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Search results; Over 1,000 homes in Oakham

Top guest favourite
Home in Oakham
Lovely & Peaceful Waterfront Vacation Retreat
4 bedrooms, 6 beds, 2.5 private bathrooms
3–8 Nov
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5.0 out of 5 average rating, 185 reviews
Guest favourite
Flat in Barre
Townhouse on the Barre Commons
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 7 beds, 1 bathroom
8–13 Jul
Top guest favourite
Home in North Brookfield
Lake Lashaway Family Retreat with Dock and Kayaks
5.0 out of 5 average rating, 6 reviews, 5 bedrooms, 9 beds, 2.5 bathrooms
9–14 Jul
Top guest favourite
Guest suite in Hubbardston
In-law Apartment, Full Kitchen, Near Mt Wachusetts
4.98 out of 5 average rating, 212 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Jul – 4 Aug
Top guest favourite
Room in Princeton
East Princeton Getaway - in historic home
4.98 out of 5 average rating, 81 reviews, 2 beds, 1 bathroom
19–24 Jul
Top guest favourite
Home in Brimfield
Brookside Cabin retreat feet from Little Alum Lake
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 4 beds, 1 bathroom
26–31 Jul
Flat in Barre
Lovely 3-bedroom City Escape
4.85 out of 5 average rating, 82 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
12–17 Jul
Top guest favourite
Rooms in Hubbardston
Welcome to Plain View Farm!
4.96 out of 5 average rating, 26 reviews, 2 bedrooms, 2 queen beds, 1.5 bathrooms
19–24 Jul
Guest favourite
Place to stay in Worcester
Comfy double room with office private bathroom WA
4.88 out of 5 average rating, 16 reviews, 1 bedroom, 2 beds, 1 bathroom
8–13 Aug
Guest favourite
Home in West Brookfield
Peaceful Cottage Retreat
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 3 beds, 1 bathroom
8–13 Jul
Guest favourite
Barn in Holden
Farm stay in a Historic Ski Lodge turned Barn
4.9 out of 5 average rating, 532 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Jul
Top guest favourite
Guest house in Spencer
Nantucket Cottage
4.91 out of 5 average rating, 87 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Home in Templeton
Private 3br & basement 3bth near Trail golf & Lake
New place to stay, 4 bedrooms, 5 beds, 3.5 bathrooms
12–17 Jul
Top guest favourite
Home in Ware
Little House Inn - Private House - Secluded
4.9 out of 5 average rating, 334 reviews, 2 bedrooms, 3 beds, 1 bathroom
26–31 Jul
Guest favourite
Cottage in Petersham
Cider House Cottage
4.98 out of 5 average rating, 250 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Aug
Guest favourite
Home in Westminster
Lakefront, view of ski mtn, firepit, kayaks, dock
4.84 out of 5 average rating, 188 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Jul – 4 Aug
Top guest favourite
Room in Spencer
Private room and bath in quiet home
4.93 out of 5 average rating, 45 reviews, 1 queen bed, 1 bathroom
16–21 Jul
Superhost
Flat in West Brookfield
Spacious Massachusetts Apartment
4.62 out of 5 average rating, 89 reviews, 3 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Top guest favourite
Cabin in New Salem
Rustic cabin with A/C at historic orchard & cidery
4.94 out of 5 average rating, 16 reviews, 1 bedroom, 2 beds, 1 bathroom
19–24 Jul