Winchendon hotels from RM351

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
24 Jan - 25 Jan
Tomorrow
25 Jan - 26 Jan
Next weekend
30 Jan - 1 Feb
In two weeks
6 Feb - 8 Feb

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Winchendon hotels

Terrace/patio

The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast
3.5 star property
Ashburnham
10.0 out of 10, Exceptional, (36 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 RM1,102
RM1,102 total
includes taxes & fees
28 Jan - 29 Jan
The Maguire House Bed & Breakfast
Lobby

Gardner Inn

Gardner Inn
2.0 star property
Gardner
5.2 out of 10, (19 reviews)
"Clean room, comfy bed, quiet guests around my room. Staff was cordial when I checked in. "
United States
Kathy
The price is RM441
RM492 total
includes taxes & fees
25 Jan - 26 Jan
Gardner Inn
Interior

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,007 reviews)
"Well-kept hotel with a great restaurant."
United States
Adam
The Colonial Hotel
Free WiFi, bed sheets

Motel 6 Leominster, MA

Motel 6 Leominster, MA
2.0 star property
Leominster
8.2 out of 10, Very good, (1,005 reviews)
"Clean room and friendly staff!"
United States
Ralph
The price is RM324
RM370 total
includes taxes & fees
2 Feb - 3 Feb
Motel 6 Leominster, MA
Lobby

Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster
4.0 star property
Leominster
8.6 out of 10, Excellent, (1,000 reviews)
"Clean room nice area close to shopping and plenty of restaurants "
United States
janine
The price is RM572
RM638 total
includes taxes & fees
1 Feb - 2 Feb
Doubletree by Hilton Hotel Leominster
Fireplace

Chocksett Inn and Restaurant

Chocksett Inn and Restaurant
3.5 star property
Sterling
8.8 out of 10, Excellent, (148 reviews)
"The staff was very accommodating and friendly. Quaint place to stay. "
United States
Helen
The price is RM677
RM756 total
includes taxes & fees
26 Jan - 27 Jan
Chocksett Inn and Restaurant
BBQ/picnic Area

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)
2.5 star property
Peterborough
9.4 out of 10, Exceptional, (444 reviews)
"Room was clean, spacious and staff was pleasant. "
United States
Susan
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Free daily full breakfast

Centennial House

Centennial House
3.5 star property
Northfield
9.6 out of 10, Exceptional, (173 reviews)
"great proprietors beautiful vintage home excellent breakfast"
United States
JAMES
The price is RM762
RM805 total
includes taxes & fees
1 Feb - 2 Feb
Centennial House
In-room safe, desk, blackout curtains, iron/ironing board

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1,000 reviews)
"Checkin was quick. I like the pre-check in process."
United States
Anthony
The price is RM324
RM351 total
includes taxes & fees
27 Jan - 28 Jan
Days Inn by Wyndham Keene NH
Front of property – evening/night

Howarth House B&B

Howarth House B&B
3.0 star property
Fitchburg
10.0 out of 10, Exceptional, (112 reviews)
"Absolutely beautiful house. The owners are so kind and the breakfast is amazing."
United States
James
Howarth House B&B
Free daily continental breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (167 reviews)
"Very helpful and welcoming host. "
United States
Bruce
The price is RM511
RM554 total
includes taxes & fees
25 Jan - 26 Jan
The Carriage Barn Inn
Exterior

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (156 reviews)
"The building and room were very nice. The location is great, very walkable to the center of town. "
United States
Rochelle
The Burrell House
Exterior

Monadnock Inn

Monadnock Inn
2.5 star property
Jaffrey
7.6 out of 10, Good, (278 reviews)
"The Inn was cozy, the room was clean and comfortable. The owner was engaging and helpful. Would definitely stay there again. "
United States
E S
Monadnock Inn
Pub

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (1,002 reviews)
"Really clean hotel, friendly staff and great location."
United States
Aaron
The price is RM721
RM782 total
includes taxes & fees
8 Feb - 9 Feb
Courtyard by Marriott Keene Downtown
Exterior

