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Search results; 352 homes in Winchendon

Top guest favourite

Place to stay in Winchendon

Enjoy your stay in an Antique Home in a Toy Museum

3 bedrooms, 3 beds, 2 private bathrooms

5–10 Aug

$2,431 SGD for 5 nights

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4.93 out of 5 average rating, 102 reviews

Superhost

Home in Rindge

Lakefront Mid-Century Cottage with Sandy Beach

2 bedrooms, 3 beds, 1 bathroom

5–10 Aug

$2,427 SGD for 5 nights

New place to stay

Superhost

Home in Winchendon

Waterfront home 2 bedrooms withdeck beach and dock

2 bedrooms, 2 beds, 1 bathroom

13–18 Sept

$1,134 SGD for 5 nights

4.8 out of 5 average rating, 348 reviews

Top guest favourite

Cabin in Winchendon

The little house on Mirror Pond

2 bedrooms, 2 queen beds, 1.5 bathrooms

20–25 Sept

$1,987 SGD for 5 nights

4.96 out of 5 average rating, 127 reviews

Top guest favourite

Home in Winchendon

Fully Renovated Cottage

2 bedrooms, 2 beds, 1 bathroom

11–16 Sept

$1,217 SGD for 5 nights

5.0 out of 5 average rating, 33 reviews

Guest favourite

Home in Winchendon

Lake Monomonac Cottage with Private Beach & Dock

1 bedroom, 1 queen bed, 1 bathroom

23–28 Aug

$1,570 SGD for 5 nights

5.0 out of 5 average rating, 8 reviews

Top guest favourite

Bed and breakfast in Rindge

Rindge Glass Flower Rm1 PvtRoom, PvtBath, King Bed

1 bedroom, 1 king bed, 1 bathroom

6–11 Aug

$998 SGD for 5 nights

4.99 out of 5 average rating, 181 reviews

Apartment in Winchendon

Private 1st Floor Apt @ Winchendon Center Town

2 bedrooms, 2 beds, 1 bathroom

22–27 Aug

$732 SGD for 5 nights

4.59 out of 5 average rating, 59 reviews

Guest favourite

Home in Ashburnham

Cozy, year-round Lakefront Retreat.

2 bedrooms, 2 queen beds, 1 bathroom

13–18 Sept

$1,334 SGD for 5 nights

5.0 out of 5 average rating, 10 reviews

Top guest favourite

Tiny home in New Ipswich

Quaint, Historic Tiny Home

1 bedroom, 1 queen bed, 1 bathroom

10–15 Aug

$1,474 SGD for 5 nights

4.98 out of 5 average rating, 54 reviews

Superhost

Home in Ashburnham

Tranquil Family Friendly Lakefront Retreat

4 bedrooms, 5 beds, 3 bathrooms

13–18 Sept

$2,494 SGD for 5 nights

4.62 out of 5 average rating, 146 reviews

Top guest favourite

Guest house in Peterborough

Dunboy House: A Bright & Playful Retreat

1 bedroom, 2 beds, 1.5 bathrooms

28 Sept – 3 Oct

$1,359 SGD for 5 nights

5.0 out of 5 average rating, 17 reviews

Top guest favourite

Room in Wilton

River Room overlooking the waterfall

1 queen bed, 1 bathroom

16–21 Aug

$1,213 SGD for 5 nights

4.91 out of 5 average rating, 346 reviews

Top guest favourite

Cottage in Orange

Lake House with view of mountain

2 bedrooms, 3 beds, 1 bathroom

28 Sept – 3 Oct

$1,844 SGD for 5 nights

4.99 out of 5 average rating, 93 reviews

Guest favourite

Cottage in Gardner

Otter's Paradise

2 bedrooms, 2 beds, 1 bathroom

16–21 Aug

$1,776 SGD for 5 nights

4.89 out of 5 average rating, 36 reviews

Top guest favourite

Home in Rindge

Cottage Cove lakefront home

3 bedrooms, 6 beds, 1 bathroom

21–26 Sept

$2,485 SGD for 5 nights

4.98 out of 5 average rating, 52 reviews

Guest favourite

Home in Winchendon

Modern Waterfront Gem w/ Dock on Lake Monomonac

2 bedrooms, 3 beds, 1 bathroom

8–15 Aug

$2,936 SGD for 7 nights

4.87 out of 5 average rating, 30 reviews

Top guest favourite

Guest house in Wilton

Cottage beside a waterfall

1 bedroom, 1 queen bed, 1 bathroom

6–11 Sept

$1,213 SGD for 5 nights

4.94 out of 5 average rating, 686 reviews

Top guest favourite

Tiny home in Greenfield

New Solar Cabin w/ outhouse, by Woodland Stream

1 bedroom, 1 bed, 1 bathroom

8–13 Aug

$688 SGD for 5 nights

4.97 out of 5 average rating, 66 reviews