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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
Townhouse on the Barre Commons
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 7 beds, 1 bathroom
19–24 Jul
Top guest favourite
Home in North Brookfield
Lake Lashaway Family Retreat with Dock and Kayaks
5.0 out of 5 average rating, 6 reviews, 5 bedrooms, 9 beds, 2.5 bathrooms
20–25 Jul
Flat in Barre
Lovely 3-bedroom City Escape
4.85 out of 5 average rating, 82 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
26–31 Jul
Guest favourite
Flat in Rutland
Worcester County• Quiet• Residential Hill Town
4.94 out of 5 average rating, 17 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Top guest favourite
Room in Spencer
Private room and bath in quiet home
4.93 out of 5 average rating, 46 reviews, 1 queen bed, 1 bathroom
16–21 Jul
Top guest favourite
Room in Princeton
East Princeton Getaway - in historic home
4.98 out of 5 average rating, 81 reviews, 2 beds, 1 bathroom
21–26 Jul
Top guest favourite
Flat in Worcester
Centrally Located Apartment in Worcester
4.95 out of 5 average rating, 104 reviews, 2 bedrooms, 2 beds, 1 bathroom
31 Jul – 5 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
Home in Hardwick
Hardwick Centerpiece
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 1 bed, 4.5 bathrooms
15–20 Jul
Top guest favourite
Home in Brimfield
Brookside Cabin retreat feet from Little Alum Lake
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 4 beds, 1 bathroom
26–31 Jul
Guest favourite
Home in West Brookfield
Waterfront New England House on Wickaboag Lake!
4.89 out of 5 average rating, 132 reviews, 4 bedrooms, 5 beds, 2 bathrooms
30 Aug – 4 Sept
Top guest favourite
Home in Sterling
Stunning Sterling Sanctuary: Unwind on the Water!
5.0 out of 5 average rating, 24 reviews, 3 bedrooms, 5 beds, 1.5 bathrooms
10–15 Oct
Top guest favourite
Flat in Templeton
Valley View
5.0 out of 5 average rating, 14 reviews, 1 bedroom, 2 beds, 1 bathroom
15–20 Jul
Guest favourite
Home in Worcester
COMFORTABLE 2ND FLOOR, FULL EQUIPPED&PET FRIENDLY
4.86 out of 5 average rating, 166 reviews, 3 bedrooms, 6 beds, 1 bathroom
18–23 Jul
Top guest favourite
Cottage in Petersham
Cider House Cottage
4.98 out of 5 average rating, 252 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Aug
Top guest favourite
Rooms in Hubbardston
Welcome to Plain View Farm!
4.96 out of 5 average rating, 27 reviews, 2 bedrooms, 2 queen beds, 1.5 bathrooms
19–24 Jul
Top guest favourite
Home in West Brookfield
Peaceful Lake Escape w/ Porch, Fire Pit & Kayak
4.91 out of 5 average rating, 106 reviews, 3 bedrooms, 5 beds, 2 bathrooms
4–9 Aug
Top guest favourite
Guest suite in Hubbardston
In-law Apartment, Full Kitchen, Near Mt Wachusetts
4.98 out of 5 average rating, 212 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Jul – 4 Aug