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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
19–24 Sept
4.85 out of 5 average rating, 82 reviews
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Guest favourite
Home in West Brookfield
Waterfront New England House on Wickaboag Lake!
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.89 out of 5 average rating, 134 reviews
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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
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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, 14 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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Guest favourite
Home in Hubbardston
4 Bedroom Lake house overlooking lake
4 bedrooms, 5 queen beds, 2 bathrooms
17–22 Sept
4.86 out of 5 average rating, 28 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
20–25 Sept
5.0 out of 5 average rating, 9 reviews
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Superhost
Home in Spencer
Contemporary Lakeside Retreat
2 bedrooms, 3 beds, 1 bathroom
19–24 Oct
4.76 out of 5 average rating, 193 reviews
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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
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Home in Holden
North Star
4 bedrooms, 4 beds, 2.5 bathrooms
25–30 Oct
4.69 out of 5 average rating, 29 reviews
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Guest favourite
Townhouse in Holden
Updated 3 Bedroom Townhouse Near Center of Holden
3 bedrooms, 3 beds, 1.5 bathrooms
16–21 Sept
4.92 out of 5 average rating, 76 reviews
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Superhost
Townhouse in West Brookfield
Luxury By The Lake
3 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.86 out of 5 average rating, 194 reviews
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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, 76 reviews
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Flat in Worcester
Cozy & Convenient Burncoat Retreat
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Sept
New place to stay
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Flat in West Brookfield
Apartment in town center
3 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.5 out of 5 average rating, 54 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, 424 reviews
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Guest favourite
Home in Worcester
COMFORTABLE 2ND FLOOR, FULL EQUIPPED&PET FRIENDLY
3 bedrooms, 6 beds, 1 bathroom
20–25 Sept
4.86 out of 5 average rating, 175 reviews
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Superhost
Room in Barre
Dharma House 3
1 bed, 1.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 5 reviews