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Vacation rentals in Phillipston

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Top-rated vacation rentals in Phillipston

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite
Cottage in Petersham
Cider House Cottage
Antique guest cottage on a country farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub.
Jun 17 – 24
$127 per night
Guest favorite
Guest suite in Ashburnham
The Ginger Bed King Suite
Come for the lovely country setting, the winter beauty, amenities, neighborhood, convenience, privacy, spaciousness, and the comfortable bed. Close to many wonderful hiking/biking paths, rail trails, Wachusett ski area, Jewel Hill, Lake Wampanoag, Kirby area. WI-FI, TV ( Hulu and Netflix), refrigerator, microwave, coffee/tea maker, reading lights, table area, continental breakfast, parking... Good for couples, solo and business travelers. (Key pad for Covid safe entry) Everyone is welcome!
Jan 8 – 15
$93 per night
Guest favorite
Guest suite in Fitzwilliam
The Carriage House in Historic Fitzwilliam
Welcome to the Carriage House! Former site of the popular Hannah Davis House Bed and Breakfast, this gorgeous space is ready for your visit! Beautiful wood beams throughout, a cozy loft bedroom, and a completely separate entrance for privacy. Short rides to Rhododendron State Park, Mount Monadnock, Gap Mountain, the Cheshire Rail Trail, Laurel Lake, and many more outdoor activities year round. Walking distance to the town common in a town where little has changed and history is preserved.
Dec 7 – 14
$81 per night

Popular amenities for Phillipston vacation rentals

Other great vacation rentals in Phillipston

Home in Winchendon
Waterfront home 2 bedrooms withdeck beach and dock
Dec 25 – Jan 1
$130 per night
Guest favorite
Guesthouse in New Ipswich
"The Porch" Your cozy home away from home!
Jan 31 – Feb 7
$74 per night
Guest favorite
Barn in Holden
Farm stay in a Historic Ski Lodge turned Barn
May 17 – 24
$142 per night
Guest favorite
Home in Westminster
Lakefront; view of ski mtn, firepit, dock, kayaks
Dec 19 – 26
$278 per night
Guest favorite
Guest suite in Warren
Craig's Cove
Jun 27 – Jul 4
$63 per night
Guest favorite
Cabin in Hubbardston
Triggers Cabin
Sep 27 – Oct 4
$135 per night
Guest favorite
Tiny home in Wilmington
Beautiful Timber Frame Retreat
Jul 31 – Aug 7
$187 per night
Guest favorite
Apartment in Winchester
Downtown Loft above Winery and Distillery
Apr 20 – 27
$73 per night
Guest favorite
Apartment in Dublin
Private Dublin apartment nestled in the woods
Apr 30 – May 7
$99 per night
Guest favorite
Home in Athol
Big Post and Beam Lake House
Feb 22 – Mar 1
$457 per night
Apartment in Athol
The Gargoyle's House 2nd floor 2-1 nest in Athol.
May 2 – 9
$72 per night
Guest favorite
Guest suite in Hubbardston
Private Entry, Full Kitchen, Close to Mt Wachuset
May 20 – 27
$89 per night

Destinations to explore