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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, 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
Top guest favourite
Guest house in Spencer
Nantucket Cottage
4.91 out of 5 average rating, 91 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 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
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 Sterling
Stunning Sterling Sanctuary: Unwind on the Water!
5.0 out of 5 average rating, 25 reviews, 3 bedrooms, 5 beds, 1.5 bathrooms
10–15 Oct
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
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
Superhost
Home in Spencer
Contemporary Lakeside Retreat
4.77 out of 5 average rating, 184 reviews, 2 bedrooms, 3 beds, 1 bathroom
25–30 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
1–6 Aug
Top guest favourite
Farm stay in Rutland
Farm Living
4.95 out of 5 average rating, 419 reviews, 1 bedroom, 6 beds, 1 bathroom
13–18 Aug
Top guest favourite
Flat in Leicester
Barred Owl Retreat: Sunny 4 Bdr Apartment
4.94 out of 5 average rating, 82 reviews, 4 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
Guest favourite
Townhouse in West Brookfield
Luxury By The Lake
4.86 out of 5 average rating, 186 reviews, 3 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Home in Worcester
Entire home in Worcester, MA
New place to stay, 4 bedrooms, 4 beds, 2.5 bathrooms
9–14 Aug
Superhost
Townhouse in Holden
Beautifully Renovated 3 Bedroom Townhome w/parking
4.89 out of 5 average rating, 53 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
1–6 Aug
Guest favourite
Home in Sterling
Pool•1000mbpsWiFi•DeepTub•Fireplace•Full Kitchen
4.89 out of 5 average rating, 19 reviews, 3 bedrooms, 4 beds, 2 bathrooms
26–31 Aug
Top guest favourite
Flat in Belchertown
Sunset Ridge
4.95 out of 5 average rating, 56 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 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
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