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Search results; Over 1,000 homes in Oakham

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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
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Flat in Barre
Lovely 3-bedroom City Escape
3 bedrooms, 3 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.85 out of 5 average rating, 82 reviews
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Guest favourite
Flat in Barre
Townhouse on the Barre Commons
3 bedrooms, 7 beds, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 16 reviews
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Guest favourite
Home in West Brookfield
Waterfront New England House on Wickaboag Lake!
4 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
4.89 out of 5 average rating, 134 reviews
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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, 49 reviews
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Top guest favourite
Home in North Brookfield
Lake Lashaway Family Retreat with Dock and Kayaks
5 bedrooms, 9 beds, 2.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Home in East Brookfield
Lakefront Retreat with Private Beach
4 bedrooms, 8 beds, 2 bathrooms
11–16 Dec
4.99 out of 5 average rating, 76 reviews
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Guest favourite
Home in Hubbardston
4 Bedroom Lake house overlooking lake
4 bedrooms, 5 queen beds, 2 bathrooms
27 Sept – 2 Oct
4.86 out of 5 average rating, 28 reviews
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Flat in West Brookfield
Apartment in town center
3 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
4.5 out of 5 average rating, 54 reviews
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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, 195 reviews
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Guest favourite
Farm stay in Rutland
Farm Living
1 bedroom, 6 beds, 1 bathroom
10–15 Oct
4.95 out of 5 average rating, 425 reviews
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Home in Holden
North Star
4 bedrooms, 4 beds, 2.5 bathrooms
12–17 Oct
4.69 out of 5 average rating, 29 reviews
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Guest favourite
Flat in Barre
Barre Common Overlook
2 bedrooms, 3 beds, 1 bathroom
3–8 Oct
5.0 out of 5 average rating, 15 reviews
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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
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Guest favourite
Room in Barre
Dharma House
1 queen bed, 1.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 12 reviews
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Home in Holden
2 Bedroom Townhouse! NEW Kitchen!
2 bedrooms, 2 beds, 1 bathroom
24–29 Sept
4.85 out of 5 average rating, 72 reviews
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Flat in Worcester
110 New apartment 2 beds + 1 bath + sofa bed
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Sept
New place to stay
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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, 48 reviews
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Guest favourite
Home in Worcester
COMFORTABLE 2ND FLOOR, FULL EQUIPPED&PET FRIENDLY
3 bedrooms, 6 beds, 1 bathroom
4–9 Oct
4.86 out of 5 average rating, 175 reviews