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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
Guest favourite
Flat in Barre
Barre Common Overlook
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 15 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
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
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
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
Superhost
Home in Spencer
Contemporary Lakeside Retreat
2 bedrooms, 3 beds, 1 bathroom
12–17 Oct
4.76 out of 5 average rating, 193 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, 102 reviews
Top guest favourite
Room in Barre
Dharma House 2
1 bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 28 reviews
Superhost
Room in Barre
Dharma House 3
1 bed, 1.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Barn in Holden
Farm stay in a Historic Ski Lodge turned Barn
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
4.9 out of 5 average rating, 544 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
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 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
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, 48 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, 469 reviews
Top guest favourite
Cottage in Petersham
Cider House Cottage
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 260 reviews
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, 225 reviews
Top guest favourite
Home in Brimfield
Cozy Log Cabin | Lake Access, Kayaks & Brook
3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 17 reviews