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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
4.85 out of 5 average rating, 82 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
5–10 Aug
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
2–7 Aug
Top guest favourite
Home in Brimfield
Brookside Cabin retreat feet from Little Alum Lake
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 4 beds, 1 bathroom
8–13 Aug
Superhost
Home in Spencer
Contemporary Lakeside Retreat
4.77 out of 5 average rating, 184 reviews, 2 bedrooms, 3 beds, 1 bathroom
31 Aug – 5 Sept
Top guest favourite
Flat in Worcester
Centrally Located Apartment in Worcester
4.95 out of 5 average rating, 106 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Aug
Guest favourite
Home in Barre
The Purple Rooster
4.94 out of 5 average rating, 33 reviews, 3 bedrooms, 5 beds, 3.5 bathrooms
1–6 Aug
Guest favourite
Cabin in Rutland
Farm Stay in Rustic Cabin (#2)
4.86 out of 5 average rating, 21 reviews, 1 bedroom, 6 beds, 1 bathroom
1–6 Aug
Home in Worcester
Entire home in Worcester, MA
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 4 beds, 2.5 bathrooms
9–14 Aug
Top guest favourite
Home in Stafford
Lakefront! Completely Renovated! Kayaks-Privacy
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
Top guest favourite
Room in Princeton
East Princeton Getaway - in historic home
4.98 out of 5 average rating, 84 reviews, 2 beds, 1 bathroom
2–7 Aug
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
10–15 Aug
Guest favourite
Guest house in Worcester
Carriage house apartment
4.82 out of 5 average rating, 329 reviews, 1 bedroom, 2 beds, 1 bathroom
9–14 Aug
Room in Worcester
Cozy Room in the City of Worcester
4.78 out of 5 average rating, 18 reviews, 1 queen bed, 1 bathroom
11–16 Aug
Guest favourite
Guest suite in Worcester
Modern 2 Bedroom Basement Suite
4.87 out of 5 average rating, 158 reviews, 2 bedrooms, 4 beds, 1 bathroom
2–7 Aug
Guest favourite
Home in Worcester
COMFORTABLE 2ND FLOOR, FULL EQUIPPED&PET FRIENDLY
4.86 out of 5 average rating, 167 reviews, 3 bedrooms, 6 beds, 1 bathroom
2–7 Aug
Guest favourite
Room in Barre
Dharma House
5.0 out of 5 average rating, 11 reviews, 1 queen bed, 1.5 bathrooms
9–14 Aug
Flat in West Brookfield
Apartment in town center
4.54 out of 5 average rating, 50 reviews, 3 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Guest favourite
Home in West Brookfield
Sun-Dappled Retreat - Walk to Wickaboag Lake!
4.93 out of 5 average rating, 45 reviews, 2 bedrooms, 4 beds, 2.5 bathrooms
18–23 Aug