Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
NEW
NEW
Experiences
Experiences, new
NEW
NEW
Services
Services, new
Start your search
Location
Homes in Winchendon
Check in / Check out
Any week
Guests
Add guests
Become a host
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
Type of place
Show map
Search results; 352 homes in Winchendon
352 homes in Winchendon
Top guest favourite
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
1–6 Aug
1–6 Aug
$2,554 SGD
Show price breakdown
for 5 nights
$2,554 SGD for 5 nights
,
·
4.93 out of 5 average rating, 102 reviews
4.93 (102)
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
13–18 Sept
13–18 Sept
$1,143 SGD
Show price breakdown
for 5 nights
$1,143 SGD for 5 nights
Free cancellation
4.8 out of 5 average rating, 343 reviews
4.8 (343)
Superhost
Superhost
Home in Winchendon
Lake Monomonac Cottage with Private Beach & Dock
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
15–20 Aug
15–20 Aug
$1,615 SGD
Show price breakdown
for 5 nights
$1,615 SGD for 5 nights
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Top guest favourite
Guest favourite
Cabin in Winchendon
The little house on Mirror Pond
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1.5 bathrooms
1.5 bathrooms
20–25 Sept
20–25 Sept
$2,004 SGD
Show price breakdown
for 5 nights
$2,004 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 126 reviews
4.96 (126)
Top guest favourite
Guest favourite
Flat in New Salem
New England Escape
2 bedrooms
2 bedrooms
,
·
2 double beds
2 double beds
,
·
1 bathroom
1 bathroom
1–6 Aug
1–6 Aug
$1,517 SGD
Show price breakdown
for 5 nights
$1,517 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 71 reviews
5.0 (71)
Top guest favourite
Guest favourite
Home in Winchendon
Fully Renovated Cottage
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
6–11 Sept
6–11 Sept
$1,166 SGD
Show price breakdown
for 5 nights
$1,166 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 32 reviews
5.0 (32)
Top guest favourite
Guest favourite
Home in Jaffrey
Willow Falls Home ~Hot tub & Waterfront
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
3 bathrooms
3 bathrooms
22–27 Aug
22–27 Aug
$3,468 SGD
Show price breakdown
for 5 nights
$3,468 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 104 reviews
4.98 (104)
Home in Jaffrey
John's Mountain Hideaway
3 bedrooms
3 bedrooms
,
·
2 bathrooms
2 bathrooms
2–7 Aug
2–7 Aug
$1,627 SGD
Show price breakdown
for 5 nights
$1,627 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Guest favourite
Guest favourite
Home in Winchendon
Modern Waterfront Gem w/ Dock on Lake Monomonac
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
8–15 Aug
8–15 Aug
$3,341 SGD
$3,005 SGD
Show price breakdown
for 7 nights
4.87 out of 5 average rating, 30 reviews
4.87 (30)
Top guest favourite
Guest favourite
Home in Jaffrey
Squantum Place
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
6–11 Sept
6–11 Sept
$1,529 SGD
Show price breakdown
for 5 nights
$1,529 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 50 reviews
4.98 (50)
Guest favourite
Guest favourite
Flat in Jaffrey
Schoolhouse No. 1
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
10–15 Aug
10–15 Aug
$1,213 SGD
Show price breakdown
for 5 nights
$1,213 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 60 reviews
4.98 (60)
Guest favourite
Guest favourite
Flat in Orange
Lakefront Orange Vacation Rental - Pet Friendly!
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
2–7 Aug
2–7 Aug
$1,141 SGD
Show price breakdown
for 5 nights
$1,141 SGD for 5 nights
5.0 out of 5 average rating, 27 reviews
5.0 (27)
Guest favourite
Guest favourite
Guest house in Gardner
Eagleview Guesthouse
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
1 bathroom
1 bathroom
1–6 Aug
1–6 Aug
$1,435 SGD
Show price breakdown
for 5 nights
$1,435 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Top guest favourite
Guest favourite
Guest suite in Hubbardston
In-law Apartment, Full Kitchen, Near Mt Wachusetts
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
20–25 Sept
20–25 Sept
$737 SGD
Show price breakdown
for 5 nights
$737 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 214 reviews
4.98 (214)
Top guest favourite
Guest favourite
Cottage in Westminster
Cottage @ Partridge Pond
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1.5 bathrooms
1.5 bathrooms
24–29 Oct
24–29 Oct
$2,426 SGD
Show price breakdown
for 5 nights
$2,426 SGD for 5 nights
4.99 out of 5 average rating, 88 reviews
4.99 (88)
Top guest favourite
Guest favourite
Flat in New Ipswich
Quiet country apartment in farmland setting.
2 beds
2 beds
,
·
1 bathroom
1 bathroom
5–10 Oct
5–10 Oct
$776 SGD
Show price breakdown
for 5 nights
$776 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 138 reviews
4.96 (138)
Guest favourite
Guest favourite
Home in Rindge
Waterfront escape
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
1–6 Sept
1–6 Sept
$2,897 SGD
Show price breakdown
for 5 nights
$2,897 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 113 reviews
4.95 (113)
Home in Templeton
Private 3BR Home & bsmt Near Golf, Trails & Shops
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3.5 bathrooms
3.5 bathrooms
18–23 Aug
18–23 Aug
$2,224 SGD
Show price breakdown
for 5 nights
$2,224 SGD for 5 nights
Free cancellation
New place to stay
New
Guest favourite
Guest favourite
Cottage in Rindge
Lakefront Escape•HOT TUB•Fishing •Swimming•Boats
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
22–27 Aug
22–27 Aug
$3,148 SGD
Show price breakdown
for 5 nights
$3,148 SGD for 5 nights
Free cancellation
4.79 out of 5 average rating, 76 reviews
4.79 (76)
1
2
3
4
…
15