Find hotels in Winchendon, MA from ￥13,771

Most hotels are fully refundable. Because flexibility matters.

Save an average of 15% on thousands of hotels with Expedia Rewards.

Search over 2.9 million properties and 550 airlines worldwide

Find properties with these dates

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

Filter by

Popular filters
Popular filters
Price per night
Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility
Traveler experience
Traveler experience

Compare 185 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Lakefront Orange Vacation Rental - Pet Friendly!
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!
Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!
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!
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
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!
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Charming Waterfront Log Cabin
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
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
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
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
Interior
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
3.5 star property
10.0 out of 10, Exceptional, (1)
"We had a truly wonderful stay. The cottage and property are beautiful, peaceful and very special. Great views! Our host thought of everything, it's very comfortable and lovely. Best place to stay in Southern Vermont! Don't miss the Tiny Bread Box on Saturdays; it's just up the road. We'll defiantly be back for another visit."
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
Penthouse, Steps to the Sandy Beach & clear water
Dishwasher
Penthouse, Steps to the Sandy Beach & clear water
10.0 out of 10, Exceptional, (5)
"The Penthouse was a great place to rent for our family get-together. The owners live nearby and are very responsive to any issues that may arise, and indeed promptly addressed questions and any issues that we had. It was a great vacation place for us (other family members rented other houses on the property from the same owner so we were able to get together and have plenty of room). The lake is perfect -- clean and beautiful, and we made the most out of boating and kayaking activities there."
Penthouse, Steps to the Sandy Beach & clear water
Historic Home w/ Modern Updates on 3.5 Acres
4 bedrooms, desk, iron/ironing board, internet
Historic Home w/ Modern Updates on 3.5 Acres
10.0 out of 10, Exceptional, (5)
"The property was awesome! Old, quaint and brought memories back of our grandparents homes…Family sat around table and enjoyed shared memories"
Historic Home w/ Modern Updates on 3.5 Acres
Waterfont log home nestled in the pines
Interior
Waterfont log home nestled in the pines
10.0 out of 10, Exceptional, (43)
"Property was perfect for a guys get away fishing trip. Alfred was very attentive and helpful. I've stayed at many Vrbo house but this is one of my favorites. Hope to stay here again soon Steve"
Waterfont log home nestled in the pines
Historic Home w/ Modern Updates on < 4 Acres
Interior
Historic Home w/ Modern Updates on < 4 Acres
3.5 star property
10.0 out of 10, Exceptional, (1)
Historic Home w/ Modern Updates on < 4 Acres
Spectacular Mountain views with all the amentities nearby
1 bedroom, iron/ironing board, free WiFi, bed sheets
Spectacular Mountain views with all the amentities nearby
9.8 out of 10, Exceptional, (39)
"We were visiting relatives and found Hickory Hill a really wonderful place to stay, both comfortable and pleasant. It is a working kennel so there were occasional barks but was very quiet at night- you can see both sunrise and sunset from the deck. The area has dark skies so the stars are really clear ... big improvement for us city folks. Very glad they board people in addition to pups! :)"
Spectacular Mountain views with all the amentities nearby
Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford
Property grounds
Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford
9.8 out of 10, Exceptional, (22)
"Our daughter just turned 43 and is severely challenged and in a wheelchair requiring her helper Staff to assist. The house had the proper h/c accommodations for this without having the appearance of such. This is not a medical facility but, a wonderful camp on a beautiful lake that allows for your needs or just a great camp with no h/c needs. You would never notice such if you didn't need the accommodation. Right on the lake yet, with the privacy we wished for. We were able to go swimming...
Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford
Main House, Relax and enjoy the scenery, go and swim, fish or start your boat
Dishwasher
Main House, Relax and enjoy the scenery, go and swim, fish or start your boat
9.8 out of 10, Exceptional, (8)
"We booked last minute to celebrate my mom’s birthday with family. Anthony was very accommodating and understanding of our family needs. He went out of his way to ensure my elderly parents were comfortable. The house was well stocked and VERY clean. We would stay again!"
Main House, Relax and enjoy the scenery, go and swim, fish or start your boat
The Carriage Barn Inn
Free daily continental breakfast
The Carriage Barn Inn
3.0 star property
9.6 out of 10, Exceptional, (121)
"Joe went above and beyond for us. I recently had surgery and needed a chair to put in the shower (not the typical request) and he found me one within ten minutes of asking. He also had a lovely breakfast and was enjoy to talk to"
The price is ￥28,685
￥31,123 total
includes taxes & fees
May 20 - May 21
The Carriage Barn Inn
The One Cat B&B
Exterior detail
The One Cat B&B
2.5 star property
9.6 out of 10, Exceptional, (66)
"This is an awesome B&B! Pat and Conrad are great hosts and they live on site so they are available if you need anything. The room was clean and very spacious. There was comfortable seating in addition to the bed. The room had it's own Keurig machine and it's own AC/heat system. Breakfast the next morning was delicious. Several food and drink options to consider. Also, Conrad bakes his own bread. I had the maple oat bread which was so good. This was my first time in Brattleboro. I will definitely...
The price is ￥26,670
￥29,336 total
includes taxes & fees
May 26 - May 27
The One Cat B&B
Cozy Updated Log Cabin with Mountain Views close to Monadnock
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 ￥20,563
￥43,271 total
includes taxes & fees
May 15 - May 16
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Centennial House
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 ￥31,000
￥32,767 total
includes taxes & fees
May 19 - May 20
Centennial House
Downtown Hot Tub Escape
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 ￥27,262
￥52,737 total
includes taxes & fees
May 16 - May 17
Downtown Hot Tub Escape
Waterfront Cottage on Scenic Sportsman Pond
Exterior
Waterfront Cottage on Scenic Sportsman Pond
9.4 out of 10, Exceptional, (34)
"Linda was wonderful in her review of the property and was very accommodating in all aspects of our stay. The cottage was well equipped and very comfortable including the mattress. We enjoyed the lake and a little fishing. The area is very nice and we did some exploring. It was very quiet and we rarely even saw anyone while we were on the lake. We hope to return in the spring or summer. Many thanks to Linda and Brad"
Waterfront Cottage on Scenic Sportsman Pond
"The Murdock Suite @ The Large House"
Fridge, microwave, oven, dishwasher
"The Murdock Suite @ The Large House"
9.4 out of 10, Exceptional, (3)
"We stayed at the Murdoch suite when we had to fly back to New Hampshire for a family funeral. The suite suited our needs well. It was clean and well stocked. The only negative is it is located on a major road, right after a round about, so there is a lot of road noise."
"The Murdock Suite @ The Large House"
Don't see what you're looking for?
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.