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Find hotels in Winchester, NH from $88

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May 11 - May 12
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Compare 379 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Property grounds
Lakefront Orange Vacation Rental - Pet Friendly!
10.0 out of 10, Exceptional, (6)
"Crystal was an exceptional hostess! "
Lakefront Orange Vacation Rental - Pet Friendly!
Interior
Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!
10.0 out of 10, Exceptional, (130)
"The property is beautiful and has so many activities from walking in the woods and going out on the water to staying inside and enjoying the game room. Highly recommend!"
Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!
Fridge, microwave, stovetop, coffee/tea maker
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
10.0 out of 10, Exceptional, (22)
"This property is fairytale cute, so welcoming and relaxing. We had a beautiful stay in Vermont thanks to this location. And there were surprise puppies on site!!!!! Honestly this was the kind of trip that gives you confidence in vacation rentals. Clean, wonderfully decorated, off the beaten path a truly relaxing stay! Go outside at night!!!! We dont have stars like that in the city."
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
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Interior
Charming Waterfront Log Cabin
10.0 out of 10, Exceptional, (24)
"Wonderful place it’s are 3rd time staying there an you can’t beat the location, pond view or the nature surrounding you. An a very fast response. I will be staying agsin!"
Charming Waterfront Log Cabin
Lake
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
10.0 out of 10, Exceptional, (8)
"The house was superb for our family visit! We enjoyed it all! Linda was a perfect hostess…,so attentive!"
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
Interior
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
3.5 star property
10.0 out of 10, Exceptional, (1)
"We had a truly wonderful stay. The cottage and property are beautiful, peaceful and very special. Great views! Our host thought of everything, it's very comfortable and lovely. Best place to stay in Southern Vermont! Don't miss the Tiny Bread Box on Saturdays; it's just up the road. We'll defiantly be back for another visit."
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
Dishwasher
Penthouse, Steps to the Sandy Beach & clear water
10.0 out of 10, Exceptional, (5)
"The Penthouse was a great place to rent for our family get-together. The owners live nearby and are very responsive to any issues that may arise, and indeed promptly addressed questions and any issues that we had. It was a great vacation place for us (other family members rented other houses on the property from the same owner so we were able to get together and have plenty of room). The lake is perfect -- clean and beautiful, and we made the most out of boating and kayaking activities there."
Penthouse, Steps to the Sandy Beach & clear water
4 bedrooms, desk, iron/ironing board, internet
Historic Home w/ Modern Updates on 3.5 Acres
10.0 out of 10, Exceptional, (5)
"The property was awesome! Old, quaint and brought memories back of our grandparents homes…Family sat around table and enjoyed shared memories"
Historic Home w/ Modern Updates on 3.5 Acres
Interior
Waterfont log home nestled in the pines
10.0 out of 10, Exceptional, (43)
"Property was perfect for a guys get away fishing trip. Alfred was very attentive and helpful. I've stayed at many Vrbo house but this is one of my favorites. Hope to stay here again soon Steve"
Waterfont log home nestled in the pines
Interior
Historic Home w/ Modern Updates on < 4 Acres
3.5 star property
10.0 out of 10, Exceptional, (1)
Historic Home w/ Modern Updates on < 4 Acres
1 bedroom, iron/ironing board, free WiFi, bed sheets
Spectacular Mountain views with all the amentities nearby
9.8 out of 10, Exceptional, (38)
"The vrbo was as-described and the hosts exceptionally personable and friendly. Exemplary!"
Spectacular Mountain views with all the amentities nearby
Property grounds
Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford
9.8 out of 10, Exceptional, (22)
"Our daughter just turned 43 and is severely challenged and in a wheelchair requiring her helper Staff to assist. The house had the proper h/c accommodations for this without having the appearance of such. This is not a medical facility but, a wonderful camp on a beautiful lake that allows for your needs or just a great camp with no h/c needs. You would never notice such if you didn't need the accommodation. Right on the lake yet, with the privacy we wished for. We were able to go swimming...
Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford
Dishwasher
Main House, Relax and enjoy the scenery, go and swim, fish or start your boat
9.8 out of 10, Exceptional, (8)
"We booked last minute to celebrate my mom’s birthday with family. Anthony was very accommodating and understanding of our family needs. He went out of his way to ensure my elderly parents were comfortable. The house was well stocked and VERY clean. We would stay again!"
Main House, Relax and enjoy the scenery, go and swim, fish or start your boat
Free daily continental breakfast
The Carriage Barn Inn
3.0 star property
9.6 out of 10, Exceptional, (120)
"The hosts were wonderfully helpful!"
The price is $217
$235 total
includes taxes & fees
May 22 - May 23
The Carriage Barn Inn
Exterior detail
The One Cat B&B
2.5 star property
9.6 out of 10, Exceptional, (65)
"This is an awesome B&B! Pat and Conrad are great hosts and they live on site so they are available if you need anything. The room was clean and very spacious. There was comfortable seating in addition to the bed. The room had it's own Keurig machine and it's own AC/heat system. Breakfast the next morning was delicious. Several food and drink options to consider. Also, Conrad bakes his own bread. I had the maple oat bread which was so good. This was my first time in Brattleboro. I will definitely...
The price is $166
$183 total
includes taxes & fees
Jun 9 - Jun 10
The One Cat B&B
Exterior
Cozy Updated Log Cabin with Mountain Views close to Monadnock
9.6 out of 10, Exceptional, (18)
"We absolutely loved the privacy and seclusion of the property. Everything was clean and tidy, minus some trash that was left around the firepit, presumably from a previous guest, that we cleaned up. The kitchen was well stocked with cooking tools and the bathroom was just big enough. Guests should take note though that the shower was definitely a tight fit for my 6'1" husband and the furniture was also a struggle for him. One of the beds was only about 4 inches off the ground and the seating was...
The price is $178
$337 total
includes taxes & fees
May 28 - May 29
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Exterior detail
Centennial House
3.5 star property
9.4 out of 10, Exceptional, (126)
"The room was exceptionally clean and cozy. Lucy the pet dog so sweet and friendly! We enjoyed conversing with Steve and Joan."
The price is $199
$210 total
includes taxes & fees
May 13 - May 14
Centennial House
Property grounds
Downtown Hot Tub Escape
9.4 out of 10, Exceptional, (3)
"Wonderfully located not to far from plenty of great restaurants and really well kept home that accomadated 9 adults for the night perfectly. Clear instructions for all the amenities in the home made it easy and fun."
The price is $169
$332 total
includes taxes & fees
May 12 - May 13
Downtown Hot Tub Escape
Exterior
Waterfront Cottage on Scenic Sportsman Pond
9.4 out of 10, Exceptional, (34)
"Linda was wonderful in her review of the property and was very accommodating in all aspects of our stay. The cottage was well equipped and very comfortable including the mattress. We enjoyed the lake and a little fishing. The area is very nice and we did some exploring. It was very quiet and we rarely even saw anyone while we were on the lake. We hope to return in the spring or summer. Many thanks to Linda and Brad"
Waterfront Cottage on Scenic Sportsman Pond
Fridge, microwave, oven, dishwasher
"The Murdock Suite @ The Large House"
9.4 out of 10, Exceptional, (3)
"We stayed at the Murdoch suite when we had to fly back to New Hampshire for a family funeral. The suite suited our needs well. It was clean and well stocked. The only negative is it is located on a major road, right after a round about, so there is a lot of road noise."
"The Murdock Suite @ The Large House"
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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.

More cheap stays in Winchester

The Covered Bridge Inn

The Covered Bridge Inn

1043 Putney Road, Brattleboro, VT
The price is $89 per night from May 22 to May 23
$89
$99 total
includes taxes & fees
May 22 - May 23
8.2/10 Very Good! (1,001 reviews)

Winchester Travel Info

Number of reviews
4,389
Accommodation
379 hotels
Highest price
$217
Lowest price
$88
Reasons to visit
Pisgah State Park, Asbury United Methodist Church and Little Monadnock Mountain

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 traveler data. Other good options for your stay in the area are The Covered Bridge Inn and Colonial Motel And Spa. See all available top hotels, or vacation rentals in Winchester.

What are some of the best vacation rentals in Winchester?

Charming Waterfront Log Cabin: You might want to consider this vacation home rental near Winchester, which is located on the waterfront and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. See all vacation rentals in Winchester.

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

Yes, most hotel reservations are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If your reservation is non-refundable, you might still have the option to cancel and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

Where can I learn more about changing or cancelling my trip to Winchester?

For more details about rescheduling or cancelling your trip to Winchester, go to https://www.expedia.com/service/.

What are some hotels with pools in Winchester?

The Colonial Hotel: Offers a sauna, an indoor pool, and free self parking. Colonial Motel And Spa and Hampton Inn Brattleboro are two additional hotels with an onsite pool. View all hotels with pools in Winchester.

What is the best hotel near Hartness State Airport (VSF)?

The Inn at Weathersfield is a popular 4-star inn featuring free breakfast and a restaurant. It's located a short 1.3 mi (2.1 km) from Hartness State Airport. Another good choice close to the airport is Hartness House Inn, located 3.7 mi (5.9 km) away.

What is staying in Winchester like?

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

What should I do while I'm visiting Winchester?

Natural beauty is on display at Pisgah State Park, Birch Point, and Rhododendron State Park. Additionally, you might want to add Ashuelot River to your itinerary. Check out what more to see and do in Expedia's Winchester guide.

What's the seasonal weather like in Winchester?

The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Winchester are January, March, February, and November, with each month seeing an average of 10 inches of snowfall.

Recent reviews of Winchester hotels
Expedia verified reviews

Colonial Motel And Spa

Colonial Motel And Spa

5/5 Excellent
" FAST FRINDLY SERVICE !!!!!!!!!!!! "
A verified traveler stayed at Colonial Motel And Spa
Posted 10 hours ago
Colonial Motel And Spa