578 homes

Cottage in Winchester
The Overlook: A Sweetwater Stay
1 bed
Oct 23 – 28
$89 per night
Superhost
Tiny home in Orange
The Writer's Retreat: A Sweetwater Stay
1 queen bed
Oct 21 – 26
$154 per night, originally $213
Superhost
Guest suite in Fitzwilliam
The Great Room in Historic Fitzwilliam
1 queen bed
Oct 23 – 28
$119 per night
Superhost
Cabin in Fitzwilliam
Cozy Log Cabin with Mountain Views
3 beds
Nov 13 – 18
$141 per night
Superhost
Townhouse in Winchester
Timber Frame Loft
1 queen bed
Oct 16 – 21
$87 per night, originally $99
Superhost
Guesthouse in Winchester
The Higgle House: A Sweetwater Farm Stay
2 queen beds
Oct 23 – 28
$69 per night
Superhost
Tiny home in Orange
The Photographer's Hut: A Sweetwater Stay
1 queen bed
Oct 25 – 30
$140 per night, originally $208
Superhost
Apartment in Winchester
Suite 2 - Stay at a craft brewery - Winchester NH
1 bed
Oct 16 – 21
$150 per night
Superhost
Guest suite in Fitzwilliam
The Carriage House in Historic Fitzwilliam
1 double bed
Oct 30 – Nov 4
$105 per night
Superhost
Cottage in Orange
The Lake Cottage: A Sweetwater Stay
2 beds
Dec 4 – 10
$144 per night
Superhost
Home in Winchester
Morning Myst Pines
5 beds
Oct 31 – Nov 5
$192 per night
Guesthouse in New Ipswich
"The Porch" Your cozy home away from home!
2 queen beds
Dec 3 – 8
$74 per night
Superhost
Farm stay in Warwick
Be Still Meadows at Chase Hill Farm - first floor
2 beds
Oct 30 – Nov 4
$146 per night
Superhost
Cottage in Warwick
Corkscrew: Lakeside Cozy Cottage in Warwick, MA
4 beds
Oct 31 – Nov 5
$160 per night
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Guesthouse in Fitzwilliam
Romantic, Tranquil Guest House on 1820s Farm
1 queen bed
Oct 23 – 28
$139 per night
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Home in Royalston
NEW! Historic Home w/ Modern Updates on 3.5 Acres
5 beds
Oct 22 – 28
$228 per night
Private room in Marlborough
The Marlborough House c.1900(Full) - NH
1 double bed
Oct 9 – 14
$65 per night
Apartment in Athol
2nd Floor Spacious 2-1 Apt. in Athol Center Town.
2 beds
Nov 12 – 17
$81 per night
Superhost
Cabin in Fitzwilliam
Charming Waterfront Log Cabin w/ Private Island!
3 queen beds
Nov 2 – 7
$207 per night
Superhost
Cottage in Winchester
Peaceful NH Lakefront Cottage w/Breathtaking Views
4 beds
Oct 16 – 23
$160 per night, originally $200
Guest suite in Orange
Downtown Victorian on the Mohawk Trail
1 double bed
Oct 9 – 14
$77 per night
Cottage in Orange
The Fishing Cottage: A Sweetwater Stay
2 beds
Oct 23 – 28
$165 per night
Superhost
Cottage in Orange
The Film Shack: A Sweetwater Stay
6 beds
Oct 28 – Nov 2
$168 per night, originally $186
Superhost
Home in Winchendon
Waterfront home 2 bedrooms withdeck beach and dock
2 beds
Oct 23 – 29
$130 per night
Superhost