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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, 185 reviews
Top guest favourite
Home in North Brookfield
Lake Lashaway Family Retreat with Dock and Kayaks
5 bedrooms, 9 beds, 2.5 bathrooms
9–14 Jul
5.0 out of 5 average rating, 6 reviews
Flat in Barre
Lovely 3-bedroom City Escape
3 bedrooms, 3 beds, 1.5 bathrooms
12–17 Jul
4.85 out of 5 average rating, 82 reviews
Guest favourite
Flat in Barre
Townhouse on the Barre Commons
3 bedrooms, 7 beds, 1 bathroom
8–13 Jul
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Hubbardston
4 Bedroom Lake house overlooking lake
4 bedrooms, 5 queen beds, 2 bathrooms
9–14 Jul
4.83 out of 5 average rating, 24 reviews
Guest favourite
Home in Barre
The Purple Rooster
3 bedrooms, 5 beds, 3.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Home in West Brookfield
FIFA 2026 Getaway | Near Stadium + Lake Access
3 bedrooms, 5 beds, 2 bathrooms
26–31 Jul
4.91 out of 5 average rating, 106 reviews
Guest favourite
Farm stay in Rutland
Spacious 3 Bedroom Home for Family Farm Stay
3 bedrooms, 6 beds, 2 bathrooms
5–10 Aug
4.9 out of 5 average rating, 122 reviews
Top guest favourite
Farm stay in Rutland
Farm Living
1 bedroom, 6 beds, 1 bathroom
21–26 Jul
4.95 out of 5 average rating, 417 reviews
Superhost
Home in Spencer
Contemporary Lakeside Retreat
2 bedrooms, 3 beds, 1 bathroom
25–30 Aug
4.77 out of 5 average rating, 184 reviews
Guest favourite
Flat in Barre
Barre Common Overlook
2 bedrooms, 3 beds, 1 bathroom
13–18 Jul
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in Worcester
Renovated Lakefront 5BR • Sunsets • Sleeps 10-12
5 bedrooms, 6 beds, 2 bathrooms
8–13 Jul
4.92 out of 5 average rating, 37 reviews
Superhost
Guest suite in Rutland
Cozy house in Rutland MA 3 beds and 1 office space
3 bedrooms, 3 queen beds, 1 bathroom
8–13 Jul
4.78 out of 5 average rating, 9 reviews
Home in Holden
2 Bedroom Townhouse! NEW Kitchen!
2 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug
4.84 out of 5 average rating, 67 reviews
Guest favourite
Home in Phillipston
Wild Blueberry Farmhouse: Nature & Sports!
3 bedrooms, 7 beds, 2 bathrooms
8–13 Jul
4.93 out of 5 average rating, 15 reviews
Guest favourite
Home in Worcester
Velocity Residence
4 bedrooms, 4 beds, 2 bathrooms
11–16 Jul
4.85 out of 5 average rating, 26 reviews
Guest favourite
Townhouse in Holden
Updated 3 Bedroom Townhouse Near Center of Holden
3 bedrooms, 3 beds, 1.5 bathrooms
11–16 Jul
4.92 out of 5 average rating, 74 reviews
Top guest favourite
Home in East Brookfield
Lakefront Retreat with Private Beach
4 bedrooms, 8 beds, 2 bathrooms
30 Sept – 5 Oct
4.99 out of 5 average rating, 70 reviews
Top guest favourite
Home in Brimfield
Brookside Cabin retreat feet from Little Alum Lake
3 bedrooms, 4 beds, 1 bathroom
26–31 Jul
5.0 out of 5 average rating, 6 reviews