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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, 185 reviews
Guest favourite
Flat in Barre
Barre Common Overlook
2 bedrooms, 3 beds, 1 bathroom
13–18 Jul
5.0 out of 5 average rating, 13 reviews
Flat in Barre
Lovely 3-bedroom City Escape
3 bedrooms, 3 beds, 1.5 bathrooms
12–17 Jul
4.85 out of 5 average rating, 82 reviews
Top guest favourite
Home in North Brookfield
Lake Lashaway Family Retreat with Dock and Kayaks
5 bedrooms, 9 beds, 2.5 bathrooms
8–13 Jul
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Room in Spencer
Private room and bath in quiet home
1 queen bed, 1 bathroom
16–21 Jul
4.93 out of 5 average rating, 45 reviews
Guest favourite
Flat in Barre
Townhouse on the Barre Commons
3 bedrooms, 7 beds, 1 bathroom
7–12 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Farm stay in Rutland
Farm Living
1 bedroom, 6 beds, 1 bathroom
21–26 Jul
4.95 out of 5 average rating, 416 reviews
Top guest favourite
Cottage in Spencer
CK Cottage | Cozy Cottage on a Peaceful Pond
3 bedrooms, 4 beds, 1.5 bathrooms
5–11 Oct
5.0 out of 5 average rating, 83 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
Top guest favourite
Guest suite in Hubbardston
In-law Apartment, Full Kitchen, Near Mt Wachusetts
1 bedroom, 1 bed, 1 bathroom
30 Jul – 4 Aug
4.98 out of 5 average rating, 212 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
Flat in Worcester
Centrally Located Apartment in Worcester
2 bedrooms, 2 queen beds, 1 bathroom
31 Jul – 5 Aug
4.95 out of 5 average rating, 104 reviews
Guest favourite
Room in Barre
Dharma House
1 queen bed, 1.5 bathrooms
19–24 Jul
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Guest house in Spencer
Nantucket Cottage
1 bedroom, 1 queen bed, 1 bathroom
19–24 Jul
4.91 out of 5 average rating, 87 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, 334 reviews
Guest favourite
Guest suite in Worcester
Modern 2 Bedroom Basement Suite
2 bedrooms, 4 beds, 1 bathroom
21–26 Jul
4.87 out of 5 average rating, 156 reviews
Guest favourite
Home in West Brookfield
Sunnybrook House
5 bedrooms, 6 beds, 3 bathrooms
7–12 Jul
4.94 out of 5 average rating, 97 reviews
Top guest favourite
Home in East Brookfield
Lakefront Retreat with Private Beach
4 bedrooms, 8 beds, 2 bathrooms
30 Sept – 5 Oct
4.99 out of 5 average rating, 70 reviews
Superhost
Townhouse in West Brookfield
Luxury By The Lake
3 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.86 out of 5 average rating, 185 reviews