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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, 193 reviews
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Flat in Barre
Lovely 3-bedroom City Escape
3 bedrooms, 3 beds
4–9 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
10–15 Oct
5.0 out of 5 average rating, 17 reviews
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Guest suite in Rutland
Cozy house in Rutland MA 3 beds and 1 office space
3 bedrooms, 4 beds
1–6 Oct
4.78 out of 5 average rating, 9 reviews
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Guest favourite
Home in Hubbardston
4 Bedroom Lake house overlooking lake
4 bedrooms, 5 queen beds
1–6 Oct
4.86 out of 5 average rating, 28 reviews
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Guest favourite
Flat in Barre
Barre Common Overlook
2 bedrooms, 3 beds
3–8 Oct
5.0 out of 5 average rating, 15 reviews
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Home in Holden
2 Bedroom Townhouse! NEW Kitchen!
2 bedrooms, 2 beds
1–6 Oct
4.85 out of 5 average rating, 72 reviews
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Superhost
Room in Barre
Dharma House 3
1 bed
1–6 Oct
5.0 out of 5 average rating, 5 reviews
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Superhost
Townhouse in West Brookfield
Luxury By The Lake
3 bedrooms, 3 beds
4–9 Oct
4.85 out of 5 average rating, 197 reviews
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Top guest favourite
Home in North Brookfield
Lake Lashaway Family Retreat with Dock and Kayaks
5 bedrooms, 9 beds
1–6 Oct
5.0 out of 5 average rating, 11 reviews
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Home in Holden
North Star
4 bedrooms, 4 beds
12–17 Oct
4.7 out of 5 average rating, 30 reviews
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Top guest favourite
Room in Barre
Dharma House 2
1 bed
1–6 Oct
5.0 out of 5 average rating, 29 reviews
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Guest favourite
Home in Rutland
The Tucked Away Farm Stay
3 bedrooms, 5 beds
14–19 Oct
4.86 out of 5 average rating, 50 reviews
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Flat in West Brookfield
Apartment in town center
3 bedrooms, 3 beds
4–9 Oct
4.52 out of 5 average rating, 56 reviews
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Home in West Brookfield
Waterfront New England House on Wickaboag Lake!
4 bedrooms, 5 beds
18–23 Oct
4.89 out of 5 average rating, 134 reviews
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Guest favourite
Home in Barre
Spacious New England Escape - Barre Common
3 bedrooms, 5 beds
1–6 Oct
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Townhouse in Holden
Updated 3 Bedroom Townhouse Near Center of Holden
3 bedrooms, 3 beds
1–6 Oct
4.92 out of 5 average rating, 76 reviews
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Top guest favourite
Home in West Brookfield
Sunnybrook House
5 bedrooms, 6 beds
1–6 Oct
4.94 out of 5 average rating, 102 reviews
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Guest favourite
Farm stay in Rutland
Spacious 3 Bedroom Home for Family Farm Stay
3 bedrooms, 6 beds
29 Oct – 3 Nov
4.9 out of 5 average rating, 126 reviews