Search Winchendon hotels

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check Winchendon hotel prices

Tonight
24 Nov - 25 Nov
Tomorrow night
25 Nov - 26 Nov
Next weekend
29 Nov - 1 Dec

Filter by

Guest rating
Guest rating
Property class

Top hotels and accommodation in Winchendon

Latchis Hotel
Interior

Latchis Hotel

2.5 star property
8.4 out of 10, Very good, (678)
"Took Amtrak and decided to spend one night in town. Hotel conveniently located to station, local bus, and shops/restaurants. Easily walkable to anywhere you need to go, and movie theater next door had convenient timings. Clean room, comfortable bed, and so much space in the room. "
The price is AU$206
includes taxes & fees
4 Dec - 5 Dec
Latchis Hotel
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, (963)
"Great rooms and service love it my favorite place to stay in Keene "
The price is AU$126
includes taxes & fees
9 Dec - 10 Dec
Days Inn by Wyndham Keene NH
Best Western Plus Keene Hotel
Exterior

Best Western Plus Keene Hotel

3.0 star property
8.2 out of 10, Very good, (1003)
"Best breakfast. Balcony is too small you can’t even put a chair on it"
The price is AU$220
includes taxes & fees
1 Dec - 2 Dec
Best Western Plus Keene Hotel
Hampton Inn & Suites Keene
Reception

Hampton Inn & Suites Keene

2.5 star property
8.8 out of 10, Excellent, (256)
"Great place!"
The price is AU$224
includes taxes & fees
2 Dec - 3 Dec
Hampton Inn & Suites Keene
Courtyard by Marriott Keene Downtown
Hypo-allergenic bedding, in-room safe, desk, laptop workspace

Courtyard by Marriott Keene Downtown

3.0 star property
8.8 out of 10, Excellent, (994)
"Well appointments room, very spacious and quiet. Fan I bathroom did not work "
The price is AU$197
includes taxes & fees
12 Dec - 13 Dec
Courtyard by Marriott Keene Downtown
Holiday Inn Express Keene, an IHG Hotel
Indoor pool

Holiday Inn Express Keene, an IHG Hotel

2.5 star property
8.4 out of 10, Very good, (799)
"Clean and comfy. The hotel location was close to many places to shop and eat. At the hotel the staff was friendly and there was hot coffee available. I think there was a remodel in progress, but you would not know that anything was going on. Breakfast was great!"
The price is AU$199
includes taxes & fees
26 Nov - 27 Nov
Holiday Inn Express Keene, an IHG Hotel
Econo Lodge Brattleboro
View from room

Econo Lodge Brattleboro

2.0 star property
5.6 out of 10, (515)
"It was fine. We just stopped in for the night after a concert"
The price is AU$137
includes taxes & fees
25 Nov - 26 Nov
Econo Lodge Brattleboro
The Inn At Crumpin Fox
Terrace/patio

The Inn At Crumpin Fox

2.5 star property
9.2 out of 10, Wonderful, (274)
"Near good dining…."
The price is AU$359
includes taxes & fees
25 Nov - 26 Nov
The Inn At Crumpin Fox
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (142)
"Lovely old BnB, easy to find, very convenient Very clean room Great continental breakfast Loved ease of walking to downtown, many stores and restaurants Informative and very friendly and helpful owner"
The price is AU$302
includes taxes & fees
25 Nov - 26 Nov
The Carriage Barn Inn
Centennial House
Exterior detail

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (145)
"Lovely bed & breakfast!!! We appreciate the hospitality and delicious breakfast. "
The price is AU$291
includes taxes & fees
25 Nov - 26 Nov
Centennial House
The One Cat B&B
Exterior detail

The One Cat B&B

2.5 star property
9.6 out of 10, Exceptional, (74)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
The One Cat B&B
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Exterior

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

9.8 out of 10, Exceptional, (6)
"Our two night stay was great. Loved how close it was to the bike path and the fire pit in the back. Clare was very responsive!"
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
The Covey House Retreat with InfraRed Sauna
Outdoor dining

The Covey House Retreat with InfraRed Sauna

10.0 out of 10, Exceptional, (3)
"We had an amazing stay, your place is awesome!"
The Covey House Retreat with InfraRed Sauna
Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!
Interior

Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!

