Winchendon Hotels

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 3 - May 4
Tomorrow
May 4 - May 5
This weekend
May 3 - May 5

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

Top 10 trending Winchendon hotels

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!
Interior
Historic Home w/ Modern Updates on 3.5 Acres
3.5 star property
10.0 out of 10, Exceptional, (1)
Historic Home w/ Modern Updates on 3.5 Acres
Free daily continental breakfast
The Carriage Barn Inn
3.0 star property
9.6 out of 10, Exceptional, (120)
"The hosts were wonderfully helpful!"
The price is P 8,918
per night
May 6 - May 7
The Carriage Barn Inn
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Exterior detail
The One Cat B&B
2.5 star property
9.6 out of 10, Exceptional, (65)
"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 P 10,703
per night
May 20 - May 21
The One Cat B&B
Exterior detail
Centennial House
3.5 star property
9.4 out of 10, Exceptional, (125)
"Loved our stay"
The price is P 11,507
per night
May 5 - May 6
Centennial House
Terrace/patio
The Inn At Crumpin Fox
2.5 star property
9.2 out of 10, Wonderful, (221)
"It was as described"
The price is P 9,787
per night
May 20 - May 21
The Inn At Crumpin Fox
Reception
Hampton Inn & Suites Keene
2.5 star property
9.0 out of 10, Wonderful, (160)
"The room was comfortable and clean. Breakfast was great "
The price is P 7,078
per night
May 23 - May 24
Hampton Inn & Suites Keene
Hypo-allergenic bedding, in-room safe, desk, laptop workspace
Courtyard by Marriott Keene Downtown
3.0 star property
8.8 out of 10, Excellent, (895)
"Cleanest hotel bathroom I've ever seen. Good food. Friendly staff. "
The price is P 7,344
per night
May 20 - May 21
Courtyard by Marriott Keene Downtown
Indoor pool
Holiday Inn Express Keene, an IHG Hotel
2.5 star property
8.4 out of 10, Very Good, (718)
"Great stay, great staff! "
The price is P 7,250
per night
May 14 - May 15
Holiday Inn Express Keene, an IHG Hotel
Interior
Latchis Hotel
2.5 star property
8.4 out of 10, Very Good, (559)
"Fun place to stay "
The price is P 6,329
per night
May 6 - May 7
Latchis Hotel
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 P 7,998
per night
May 6 - May 7
Best Western Plus Keene Hotel
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, (871)
"Had a nice stay. Nice and quiet, bed was comfortable and shower had great pressure. The furniture was outdated, but everything was clean and functioned well. Near stores and restaurants and the main roads. The breakfast was a bit lacking, but the coffee was good. "
The price is P 4,891
per night
May 9 - May 10
Days Inn by Wyndham Keene NH
View from room
Econo Lodge Brattleboro
2.0 star property
5.8 out of 10, (485)
"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 P 6,525
per night
May 6 - May 7
Econo Lodge Brattleboro
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.

More cheap stays in Winchendon

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road, Keene, NH
The price is P4,891 per night from May 9 to May 10
P4,891
per night
9 May - 10 May
7.2/10 Good! (868 reviews)

Near an Attraction

Image for Lake Dennison State Recreation Area

Lake Dennison State Recreation Area

Explore the great outdoors at Lake Dennison State Recreation Area, a lovely green space in Winchendon. Discover the area's waterfalls and mountain views.

See properties
Lake Dennison State Recreation Area

Winchendon hotels information

Number of reviews
3,689
Accommodation
184 hotels
Lowest Price
P4,891
Highest Price
P11,507

Frequently asked questions

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 9 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, March, February, and November, with each month seeing an average of 7 inches of snowfall.

Recent Reviews in Winchendon
Expedia verified reviews

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

5/5 Excellent
"The room was comfortable and clean. Breakfast was great "
A verified traveler stayed at Hampton Inn & Suites Keene
Posted 3 days ago
Hampton Inn & Suites Keene