Find hotels in Winchendon, MA from ￥14,254

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Dec 24 - Dec 25
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Dec 25 - Dec 26
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Dec 26 - Dec 28
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Our top choices for Winchendon hotels

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, (967)
"The room was perfect, and the food was great "
United States
Paul
The price is ￥18,391
￥19,954 total
includes taxes & fees
Dec 29 - Dec 30
Keene Elm City Hotel, an Ascend Collection Hotel
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)
"The hotel was very nice and the restaurant was a nice establishment. "
United States
Dina
The price is ￥20,483
￥22,879 total
includes taxes & fees
Dec 30 - Dec 31
Doubletree by Hilton Hotel Leominster
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 ￥18,702
￥20,292 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Carriage Barn Inn
Lobby
Motel 6 Leominster, MA

Motel 6 Leominster, MA

Motel 6 Leominster, MA
2.0 star property
Leominster
8.2 out of 10, Very Good, (1003)
"Very clean room and helpful, friendly staff !"
United States
Ralph
The price is ￥12,644
￥14,436 total
includes taxes & fees
Dec 29 - Dec 30
Motel 6 Leominster, MA
Interior
The Colonial Hotel

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1002)
"Easy checkin, pleasant staff and clean room. "
United States
Susan
The Colonial Hotel
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, (1001)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is ￥21,701
￥23,546 total
includes taxes & fees
Dec 29 - Dec 30
Best Western Plus Keene Hotel
In-room safe, desk, blackout drapes, 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, (1000)
"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 ￥13,137
￥14,254 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Days Inn by Wyndham Keene NH
Reception
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (358)
"Clean comfy nice staff "
United States
Katherine
The price is ￥26,284
￥28,518 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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, (758)
"Room spacious, breakfast good, poor directions to parking, snow covered disability ramp."
United States
Stephanie
The price is ￥28,102
￥30,491 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Fairfield Inn & Suites by Marriott Keene Downtown
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 ￥24,823
￥27,727 total
includes taxes & fees
Dec 25 - Dec 26
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, (437)
"Super cute place! Would stay here again"
United States
Danielle
Riverhouse by Weekender (Formerly Jack Daniels 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
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, (1002)
"Very comfortable and clean."
United States
Christina
The price is ￥28,102
￥30,491 total
includes taxes & fees
Dec 30 - Dec 31
Courtyard by Marriott Keene Downtown
Dinner served, farm to table cuisine
The Birchwood Inn

The Birchwood Inn

The Birchwood Inn
3.5 star property
Temple
9.4 out of 10, Exceptional, (225)
"A wonderful historic Inn. Great resturant and lovely accommodations . A very gracious host."
United States
Anonymous traveler
The price is ￥26,540
￥28,796 total
includes taxes & fees
Dec 25 - Dec 26
The Birchwood Inn
4 indoor pools, seasonal outdoor 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, (1005)
"Nice place "
United States
Daniel
The price is ￥25,150
￥28,093 total
includes taxes & fees
Jan 22 - Jan 23, 2026
Great Wolf Lodge Boston / Fitchburg, MA
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 ￥28,925
￥30,573 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Centennial House
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 ￥38,641
￥38,641 total
includes taxes & fees
Jan 7 - Jan 8, 2026
The Maguire House Bed & Breakfast
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
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 ￥15,456
￥17,264 total
includes taxes & fees
Dec 28 - Dec 29
Gardner Inn
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
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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Wendall P. Clark Memorial

After visiting Wendall P. Clark Memorial, make a plan to see the other sights and activities 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 Center, 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

Motel 6 Leominster, MA

Motel 6 Leominster, MA

10/10 Excellent
"Perfect...they let me check in early too at no charge "
PAUL 1-night trip
Posted 2 days ago
Motel 6 Leominster, MA

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 ￥13,137 per night from Dec 31 to Jan 1
￥13,137
￥14,254 total
Dec 31 - Jan 1, 2026
includes taxes & fees
7/10 Good! (999 reviews)

Frequently asked questions

What's the best place to stay in Winchendon?
Based on Expedia's traveler preferences, Cozy Lakefront Cottage is a top place to stay in Winchendon. Other good choices for your trip to 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.
What are some of the best vacation rentals in Winchendon?
Cozy Lakefront Cottage: Visitors like this Winchendon vacation home rental. It is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of books. 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 that most hotel room reservations are fully refundable if cancelled prior to the hotel's cancellation deadline, which often is within 24-48 hours of your check-in date. If you booked a non-refundable reservation, it may still be possible to cancel it and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchendon.
Where can I learn more about changing or cancelling my trip to Winchendon?
To access more information about updating your trip to Winchendon or cancelling it, click here.
What's the best place to stay near Lake Dennison State Recreation Area?
The Colonial Hotel is one of the top choices for your stay based on our traveler data, and this 3-star hotel offers a restaurant and an indoor pool. You'll find it 9 mi (14.5 km) from Lake Dennison State Recreation Area. Other good options in the area include Super 8 by Wyndham Gardner and The Maguire House Bed & Breakfast.
What are some hotels with pools in Winchendon?
Great Wolf Lodge Boston / Fitchburg, MA: Resort, 9-minute walk from Great Wolf Lodge Waterpark. Features 4 indoor pools, a children's pool, and free water-park access. Doubletree by Hilton Hotel Leominster and The Colonial Hotel are two additional hotels that offer an onsite pool. View all hotels with pools in Winchendon.
What's the best accommodation near Worcester Regional Airport (ORH)?
Hilton Garden Inn Worcester is one of the top choices for your stay and is a popular 3-star hotel featuring a restaurant and an indoor pool. It's located 3.7 mi (5.9 km) from Worcester Regional Airport. Other choices near the airport include Holiday Inn Express Worcester Downtown and AC Hotel by Marriott Worcester.
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 accommodations to choose from. Find out more about Winchendon.
What should I see while I'm in Winchendon?
Natural beauty is on display at Wendall P. Clark Memorial, Millers River, and Hyde Park. A couple of additional sights to add to your agenda are Lake Dennison State Recreation Area and Winchendon Town Hall. Check out what more to see and do in Expedia's Winchendon guide.
What's the weather like in Winchendon?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Winchendon are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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