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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
1–6 Oct
4.85 out of 5 average rating, 82 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
1–6 Oct
5.0 out of 5 average rating, 10 reviews
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Guest favourite
Flat in Barre
Townhouse on the Barre Commons
3 bedrooms, 7 beds, 1 bathroom
10–15 Oct
5.0 out of 5 average rating, 17 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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Guest favourite
Home in West Brookfield
Peaceful Cottage Retreat
2 bedrooms, 3 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Home in West Brookfield
Sunnybrook House
5 bedrooms, 6 beds, 3 bathrooms
1–6 Oct
4.94 out of 5 average rating, 102 reviews
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Home in Sturbridge
Charming retreat
2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
4.74 out of 5 average rating, 58 reviews
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Top guest favourite
Farm stay in Paxton
Glamping at Turn Back Time Farm
3 bedrooms, 6 bunk beds, 2 bathrooms
10–15 Jan
5.0 out of 5 average rating, 48 reviews
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Top guest favourite
Guest house in Spencer
Nantucket Cottage
1 bedroom, 1 queen bed, 1 bathroom
24–29 Oct
4.92 out of 5 average rating, 104 reviews
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Guest favourite
Guest house in Worcester
Carriage house apartment
1 bedroom, 2 beds, 1 bathroom
8–13 Oct
4.82 out of 5 average rating, 335 reviews
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Superhost
Room in Barre
Dharma House 3
1 bed, 1.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Guest suite in Hubbardston
In-law Apartment, Full Kitchen, Near Mt Wachusetts
1 bedroom, 1 bed, 1 bathroom
14–19 Oct
4.98 out of 5 average rating, 228 reviews
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Top guest favourite
Room in Barre
Dharma House 2
1 bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 29 reviews
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Home in Holden
North Star
4 bedrooms, 4 beds, 2.5 bathrooms
12–17 Oct
4.7 out of 5 average rating, 30 reviews
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Guest favourite
Home in West Brookfield
Waterfront New England House on Wickaboag Lake!
4 bedrooms, 5 beds, 2 bathrooms
18–23 Oct
4.89 out of 5 average rating, 134 reviews
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Top guest favourite
Cabin in Sturbridge
Mermaid Cove | Private Lakefront Escape
2 bedrooms, 7 beds, 1 bathroom
1–6 Oct
4.91 out of 5 average rating, 11 reviews
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Guest favourite
Farm stay in Rutland
Spacious 3 Bedroom Home for Family Farm Stay
3 bedrooms, 6 beds, 2 bathrooms
29 Oct – 3 Nov
4.9 out of 5 average rating, 126 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, 77 reviews