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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
,
5.0 out of 5 average rating, 185 reviews
Flat in Barre
Lovely 3-bedroom City Escape
4.85 out of 5 average rating, 82 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
5–10 Jul
Top guest favourite
Home in North Brookfield
Lake Lashaway Family Retreat with Dock and Kayaks
5.0 out of 5 average rating, 5 reviews, 5 bedrooms, 9 beds, 2.5 bathrooms
6–11 Jul
Guest favourite
Flat in Barre
Townhouse on the Barre Commons
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 7 beds, 1 bathroom
5–10 Jul
Guest favourite
Farm stay in Rutland
Farm Living
4.95 out of 5 average rating, 415 reviews, 1 bedroom, 6 beds, 1 bathroom
21–26 Jul
Guest favourite
Home in Hubbardston
4 Bedroom Lake house overlooking lake
4.83 out of 5 average rating, 24 reviews, 4 bedrooms, 5 beds, 2 bathrooms
6–11 Jul
Top guest favourite
Home in West Brookfield
FIFA 2026 Getaway | Near Stadium + Lake Access
4.9 out of 5 average rating, 105 reviews, 3 bedrooms, 5 beds, 2 bathrooms
12–17 Jul
Guest favourite
Flat in Barre
Barre Common Overlook
5.0 out of 5 average rating, 13 reviews, 2 bedrooms, 3 beds, 1 bathroom
13–18 Jul
Guest favourite
Home in Rutland
The Tucked Away Farm Stay
4.91 out of 5 average rating, 46 reviews, 3 bedrooms, 5 beds, 2 bathrooms
25–30 Aug
Guest favourite
Home in Worcester
Renovated Lakefront 5BR • Sunsets • Sleeps 10-12
4.92 out of 5 average rating, 36 reviews, 5 bedrooms, 6 beds, 2 bathrooms
5–10 Jul
Superhost
Guest suite in Rutland
Cozy house in Rutland MA 3 beds and 1 office space
4.78 out of 5 average rating, 9 reviews, 3 bedrooms, 3 beds, 1 bathroom
5–10 Jul
Guest favourite
Home in Barre
The Purple Rooster
5.0 out of 5 average rating, 32 reviews, 3 bedrooms, 5 beds, 3.5 bathrooms
8–13 Jul
Top guest favourite
Home in Spencer
Luxury Tuscan Themed Getaway
4.97 out of 5 average rating, 31 reviews, 5 bedrooms, 5 beds, 3.5 bathrooms
16–21 Jul
Top guest favourite
Cottage in Spencer
CK Cottage | Cozy Cottage on a Peaceful Pond
5.0 out of 5 average rating, 83 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
5–11 Oct
Top guest favourite
Home in East Brookfield
Lakefront Retreat with Private Beach
4.99 out of 5 average rating, 70 reviews, 4 bedrooms, 8 beds, 2 bathrooms
30 Sept – 5 Oct
Guest favourite
Home in Phillipston
Wild Blueberry Farmhouse: Nature & Sports!
4.93 out of 5 average rating, 15 reviews, 3 bedrooms, 7 beds, 2 bathrooms
5–10 Jul
Guest favourite
Home in Worcester
Velocity Residence
4.84 out of 5 average rating, 25 reviews, 4 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
Guest favourite
Home in Petersham
Beautiful Farm in Central Massachusetts
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
8–13 Jul
Guest favourite
Home in Sterling
Pool•1000mbpsWiFi•DeepTub•Fireplace•Full Kitchen
4.88 out of 5 average rating, 16 reviews, 3 bedrooms, 4 beds, 2 bathrooms
31 Aug – 5 Sept