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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, 189 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, 9 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, 11 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, 85 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, 108 reviews
Superhost
Home in Spencer
Contemporary Lakeside Retreat
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.77 out of 5 average rating, 184 reviews
Cabin in Wilbraham
4BR Lakefront Cabin with Private Dock & Beach
4 bedrooms, 4 beds, 1 bathroom
10–15 Aug
New place to stay
Guest favourite
Guest house in Gardner
Eagleview Guesthouse
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 8 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
Superhost
Room in Spencer
Private room and bath in quiet home
1 queen bed, 1 bathroom
10–15 Aug
4.93 out of 5 average rating, 46 reviews
Guest favourite
Home in Barre
The Purple Rooster
3 bedrooms, 5 beds, 3.5 bathrooms
4–9 Aug
4.94 out of 5 average rating, 33 reviews
Top guest favourite
Rooms in Hubbardston
Welcome to Plain View Farm!
2 bedrooms, 2 queen beds, 1.5 bathrooms
8–13 Aug
4.97 out of 5 average rating, 30 reviews
Top guest favourite
Guest suite in Warren
Craig's Cove
1 bedroom, 1 queen bed, 1 bathroom
2–7 Aug
4.95 out of 5 average rating, 339 reviews
Top guest favourite
Room in Barre
Dharma House 2
1 bed, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Farm stay in Rutland
Farm Living
1 bedroom, 6 beds, 1 bathroom
24–29 Aug
4.95 out of 5 average rating, 420 reviews
Guest favourite
Home in West Brookfield
Sun-Dappled Retreat - Walk to Wickaboag Lake!
2 bedrooms, 4 beds, 2.5 bathrooms
18–23 Aug
4.93 out of 5 average rating, 45 reviews
Top guest favourite
Guest house in Shrewsbury
Luxury Spacious 2BR • King & Queen Beds • 2 Baths
2 bedrooms, 2 bathrooms
8–13 Aug
4.82 out of 5 average rating, 117 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