We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Search results; 346 homes in Winchendon

Photo 1 of 29

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

,

4.96 out of 5 average rating, 137 reviews

Photo 1 of 29

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

Photo 1 of 9

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

Photo 1 of 16

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

Photo 1 of 27

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

Photo 1 of 29

Home in Ashburnham

Walk to Cushing Academy | Sleeps 10

4 bedrooms, 4 beds, 3.5 bathrooms

1–6 Oct

New place to stay

Photo 1 of 23

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

Photo 1 of 29

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

Photo 1 of 24

Guest favourite

Home in Winchendon

Modern Waterfront Gem w/ Dock on Lake Monomonac

2 bedrooms, 3 beds, 1 bathroom

4–9 Oct

$2,071 SGD for 5 nights

4.88 out of 5 average rating, 33 reviews

Photo 1 of 22

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

Photo 1 of 29

Top guest favourite

Home in Ashburnham

Charming carriage house in woods with lake access

3 bedrooms, 7 beds, 1 bathroom

11–16 Oct

$1,574 SGD for 5 nights

4.97 out of 5 average rating, 31 reviews

Photo 1 of 29

Top guest favourite

Bed and breakfast in Rindge

Rindge Glass Flower Rm 2: Pvt Room&Bath Queen Bed

1 bedroom, 1 bed, 1 bathroom

2–7 Nov

$790 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 102 reviews

Photo 1 of 29

Home in Templeton

Private 3br & basement 3bth near Trail golf & Lake

4 bedrooms, 3 beds, 1 bathroom

11–16 Oct

$2,440 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 4 reviews

Photo 1 of 29

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

Photo 1 of 17

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

Photo 1 of 29

Guest favourite

Guest suite in Jaffrey

Lucy's Lodge - Host lives onsite in secondary unit

4 bedrooms, 11 beds, 2.5 bathrooms

21–26 Oct

$2,292 SGD for 5 nights

Free cancellation

4.93 out of 5 average rating, 30 reviews

Photo 1 of 29

Home in Royalston

Historic Home w/ Modern Updates on < 4 Acres

4 bedrooms, 5 beds, 2 bathrooms

11–16 Oct

$2,521 SGD for 5 nights

4.94 out of 5 average rating, 77 reviews

Photo 1 of 29

Home in Athol

The Rafors Lake House

4 bedrooms, 7 queen beds, 3.5 bathrooms

4–9 Oct

$3,072 SGD for 5 nights

Free cancellation

New place to stay

Photo 1 of 29

Guest favourite

Flat in Barre

Townhouse on the Barre Commons

3 bedrooms, 7 beds, 1 bathroom

10–15 Oct

$2,596 SGD for 5 nights

5.0 out of 5 average rating, 17 reviews