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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
3 bedrooms, 7 beds
19–24 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Room in Princeton
East Princeton Getaway - in historic home
2 beds
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
26–31 Jul
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Rooms in Hubbardston
Welcome to Plain View Farm!
2 bedrooms, 2 queen beds
19–24 Jul
4.96 out of 5 average rating, 27 reviews
Top guest favourite
Home in North Brookfield
Lake Lashaway Family Retreat with Dock and Kayaks
5 bedrooms, 9 beds
20–25 Jul
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Stafford
Lakefront! Completely Renovated! Kayaks-Privacy
3 bedrooms, 4 beds
4–9 Oct
5.0 out of 5 average rating, 7 reviews
Home in Worcester
Entire home in Worcester, MA
4 bedrooms, 4 beds
18–23 Jul
New place to stay
Top guest favourite
Cottage in Petersham
Cider House Cottage
1 bedroom, 1 queen bed
24–29 Aug
4.98 out of 5 average rating, 252 reviews
Flat in Barre
Lovely 3-bedroom City Escape
3 bedrooms, 3 beds
26–31 Jul
4.85 out of 5 average rating, 82 reviews
Top guest favourite
Home in Sterling
Stunning Sterling Sanctuary: Unwind on the Water!
3 bedrooms, 5 beds
10–15 Oct
5.0 out of 5 average rating, 24 reviews
Guest favourite
Home in West Brookfield
Peaceful Cottage Retreat
2 bedrooms, 3 beds
18–23 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Cottage in Spencer
CK Cottage | Cozy Cottage on a Peaceful Pond
3 bedrooms, 4 beds
5–11 Oct
5.0 out of 5 average rating, 83 reviews
Guest favourite
Room in Barre
Dharma House
1 queen bed
19–24 Jul
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Flat in Templeton
Valley View
1 bedroom, 2 beds
17–22 Jul
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Cabin in Union
Private Mountain Escape, 50+ Acres, Hiking Trails
3 bedrooms, 3 beds
20–25 Jul
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Guest suite in Hubbardston
In-law Apartment, Full Kitchen, Near Mt Wachusetts
1 bedroom, 1 bed
30 Jul – 4 Aug
4.98 out of 5 average rating, 212 reviews
Guest favourite
Home in Hardwick
Hardwick Centerpiece
3 bedrooms, 1 bed
17–22 Jul
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Guest house in Spencer
Nantucket Cottage
1 bedroom, 1 queen bed
19–24 Jul
4.91 out of 5 average rating, 89 reviews