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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
Guest favourite
Home in Brimfield
Little House Inn - Brimmy - Private Home
2 bedrooms, 5 beds, 1 bathroom
28 Aug – 2 Sept
4.86 out of 5 average rating, 307 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
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
Tiny home in Pelham
Cabin Camp Valley Retreat
1 bedroom, 2 beds, 1 bathroom
19–24 Aug
4.94 out of 5 average rating, 36 reviews
Guest favourite
Farm stay in Rutland
Farm Living
1 bedroom, 6 beds, 1 bathroom
13–18 Aug
4.95 out of 5 average rating, 421 reviews
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
Guest favourite
Room in Barre
Dharma House
1 queen bed, 1.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 11 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, 31 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
Room in Worcester
Cozy Room in the City of Worcester
1 queen bed, 1 bathroom
11–16 Aug
4.73 out of 5 average rating, 22 reviews
Top guest favourite
Room in Monson
Paradise Lake Sanctuary Blue Room
1 bed, 1 bathroom
17–22 Aug
5.0 out of 5 average rating, 11 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
Guest favourite
Cabin in Rutland
Farm Stay in Rustic Cabin (#2)
1 bedroom, 6 beds, 1 bathroom
7–12 Aug
4.86 out of 5 average rating, 21 reviews
Top guest favourite
Cottage in Sturbridge
Cozy Cottage on Cedar Lake- "Cottage Cheeze"
2 bedrooms, 2 beds, 1 bathroom
26–31 Aug
4.92 out of 5 average rating, 183 reviews
Guest favourite
Home in Gardner
Lodge at Kendall Pond
3 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
4.85 out of 5 average rating, 13 reviews
Top guest favourite
Bed and breakfast in Brimfield
New England Escape
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.96 out of 5 average rating, 459 reviews
Top guest favourite
Home in Shrewsbury
Historical New England retreat
3 bedrooms, 3 beds, 2.5 bathrooms
20–25 Sept
4.98 out of 5 average rating, 44 reviews