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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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5.0 out of 5 average rating, 186 reviews
Guest favourite
Flat in Barre
Townhouse on the Barre Commons
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 7 beds, 1 bathroom
20–25 Jul
Top guest favourite
Room in Princeton
East Princeton Getaway - in historic home
4.98 out of 5 average rating, 82 reviews, 2 beds, 1 bathroom
21–26 Jul
Top guest favourite
Guest suite in Hubbardston
In-law Apartment, Full Kitchen, Near Mt Wachusetts
4.98 out of 5 average rating, 212 reviews, 1 bedroom, 1 bed, 1 bathroom
20–25 Sept
Flat in Barre
Lovely 3-bedroom City Escape
4.85 out of 5 average rating, 82 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
26–31 Jul
Guest favourite
Barn in Holden
Farm stay in a Historic Ski Lodge turned Barn
4.9 out of 5 average rating, 532 reviews, 1 bedroom, 1 bed, 1 bathroom
20–25 Sept
Top guest favourite
Home in Sterling
Stunning Sterling Sanctuary: Unwind on the Water!
5.0 out of 5 average rating, 24 reviews, 3 bedrooms, 5 beds, 1.5 bathrooms
10–15 Oct
Guest favourite
Flat in Rutland
Worcester County• Quiet• Residential Hill Town
4.94 out of 5 average rating, 18 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
Top guest favourite
Home in North Brookfield
Lake Lashaway Family Retreat with Dock and Kayaks
5.0 out of 5 average rating, 6 reviews, 5 bedrooms, 9 beds, 2.5 bathrooms
21–26 Jul
Top guest favourite
Home in Stafford
Lakefront! Completely Renovated! Kayaks-Privacy
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
Top guest favourite
Farm stay in Rutland
Farm Living
4.95 out of 5 average rating, 419 reviews, 1 bedroom, 6 beds, 1 bathroom
13–18 Aug
Top guest favourite
Rooms in Hubbardston
Welcome to Plain View Farm!
4.96 out of 5 average rating, 28 reviews, 2 bedrooms, 2 queen beds, 1.5 bathrooms
26–31 Jul
Top guest favourite
Room in Belchertown
The Lacey Rose - A Victorian Suite
5.0 out of 5 average rating, 257 reviews, 1 king bed, 1.5 bathrooms
1–6 Aug
Room in Worcester
Cozy Room in the City of Worcester
4.76 out of 5 average rating, 17 reviews, 1 queen bed, 1 bathroom
6–11 Aug
Guest favourite
Guest suite in Worcester
Modern 2 Bedroom Basement Suite
4.87 out of 5 average rating, 157 reviews, 2 bedrooms, 4 beds, 1 bathroom
21–26 Jul
Guest favourite
Cottage in Petersham
Cider House Cottage
4.98 out of 5 average rating, 252 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Aug
Guest favourite
Townhouse in West Brookfield
Luxury By The Lake
4.86 out of 5 average rating, 186 reviews, 3 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Superhost
Home in Spencer
Contemporary Lakeside Retreat
4.77 out of 5 average rating, 184 reviews, 2 bedrooms, 3 beds, 1 bathroom
25–30 Aug
Top guest favourite
Cottage in Sturbridge
Cozy Cottage on Cedar Lake- "Cottage Cheeze"
4.92 out of 5 average rating, 182 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug