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Search results; Over 1,000 homes in Oakham

Descriptions are based on details hosts provide
Top guest favourite
Home in Oakham
Lovely & Peaceful Waterfront Vacation Retreat
4 bedrooms, 6 beds, 2.5 private bathrooms
3–8 Nov
,
5.0 out of 5 average rating, 185 reviews
Guest favourite
Flat in Barre
Townhouse on the Barre Commons
3 bedrooms, 7 beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in North Brookfield
Lake Lashaway Family Retreat with Dock and Kayaks
5 bedrooms, 9 beds, 2.5 bathrooms
20–25 Jul
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Room in Princeton
East Princeton Getaway - in historic home
2 beds, 1 bathroom
21–26 Jul
4.98 out of 5 average rating, 81 reviews
Top guest favourite
Home in Brimfield
Brookside Cabin retreat feet from Little Alum Lake
3 bedrooms, 4 beds, 1 bathroom
26–31 Jul
5.0 out of 5 average rating, 7 reviews
Guest favourite
Flat in Rutland
Worcester County• Quiet• Residential Hill Town
1 bedroom, 1 bed, 1 bathroom
16–21 Aug
4.94 out of 5 average rating, 17 reviews
Top guest favourite
Home in Stafford
Lakefront! Completely Renovated! Kayaks-Privacy
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 6 reviews
Flat in Barre
Lovely 3-bedroom City Escape
3 bedrooms, 3 beds, 1.5 bathrooms
26–31 Jul
4.85 out of 5 average rating, 82 reviews
Home in Worcester
Fireplace, piano, and a private backyard
4 bedrooms, 4 beds, 2.5 bathrooms
18–23 Jul
New place to stay
Top guest favourite
Cottage in Petersham
Antique post-and-beam cottage with pond views
1 bedroom, 1 queen bed, 1 bathroom
24–29 Aug
4.98 out of 5 average rating, 252 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, 24 reviews
Top guest favourite
Rooms in Hubbardston
Welcome to Plain View Farm!
2 bedrooms, 2 queen beds, 1.5 bathrooms
19–24 Jul
4.96 out of 5 average rating, 27 reviews
Top guest favourite
Flat in Templeton
Valley View
1 bedroom, 2 beds, 1 bathroom
15–20 Jul
5.0 out of 5 average rating, 14 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
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, 116 reviews
Top guest favourite
Flat in Leicester
3 acres with ponds, streams, and gardens
4 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
4.94 out of 5 average rating, 82 reviews
Top guest favourite
Cottage in Spencer
Renovated pond-front cottage with a dock
3 bedrooms, 4 beds, 1.5 bathrooms
5–11 Oct
5.0 out of 5 average rating, 83 reviews
Top guest favourite
Flat in Worcester
1910 duplex with 1 Gbps WiFi
2 bedrooms, 2 queen beds, 1 bathroom
31 Jul – 5 Aug
4.95 out of 5 average rating, 104 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, 89 reviews