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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, 1.5 bathrooms
19–24 Sept
4.85 out of 5 average rating, 82 reviews
Guest favourite
Flat in Barre
Townhouse on the Barre Commons
3 bedrooms, 7 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 14 reviews
Home in Holden
North Star
4 bedrooms, 4 beds, 2.5 bathrooms
13–18 Sept
4.69 out of 5 average rating, 29 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
Guest favourite
Home in Rutland
The Tucked Away Farm Stay
3 bedrooms, 5 beds, 2 bathrooms
14–19 Oct
4.9 out of 5 average rating, 48 reviews
Guest favourite
Home in Hubbardston
4 Bedroom Lake house overlooking lake
4 bedrooms, 5 queen beds, 2 bathrooms
14–19 Sept
4.85 out of 5 average rating, 27 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
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
Guest favourite
Room in Barre
Dharma House
1 queen bed, 1.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Worcester
COMFORTABLE 2ND FLOOR, FULL EQUIPPED&PET FRIENDLY
3 bedrooms, 6 beds, 1 bathroom
13–18 Sept
4.87 out of 5 average rating, 173 reviews
Guest favourite
Home in West Brookfield
Sun-Dappled Retreat - Walk to Wickaboag Lake!
2 bedrooms, 4 beds, 2.5 bathrooms
13–18 Oct
4.94 out of 5 average rating, 47 reviews
Superhost
Home in Spencer
Contemporary Lakeside Retreat
2 bedrooms, 3 beds, 1 bathroom
12–17 Oct
4.76 out of 5 average rating, 193 reviews
Guest favourite
Flat in Barre
Barre Common Overlook
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in East Brookfield
Lakefront Retreat with Private Beach
4 bedrooms, 8 beds, 2 bathrooms
10–15 Dec
4.99 out of 5 average rating, 74 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
Top guest favourite
Home in West Brookfield
Peaceful Lake Escape w/ Porch, Fire Pit & Kayak
3 bedrooms, 5 beds, 2 bathrooms
25–30 Oct
4.91 out of 5 average rating, 110 reviews
Top guest favourite
Home in New Salem
Stone n' Sky Lodge
5 bedrooms, 7 beds, 3 bathrooms
27 Oct – 1 Nov
4.91 out of 5 average rating, 253 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, 17 reviews