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Featured Cottages in Winchendon

Cottage on Partridge Pond

Cottage on Partridge Pond

Westminster
Located in Westminster, this cottage is on the waterfront, within a 15-minute drive of 1761 Old Mill Gift Shop and Dunn State Park.
Cottage on Partridge Pond
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

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

Westminster
The price is AU$601 per night from 16 Jan to 17 Jan
AU$601
includes taxes & fees
16 Jan - 17 Jan 2025
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 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
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VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula

VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula

Winchendon
With a stay at this cottage in Winchendon, you'll be within a 5-minute drive of Winchendon Community Park and Blueberry Island.
VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula
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
Cottage on Laurel Lake, Private lake access, picture perfect sunsets

Cottage on Laurel Lake, Private lake access, picture perfect sunsets

Fitzwilliam
Located in Fitzwilliam, this cottage is on a lake, a 1-minute drive from Laurel Lake and 6 minutes from Sportsman Pond.
Cottage on Laurel Lake, Private lake access, picture perfect sunsets
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
Charming Jaffrey Cottage w/ Deck & Grill!

Charming Jaffrey Cottage w/ Deck & Grill!

Jaffrey
With a stay at this cottage in Jaffrey, you'll be in the mountains, just steps from Shattuck Golf Course and a 5-minute drive from Jaffrey Civic Center.
Charming Jaffrey Cottage w/ Deck & Grill!
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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
21 Cottages
Lowest Price
AU$381
Highest Price
AU$601
Popular accommodation
Cottage on Partridge Pond, Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board, 2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock, VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula , Waterfront Cottage on Scenic Sportsman Pond, Cottage on Laurel Lake, Private lake access, picture perfect sunsets, Vacationer's oasis on the waterfront of picturesque Pearly Pond., Waterfront Cottage 5 minutes to Mount Wachusett, Dock, Pet Friendly, Kayaks, Charming Jaffrey Cottage w/ Deck & Grill!

Top trending hotels in Winchendon

VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac

VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac

Winchendon
Located in Winchendon, this vacation home is within a 5-minute drive of Winchendon Community Park and Blueberry Island.
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place

Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place

Winchendon
When you stay at this vacation home in Winchendon, you'll be on the waterfront, within a 5-minute drive of Winchendon Community Park and Blueberry Island.
Amazing Lakefront property, Private Pool on Lake Monomonac at Tatum's Place
VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula

VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula

Winchendon
With a stay at this cottage in Winchendon, you'll be within a 5-minute drive of Winchendon Community Park and Blueberry Island.
VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula
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
The price is AU$381 per night from 6 Jan to 7 Jan
AU$381
includes taxes & fees
6 Jan - 7 Jan 2025
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
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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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^Subject to availability and chosen travel dates.