Find hotels in Winchendon, MA from ￥16,425

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Oct 28 - Oct 29
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Oct 31 - Nov 2
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Compare 210 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Reception
Doubletree by Hilton Hotel Leominster
Doubletree by Hilton Hotel Leominster
4.0 star property
8.6 out of 10, Excellent, (1005)
"Very nice and clean hotel "
United States
octavio
The price is ￥20,540
￥22,944 total
includes taxes & fees
Nov 25 - Nov 26
Doubletree by Hilton Hotel Leominster
Interior
The Colonial Hotel
The Colonial Hotel
3.0 star property
8.8 out of 10, Excellent, (1008)
"Great hotel, fantastic restaurant, wonderful place!"
United States
Kate
The Colonial Hotel
Premium bedding, individually decorated, individually furnished, desk
Best Western Plus Keene Hotel
Best Western Plus Keene Hotel
3.0 star property
8.4 out of 10, Very Good, (1002)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is ￥22,758
￥24,693 total
includes taxes & fees
Oct 29 - Oct 30
Best Western Plus Keene Hotel
Fireplace
Chocksett Inn and Restaurant
Chocksett Inn and Restaurant
3.5 star property
8.6 out of 10, Excellent, (138)
"Good price very clean will stay there again "
United States
Brittany
The price is ￥24,286
￥27,127 total
includes taxes & fees
Oct 30 - Oct 31
Chocksett Inn and Restaurant
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
7.0 out of 10, Good, (1003)
"Would stay again"
United States
Judy
The price is ￥15,450
￥16,763 total
includes taxes & fees
Nov 2 - Nov 3
Days Inn by Wyndham Keene NH
Lobby
Motel 6 Leominster, MA
Motel 6 Leominster, MA
2.0 star property
8.0 out of 10, Very Good, (1026)
"Clean room, quiet Walk to restaurants and shops, Reliable Internet Perfect place to stay while visiting family in the area"
United States
Jennifer
The price is ￥14,432
￥16,425 total
includes taxes & fees
Nov 4 - Nov 5
Motel 6 Leominster, MA
Indoor pool
Keene Elm City Hotel, an Ascend Collection Hotel
Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
8.4 out of 10, Very Good, (936)
"Nice place to stay "
United States
James
The price is ￥19,108
￥20,732 total
includes taxes & fees
Nov 11 - Nov 12
Keene Elm City Hotel, an Ascend Collection Hotel
Single Room | Free WiFi
Gardner Inn
Gardner Inn
2.0 star property
5.6 out of 10, (11)
"The property needs work but hte staff was pleasant and the facility was quiet. "
United States
Lou
The price is ￥15,121
￥16,890 total
includes taxes & fees
Nov 2 - Nov 3
Gardner Inn
Exterior
Fairfield Inn & Suites by Marriott Keene Downtown
Fairfield Inn & Suites by Marriott Keene Downtown
2.5 star property
8.8 out of 10, Excellent, (746)
"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 ￥25,813
￥28,007 total
includes taxes & fees
Nov 4 - Nov 5
Fairfield Inn & Suites by Marriott Keene Downtown
Breakfast area
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Riverhouse by Weekender (Formerly Jack Daniels Inn)
2.5 star property
9.4 out of 10, Exceptional, (431)
"Super cute place! Would stay here again"
United States
Danielle
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Reception
Hampton Inn & Suites Keene
Hampton Inn & Suites Keene
2.5 star property
8.8 out of 10, Excellent, (342)
"Nice place to stay, nice area, will stay again."
United States
Catherine
The price is ￥25,173
￥27,312 total
includes taxes & fees
Nov 16 - Nov 17
Hampton Inn & Suites Keene
Reception
Courtyard by Marriott Keene Downtown
Courtyard by Marriott Keene Downtown
3.0 star property
8.8 out of 10, Excellent, (1002)
"Lovely hotel"
United States
ronald
The price is ￥25,202
￥27,344 total
includes taxes & fees
Nov 26 - Nov 27
Courtyard by Marriott Keene Downtown
Free daily continental breakfast
The Carriage Barn Inn
The Carriage Barn Inn
3.0 star property
9.6 out of 10, Exceptional, (163)
"Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!"
United States
natalia
The price is ￥27,621
￥29,969 total
includes taxes & fees
Nov 20 - Nov 21
The Carriage Barn Inn
Garden
Howarth House B&B
Howarth House B&B
3.0 star property
10.0 out of 10, Exceptional, (109)
"Beautiful gardens"
United States
Christine
Howarth House B&B
Exterior
The Burrell House
The Burrell House
2.5 star property
9.6 out of 10, Exceptional, (152)
"Very helpful, kind staff"
United States
Paitris
The Burrell House
Free daily full breakfast
Centennial House
Centennial House
3.5 star property
9.6 out of 10, Exceptional, (171)
"The property was wonderful and the hosts exceptional❤️"
United States
Susan
The price is ￥27,355
￥28,915 total
includes taxes & fees
Oct 29 - Oct 30
Centennial House
Lunch, dinner, brunch served; farm to table cuisine
The Birchwood Inn
The Birchwood Inn
3.5 star property
9.4 out of 10, Exceptional, (218)
"The Innkeeper was very pleasant and considerate of my schedule and had fresh bread for me."
United States
Pamela
The price is ￥25,966
￥28,173 total
includes taxes & fees
Oct 29 - Oct 30
The Birchwood Inn
Exterior
Monadnock Inn
Monadnock Inn
2.5 star property
7.6 out of 10, Good, (272)
"It is a Beautiful Old Charm Inn. Everything was great. I would definitely come back and stay there again. "
United States
Sharon-Ann C
The price is ￥20,925
￥22,703 total
includes taxes & fees
Nov 2 - Nov 3
Monadnock Inn
Property grounds
The Maguire House Bed & Breakfast
The Maguire House Bed & Breakfast
3.5 star property
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 ￥38,645
￥38,645 total
includes taxes & fees
Nov 12 - Nov 13
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.
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

Top Winchendon Hotel Reviews

The Colonial Hotel

The Colonial Hotel

10/10 Excellent
"N/A"
Charlene 1-night trip
Posted 19 hours ago
The Colonial Hotel

More cheap stays in Winchendon

Motel 6 Leominster, MA

Motel 6 Leominster, MA

48 Commercial Rd, Leominster, MA
The price is ￥14,432 per night from Nov 4 to Nov 5
￥14,432
￥16,425 total
Nov 4 - Nov 5
includes taxes & fees
8/10 Very Good! (1,026 reviews)

Frequently asked questions

What's the best place to stay in Winchendon?
Based on Expedia's traveler preferences, Modern Waterfront Gem w/ Dock on Lake Monomonac is a top place to stay in Winchendon. Other good choices for your trip to the area are The Colonial Hotel and Motel 6 Leominster, MA. See all available top hotels, or vacation rentals in Winchendon.
What are some of the best vacation rentals in Winchendon?
Charming Waterfront Log Cabin: This vacation home rental outside Winchendon is located on the waterfront and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. 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?
The Colonial Hotel: Features a sauna, an indoor pool, and free self parking. Doubletree by Hilton Hotel Leominster 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 10 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 Millers River, V F W Park, and Blueberry Island. A couple of additional sights to add to your agenda are Lake Dennison State Recreation Area and Wetmore Trailhead. 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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