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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, 189 reviews
Flat in Barre
Lovely 3-bedroom City Escape
3 bedrooms, 3 beds, 1.5 bathrooms
7–12 Aug
4.85 out of 5 average rating, 82 reviews
Cabin in Wilbraham
4BR Lakefront Cabin with Private Dock & Beach
4 bedrooms, 4 beds, 1 bathroom
8–13 Oct
New place to stay
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
Home in Sterling
Stunning Sterling Sanctuary: Unwind on the Water!
3 bedrooms, 5 beds, 1.5 bathrooms
10–15 Oct
5.0 out of 5 average rating, 28 reviews
Superhost
Home in Spencer
Contemporary Lakeside Retreat
2 bedrooms, 3 beds, 1 bathroom
25–30 Aug
4.77 out of 5 average rating, 185 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
Guest favourite
Flat in Barre
Townhouse on the Barre Commons
3 bedrooms, 7 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Guest house in Worcester
Carriage house apartment
1 bedroom, 2 beds, 1 bathroom
10–15 Aug
4.82 out of 5 average rating, 329 reviews
Top guest favourite
Flat in Belchertown
Sunset Ridge
1 bedroom, 2 beds, 1 bathroom
15–20 Aug
4.95 out of 5 average rating, 58 reviews
Room in Worcester
Clean & Cozy Private- 3 floor_R 3
1 queen bed, 1 bathroom
8–13 Aug
4.75 out of 5 average rating, 8 reviews
Top guest favourite
Room in Princeton
East Princeton Getaway - in historic home
2 beds, 1 bathroom
9–14 Aug
4.98 out of 5 average rating, 86 reviews
Superhost
Room in Spencer
Private room and bath in quiet home
1 queen bed, 1 bathroom
17–22 Aug
4.93 out of 5 average rating, 46 reviews
Guest favourite
Home in Worcester
Velocity Residence
4 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.86 out of 5 average rating, 28 reviews
Top guest favourite
Cottage in Petersham
Cider House Cottage
1 bedroom, 1 queen bed, 1 bathroom
24–29 Aug
4.98 out of 5 average rating, 254 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
Home in Athol
The Rafors Lake House
4 bedrooms, 4 queen beds, 3.5 bathrooms
16–21 Aug
New place to stay
Top guest favourite
Guest house in Spencer
Nantucket Cottage
1 bedroom, 1 queen bed, 1 bathroom
13–18 Aug
4.91 out of 5 average rating, 93 reviews
Top guest favourite
Cottage in Westminster
Cottage @ Partridge Pond
3 bedrooms, 4 beds, 1.5 bathrooms
30 Sept – 5 Oct
4.99 out of 5 average rating, 91 reviews