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

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Winchester 3-star hotels

A cozy living room with a fireplace, a coffee station, and a view of the outside.

1. Colonial Motel

Colonial Motel
3.0 star property
Brattleboro
6.4 out of 10, (108 reviews)
"Value for money. Clean and conveniently located. Friendly staff."
United States
Swaraj
$95 nightly
The price is $105
Nov 1 - Nov 2
Total with taxes and fees
Colonial Motel
A grand lobby with a staircase, a piano, comfortable seating, and large windows.

2. The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
9.0 out of 10, Wonderful, (1,002 reviews)
"We love this hotel! We stay every year when we go to Wachusett Mountain"
United States
Mollie
$122 nightly
The price is $137
Nov 1 - Nov 2
Total with taxes and fees
The Colonial Hotel
A bar area with a high ceiling and stained glass windows, bar stools, and a checkered floor.

3. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,005 reviews)
"Great place to go"
United States
Ruddy
$142 nightly
The price is $154
Nov 1 - Nov 2
Total with taxes and fees
Best Western Plus Keene Hotel
A historic building with a covered porch, American flags, and a sign reading 'Deerfield Inn.'

4. Deerfield Inn

Deerfield Inn
3.0 star property
Deerfield
9.8 out of 10, Exceptional, (39 reviews)
"Excellent stay!"
United States
Debbie
$250 nightly
The price is $307
Nov 4 - Nov 5
Total with taxes and fees
Deerfield Inn
A bar area with a dark tiled backsplash, multiple stools, and a variety of bottles and glasses on the counter.

5. Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.6 out of 10, Excellent, (1,000 reviews)
"Comfortable, clean room. Helpful and friendly staff. Convenient location."
United States
Deborah
$189 nightly
The price is $205
Nov 3 - Nov 4
Total with taxes and fees
Courtyard by Marriott Keene Downtown
Exterior

6. 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, (807 reviews)
"Looking for a quite stay there perfect"
United States
Christopher
$194 nightly
The price is $210
Nov 3 - Nov 4
Total with taxes and fees
Fairfield Inn & Suites by Marriott Keene Downtown
A two-story house with a porch, a balcony, and a chimney.

7. Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (151 reviews)
"Like the ambiance as well as the decor! The location was perfect for walking around town!"
United States
Robert
$131 nightly
The price is $140
Nov 22 - Nov 23
Total with taxes and fees
Blooming Inn
A two-story house with a red door, green shutters, and a snow-covered front yard.

8. Centennial House

Centennial House
3.5 star property
Northfield
9.6 out of 10, Exceptional, (190 reviews)
"Excellent host making us feel very welcome. Very nice room and really lovely breakfast. Would certainly stay again if we are in the area."
United Kingdom
Alan
$164 nightly
The price is $173
Nov 4 - Nov 5
Total with taxes and fees
Centennial House
A wooden table set with plates, cutlery, and a folded napkin.

9. The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (177 reviews)
"Clean,quiet, beautiful inn in the heart of downtown Keene,NH. Joe was friendly and accommodating and a hell of a great guy. A+++++++"
United States
Richard
$169 nightly
The price is $183
Nov 22 - Nov 23
Total with taxes and fees
The Carriage Barn Inn
A large white building with a stone wall and a lawn covered in fallen leaves.

10. Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (363 reviews)
"Beautiful grounds, nice walking trails, comfortable bed, excellent breakfast."
United States
Amy
$146 nightly
The price is $161
Oct 28 - Oct 29
Total with taxes and fees
Colonel Williams Inn
A covered porch with Adirondack chairs and a table with wine glasses, overlooking a lake and lush greenery.

11. The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast
3.5 star property
Ashburnham
10.0 out of 10, Exceptional, (41 reviews)
"Terry and Paul are wonderful warm Innkeepers. The inn is classically New England charming. The lake view is stunning. Appreciated the little touches like nighty cookies, water and snacks in the room."
United States
Jeffrey
$274 nightly
The price is $274
Nov 5 - Nov 6
Total with taxes and fees
The Maguire House Bed & Breakfast
A two-story house with a covered porch, a staircase leading to the upper level, and a well-maintained garden with trees and shrubs.

