Winchendon Hotels from ₹7,975

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Check prices for these dates

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10 Dec - 11 Dec
Tomorrow
11 Dec - 12 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

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Our top choices for Winchendon hotels

Reception
Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster
4.0 star property
Leominster
8.6 out of 10, Excellent, (1001)
"Rooms clean, staff friendly. Nice bar, great breakfast buffet"
United States
Leah
The price is ₹11,351
₹12,679 total
includes taxes & fees
21 Dec - 22 Dec
Doubletree by Hilton Hotel Leominster
4 indoor pools, seasonal outdoor pool, pool cabanas (surcharge)
Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA
3.5 star property
Fitchburg
8.6 out of 10, Excellent, (1002)
"Everything good 👌"
United States
Alexandra
The price is ₹14,885
₹16,626 total
includes taxes & fees
8 Jan - 9 Jan 2026
Great Wolf Lodge Boston / Fitchburg, MA
Interior
The Colonial Hotel

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1007)
"The perfect hotel!"
United States
Elizabeth
The Colonial Hotel
Lobby
Motel 6 Leominster, MA

Motel 6 Leominster, MA

Motel 6 Leominster, MA
2.0 star property
Leominster
8.0 out of 10, Very good, (1005)
"Not like other Motel 6 hotels that I have stayed at. Room was clean and friendly staff. Restaurants nearby to walk to."
United States
Mike
The price is ₹7,280
₹8,312 total
includes taxes & fees
14 Dec - 15 Dec
Motel 6 Leominster, MA
Premium bedding, individually decorated, individually furnished, desk
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1000)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is ₹12,494
₹13,556 total
includes taxes & fees
11 Dec - 12 Dec
Best Western Plus Keene Hotel
Fireplace
Chocksett Inn and Restaurant

Chocksett Inn and Restaurant

Chocksett Inn and Restaurant
3.5 star property
Sterling
8.6 out of 10, Excellent, (144)
"Fine for an overnight stay. Seems to be one of the better options in the area. Room clean and spacious. "
United States
Ayah
The price is ₹14,292
₹15,963 total
includes taxes & fees
11 Dec - 12 Dec
Chocksett Inn and Restaurant
Breakfast area
Riverhouse by Weekender (Formerly Jack Daniels Inn)

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, (435)
"Super cute place! Would stay here again"
United States
Danielle
Riverhouse by Weekender (Formerly Jack Daniels Inn)
In-room safe, desk, blackout curtains, iron/ironing board
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1001)
"Not exactly spotless by the experience was better than at the Courtyard by Marriott on Railroad St. in Keene NH."
United States
Miroslaw
The price is ₹7,351
₹7,975 total
includes taxes & fees
18 Dec - 19 Dec
Days Inn by Wyndham Keene NH
Double Room | Free WiFi
Gardner Inn

Gardner Inn

Gardner Inn
2.0 star property
Gardner
5.6 out of 10, (17)
"The property needs work but hte staff was pleasant and the facility was quiet. "
United States
Lou
The price is ₹8,009
₹8,946 total
includes taxes & fees
4 Jan - 5 Jan 2026
Gardner Inn
Reception
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (353)
"Clean comfy nice staff "
United States
Katherine
The price is ₹13,231
₹14,356 total
includes taxes & fees
23 Dec - 24 Dec
Hampton Inn & Suites Keene
Exterior
Fairfield Inn & Suites by Marriott Keene Downtown

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, (755)
"Front desk pleasant and helpful Breakfast was good Room was spacious and clean Able to walk to shopping and dining. "
United States
Stephen
The price is ₹16,179
₹17,554 total
includes taxes & fees
1 Jan - 2 Jan 2026
Fairfield Inn & Suites by Marriott Keene Downtown
Indoor pool
Keene Elm City Hotel, an Ascend Collection Hotel

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, (960)
"Enjoyed the breakfast options and the very comfortable bed. "
Canada
Nancy
The price is ₹9,788
₹10,620 total
includes taxes & fees
30 Dec - 31 Dec
Keene Elm City Hotel, an Ascend Collection Hotel
Garden
Howarth House B&B

Howarth House B&B

Howarth House B&B
3.0 star property
Fitchburg
10.0 out of 10, Exceptional, (110)
"Beautiful place, great hospitality! "
United States
andrew
Howarth House B&B
Reception
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (1004)
"Very comfortable and clean."
United States
Christina
The price is ₹16,179
₹17,554 total
includes taxes & fees
19 Dec - 20 Dec
Courtyard by Marriott Keene Downtown
Farm to table cuisine
The Birchwood Inn

The Birchwood Inn

The Birchwood Inn
3.5 star property
Temple
9.4 out of 10, Exceptional, (224)
"A wonderful historic Inn. Great resturant and lovely accommodations . A very gracious host."
United States
Anonymous traveller
The price is ₹15,280
₹16,579 total
includes taxes & fees
11 Dec - 12 Dec
The Birchwood Inn
Exterior
The Burrell House

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (155)
"Very helpful, kind staff"
United States
Paitris
The Burrell House
Free daily continental breakfast
The Carriage Barn Inn

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (165)
"Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!"
United States
natalia
The price is ₹11,340
₹12,304 total
includes taxes & fees
31 Dec - 1 Jan 2026
The Carriage Barn Inn
Free daily full breakfast
Centennial House

Centennial House

Centennial House
3.5 star property
Northfield
9.6 out of 10, Exceptional, (173)
"The house was cozy and inviting. Felt the history all around me and the breakfast made and served by Joan was great. We recommend this place for those looking for that historical b&b experience. "
United States
Paul
The price is ₹17,739
₹18,750 total
includes taxes & fees
28 Dec - 29 Dec
Centennial House
Exterior
Monadnock Inn

Monadnock Inn

Monadnock Inn
2.5 star property
Jaffrey
7.6 out of 10, Good, (277)
"It is a Beautiful Old Charm Inn. Everything was great. I would definitely come back and stay there again. "
United States
Sharon-Ann C
Monadnock Inn
Property grounds
The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast
3.5 star property
Ashburnham
10.0 out of 10, Exceptional, (36)
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
United States
Ranjit
The price is ₹24,224
₹24,224 total
includes taxes & fees
7 Jan - 8 Jan 2026
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

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.
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Hyde Park

Explore the great outdoors at Hyde Park, a lovely green space in Winchendon. While you're in the area, wander around the parks.
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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

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

10/10 Excellent
"The room had extra amenities besides a Keurig, refrigerator, and microwave. These included make-up removal wipes, hand lotion, and seasonal decor plus a working desk and dining table. The owners of Riverhouse also equipped the lobby with coffee and tea, mini bagels with butter and cream cheese, granola bars, fresh fruit, and yogurt. Brochures of local attractions were on display. The friendly owners of Riverhouse made me feel right at home! Thank you!"
Amanda 2-night trip
Posted 2 days ago
Riverhouse by Weekender (Formerly Jack Daniels Inn)

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 ₹7,351 per night from 18 Dec to 19 Dec
₹7,351
₹7,975 total
18 Dec - 19 Dec
includes taxes & fees
7/10 Good! (1,000 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 Doubletree by Hilton Hotel Leominster. 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: Features 4 indoor swimming pools, a children's pool and free water park access. Doubletree by Hilton Hotel Leominster 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 9 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 Millers River. A couple of additional sights to add to your itinerary are Lake Dennison State Recreation Area 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.

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