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
2.5 star property
Keene
8.8 out of 10, Excellent, (759 reviews)
"Everything was clean, comfortable and the staff quite conversational"
United States
Diane
The price is RM706
RM766 total
includes taxes & fees
30 Jan - 31 Jan
Fairfield Inn & Suites by Marriott Keene Downtown
Fitness facility

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.4 out of 10, Very good, (979 reviews)
"Reasonably priced and clean."
United States
Justin
The price is RM497
RM539 total
includes taxes & fees
25 Jan - 26 Jan
Keene Elm City Hotel, an Ascend Collection Hotel
Free daily buffet breakfast

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (364 reviews)
"Room is very clean , breakfast is good and fresh .coffee serve well all time . Will back to stay again . "
United States
Raymond
The price is RM678
RM736 total
includes taxes & fees
22 Feb - 23 Feb
Hampton Inn & Suites Keene
Restaurant

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,002 reviews)
"Great stay pool was very nice"
United States
Patrick
The price is RM557
RM604 total
includes taxes & fees
25 Jan - 26 Jan
Best Western Plus Keene Hotel
Farm to table cuisine

The Birchwood Inn

The Birchwood Inn
3.5 star property
Temple
9.4 out of 10, Exceptional, (225 reviews)
"Very comfortable bed. Best out of the last 50 hotels we have stayed in."
United States
Rungnapha
The price is RM701
RM761 total
includes taxes & fees
28 Jan - 29 Jan
The Birchwood Inn
Water park

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA
3.5 star property
Fitchburg
8.6 out of 10, Excellent, (1,008 reviews)
"The room was clean, the staff was very nice!"
United States
Entela
The price is RM717
RM801 total
includes taxes & fees
28 Jan - 29 Jan
Great Wolf Lodge Boston / Fitchburg, MA
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Stay near popular Winchendon attractions

Lake Dennison State Recreation Area

This serene 85-acre lake offers swimming, fishing, and access to 50+ miles of mountain biking trails. Reserve one of the 150 wooded campsites early for a prime lakeside spot to fully experience this natural retreat.
See properties

Winchendon Town Hall

The Winchendon Municipal Building serves as the town's administrative centre. Visitors can observe civic operations during business hours and occasionally attend public meetings.
See properties

Learn more about Winchendon

Toy Town's charm comes alive at the Old Murdock Senior Centre, where the town's unique toy-making history is celebrated. Lake Dennison Recreation Area offers perfect summer swimming, while winter visitors can explore nearby Wachusett Mountain for skiing in Princeton.

See all hotels in Winchendon
The Millers River in Winchendon, Massachusetts

Top Winchendon Hotel Reviews

The Colonial Hotel

The Colonial Hotel

10/10 Excellent
"Yes"
licia 1-night trip
Posted 5 days ago
The Colonial Hotel

More cheap stays in Winchendon

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
The price is RM324 per night from 27 Jan to 28 Jan
RM324
RM351 total
27 Jan - 28 Jan
includes taxes & fees
7/10 Good! (999 reviews)

Frequently asked questions

What's the best place to stay in Winchendon?
Based on Expedia's traveller preferences, Modern Waterfront Gem w/ Dock on Lake Monomonac is a top place to stay in Winchendon. Other good choices for your stay in the area are Great Wolf Lodge Boston / Fitchburg, MA and The Colonial Hotel. See all available top hotels, or 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: Resort steps from Great Wolf Lodge Waterpark. Offers 4 indoor swimming pools, a children's pool and free water park access. The Colonial Hotel and Doubletree by Hilton Hotel Leominster 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 11 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 Wendall P. Clark Memorial, Hyde Park and Militia Training Field. A couple of additional sights to add to your itinerary are Lake Dennison State Recreation Area and Otter River State Forest. 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.

Explore a world of travel with Expedia