12. Lakeside Spofford Retreat Near Hiking & Boating!

Lakeside Spofford Retreat Near Hiking & Boating!
3.0 star property
Spofford
Lakeside Spofford Retreat Near Hiking & Boating!
A spacious attic room with a sloped wooden ceiling, large windows, and a view of the outdoors.

13. 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!
Children's play area - outdoor

14. 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
A lakeside view with a red building, trees, and a calm lake.

15. 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!
A cozy living room with wooden furniture, a sofa, a coffee table, and a bookshelf.

16. 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
A picnic setup with a wooden table, cheese, bread, and a basket of bread rolls, overlooking a waterfall and a rustic building.

17. Green River Bridge Inn

Green River Bridge Inn
3.0 star property
Guilford
8.4 out of 10, Very good, (13 reviews)
"Beautiful Inn and property"
United States
JaDean
Green River Bridge Inn
A cozy room with a large bed, a wooden ceiling, a TV, and a desk with a chair.

18. Cavalier Cottage B&B

Cavalier Cottage B&B
3.0 star property
Shelburne Falls
9.4 out of 10, Exceptional, (3 reviews)
"Cavalier Cottage was perfect for my two-night stay. It was very spacious and clean. Patricia was an excellent host, and provided delicious, warm home-made scones each morning which was a really nice touch!"
United States
Kathryn
Cavalier Cottage B&B
A rural road sign for Fiddlehead Farm.

19. 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!
A house with a deck overlooking a lake, a chimney, and a stone foundation.

20. Modern Waterfront Gem w/ Dock on Lake Monomonac

Modern Waterfront Gem w/ Dock on Lake Monomonac
3.0 star property
Winchendon
Modern Waterfront Gem w/ Dock on Lake Monomonac
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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
$99 nightly
The price is $107 total per night from Nov 2 to Nov 3
$107 total
Nov 2 - Nov 3
Total with taxes and fees
9.8/10 Exceptional! (63 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 bridge over a river with a red roof, surrounded by trees and buildings.

Top Winchester Hotel Reviews

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"Breakfast was exceptional. Lori keeps everything clean and organized. We have never been to a hotel breakfast that comes close."
elizabeth 4-night trip
Posted 1 day ago
Best Western Plus Keene Hotel
The Colonial Hotel

The Colonial Hotel

8/10 Good
"This is a dated, solid 3-star hotel. The interior finishes all need a serious refresh. I was on the ground floor in a nice room, but the Wi-Fi was terrible and they stuck me down by the mechanical plant and housekeeping offices. Normally not a bid deal but they left the doors open to the mechanical room the entire time I was in my room. They also need to update the quality and number of WAPs. They were confused when I asked if they had a "business center" because they don't. Given the quality of the Wi-Fi in my room, it would've been nice if they had one.😊 The Colonial Grille is awesome; it is a shining star for this somewhat tired hotel. The restuarant/bar staff are awesome, and the food is good American fare. The bar is a lot of fun, and it's big. This is a local destination for weddings. I was there from Friday to Sunday in late October and I think there were not less than 3 weddings."
David 2-night trip
Posted 2 days ago
The Colonial Hotel

Find out more about Winchester

Three Star Hotel Guide for Winchester

There’s a reason the top 3 star hotels in Winchester, New Hampshire are so incredibly popular: They combine comforting amenities and just-for-you service with some of the best rates and discounts the area has to offer. When you book a stay at a three star hotel in Winchester, you’ll get access to perfect little perks like on-site restaurants and cocktail bars, well-appointed fitness centers, and spacious rooms.

Search for a cheap deal on a 3 star upscale hotel in Winchester for the most elegant experience, or grab a low rate on one of the cheap 3 star hotels in Winchester near the local attractions, if you want something a touch more unassuming. Whatever your traveling style, make sure to use the search tools at Expedia to track down prices, read more about amenities, and score a few local discounts.

From business trips to family getaways, the Winchester 3 star hotels offer a fantastic home base for any type of vacation.

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.

  • Search for the lowest price per night right now from $107

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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