NH
Monadnock Inn
Exterior

Monadnock Inn

2.5 star property
7.6 out of 10, Good, (267)
"It was very personable. They were very flexible with check-in. Quiet and homie. "
Monadnock Inn
Comfort Inn & Suites Brattleboro I-91
Lobby

Comfort Inn & Suites Brattleboro I-91

2.5 star property
8.6 out of 10, Excellent, (674)
"Great place for a quick stay with my son on the way to Maine. "
The price is NZ$259
includes taxes & fees
21 Aug - 22 Aug
Comfort Inn & Suites Brattleboro I-91
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (153)
"Loved our stay. Beautifully decorated and I was able to play the house guitar in common room which was a unique touch I really enjoyed. Would gladly stay here again."
The price is NZ$321
includes taxes & fees
4 Sept - 5 Sept
The Carriage Barn Inn
Black Mountain Inn
Front of property

Black Mountain Inn

2.0 star property
7.4 out of 10, Good, (459)
"The bed was super comfortable and the sheets were very soft and also comfortable. "
The price is NZ$232
includes taxes & fees
26 Aug - 27 Aug
Black Mountain Inn
Hampton Inn & Suites Greenfield
Room, 2 Queen Beds, Non Smoking

Hampton Inn & Suites Greenfield

2.5 star property
8.6 out of 10, Excellent, (834)
"Great place with a walkable eating option"
The price is NZ$287
includes taxes & fees
1 Sept - 2 Sept
Hampton Inn & Suites Greenfield
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (313)
"I enjoyed my stay and found the room more than adequately furnished. Wished the bed could be firmer and they could supply meals other than just breakfast."
The price is NZ$290
includes taxes & fees
31 Aug - 1 Sept
Colonel Williams Inn
Riverside Hotel, Ascend Hotel Collection
Sundeck

Riverside Hotel, Ascend Hotel Collection

2.5 star property
9.6 out of 10, Exceptional, (589)
"Lovely, and very peaceful stay nestled beside the Connecticut River"
The price is NZ$279
includes taxes & fees
25 Aug - 26 Aug
Riverside Hotel, Ascend Hotel Collection
The Colonial Hotel
Interior

The Colonial Hotel

3.0 star property
8.8 out of 10, Excellent, (1003)
"We have stayed at this property a few times and it is always a pleasant experience. "
The Colonial Hotel
Travelodge by Wyndham Brattleboro VT
Reception

Travelodge by Wyndham Brattleboro VT

2.5 star property
6.0 out of 10, (695)
"I was only there for a few hours sleep "
The price is NZ$132
includes taxes & fees
19 Aug - 20 Aug
Travelodge by Wyndham Brattleboro VT
The Burrell House
Exterior

The Burrell House

2.5 star property
9.6 out of 10, Exceptional, (134)
"Very nice property. Highly recommend. "
The Burrell House
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Free daily on-the-go breakfast

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 star property
9.4 out of 10, Exceptional, (417)
"Highly recommend PEARL restaurant nearby! Always comfortable accommodations. "
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Free daily on-the-go breakfast

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 star property
8.8 out of 10, Excellent, (1001)
"Good room, great breakfast options "
The price is NZ$299
includes taxes & fees
24 Aug - 25 Aug
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Hampton Inn Brattleboro
Free breakfast

Hampton Inn Brattleboro

2.5 star property
8.2 out of 10, Very good, (866)
"Great beach and nice rooms Breakfast can improve and pool is small "
The price is NZ$227
includes taxes & fees
2 Sept - 3 Sept
Hampton Inn Brattleboro
Vikings Villages Resort
Deluxe Chalet

Vikings Villages Resort

2.0 star property
10.0 out of 10, Exceptional, (119)
"My family and I loved staying here! The cabin was very clean, nicely decorated, comfy beds. Hope to be back during the winter b/c I’m sure it's absolutely magical with snow on the ground"
The price is NZ$389
includes taxes & fees
19 Aug - 20 Aug
Vikings Villages Resort
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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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
Photo by Donny Campos
Open Photo by Donny Campos

Top Winchester Hotel Reviews

The Colonial Hotel

The Colonial Hotel

10/10 Excellent
"This is a greag property with plenty of historic charm. The staff are all friendly and helpful. This was my second stay here and I'll definitely be back. "
Ryan 1-night trip
Posted 1 day ago
The Colonial Hotel

Frequently asked questions

What's the best place to stay in Winchester?

The Colonial Hotel, located 26.3 mi (42.3 km) from the heart of Winchester, is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Colonial Motel And Spa and Hampton Inn Brattleboro. See all available top hotels, or vacation rentals in Winchester.

What are some of the best holiday rentals that Winchester has to offer?

Lovely 2nd Floor Apartment: This holiday home rental outside of Winchester offers a garden, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. See all vacation rentals in Winchester.

If I need to cancel my hotel reservation in Winchester, will I receive a refund?

Yes, the majority of hotel reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your arrival date. If you have a non-refundable reservation, you may still be able to cancel and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

What are some hotels with pools in Winchester?

The Colonial Hotel: Features a sauna, an indoor pool and free self parking. Colonial Motel And Spa and Hampton Inn Brattleboro are a couple of other choices that offer an on-site pool. View all hotels with pools in Winchester.

What is staying in Winchester like?

Visitors to Winchester will definitely enjoy the lakeside setting. Tourists can also enjoy so much more including its forests. In Winchester, there are 6 hotels and other accommodation options to choose from. Find out more about Winchester.

What are the top places to visit in Winchester?

Natural beauty is on display at Richmond Wildlife Manangement Area, Rhododendron State Park and Ashuelot River. A couple of additional sights to add to your itinerary are New England Sweetwater Farm & Distillery and Pisgah State Park. Take a look at what more there is to see and do in Expedia's Winchester guide.

What's the weather like in Winchester?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Winchester are January, March, February and November, with each month seeing an average of 26 cm of snowfall.