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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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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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Top guest favourite
Barn in Holden
Farm stay in a Historic Ski Lodge turned Barn
1 bedroom, 1 queen bed, 1 bathroom
31 Oct – 5 Nov
4.9 out of 5 average rating, 544 reviews
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Guest favourite
Home in Petersham
Beautiful Farm in Central Massachusetts
3 bedrooms, 3 beds, 2.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Flat in Leicester
Barred Owl Retreat: Sunny 4 Bdr Apartment
4 bedrooms, 4 beds, 2 bathrooms
3–8 Dec
4.94 out of 5 average rating, 84 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
17–22 Sept
5.0 out of 5 average rating, 5 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
27 Oct – 1 Nov
4.9 out of 5 average rating, 125 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, 15 reviews
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Top guest favourite
Home in Hardwick
Hardwick Centerpiece
3 bedrooms, 1 bed, 4.5 bathrooms
22–27 Sept
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Room in Barre
Dharma House 2
1 bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 28 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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Home in Sturbridge
Charming retreat
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.74 out of 5 average rating, 58 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, 10 reviews
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Top guest favourite
Yurt in Wendell
Cozy yurt in the woods.
1 bedroom, 1 bed, WC
19–24 Sept
5.0 out of 5 average rating, 36 reviews
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Top guest favourite
Guest house in Spencer
Nantucket Cottage
1 bedroom, 1 queen bed, 1 bathroom
28 Sept – 3 Oct
4.92 out of 5 average rating, 103 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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Guest suite in Rutland
Cozy house in Rutland MA 3 beds and 1 office space
3 bedrooms, 4 beds, 1 bathroom
17–22 Sept
4.78 out of 5 average rating, 9 reviews