A hilly landscape with a tower on top, dense forest, and a cloudy sky.

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Check prices for these dates

Next weekend
10 Jul - 12 Jul
In two weeks
17 Jul - 19 Jul

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Star rating

Our top choices for Winchendon hotels

Lobby

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.6 out of 10, Excellent, (1,004 reviews)
"Good stay everything you could ask for from a budget friendly hotel."
United States
Stephen
The price is ąøæ3,948
ąøæ4,284 total
includes taxes & fees
6 Jul - 7 Jul
Keene Elm City Hotel, an Ascend Collection Hotel
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, (1,004 reviews)
"This place is awesome"
United States
Deserie
The price is ąøæ4,943
ąøæ5,522 total
includes taxes & fees
30 Jul - 31 Jul
Great Wolf Lodge Boston / Fitchburg, MA
Restaurant

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,003 reviews)
"Best place to stay the food was good and we had a wonderful stay. Swimming pool was fun and safe for kids"
United States
Nidia Ruby
The price is ąøæ4,220
ąøæ4,579 total
includes taxes & fees
8 Jul - 9 Jul
Best Western Plus Keene Hotel
Interior

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,005 reviews)
"Good place to stay "
United States
Glenn
The price is ąøæ5,074
ąøæ5,668 total
includes taxes & fees
7 Jul - 8 Jul
The Colonial Hotel
Lobby

Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster
4.0 star property
Leominster
8.6 out of 10, Excellent, (1,001 reviews)
"Best place in central mass to stay!"
United States
Linda
The price is ąøæ5,550
ąøæ6,199 total
includes taxes & fees
26 Jul - 27 Jul
Doubletree by Hilton Hotel Leominster
Free WiFi, bed sheets

Motel 6 Leominster, MA

Motel 6 Leominster, MA
2.0 star property
Leominster
8.2 out of 10, Very good, (1,000 reviews)
"Once again it was another great stay"
United States
alice
The price is ąøæ3,593
ąøæ4,079 total
includes taxes & fees
2 Aug - 3 Aug
Motel 6 Leominster, MA
Free daily buffet breakfast

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (390 reviews)
"Clean rooms, good location, easy parking, excellent service!"
United States
Kerry
The price is ąøæ6,379
ąøæ6,921 total
includes taxes & fees
12 Jul - 13 Jul
Hampton Inn & Suites Keene
Front of property ā€“ evening/night

Howarth House B&B

Howarth House B&B
3.0 star property
Fitchburg
10.0 out of 10, Exceptional, (115 reviews)
"Ryan and Sarah were so nice! They made our one night stay feel like we stayed at a friend's home. Their Bed and Breakfast was so quaint and charming. Our room was very comfortable with the jacuzzi bath. The breakfast was delicious. You get to choose what you prefer either an omelette, pancakes, waffles, or any egg style. It was so nice to wake up to a great breakfast. My wife and I were so impressed with everything they did, we highly recommend staying here if you are in the area of...
United States
Mark
The price is ąøæ7,017
ąøæ7,017 total
includes taxes & fees
12 Jul - 13 Jul
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, (174 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is ąøæ5,999
ąøæ6,509 total
includes taxes & fees
7 Jul - 8 Jul
The Carriage Barn Inn
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, (1,001 reviews)
"Great breakfast, friendly staff and good place to stay."
United States
Michael
The price is ąøæ2,933
ąøæ3,182 total
includes taxes & fees
30 Jul - 31 Jul
Days Inn by Wyndham Keene NH
Standard Room, 1 King Bed, Non Smoking | Free WiFi, bed sheets, alarm clocks

Econo Lodge

Econo Lodge
2.0 star property
Westminster
6.4 out of 10, (319 reviews)
"Clean rooms and friendly staff "
United States
Steven
The price is ąøæ4,943
ąøæ5,423 total
includes taxes & fees
6 Jul - 7 Jul
Econo Lodge
Front of property

Gardner Inn

Gardner Inn
2.0 star property
Gardner
7.4 out of 10, Good, (33 reviews)
"Great for a quick stay while passing through!"
United States
Cristen
The price is ąøæ3,669
ąøæ4,098 total
includes taxes & fees
6 Jul - 7 Jul
Gardner Inn
Fireplace

