A snow-covered town with a river running through it, surrounded by mountains and trees.

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Check availability on Winchester 3 Star Hotels

Our top choices for Winchester 3-star hotels

Interior

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
9.0 out of 10, Wonderful, (1,009 reviews)
"Food at restaurant was phenomenal"
United States
Zachary
The price is SAR 574
SAR 642 total
includes taxes & fees
26 Jul - 27 Jul
The Colonial Hotel
Restaurant

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1,008 reviews)
"Staff was very friendly, accommodating, and attentive to our needs. Room was clean and comfortable!"
United States
Helen
The price is SAR 522
SAR 566 total
includes taxes & fees
23 Jul - 24 Jul
Best Western Plus Keene Hotel
Lobby

Colonial Motel

Colonial Motel
3.0 star property
Brattleboro
6.0 out of 10, (24 reviews)
"Clean room ez checkin, coffee at breakfast good!"
United States
James
The price is SAR 287
SAR 316 total
includes taxes & fees
2 Aug - 3 Aug
Colonial Motel
Indoor pool

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.6 out of 10, Excellent, (1,000 reviews)
"Friendly staff"
United States
Nicholas Hamilton
The price is SAR 674
SAR 732 total
includes taxes & fees
11 Aug - 12 Aug
Courtyard by Marriott Keene Downtown
Exterior

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (785 reviews)
"My favorite hotel!!!!"
United States
Brian
The price is SAR 603
SAR 655 total
includes taxes & fees
9 Aug - 10 Aug
Fairfield Inn & Suites by Marriott Keene Downtown
Superior Single Room, 1 Queen Bed | Iron/ironing board, travel crib, WiFi (free), bed sheets

Deerfield Inn

Deerfield Inn
3.0 star property
Deerfield
10.0 out of 10, Exceptional, (4 reviews)
"The Inn was quiet, convenient and offered excellent food."
United States
Jay
The price is SAR 894
SAR 1,159 total
includes taxes & fees
3 Aug - 4 Aug
Deerfield Inn
Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (357 reviews)
"A very historic and well maintained bed and breakfast. The owners are wonderful and the rooms were cozy. The hand made breakfast was a highlight"
United States
Robert
The price is SAR 571
SAR 628 total
includes taxes & fees
3 Aug - 4 Aug
Colonel Williams Inn
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (142 reviews)
"Appealing common spaces, lovely selections at the coffee/tea station, library and games. Everything for a cozy respite in a great location. Walk to the local village and attractions, central to exploring the Mohawk Trail."
United States
Annette
The price is SAR 411
SAR 643 total
includes taxes & fees
19 Aug - 20 Aug
Blooming Inn
Free daily continental breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (175 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is SAR 604
SAR 656 total
includes taxes & fees
23 Jul - 24 Jul
The Carriage Barn Inn
Terrace/patio

The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast
3.5 star property
Ashburnham
10.0 out of 10, Exceptional, (38 reviews)
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
United States
Ranjit
The price is SAR 985
SAR 985 total
includes taxes & fees
12 Aug - 13 Aug
The Maguire House Bed & Breakfast
Children's play area - outdoor

The Inn at Kampfires

The Inn at Kampfires
3.5 star property
Brattleboro
9.4 out of 10, Exceptional, (43 reviews)
"The guest house and as new. It was very comfortable for the entire family and we would go back again."
United States
Nancy E
The Inn at Kampfires
Cottage (2 Bedrooms) | Interior

4 Mi to Lake Raponda! Secluded Family Cottage

4 Mi to Lake Raponda! Secluded Family Cottage
3.0 star property
Wilmington
4 Mi to Lake Raponda! Secluded Family Cottage
Apartment (1 Bedroom) | Interior

Lakefront Orange Vacation Rental - Pet Friendly!

Lakefront Orange Vacation Rental - Pet Friendly!
3.0 star property
Orange
10.0 out of 10, Exceptional, (1 review)
"Lovely, very clean, and well appointed. Host was amazing, 2 rocking chairs on front stoop overlooking the water was beautiful, peaceful.The interiorand decor was beautiful and very comfortable. We used our kayaks, which was great. It is an in̈cline downhill to carry your kayak. "
United States
Jean
Lakefront Orange Vacation Rental - Pet Friendly!
House (2 Bedrooms) | Interior

Hiking Trails On-site: Cozy Falls Brook Cabin

Hiking Trails On-site: Cozy Falls Brook Cabin
3.0 star property
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
United States
sarah
The price is SAR 680
SAR 1,542 total
includes taxes & fees
5 Aug - 6 Aug
Hiking Trails On-site: Cozy Falls Brook Cabin
Apartment (0 Bedroom) | Interior

Studio w/ Trail Access ~ 10 Mi to Brattleboro!

