Find hotels in Winchendon, MA from CA $121

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May 13 - May 14
Tomorrow
May 14 - May 15
This weekend
May 17 - May 19
Next weekend
May 24 - May 26

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Top 10 Winchendon hotels and places to stay

In-room safe, desk, blackout drapes, iron/ironing board
Days Inn by Wyndham Keene NH
2.0 star property
7.4 out of 10, Good, (873)
"It is obvious this is an older property. The small refrigerator and the microwave were plugged into an extension cord (not sure how safe that is.....). Overall it was clean and reception desk was very nice. No overall issues. I would recommend"
The price is CA $121
CA $131 total
includes taxes & fees
May 21 - May 22
Days Inn by Wyndham Keene NH
Hypo-allergenic bedding, in-room safe, desk, laptop workspace
Courtyard by Marriott Keene Downtown
3.0 star property
8.8 out of 10, Excellent, (902)
"The beds were comfy, the whole place was extremely clean and every employee we encountered was wonderful. I highly recommend a stay at this hotel, I know I’ll stay there again."
The price is CA $187
CA $203 total
includes taxes & fees
Jun 2 - Jun 3
Courtyard by Marriott Keene Downtown
Interior entrance
Best Western Plus Keene Hotel
3.0 star property
8.2 out of 10, Very good, (1002)
"breakfast area was the best equipped of any I have ever stayed at!"
The price is CA $190
CA $206 total
includes taxes & fees
May 14 - May 15
Best Western Plus Keene Hotel
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Indoor pool
Holiday Inn Express Keene, an IHG Hotel
2.5 star property
8.4 out of 10, Very good, (719)
"The place is in the middle of construction. It was quiet and clean"
The price is CA $172
CA $187 total
includes taxes & fees
May 19 - May 20
Holiday Inn Express Keene, an IHG Hotel
Reception
Hampton Inn & Suites Keene
2.5 star property
9.0 out of 10, Wonderful, (167)
"The hotel is beautiful. All the staff were very friendly and professional. The breakfast was top notch. "
The price is CA $164
CA $178 total
includes taxes & fees
Jun 2 - Jun 3
Hampton Inn & Suites Keene
View from room
Econo Lodge Brattleboro
2.0 star property
5.8 out of 10, (486)
"Clean quiet and affordable place with a friendly staff. Small critique: put a small shelf in the shower for shampoo/soap etc. "
The price is CA $122
CA $134 total
includes taxes & fees
May 14 - May 15
Econo Lodge Brattleboro
Terrace/patio
The Inn At Crumpin Fox
2.5 star property
9.2 out of 10, Wonderful, (223)
"Very clean warm comfortable very good atmosphere "
The price is CA $233
CA $260 total
includes taxes & fees
May 28 - May 29
The Inn At Crumpin Fox
Free daily continental breakfast
The Carriage Barn Inn
3.0 star property
9.6 out of 10, Exceptional, (121)
"The hosts were wonderfully helpful!"
The price is CA $252
CA $274 total
includes taxes & fees
May 26 - May 27
The Carriage Barn Inn
Interior
Latchis Hotel
2.5 star property
8.4 out of 10, Very good, (564)
"We decided to stay at the Latchis because the unique art deco exterior has intrigued us for many years, and the interior more than lived up to the promise of time travel back to the 1930s. Some of the reviewers appear to have gotten lost on their way to a Holiday Inn Express, finding fault with the rugs or the mattresses or the cleaning, and missed the fact that we were in one of the most unique hotels in New England—a loving if not lavish restoration—for the same price. If only more hoteliers...
The price is CA $178
CA $196 total
includes taxes & fees
May 14 - May 15
Latchis Hotel
Exterior detail
Centennial House
3.5 star property
9.4 out of 10, Exceptional, (127)
"The room was exceptionally clean and cozy. Lucy the pet dog so sweet and friendly! We enjoyed conversing with Steve and Joan."
The price is CA $272
CA $288 total
includes taxes & fees
May 14 - May 15
Centennial House
Exterior detail
The One Cat B&B
2.5 star property
9.6 out of 10, Exceptional, (66)
"Wonderful selection of books, friendly hosts, happy colors."
The price is CA $251
CA $277 total
includes taxes & fees
May 28 - May 29
The One Cat B&B
Property grounds
Lakefront Orange Vacation Rental - Pet Friendly!
10.0 out of 10, Exceptional, (6)
"Crystal was an exceptional hostess! "
Lakefront Orange Vacation Rental - Pet Friendly!
Interior