Chocksett Inn and Restaurant

Chocksett Inn and Restaurant
3.5 star property
Sterling
8.8 out of 10, Excellent, (169 reviews)
"Beautiful inn, nice room, friendly staff."
United States
Annemarie
The price is ąøæ5,275
ąøæ5,892 total
includes taxes & fees
7 Jul - 8 Jul
Chocksett Inn and Restaurant
Lobby

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.6 out of 10, Excellent, (1,000 reviews)
"Na no breakfast parking easy no cost "
United States
John
The price is ąøæ6,270
ąøæ6,803 total
includes taxes & fees
7 Jul - 8 Jul
Courtyard by Marriott Keene Downtown
Dinner served

The Birchwood Inn

The Birchwood Inn
3.5 star property
Temple
9.4 out of 10, Exceptional, (231 reviews)
"A true old inn, private bathrooms, sitting room and a comfortable bed. Coffee, snacks and breakfast items in each room. The food in the restaurant was exceptional. Friendly staff."
United States
Mark
The price is ąøæ5,806
ąøæ6,299 total
includes taxes & fees
8 Jul - 9 Jul
The Birchwood Inn
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, (783 reviews)
"My favorite hotel!!!!"
United States
Brian
The price is ąøæ5,471
ąøæ5,936 total
includes taxes & fees
29 Jul - 30 Jul
Fairfield Inn & Suites by Marriott Keene Downtown
Exterior

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (172 reviews)
"Self check-in and checkout. Room was very clean but a bit too much potpourri for my allergies. Will stay here again when in Keene. "
United States
Charles
The price is ąøæ4,882
ąøæ5,443 total
includes taxes & fees
8 Jul - 9 Jul
The Burrell House
Exterior

Monadnock Inn

Monadnock Inn
2.5 star property
Jaffrey
7.8 out of 10, Good, (287 reviews)
"Lots of character and run by a great family!"
United States
Evan
The price is ąøæ5,460
ąøæ5,924 total
includes taxes & fees
16 Jul - 17 Jul
Monadnock Inn
BBQ/picnic Area

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)
2.5 star property
Peterborough
9.2 out of 10, Wonderful, (468 reviews)
"I love this place."
United States
Tracy
The price is ąøæ5,927
ąøæ6,791 total
includes taxes & fees
4 Aug - 5 Aug
Riverhouse by Weekender (Formerly Jack Daniels 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 ąøæ9,455
ąøæ9,455 total
includes taxes & fees
5 Aug - 6 Aug
The Maguire House Bed & Breakfast
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.
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Stay near popular Winchendon attractions

Lake Dennison State Recreation Area

10.0/10 (1 review)
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

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
A river reflecting autumn trees and a dense forest.

Top Winchendon Hotel Reviews

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"A perfect place for 30 members of our clan to gather as we attended wedding festivities 1/2 hour away at Cobb Hill over three days. The breakfast (complimentary) had tons of choices, the pool was fun, the snacks near the front desk were perfect and most of all, the staff was very kind. My daughter with her husband and three children were in a huge room!"
Kate 3-night trip
Posted 10 hours ago
Best Western Plus Keene 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 ąøæ2,933 per night from 30 Jul to 31 Jul
ąøæ2,933
ąøæ3,182 total
30 Jul - 31 Jul
includes taxes & fees
7/10 Good! (1,001 reviews)

Frequently asked questions

What's the best place to stay in Winchendon?
Great Wolf Lodge Boston / Fitchburg, MA, located 13.6 mi (21.9 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 Keene Elm City Hotel, an Ascend Collection 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. Features 4 indoor swimming pools, a children's pool and free water park access. The Colonial Hotel and Keene Elm City Hotel, an Ascend Collection 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 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 Blueberry Island, Millers River and Hyde Park. A couple of additional sights to add to your itinerary are Lake Dennison State Recreation Area and Beals Memorial Library. 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 19Ā°C, while the coldest months are January and February, with an average of -2Ā°C. The snowiest months in Winchendon are January, March, February and November, with each month seeing an average of 19 cm of snowfall.