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Search results; Over 1,000 homes in Oakham

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
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
Guest favourite
Flat in Barre
Townhouse on the Barre Commons
3 bedrooms, 7 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Worcester
Centrally Located Apartment in Worcester
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Oct
4.96 out of 5 average rating, 114 reviews
Guest favourite
Flat in Barre
Barre Common Overlook
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 15 reviews
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
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
Guest favourite
Cabin in Rutland
Farm Stay in Rustic Cabin (#2)
1 bedroom, 6 beds, 1 bathroom
9–14 Sept
4.86 out of 5 average rating, 21 reviews
Superhost
Townhouse in West Brookfield
Luxury By The Lake
3 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.85 out of 5 average rating, 193 reviews
Home in Barre
Spacious New England Escape - Barre Common
3 bedrooms, 5 beds, 2.5 bathrooms
22–27 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Brimfield
Cozy Log Cabin | Lake Access, Kayaks & Brook
3 bedrooms, 4 beds, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 16 reviews
Guest favourite
Cottage in Sturbridge
Cozy Cottage on Cedar Lake- "Cottage Cheeze"
2 bedrooms, 2 beds, 1 bathroom
26 Sept – 1 Oct
4.92 out of 5 average rating, 186 reviews
Top guest favourite
Flat in Leicester
Sunny 2-Bdrm Apartment at the Barred Owl Retreat
2 bedrooms, 2 beds, 1 bathroom
11–16 Oct
4.98 out of 5 average rating, 96 reviews
Top guest favourite
Home in Sturbridge
Newly Built, Stunning, Lake Front Retreat!
2 bedrooms, 5 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 81 reviews
Top guest favourite
Home in Sterling
Stunning Sterling Sanctuary: Unwind on the Water!
3 bedrooms, 5 beds, 1.5 bathrooms
31 Oct – 5 Nov
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Guest house in Spencer
Nantucket Cottage
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.92 out of 5 average rating, 101 reviews
Guest favourite
Home in Sturbridge
Chic & Modern Studio Lakefront House with Loft
3 beds, 1 bathroom
20–25 Sept
4.86 out of 5 average rating, 91 reviews
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, 74 reviews
Top guest favourite
Bed and breakfast in Brimfield
New England Escape
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.96 out of 5 average rating, 467 reviews