Enjoy your stay in an antique home in an antique toy museum!
9.2 out of 10, Wonderful, (7)
"A unique enjoyable experience "
The price is CA $540
CA $715 total
includes taxes & fees
May 14 - May 15
Enjoy your stay in an antique home in an antique toy museum!
Interior
Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!
10.0 out of 10, Exceptional, (130)
"The property is beautiful and has so many activities from walking in the woods and going out on the water to staying inside and enjoying the game room. Highly recommend!"
Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!
Fridge, microwave, stovetop, coffee/tea maker
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
10.0 out of 10, Exceptional, (22)
"This property is fairytale cute, so welcoming and relaxing. We had a beautiful stay in Vermont thanks to this location. And there were surprise puppies on site!!!!! Honestly this was the kind of trip that gives you confidence in vacation rentals. Clean, wonderfully decorated, off the beaten path a truly relaxing stay! Go outside at night!!!! We dont have stars like that in the city."
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
1 bedroom, iron/ironing board, free WiFi, bed sheets
Spectacular Mountain views with all the amentities nearby
9.8 out of 10, Exceptional, (39)
"The vrbo was as-described and the hosts exceptionally personable and friendly. Exemplary!"
Spectacular Mountain views with all the amentities nearby
Property grounds
Downtown Hot Tub Escape
9.4 out of 10, Exceptional, (3)
"Wonderfully located not to far from plenty of great restaurants and really well kept home that accomadated 9 adults for the night perfectly. Clear instructions for all the amenities in the home made it easy and fun."
The price is CA $239
CA $463 total
includes taxes & fees
May 16 - May 17
Downtown Hot Tub Escape
Exterior
Cozy Updated Log Cabin with Mountain Views close to Monadnock
9.6 out of 10, Exceptional, (18)
"We absolutely loved the privacy and seclusion of the property. Everything was clean and tidy, minus some trash that was left around the firepit, presumably from a previous guest, that we cleaned up. The kitchen was well stocked with cooking tools and the bathroom was just big enough. Guests should take note though that the shower was definitely a tight fit for my 6'1" husband and the furniture was also a struggle for him. One of the beds was only about 4 inches off the ground and the seating was...
The price is CA $180
CA $380 total
includes taxes & fees
May 15 - May 16
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Interior
Charming Waterfront Log Cabin
10.0 out of 10, Exceptional, (24)
"Wonderful place it’s are 3rd time staying there an you can’t beat the location, pond view or the nature surrounding you. An a very fast response. I will be staying agsin!"
Charming Waterfront Log Cabin
Lake
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
10.0 out of 10, Exceptional, (8)
"The house was superb for our family visit! We enjoyed it all! Linda was a perfect hostess…,so attentive!"
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
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See all available properties in Winchendon
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.

Frequently asked questions

What's the best place to stay in Winchendon?

Based on Expedia's traveler preferences, Enjoy your stay in an antique home in an antique toy museum! 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 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 of 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?

Great Wolf Lodge Boston / Fitchburg, MA: Offers 4 indoor pools, a children's pool, and free water-park access. The Colonial Hotel and Doubletree by Hilton Hotel Leominster 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 8 hotels and other accommodations to choose from. Find out more about Winchendon.

What should I see while I'm in Winchendon?

The picturesque setting of Lake Dennison State Recreation Area and Millers River exemplify the area's natural beauty. Additionally, you might want to add Wetmore Trailhead to your itinerary. 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, April, March, and February, with each month seeing an average of 9 inches of snowfall.