Studio w/ Trail Access ~ 10 Mi to Brattleboro!
3.0 star property
Vernon
10.0 out of 10, Exceptional, (1 review)
"Perfect nature getaway! The small cabin has all of the essentials, great heat and water and excellent WiFi was a bonus. Location is ideal for hiking the local town forest and easy to drive into Brattleboro for local shopping. Very quiet and peaceful neighborhood."
United States
Charlene
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
28-inch flat-screen TV with satellite channels, TV, DVD player

Cavalier Cottage B&B

Cavalier Cottage B&B
3.0 star property
Shelburne Falls
9.0 out of 10, Wonderful, (2 reviews)
"Perfect for a quiet, weekend getaway. We went to celebrate our 5 year anniversary and brought our dog, Ollie. Ollie's a very timid and nervous guy, but he felt very comfortable here. We went during the winter, but would be interested in returning in the summer because there seems to be a lot of outdoor activities (white water rafting, fishing, hiking). "
United States
jennifer
Cavalier Cottage B&B
Apartment (2 Bedrooms) | Interior

Deck, Mountain Views: Colorful Retreat in Vernon!

Deck, Mountain Views: Colorful Retreat in Vernon!
3.0 star property
Vernon
10.0 out of 10, Exceptional, (1 review)
"The property was exquisite, affordable and amazing, me and the family enjoyed everything. Thank you to our host for you professional demeanor and hospitality."
United States
Michael
Deck, Mountain Views: Colorful Retreat in Vernon!
House (2 Bedrooms) | Interior

Furnished Deck + Views: Walpole Cabin Retreat

Furnished Deck + Views: Walpole Cabin Retreat
3.0 star property
Walpole
10.0 out of 10, Exceptional, (1 review)
"The property is lovely with amazing views. All the detailed touches that make the property what it is makes for a unique and memorable experience. The host provided extra touches such as flowers, sweets and champagne for our anniversary. The view is just breathtaking. One can see 7 ski mountains in the winter. The sky is so clear at night, the stars are in view. Wonderful stay!"
United States
Lisa
Furnished Deck + Views: Walpole Cabin Retreat
House (3 Bedrooms) | Interior

Wilmington Home on 18 Acres ~ 9 Mi to Skiing!

Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
House, 4 Bedrooms | Private kitchen | Coffee/tea maker, fridge, oven, toaster

Cushing Home Family Cabin Near Wachusett Mtn 4 Bedroom Home

Cushing Home Family Cabin Near Wachusett Mtn 4 Bedroom Home
3.0 star property
Ashburnham
Cushing Home Family Cabin Near Wachusett Mtn 4 Bedroom Home
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 3-star hotels. See all 4-star hotels in Winchester.
Four Columns Inn

Four Columns Inn

21 West Street Newfane VT
The price is SAR 737 per night from Jul 28 to Jul 29
SAR 737
SAR 803 total
28 Jul - 29 Jul
includes taxes & fees
9.8/10 Exceptional! (47 reviews)
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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.

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 downtown district with its charming 19th-century architecture and local shops selling New Hampshire maple products.

See all hotels in Winchester
A snow-covered town with a river running through it, surrounded by mountains and trees.

Top Winchester Hotel Reviews

The Colonial Hotel

The Colonial Hotel

10/10 Excellent
"Always clean rooms and accommodating staff!"
Diane 1-night trip
Posted 10 hours ago
The Colonial Hotel
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

10/10 Excellent
"Friendly staff"
Nicholas Hamilton 1-night trip
Posted 6 days ago
Courtyard by Marriott Keene Downtown

Frequently asked questions

How much does it cost to stay in a 3-star hotel in Winchester?
To lock in a great-value 3-star hotel in Winchester, use our convenient filter tools. Determine your budget, choose your desired amenities and lots more. You can also arrange your search results so the cheapest options are at the top.

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What is the difference between a 4-star and 3-star hotel in Winchester?
Book a stay at a 3-star hotel and you can look forward to comfortable and well-kept rooms and conveniences such as free WiFi, fitness equipment and tea and coffee making facilities. These lodgings may also feature a restaurant and bar on-site. Elevate your Winchester trip by opting for a 4-star hotel. With things like a spa, round-the-clock room service and premium toiletries, you'll experience a higher level of relaxation and comfort.
What is the difference between a 3-star hotel and a motel in Winchester?
Motels typically offer lower rates than hotels, which makes them great if you're exploring around Winchester on a shoestring. A sought-after pick for overnight stays, these roadside accommodations have simply furnished rooms, basic services and on-site parking. Book a 3-star hotel and you can expect to pay more for additional comfort, space and conveniences. Guests can make use of things like free WiFi, a lobby and business facilities at this kind of property.

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