Hotels in Winchendon

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Next weekend
Jun 19 - Jun 21
In two weeks
Jun 26 - Jun 28

Where to stay in Winchendon?

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, (1,003 reviews)
Escape to this welcoming hotel in Keene, where you'll find an indoor pool and fitness center near local shops and eateries. Despite its commercial location, guests enjoy a quiet atmosphere, free breakfast, and helpful staff to enhance your stay.
The price is $109
$118 total
includes taxes & fees
Jun 14 - Jun 15
Keene Elm City Hotel, an Ascend Collection Hotel
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)
Quiet rooms welcome travelers to this restful retreat near the Ashuelot River and Thorne Sagendorph Art Gallery. The restaurant and bar provide delicious meals, while fellow guests rave about the free breakfast and helpful staff.
The price is $119
$129 total
includes taxes & fees
Jun 14 - Jun 15
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
2.0 star property
Keene
7.0 out of 10, Good, (1,006 reviews)
The price is $88
$96 total
includes taxes & fees
Jun 15 - Jun 16
Days Inn by Wyndham Keene NH
Interior

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,006 reviews)
Discover a peaceful retreat with Swedish spa services and a welcoming bar. Near Wachusett Mountain Ski Area, this countryside haven offers in-room refrigerators and convenient access to scenic Dunn State Park. Guests rave about the restaurant and attentive staff.
The price is $170
$190 total
includes taxes & fees
Jun 14 - Jun 15
The Colonial Hotel
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, (308 reviews)
The price is $139
$152 total
includes taxes & fees
Jun 14 - Jun 15
Econo Lodge
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, (1,016 reviews)
Escape to this woodland retreat near Wachusett Mountain Ski Area, where adventure awaits with a lazy river, water park, and 4 indoor pools. Lodge Wood Fired Grill serves American cuisine while comfortable rooms include refrigerators and microwaves.
The price is $149
$166 total
includes taxes & fees
Jun 14 - Jun 15
Great Wolf Lodge Boston / Fitchburg, MA
Exterior

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (170 reviews)
Tucked into walkable Keene, this cozy guesthouse offers free WiFi and convenient self parking. Explore nearby Central Square and local shops, then unwind in the peaceful picnic area after a day of adventures.
The price is $142
$158 total
includes taxes & fees
Jun 14 - Jun 15
The Burrell House
Fireplace

Chocksett Inn and Restaurant

Chocksett Inn and Restaurant
3.5 star property
Sterling
8.8 out of 10, Excellent, (158 reviews)
Rustic charm meets modern comfort at this Sterling retreat featuring on-site dining at Chocksett Cellar Grille. Enjoy free WiFi, parking, and room service while exploring nearby Mary Had a Little Lamb Statue and Davis' Farmland & Mega Maze.
The price is $159
$178 total
includes taxes & fees
Jun 16 - Jun 17
Chocksett Inn and Restaurant
Front of property

Gardner Inn

Gardner Inn
2.0 star property
Gardner
6.0 out of 10, (37 reviews)
Set near Dunn State Park, this hotel offers free WiFi and parking for hassle-free exploration. A 24-hour front desk ensures support at any hour, while the Old Mill Gift Shop provides local shopping opportunities just minutes away.
The price is $99
$111 total
includes taxes & fees
Jun 14 - Jun 15
Gardner Inn
Dinner served

The Birchwood Inn

The Birchwood Inn
3.5 star property
Temple
9.4 out of 10, Exceptional, (228 reviews)
Nestled in Temple, this Colonial inn features a farm-to-table restaurant, bar, and outdoor terrace. Rooms come equipped with refrigerators and microwaves, while free breakfast, WiFi, and parking enhance the experience. Temple Mountain awaits nearby.
The price is $175
$190 total
includes taxes & fees
Jun 24 - Jun 25
The Birchwood Inn
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)
The price is $167
$187 total
includes taxes & fees
Jul 12 - Jul 13
Doubletree by Hilton Hotel Leominster
Free daily buffet breakfast

