Hot Winchendon Cottage Rates

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Cottages in Winchendon

Cottage beside a waterfall

Cottage beside a waterfall

Wilton
With a stay at this vacation home in Wilton, you'll be within a 10-minute drive of Solon Mansfield Memorial Library and Temple Town Hall.
Cottage beside a waterfall
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

Westminster
When you stay at this cottage in Westminster, you'll be in the mountains, within a 5-minute drive of Wachusett Mountain State Reservation and Polar Express.
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
2 queen and 2 twin beds

2 queen and 2 twin beds

Milford
Located in Milford, this cottage is within a 5-minute drive of Harlan Burns Forest and Hazel Adams Burns Park.
2 queen and 2 twin beds
Save an average of 15% on thousands of hotels when you're signed in
Waterfront Cottage on Scenic Sportsman Pond

Waterfront Cottage on Scenic Sportsman Pond

Fitzwilliam
With a stay at this cottage in Fitzwilliam, you'll be on the waterfront, just steps from Sportsman Pond and a 4-minute drive from Lawrence Brook WMA.
Waterfront Cottage on Scenic Sportsman Pond
Vacationer's oasis on the waterfront of picturesque Pearly Pond.

Vacationer's oasis on the waterfront of picturesque Pearly Pond.

Rindge
When you a stay at this cottage in Rindge, you'll be on the beach, just steps from Franklin Pierce University and Pearly Lake.
Vacationer's oasis on the waterfront of picturesque Pearly Pond.
Waterfront Cottage 5 minutes to Mount Wachusett, Dock, Pet Friendly, Kayaks

Waterfront Cottage 5 minutes to Mount Wachusett, Dock, Pet Friendly, Kayaks

Westminster
With a stay at this cottage in Westminster, you'll be within a 5-minute drive of Wachusett Mountain State Reservation and Polar Express.
Waterfront Cottage 5 minutes to Mount Wachusett, Dock, Pet Friendly, Kayaks
Beautiful Waterfront Cottage With a HOT TUB For Your Family Getaway!

Beautiful Waterfront Cottage With a HOT TUB For Your Family Getaway!

Rindge
With a stay at this cottage in Rindge, you'll be on the waterfront, just steps from Pearly Lake and a 3-minute drive from Franklin Pierce University.
Beautiful Waterfront Cottage With a HOT TUB For Your Family Getaway!
Finnish Cabin with Sauna on Lake Monomonac

Finnish Cabin with Sauna on Lake Monomonac

2 out of 5
Rindge
Located in Rindge, this cottage is on a lake, a 1-minute drive from Wellington Park and 5 minutes from Rindge Historcal Museum.
Finnish Cabin with Sauna on Lake Monomonac
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

Rindge
When you stay at this cottage in Rindge, you'll be on the waterfront, within a 5-minute drive of Contoocook Lake and Contoocook River.
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Don't see what you're looking for?
See all available properties in Winchendon
View all properties
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.

Winchendon Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Winchendon will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Winchendon definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Winchendon, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Winchendon Cottages essential information

Accommodation
23 Cottages
Lowest Price
Highest Price
Popular accommodation
Cottage beside a waterfall, Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board, 2 queen and 2 twin beds, Waterfront Cottage on Scenic Sportsman Pond, Vacationer's oasis on the waterfront of picturesque Pearly Pond., Waterfront Cottage 5 minutes to Mount Wachusett, Dock, Pet Friendly, Kayaks, Beautiful Waterfront Cottage With a HOT TUB For Your Family Getaway!, Finnish Cabin with Sauna on Lake Monomonac, 2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

Top trending hotels in Winchendon

Modern Waterfront Gem w/ Dock on Lake Monomonac

Modern Waterfront Gem w/ Dock on Lake Monomonac

Winchendon
Located in Winchendon, this vacation home is on the waterfront, a 1-minute drive from Blueberry Island and 6 minutes from Winchendon Community Park.
Modern Waterfront Gem w/ Dock on Lake Monomonac
Modern Waterfront Gem w/ Dock on Lake Monomonac

Modern Waterfront Gem w/ Dock on Lake Monomonac

3 out of 5
Winchendon
Located in Winchendon, this cottage is a 1-minute drive from Blueberry Island and 6 minutes from Winchendon Community Park.
Modern Waterfront Gem w/ Dock on Lake Monomonac
The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road, Gardner, MA
Fully refundableReserve now, pay when you stay
Located in Gardner, The Colonial Hotel is a 2-minute drive from Dunn State Park and 6 minutes from Mount Wachusett Community College.
The Colonial Hotel
Save an average of 15% on thousands of hotels when you're signed in
Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 out of 5
150 Great Wolf Dr, Fitchburg, MA
Fully refundableReserve now, pay when you stay
With a stay at Great Wolf Lodge Boston / Fitchburg, MA in Fitchburg, you'll be within a 5-minute drive of Great Wolf Lodge Waterpark and Wachusett Brewing ...
Great Wolf Lodge Boston / Fitchburg, MA
Don't see what you're looking for?
See all available properties in Winchendon
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.