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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
Flat in Barre
Lovely 3-bedroom City Escape
3 bedrooms, 3 beds
19–24 Sept
4.85 out of 5 average rating, 82 reviews
Guest favourite
Home in Petersham
Beautiful Farm in Central Massachusetts
3 bedrooms, 3 beds
12–17 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in North Brookfield
Lake Lashaway Family Retreat with Dock and Kayaks
5 bedrooms, 9 beds
20–25 Sept
5.0 out of 5 average rating, 9 reviews
Home in Barre
Spacious New England Escape - Barre Common
3 bedrooms, 5 beds
22–27 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Barre
Townhouse on the Barre Commons
3 bedrooms, 7 beds
13–18 Sept
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in West Brookfield
Waterfront New England House on Wickaboag Lake!
4 bedrooms, 5 beds
13–18 Sept
4.89 out of 5 average rating, 134 reviews
Guest favourite
Home in Rutland
The Tucked Away Farm Stay
3 bedrooms, 5 beds
14–19 Sept
4.9 out of 5 average rating, 48 reviews
Guest favourite
Farm stay in Rutland
Spacious 3 Bedroom Home for Family Farm Stay
3 bedrooms, 6 beds
14–19 Oct
4.9 out of 5 average rating, 125 reviews
Home in Holden
North Star
4 bedrooms, 4 beds
13–18 Sept
4.69 out of 5 average rating, 29 reviews
Flat in Worcester
Cozy & Convenient Burncoat Retreat
2 bedrooms, 3 queen beds
15–20 Sept
New place to stay
Superhost
Townhouse in West Brookfield
Luxury By The Lake
3 bedrooms, 3 beds
27 Sept – 2 Oct
4.85 out of 5 average rating, 193 reviews
Top guest favourite
Home in New Salem
Stone n' Sky Lodge
5 bedrooms, 7 beds
27 Oct – 1 Nov
4.91 out of 5 average rating, 253 reviews
Guest favourite
Townhouse in Holden
Updated 3 Bedroom Townhouse Near Center of Holden
3 bedrooms, 3 beds
10–15 Sept
4.92 out of 5 average rating, 76 reviews
Guest favourite
Home in Leicester
Scenic Lakehouse w/ Kayaking & Canoeing
3 bedrooms, 3 beds
10–15 Nov
4.82 out of 5 average rating, 72 reviews
Guest favourite
Home in Hubbardston
4 Bedroom Lake house overlooking lake
4 bedrooms, 5 queen beds
13–18 Sept
4.85 out of 5 average rating, 27 reviews
Top guest favourite
Farm stay in Sutton
Stevenson Farm / Way Back Home
6 bedrooms, 7 beds
13–18 Sept
4.94 out of 5 average rating, 53 reviews
Top guest favourite
Home in Brimfield
Cozy Log Cabin | Lake Access, Kayaks & Brook
3 bedrooms, 4 beds
12–17 Sept
5.0 out of 5 average rating, 16 reviews
Guest favourite
Farm stay in Rutland
Farm Living
1 bedroom, 6 beds
10–15 Oct
4.95 out of 5 average rating, 424 reviews