Book Holiday Homes in Winchendon

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Featured Holiday Homes in Winchendon

Lovely 3-bedroom City Escape

Lovely 3-bedroom City Escape

Barre
Stay at this vacation home in Barre. Enjoy free WiFi and air conditioning. Popular attractions Barre Historical Society and Barre Common District are located ...
Lovely 3-bedroom City Escape
Charming barn studio apt,  in lovely Peterborough NH overlooking the downtown.

Charming barn studio apt, in lovely Peterborough NH overlooking the downtown.

2 out of 5
Peterborough
Enjoy an in-room coffeemaker, in-room fireplaces, and air conditioning. Popular attractions Mariposa Museum and World Cultures Center and The Monadnock Center ...
Charming barn studio apt, in lovely Peterborough NH overlooking the downtown.
Lake Adjacent Family Home Ready To Host Your Next Trip To Wachusett Mountain!

Lake Adjacent Family Home Ready To Host Your Next Trip To Wachusett Mountain!

Westminster
Book a stay at this family-friendly vacation home in Westminster. Enjoy free WiFi, a water park, and a garden. Popular attractions Wachusett Brewing Company ...
Lake Adjacent Family Home Ready To Host Your Next Trip To Wachusett Mountain!
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Welcome to your dream lake getaway! Lovely views of 150 feet lakefront bliss!

Welcome to your dream lake getaway! Lovely views of 150 feet lakefront bliss!

Westminster
Book a stay at this ski vacation home in Westminster. Enjoy free WiFi, a water park, and a garden. Popular attractions Redemption Rock and Monadnock Triple Ski ...
Welcome to your dream lake getaway! Lovely views of 150 feet lakefront bliss!
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

Fitchburg
Stay at this vacation home in Fitchburg. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Doyle Community Park and Fitchburg Art Museum ...
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

Westminster
Stay at this vacation home in Westminster. Enjoy a sauna, a garden, and patios. Popular attractions Redemption Rock and Monadnock Triple Ski Lift are located ...
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!

Spacious Estate With Mtn Views! Private Setting, Great Family Home!!

Peterborough
Stay at this vacation home in Peterborough. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Sharon Arts Center and Ava Marie Handmade ...
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
Private Field House - Spacious 4 Bedroom Home

Private Field House - Spacious 4 Bedroom Home

Dublin
Stay at this vacation home in Dublin. Enjoy free WiFi, a garden, and balconies. Popular attractions Friendly Farm and Monadnock State Park are located ...
Private Field House - Spacious 4 Bedroom Home
Cozy 3 bedroom home

Cozy 3 bedroom home

Barre
Stay at this vacation home in Barre. Enjoy air conditioning. Popular attractions Barre Historical Society and Barre Common District are located nearby.
Cozy 3 bedroom home
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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 Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Winchendon vacation homes are the perfect way for you to wing it.

Holiday houses in Winchendon let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Winchendon in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Winchendon adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Winchendon with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Winchendon vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Winchendon Holiday Homes essential information

Accommodation
41 Holiday Homes
Lowest Price
NZ$306
Highest Price
NZ$306
Popular accommodation
Lovely 3-bedroom City Escape, Charming barn studio apt, in lovely Peterborough NH overlooking the downtown., Lake Adjacent Family Home Ready To Host Your Next Trip To Wachusett Mountain!, Welcome to your dream lake getaway! Lovely views of 150 feet lakefront bliss!, Dog-Friendly Fitchburg Vacation Rental, Hike & Ski, Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower, Spacious Estate With Mtn Views! Private Setting, Great Family Home!!, Private Field House - Spacious 4 Bedroom Home, Cozy 3 bedroom home

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
Book a stay at this family-friendly cottage in Winchendon. Enjoy a sauna, a garden, and patios. Popular attractions Blueberry Island and Paradise Island are ...
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
Book a stay at this family-friendly vacation home in Winchendon. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions 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
Book a stay at this family-friendly cottage in Winchendon. Enjoy a fitness center, an in-room coffeemaker, and in-room fireplaces. Popular attractions Blueberry ...
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 NZ$306 per night from 2 Dec to 3 Dec
NZ$306
includes taxes & fees
2 Dec - 3 Dec
Stay at this 3.5-star family-friendly resort in Fitchburg. Enjoy 4 indoor pools, free water park access, and room service. Our guests praise the helpful staff ...
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.