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Search results; 342 homes in Winchendon

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Guest favourite

Cabin in Winchendon

The little house on Mirror Pond

2 bedrooms, 2 beds, 1.5 private bathrooms

25–30 Oct

$1,544 SGD for 5 nights

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4.96 out of 5 average rating, 137 reviews

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Guest favourite

Place to stay in Winchendon

Enjoy your stay in an Antique Home in a Toy Museum

3 bedrooms, 3 beds, 2 bathrooms

1–6 Oct

$2,528 SGD for 5 nights

4.9 out of 5 average rating, 106 reviews

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Superhost

Home in Winchendon

Waterfront home 2 bedrooms withdeck beach and dock

2 bedrooms, 2 beds, 1 bathroom

4–9 Oct

$960 SGD for 5 nights

Free cancellation

4.79 out of 5 average rating, 363 reviews

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Superhost

Home in Rindge

Pine and Pond Retreat

3 bedrooms, 4 beds, 2 bathrooms

1–6 Oct

$2,307 SGD for 5 nights

New place to stay

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Apartment in Winchendon

Private 1st Floor Apt @ Winchendon Center Town

2 bedrooms, 2 beds, 1 bathroom

11–16 Oct

$621 SGD for 5 nights

4.62 out of 5 average rating, 65 reviews

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Guest favourite

Home in Winchendon

Fully Renovated Cottage

2 bedrooms, 2 beds, 1 bathroom

26–31 Oct

$986 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 40 reviews

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Guest favourite

Home in Rindge

Lakefront Mid-Century Cottage with Sandy Beach

2 bedrooms, 3 beds, 1 bathroom

4–9 Oct

$1,549 SGD for 5 nights

4.83 out of 5 average rating, 6 reviews

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Cabin in New Ipswich

Bungalow

1 bedroom, 2 beds, 1 bathroom

4–9 Oct

$1,874 SGD for 5 nights

Free cancellation

4.84 out of 5 average rating, 49 reviews

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Top guest favourite

Home in Ashburnham

Escape to the Lake!

3 bedrooms, 5 beds, 2 bathrooms

19–24 Oct

$2,430 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 70 reviews

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Superhost

Home in Ashburnham

Tranquil Family Friendly Lakefront Retreat

4 bedrooms, 5 beds, 3 bathrooms

12–17 Oct

$2,422 SGD for 5 nights

Free cancellation

4.63 out of 5 average rating, 148 reviews

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Guest favourite

Home in Winchendon

Top 10 VRBO Copley's Lakefront Cottage+Guesthouse

4 bedrooms, 9 beds, 4 bathrooms

17–22 Oct

$9,395 SGD for 5 nights

4.91 out of 5 average rating, 45 reviews

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Barn in Ashburnham

Beautiful, Modern Farmhouse, Walk to Cushing!

3 bedrooms, 3 beds, 1.5 bathrooms

1–6 Oct

$2,880 SGD for 5 nights

New place to stay

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Home in Ashburnham

Walk to Cushing Academy | Sleeps 10

4 bedrooms, 4 beds, 3.5 bathrooms

1–6 Oct

New place to stay

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Superhost

Bed and breakfast in Rindge

Rindge Glass Flower Rm3, PvtRoom Pvt Bath King bed

1 bedroom, 1 king bed, 1 bathroom

1–6 Oct

$893 SGD for 5 nights

Free cancellation

New place to stay

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Top guest favourite

Cottage in Winchendon

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

3 bedrooms, 7 beds, 3 bathrooms

1–6 Oct

$7,088 SGD for 5 nights

4.98 out of 5 average rating, 59 reviews

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Top guest favourite

Home in Jaffrey

Willow Falls Home ~Hot tub & Waterfront

3 bedrooms, 3 beds, 3 bathrooms

5–10 Oct

$3,363 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 108 reviews

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Cabin in Rindge

Secluded Lake Cabin Perfect for Family Fun!

3 bedrooms, 3 queen beds, 1 bathroom

5–10 Oct

$2,394 SGD for 5 nights

4.8 out of 5 average rating, 25 reviews

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Guest favourite

Home in Winchendon

Lake Monomonac Cottage with Private Beach & Dock

1 bedroom, 1 queen bed, 1 bathroom

1–8 Oct

Weekly discount

5.0 out of 5 average rating, 16 reviews

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Guest favourite

Home in Rindge

Wake Up on the Water | Private Beach & Dock

3 bedrooms, 7 beds, 2 bathrooms

4–9 Oct

$3,523 SGD for 5 nights

4.95 out of 5 average rating, 58 reviews