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

Find hotels in Winchendon, MA from ￥14,431

  • 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
Aug 23 - Aug 24
Tomorrow
Aug 24 - Aug 25
Next weekend
Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6

Filter by

Property class

Guest rating

Our top choices for Winchendon hotels

Interior
Front of property
Outdoor wedding area
Indoor pool

1. The Colonial Hotel

The Colonial Hotel
Gardner
United States
Mark
￥24,311
￥27,156 total
includes taxes & fees
Aug 25 - Aug 26
The Colonial Hotel
Water park
Deluxe Queen Suite
Children's activities
Children's activities

2. Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA
Fitchburg
United States
Jose
￥29,088
￥32,491 total
includes taxes & fees
Aug 24 - Aug 25
Great Wolf Lodge Boston / Fitchburg, MA
Bar (on property)
Presidential Suite, 1 King Bed, Non Smoking | Living area
Fitness facility
Breakfast area

3. Doubletree by Hilton Hotel Leominster

Doubletree by Hilton Hotel Leominster
Leominster
United Kingdom
Elizabeth
￥25,286
￥28,244 total
includes taxes & fees
Aug 30 - Aug 31
Doubletree by Hilton Hotel Leominster
Room
Vending machine
Property entrance
Lobby

4. Motel 6 Leominster, MA

Motel 6 Leominster, MA
Leominster
United States
Linda
￥12,635
￥14,431 total
includes taxes & fees
Aug 26 - Aug 27
Motel 6 Leominster, MA
Front of property
Front of property
Front of property
Double Room

5. Gardner Inn

Gardner Inn
Gardner
United States
Vicki
￥15,736
￥17,577 total
includes taxes & fees
Aug 24 - Aug 25
Gardner Inn
Restaurant
Property amenity
Lobby
Room

6. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
Keene
United States
Karen
￥23,684
￥25,698 total
includes taxes & fees
Aug 24 - Aug 25
Best Western Plus Keene Hotel
Front of property - evening/night
Garden
Outdoor pool
Interior

7. Howarth House B&B

Howarth House B&B
Fitchburg
United States
David
￥33,618
￥33,618 total
includes taxes & fees
Aug 24 - Aug 25
Howarth House B&B
Bar (on property)
Breakfast meal
Room
Pool

8. Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
Keene
United States
Deborah
￥28,539
￥30,965 total
includes taxes & fees
Aug 30 - Aug 31
Courtyard by Marriott Keene Downtown
Lobby
Standard Room, 1 King Bed, Non Smoking
Pool
Breakfast area

9. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
Keene
United States
James
￥19,074
￥20,695 total
includes taxes & fees
Sep 1 - Sep 2
Keene Elm City Hotel, an Ascend Collection Hotel
Terrace/patio
Room
Property grounds
Superior Room, 1 Queen Bed, Private Bathroom (Wisteria Room)

10. The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast
Ashburnham
United States
Ranjit
￥42,130
￥42,130 total
includes taxes & fees
Aug 26 - Aug 27
The Maguire House Bed & Breakfast
Breakfast area
Reception
Pool
Snack bar

11. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
Keene
United States
Christopher
￥23,982
￥26,021 total
includes taxes & fees
Sep 1 - Sep 2
Hampton Inn & Suites Keene
Standard Room, 1 King Bed, Non Smoking
Lobby
Lobby
Lobby

12. Econo Lodge

Econo Lodge
Westminster
United States
Chauncey
￥17,429
￥19,120 total
includes taxes & fees
Sep 21 - Sep 22
Econo Lodge
Exterior
Lobby
Lobby
Exterior

13. Monadnock Inn

Monadnock Inn
Jaffrey
United States
Saif
￥26,158
￥28,382 total
includes taxes & fees
Aug 26 - Aug 27
Monadnock Inn
Exterior
Lobby
Lobby
Lobby

14. Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
Keene
United States
James
￥28,539
￥30,965 total
includes taxes & fees
Aug 30 - Aug 31
Fairfield Inn & Suites by Marriott Keene Downtown
Restaurant
Cambridge Suite, 1 Queen bed
Traditional Room, 1 Bedroom, Accessible
Interior entrance

15. The Birchwood Inn

The Birchwood Inn
Temple
United States
Karen
￥27,816
￥30,181 total
includes taxes & fees
Aug 25 - Aug 26
The Birchwood Inn
Breakfast area
Restaurant
Lounge
Exterior

16. The Carriage Barn Inn

The Carriage Barn Inn
Keene
United States
Jonathan
￥22,067
￥23,942 total
includes taxes & fees
Aug 24 - Aug 25
The Carriage Barn Inn
Fireplace
Interior entrance
Interior detail
Hallway

17. Chocksett Inn and Restaurant

Chocksett Inn and Restaurant
Sterling
United States
Beth
￥25,273
￥28,229 total
includes taxes & fees
Aug 24 - Aug 25
Chocksett Inn and Restaurant
Room
Fitness facility
Breakfast area
Lobby

18. Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
Keene
United States
Michael
￥15,404
￥16,713 total
includes taxes & fees
Sep 16 - Sep 17
Days Inn by Wyndham Keene NH
BBQ/picnic area
Guesthouse B
Front of property
Breakfast area

19. Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)
Peterborough
United States
Tracy
￥22,351
￥25,974 total
includes taxes & fees
Sep 23 - Sep 24
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Exterior
Exterior
Staircase
Deluxe Double Room | Private kitchenette

20. The Burrell House

The Burrell House
Keene
United States
Justin
￥19,946
￥22,239 total
includes taxes & fees
Sep 1 - Sep 2
The Burrell House
View all properties
Save an average of 15% on thousands of hotels when you're signed in

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

Blueberry Island

Blueberry Island sits privately in Lake Monomonac, spanning the NH-MA border. While enjoying the lake's recreational offerings, respect the island's residential nature and focus on surrounding public areas instead.
See properties

Winchendon Community Park

Winchendon Community Park offers a picturesque amphitheater for concerts and community events during warmer months. Enjoy dog-friendly trails before settling in for performances under the stars.
See properties

Winchendon Town Hall

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

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.
See properties

Beals Memorial Library

This historic library houses literary treasures and sensory-friendly programs for neurodivergent visitors. Browse the collection, join a book club, or borrow unique items from their "Library of Things" like telescopes.
See properties

Wetmore Trailhead

Wetmore Trailhead opens to miles of serene forest and wetland paths in Birch Hill Wildlife Management Area. Bring sturdy shoes and binoculars for spotting native birds along the well-maintained trails.
See properties

Monument Park

Monument Park is just one of the places to see in Winchendon, so why not enjoy the other things to explore during your travels? While you're in the area, wander around the parks.
See properties

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
A river reflecting autumn trees and a dense forest.

Top Winchendon Hotel Reviews

The Burrell House

The Burrell House

10/10 Excellent
"Quaint very clean room walking distance to centre of town"
Matthew 2-night trip
Posted 13 hours ago
The Burrell House
Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

10/10 Excellent
"Right in the middle of town. Very comfortable. Nice breakfast in the morning. Liked the candy in the lobby."
James 2-night trip
Posted 13 hours ago
Fairfield Inn & Suites by Marriott Keene Downtown
Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

10/10 Excellent
"Good place with the kids"
Teles 2-night trip
Posted 18 hours ago
Great Wolf Lodge Boston / Fitchburg, MA
Motel 6 Leominster, MA

Motel 6 Leominster, MA

10/10 Excellent
"Staff is always accomadating"
PAUL 1-night trip
Posted 20 hours ago
Motel 6 Leominster, MA
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

10/10 Excellent
"The location was good and walkable to the downtown restaurants and shops. The room was clean and comfortable and the staff was very helpful with advising on area hikes. The only negative was the outside of the property could have more attention to detail. Will definitely go back next time in Peterborough NH."
William and Susan 2-night trip
Posted 2 days ago
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

10/10 Excellent
"Comfortable, clean room. Helpful and friendly staff. Convenient location."
Deborah 3-night trip
Posted 4 days ago
Courtyard by Marriott Keene Downtown
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

8/10 Good
"It was a very pleasant stay"
Joseph 1-night trip
Posted 7 days ago
Days Inn by Wyndham Keene NH
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

10/10 Excellent
"Quiet place and clean. Efficient and helpful staff."
William 1-night trip
Posted 7 days ago
Hampton Inn & Suites Keene
Enjoy your stay in an antique home in an antique toy museum!

Enjoy your stay in an antique home in an antique toy museum!

10/10 Excellent
"An outstanding property filled with history, beautiful furniture and highly recommended"
Eileen L. 1-night trip
Posted 11 days ago
Enjoy your stay in an antique home in an antique toy museum!

More cheap stays in Winchendon

Motel 6 Leominster, MA

Motel 6 Leominster, MA

48 Commercial Rd Leominster MA
￥12,635
￥14,431 total
Aug 26 - Aug 27
includes taxes & fees
8.2/10 Very Good! (1,014 reviews)
Motel 6 Leominster, MA
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
￥15,404
￥16,713 total
Sep 16 - Sep 17
includes taxes & fees
7/10 Good! (1,004 reviews)
Days Inn by Wyndham Keene NH
Gardner Inn

Gardner Inn

22 Pearson Blvd Gardner MA
￥15,736
￥17,577 total
Aug 24 - Aug 25
includes taxes & fees
Gardner Inn
Econo Lodge

Econo Lodge

183 Main St Westminster MA
￥17,429
￥19,120 total
Sep 21 - Sep 22
includes taxes & fees
6.4/10 (325 reviews)
Econo Lodge
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH
￥19,074
￥20,695 total
Sep 1 - Sep 2
includes taxes & fees
Keene Elm City Hotel, an Ascend Collection Hotel
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

126 Key Rd Keene NH
￥23,982
￥26,021 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (406 reviews)
Hampton Inn & Suites Keene

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 traveler data. Other good choices for your trip to 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.
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 steps from Great Wolf Lodge Waterpark. Provides 4 indoor 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 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 11 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 Blueberry Island, Millers River, and Hyde Park. A couple of additional sights to add to your agenda are Lake Dennison State Recreation Area and Beals Memorial Library. 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.

Explore a world of travel with Expedia