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (387 reviews)
Located in Keene with easy access to Cheshire Children's Museum, this hotel offers a refreshing indoor pool and 24-hour fitness center. Enjoy complimentary breakfast, free parking, and attentive staff to enhance your stay while exploring nearby attractions.
The price is $169
$184 total
includes taxes & fees
Jun 28 - Jun 29
Hampton Inn & Suites Keene
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, (780 reviews)
The price is $180
$195 total
includes taxes & fees
Jun 28 - Jun 29
Fairfield Inn & Suites by Marriott Keene Downtown
Free daily continental breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (172 reviews)
Wake up to continental breakfast at this cozy Keene B&B, located near the Thorne-Sagendorph Art Gallery. Enjoy free WiFi and parking while exploring the area, with Manchester-Boston Regional Airport and Brattleboro Station both accessible for day trips.
The price is $181
$196 total
includes taxes & fees
Jul 12 - Jul 13
The Carriage Barn Inn
Accessible bathroom

Motel 6 Leominster, MA

Motel 6 Leominster, MA
2.0 star property
Leominster
8.2 out of 10, Very Good, (1,023 reviews)
This well-positioned motel offers convenient access to North Leominster Station, just a 14-minute walk away. Clean rooms with daily housekeeping provide comfort while The Mall at Whitney Field and Doyle Community Park await nearby.
The price is $131
$148 total
includes taxes & fees
Jun 17 - Jun 18
Motel 6 Leominster, MA
Exterior

Monadnock Inn

Monadnock Inn
2.5 star property
Jaffrey
7.6 out of 10, Good, (284 reviews)
Feel the enchantment at this mountain B&B adjacent to Shattuck Golf Course. Explore nearby hiking trails and mountain biking routes, then unwind in this historic inn. Free WiFi and parking add convenience while Jaffrey Civic Center offers cultural intrigue.
The price is $183
$198 total
includes taxes & fees
Jun 15 - Jun 16
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, (464 reviews)
The price is $225
$255 total
includes taxes & fees
Jun 22 - Jun 23
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Front of property - evening/night

Howarth House B&B

Howarth House B&B
3.0 star property
Fitchburg
10.0 out of 10, Exceptional, (114 reviews)
Howarth House B&B offers a quiet retreat with soft pillows and jetted tubs for ultimate relaxation. Just a 16-minute walk from Fitchburg Station and near hiking trails, enjoy free breakfast, WiFi and parking during your rejuvenating escape.
The price is $235
$235 total
includes taxes & fees
Jun 18 - Jun 19
Howarth House B&B
Lobby

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (1,003 reviews)
Located in downtown Keene, this Art Deco hotel offers an indoor pool and 24-hour fitness center. Grab a bite at the coffee shop or unwind with drinks at the bar. Near Colonial Theatre and Central Square, enjoy free WiFi and parking during your stay.
The price is $180
$195 total
includes taxes & fees
Jun 28 - Jun 29
Courtyard by Marriott Keene Downtown
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

Top landmarks in Winchendon

Lake Dennison State Recreation Area

5.0/5 (1 review)
Lake Dennison State Recreation Area is 3.5 mi (5.6 km) from central Winchendon, why not stop by during your stay.
See properties

Learn more about Winchendon

Winchendon is well-known for its attractions such as Lake Dennison State Recreation Area and Millers River.

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

Check out reviews of Winchendon hotels guests love

Motel 6 Leominster, MA

Motel 6 Leominster, MA

2/10 Terrible
"Drugs being sold outside Dirty room Smelled like smoke"
Earl 3-night trip
Posted 5 hours ago
Motel 6 Leominster, MA

Frequently asked questions

What accommodations do travelers recommend in Winchendon?
Guests like The Colonial Hotel, Gardner Inn and Monadnock Inn.
Can I book a refundable hotel in Winchendon?
If you're looking for the flexibility to change your travel plans to Winchendon, most accommodations provide refundable* bookable rates. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Winchendon if I want a vacation home instead of a traditional hotel?
Browse 7 vacation homes on our site.
What will the weather in Winchendon be like during my vacation?
The warmest months in Winchendon are usually July and August with an average temp of 66°F. January and February are the chilliest months when the average temp is 28°F. The rainiest months are July and October.
Why should I book my Winchendon hotel through Hotels.com?
There are plenty of reasons to book your Winchendon travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.