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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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4.99 out of 5 average rating, 192 reviews
Guest favourite
Flat in Barre
Barre Common Overlook
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 15 reviews
Guest favourite
Flat in Barre
Townhouse on the Barre Commons
3 bedrooms, 7 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in North Brookfield
Lake Lashaway Family Retreat with Dock and Kayaks
5 bedrooms, 9 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 9 reviews
Superhost
Room in Spencer
Private room and bath in quiet home
1 queen bed, 1 bathroom
5–10 Oct
4.94 out of 5 average rating, 48 reviews
Flat in Barre
Lovely 3-bedroom City Escape
3 bedrooms, 3 beds, 1.5 bathrooms
19–24 Sept
4.85 out of 5 average rating, 82 reviews
Top guest favourite
Room in Barre
Dharma House 2
1 bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 28 reviews
Guest favourite
Home in Sturbridge
Chic & Modern Studio Lakefront House with Loft
3 beds, 1 bathroom
20–25 Sept
4.86 out of 5 average rating, 91 reviews
Superhost
Townhouse in West Brookfield
Luxury By The Lake
3 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.85 out of 5 average rating, 193 reviews
Top guest favourite
Home in West Brookfield
Sunnybrook House
5 bedrooms, 6 beds, 3 bathrooms
30 Sept – 5 Oct
4.94 out of 5 average rating, 100 reviews
Home in Holden
North Star
4 bedrooms, 4 beds, 2.5 bathrooms
25–30 Oct
4.69 out of 5 average rating, 29 reviews
Home in Barre
Spacious New England Escape - Barre Common
3 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 4 reviews
Guest suite in Rutland
Cozy house in Rutland MA 3 beds and 1 office space
3 bedrooms, 4 beds, 1 bathroom
14–19 Sept
4.78 out of 5 average rating, 9 reviews
Top guest favourite
Guest house in Spencer
Nantucket Cottage
1 bedroom, 1 queen bed, 1 bathroom
28 Sept – 3 Oct
4.92 out of 5 average rating, 103 reviews
Superhost
Room in Barre
Dharma House 3
1 bed, 1.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Sturbridge
Newly Built, Stunning, Lake Front Retreat!
2 bedrooms, 5 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 81 reviews
Guest favourite
Farm stay in Rutland
Farm Living
1 bedroom, 6 beds, 1 bathroom
10–15 Oct
4.95 out of 5 average rating, 424 reviews
Top guest favourite
Home in Brimfield
Cozy Log Cabin | Lake Access, Kayaks & Brook
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 18 reviews
Guest favourite
Farm stay in Brimfield
Classic New England horse farm
3 bedrooms, 5 beds, 1.5 bathrooms
14–19 Sept
4.98 out of 5 average rating, 54 reviews