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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, 1.5 bathrooms
4–9 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, 11 reviews
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Superhost
Home in Southbridge
Dog-Friendly 3 BR Townhome w/Vintage Charm
3 bedrooms, 3 beds, 1.5 bathrooms
1–6 Oct
New place to stay
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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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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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Top guest favourite
Rooms in Hubbardston
Welcome to Plain View Farm!
2 bedrooms, 2 queen beds, 1.5 bathrooms
18–23 Oct
4.97 out of 5 average rating, 33 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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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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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 house in Spencer
Nantucket Cottage
1 bedroom, 1 queen bed, 1 bathroom
24–29 Oct
4.92 out of 5 average rating, 106 reviews
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Guest favourite
Home in Rutland
The Tucked Away Farm Stay
3 bedrooms, 5 beds, 2 bathrooms
14–19 Oct
4.86 out of 5 average rating, 50 reviews
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Home in Sturbridge
Charming retreat
2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
4.75 out of 5 average rating, 59 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
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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Top guest favourite
Guest suite in Warren
Craig's Cove
1 bedroom, 1 queen bed, 1 bathroom
25–30 Oct
4.95 out of 5 average rating, 351 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 bathroom
1–6 Oct
4.78 out of 5 average rating, 9 reviews
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Top guest favourite
Cottage in Sturbridge
Cedar Sunrise
2 bedrooms, 3 beds, 1 bathroom
1–6 Oct
4.97 out of 5 average rating, 175 reviews