10.0 out of 10, Exceptional, (142)
"Mother-of-bride: Since everyone attending my daughter's wedding in NH came from a different state I wanted a place where she and her bridesmaids could spend the night together before the wedding and have plenty of room to get ready on the big day. It was a generous and very awesome gift to be able to give our princess a castle for the night! TY Hunt Castle, you did not disappoint. Everyone was in awe of this spectacular home."
Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!
Lakefront Orange Vacation Rental - Pet Friendly!
Outdoor dining

Lakefront Orange Vacation Rental - Pet Friendly!

10.0 out of 10, Exceptional, (11)
"Great host communication, everything we needed, unexpected extras (like dog treats), and a beautiful view. Would gladly stay again!"
Lakefront Orange Vacation Rental - Pet Friendly!
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Exterior

Cozy Updated Log Cabin with Mountain Views close to Monadnock

9.4 out of 10, Exceptional, (20)
"Very nice, clean, and great area. We enjoyed it very much!"
The price is AU$428
includes taxes & fees
26 Nov - 27 Nov
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Spectacular Mountain views with all the amentities nearby
Smart TV

Spectacular Mountain views with all the amentities nearby

9.8 out of 10, Exceptional, (51)
"What a wonderful place to stay!! We were in town for my 50th high school reunion, hadn’t been back to the area in 35 years. Our accommodations enhanced a beautiful weekend, and the foliage was the cherry on top! Spacious, clean, tastefully furnished and decorated. Well equipped with every utensil, and kitchen appliance you could need! Comfy bed, great shower & good water pressure too! Secluded and quiet, but very convenient to Bernardston, Northfield and Greenfield as well as I-91. Highly...
Spectacular Mountain views with all the amentities nearby
Downtown Hot Tub Escape
Fridge, microwave, oven, stovetop

Downtown Hot Tub Escape

9.4 out of 10, Exceptional, (9)
"Brought my parents and my Brother to this rental - It was a nice place."
The price is AU$574
includes taxes & fees
25 Nov - 26 Nov
Downtown Hot Tub Escape
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
Lake

Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby

9.8 out of 10, Exceptional, (15)
"Very nice house and property! "
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
Charming Waterfront Log Cabin
3 bedrooms, travel cot, free WiFi, bed sheets

Charming Waterfront Log Cabin

9.4 out of 10, Exceptional, (36)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin
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.
Don't see what you're looking for?
See all available properties in Winchendon
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Frequently asked questions

What's the best place to stay in Winchendon?

Great Wolf Lodge Boston / Fitchburg, MA, located 13.8 mi (22.2 km) from the heart of Winchendon, is a top choice for your stay, based on our traveller data. Other good choices for your stay in the area are The Colonial Hotel and Doubletree by Hilton Hotel Leominster. See all available top hotels, or vacation rentals in Winchendon.

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

VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac: This highly rated holiday home rental in Winchendon offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. Another good choice for your trip to Winchendon is Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place. See all vacation rentals in Winchendon.

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

Yes, you'll find most room reservations are fully refundable if you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a reservation that's non-refundable, you might be able to cancel it and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchendon.

What are some hotels with pools in Winchendon?

Great Wolf Lodge Boston / Fitchburg, MA: Offers 4 indoor swimming pools, a children's pool and free water park access. Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place and The Colonial Hotel are two additional hotels with an on-site pool. View all hotels with pools in Winchendon.

What is staying in Winchendon like?

Visitors can enjoy all that Winchendon has to offer, including its parks. In Winchendon, there are 6 hotels and other accommodation options to choose from. Find out more about Winchendon.

What are the top places to visit in Winchendon?

Natural beauty is on display at Lake Dennison State Recreation Area, Wendall P. Clark Memorial and Monument Park. A couple of additional sights to add to your itinerary are Beals Memorial Library and Winchendon Town Hall. Take a look at what more there is to see and do in Expedia's Winchendon guide.

What's the seasonal weather in Winchendon?

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 Winchendon are January, March, February and November, with each month seeing an average of 19 cm of snowfall.