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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
26–31 Aug
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5.0 out of 5 average rating, 187 reviews
Flat in Barre
Lovely 3-bedroom City Escape
3 bedrooms, 3 beds, 1.5 bathrooms
5–10 Aug
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
2–7 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Brimfield
Brookside Cabin retreat feet from Little Alum Lake
3 bedrooms, 4 beds, 1 bathroom
8–13 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Barre
The Purple Rooster
3 bedrooms, 5 beds, 3.5 bathrooms
1–6 Aug
4.94 out of 5 average rating, 33 reviews
Top guest favourite
Home in Stafford
Lakefront! Completely Renovated! Kayaks-Privacy
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Room in Belchertown
The Lacey Rose - A Victorian Suite
1 king bed, 1.5 bathrooms
10–15 Aug
5.0 out of 5 average rating, 257 reviews
Top guest favourite
Flat in Worcester
Centrally Located Apartment in Worcester
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Aug
4.95 out of 5 average rating, 106 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
Cabin in Rutland
Farm Stay in Rustic Cabin (#2)
1 bedroom, 6 beds, 1 bathroom
1–6 Aug
4.86 out of 5 average rating, 21 reviews
Top guest favourite
Flat in Belchertown
Sunset Ridge
1 bedroom, 2 beds, 1 bathroom
2–7 Aug
4.95 out of 5 average rating, 56 reviews
Top guest favourite
Flat in Leicester
Barred Owl Retreat: Sunny 4 Bdr Apartment
4 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
4.94 out of 5 average rating, 82 reviews
Top guest favourite
Farm stay in Rutland
Farm Living
1 bedroom, 6 beds, 1 bathroom
13–18 Aug
4.95 out of 5 average rating, 419 reviews
Home in Worcester
Entire home in Worcester, MA
4 bedrooms, 4 beds, 2.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Flat in Shrewsbury
Clean & Cozy 2BR | Great Central Location
2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
4.9 out of 5 average rating, 141 reviews
Top guest favourite
Room in Princeton
East Princeton Getaway - in historic home
2 beds, 1 bathroom
2–7 Aug
4.98 out of 5 average rating, 84 reviews
Guest favourite
Home in Worcester
COMFORTABLE 2ND FLOOR, FULL EQUIPPED&PET FRIENDLY
3 bedrooms, 6 beds, 1 bathroom
2–7 Aug
4.86 out of 5 average rating, 167 reviews
Guest favourite
Townhouse in West Brookfield
Luxury By The Lake
3 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.86 out of 5 average rating, 186 reviews
Guest favourite
Guest house in Worcester
Carriage house apartment
1 bedroom, 2 beds, 1 bathroom
9–14 Aug
4.82 out of 5 average rating, 329 reviews