Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
Experiences
Experiences
Services
Services
Start your search
Location
Homes in Winchendon
Check in / Check out
Any week
Guests
Add guests
Log in or sign up
Help Centre
Become a host
It’s easy to start hosting and earn extra income.
Refer a host
Find a co-host
Log in or sign up
filters
Filters
Price
Price filter
Type of place
Type of place filter
Show map
Search results; 345 homes in Winchendon
345 homes in Winchendon
Photo 1 of 29
Guest favourite
Guest favourite
Cabin in Winchendon
The little house on Mirror Pond
2 bedrooms
,
·
2 beds
,
·
1.5 private bathrooms
25–30 Oct
25–30 Oct
$1,745 SGD
$1,538 SGD
Show price breakdown
for 5 nights
,
·
4.96 out of 5 average rating, 137 reviews
4.96 (137)
Photo 1 of 29
Guest favourite
Guest favourite
Place to stay in Winchendon
Enjoy your stay in an Antique Home in a Toy Museum
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
1–6 Oct
1–6 Oct
$2,519 SGD
Show price breakdown
for 5 nights
$2,519 SGD for 5 nights
Free cancellation
4.9 out of 5 average rating, 105 reviews
4.9 (105)
Photo 1 of 9
Superhost
Superhost
Home in Winchendon
Waterfront home 2 bedrooms withdeck beach and dock
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
4–9 Oct
4–9 Oct
$1,097 SGD
$957 SGD
Show price breakdown
for 5 nights
Free cancellation
4.79 out of 5 average rating, 363 reviews
4.79 (363)
Photo 1 of 27
Superhost
Superhost
Home in Rindge
Pine and Pond Retreat
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
1–6 Oct
1–6 Oct
$2,321 SGD
Show price breakdown
for 5 nights
$2,321 SGD for 5 nights
New place to stay
New
Photo 1 of 16
Apartment in Winchendon
Private 1st Floor Apt @ Winchendon Center Town
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
11–16 Oct
11–16 Oct
$616 SGD
Show price breakdown
for 5 nights
$616 SGD for 5 nights
4.62 out of 5 average rating, 65 reviews
4.62 (65)
Photo 1 of 21
Cabin in New Ipswich
Bungalow
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
1–6 Oct
1–6 Oct
$1,867 SGD
Show price breakdown
for 5 nights
$1,867 SGD for 5 nights
Free cancellation
4.84 out of 5 average rating, 49 reviews
4.84 (49)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Rindge
Lakefront Mid-Century Cottage with Sandy Beach
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
4–9 Oct
4–9 Oct
$1,566 SGD
Show price breakdown
for 5 nights
$1,566 SGD for 5 nights
4.83 out of 5 average rating, 6 reviews
4.83 (6)
Photo 1 of 29
Home in Ashburnham
Walk to Cushing Academy | Sleeps 10
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
3.5 bathrooms
3.5 bathrooms
1–6 Oct
1–6 Oct
$2,983 SGD
$2,397 SGD
Show price breakdown
for 5 nights
Free cancellation
New place to stay
New
Photo 1 of 23
Guest favourite
Guest favourite
Home in Winchendon
Fully Renovated Cottage
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
26–31 Oct
26–31 Oct
$1,106 SGD
$982 SGD
Show price breakdown
for 5 nights
Free cancellation
4.98 out of 5 average rating, 40 reviews
4.98 (40)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Ashburnham
Escape to the Lake!
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
19–24 Oct
19–24 Oct
$2,744 SGD
$2,421 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 70 reviews
5.0 (70)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Winchendon
Top 10 VRBO Copley's Lakefront Cottage+Guesthouse
4 bedrooms
4 bedrooms
,
·
9 beds
9 beds
,
·
4 bathrooms
4 bathrooms
17–22 Oct
17–22 Oct
$9,359 SGD
Show price breakdown
for 5 nights
$9,359 SGD for 5 nights
4.91 out of 5 average rating, 45 reviews
4.91 (45)
Photo 1 of 22
Superhost
Superhost
Home in Ashburnham
Tranquil Family Friendly Lakefront Retreat
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
12–17 Oct
12–17 Oct
$2,436 SGD
Show price breakdown
for 5 nights
$2,436 SGD for 5 nights
Free cancellation
4.63 out of 5 average rating, 148 reviews
4.63 (148)
Photo 1 of 18
Barn in Ashburnham
Beautiful, Modern Farmhouse, Walk to Cushing!
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
1–6 Oct
1–6 Oct
$3,617 SGD
$2,869 SGD
Show price breakdown
for 5 nights
Free cancellation
New place to stay
New
Photo 1 of 29
Guest favourite
Guest favourite
Cabin in Rindge
Cabin & Sauna on Lake Monomonac
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
12–17 Oct
12–17 Oct
$1,560 SGD
Show price breakdown
for 5 nights
$1,560 SGD for 5 nights
Free cancellation
4.87 out of 5 average rating, 38 reviews
4.87 (38)
Photo 1 of 29
Top guest favourite
Guest favourite
Cottage in Winchendon
Top 10 of VRBO -Copley's Lakefront Cottage on Lake
3 bedrooms
3 bedrooms
,
·
7 beds
7 beds
,
·
3 bathrooms
3 bathrooms
1–6 Oct
1–6 Oct
$7,326 SGD
Show price breakdown
for 5 nights
$7,326 SGD for 5 nights
4.98 out of 5 average rating, 59 reviews
4.98 (59)
Photo 1 of 15
Guest favourite
Guest favourite
Home in Winchendon
Lake Monomonac Cottage with Private Beach & Dock
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
1–8 Oct
1–8 Oct
$1,968 SGD
$1,784 SGD
Show price breakdown
for 7 nights
Weekly discount
5.0 out of 5 average rating, 16 reviews
5.0 (16)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Rindge
Wake Up on the Water | Private Beach & Dock
3 bedrooms
3 bedrooms
,
·
7 beds
7 beds
,
·
2 bathrooms
2 bathrooms
4–9 Oct
4–9 Oct
$3,975 SGD
$3,509 SGD
Show price breakdown
for 5 nights
4.95 out of 5 average rating, 58 reviews
4.95 (58)
Photo 1 of 17
Top guest favourite
Guest favourite
Home in Fitzwilliam
Lakefront Home | Near Monadnock
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
1.5 bathrooms
1.5 bathrooms
1–6 Oct
1–6 Oct
$3,488 SGD
$3,061 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 21 reviews
5.0 (21)
Photo 1 of 17
Cabin in Rindge
Secluded Lake Cabin Perfect for Family Fun!
3 bedrooms
3 bedrooms
,
·
3 queen beds
3 queen beds
,
·
1 bathroom
1 bathroom
5–10 Oct
5–10 Oct
$2,399 SGD
Show price breakdown
for 5 nights
$2,399 SGD for 5 nights
4.8 out of 5 average rating, 25 reviews
4.8 (25)
1
2
3
4
…
15