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Search results; 986 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, 190 reviews
Top guest favourite
Home in Brimfield
Cozy Log Cabin | Lake Access, Kayaks & Brook
3 bedrooms, 4 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 13 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, 31 reviews
Guest favourite
Home in Shutesbury
Cute A-frame near Lake Wyola!
2 bedrooms, 4 beds, 1 bathroom
27 Oct – 1 Nov
5.0 out of 5 average rating, 5 reviews
Home in Northborough
Spacious 5BR/3BA Family Home Near Sports Fields
5 bedrooms, 6 beds, 3 bathrooms
16–21 Aug
New place to stay
Guest favourite
Flat in Barre
Townhouse on the Barre Commons
3 bedrooms, 7 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 11 reviews
Cabin in Wilbraham
4BR Lakefront Cabin with Private Dock & Beach
4 bedrooms, 4 beds, 1 bathroom
19–24 Oct
5.0 out of 5 average rating, 3 reviews
Flat in Barre
Lovely 3-bedroom City Escape
3 bedrooms, 3 beds, 1.5 bathrooms
23–28 Aug
4.85 out of 5 average rating, 82 reviews
Top guest favourite
Tower in Amherst
The Silo | Rare Architectural Retreat Near UMass
1 bedroom, 2 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 22 reviews
Superhost
Home in Spencer
Contemporary Lakeside Retreat
2 bedrooms, 3 beds, 1 bathroom
25–30 Aug
4.77 out of 5 average rating, 186 reviews
Top guest favourite
Home in Shrewsbury
Park View Cottage
3 bedrooms, 4 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Farm stay in Rutland
Farm Living
1 bedroom, 6 beds, 1 bathroom
7–12 Sept
4.95 out of 5 average rating, 421 reviews
Guest favourite
Cabin in Rutland
Farm Stay in Rustic Cabin (#2)
1 bedroom, 6 beds, 1 bathroom
5–10 Sept
4.86 out of 5 average rating, 21 reviews
Guest favourite
Home in Brimfield
Little House Inn - Brimmy - Private Home
2 bedrooms, 5 beds, 1 bathroom
30 Aug – 4 Sept
4.86 out of 5 average rating, 311 reviews
Top guest favourite
Room in Princeton
East Princeton Getaway - in historic home
2 beds, 1 bathroom
7–12 Sept
4.98 out of 5 average rating, 89 reviews
Superhost
Townhouse in West Brookfield
Luxury By The Lake
3 bedrooms, 3 beds, 1 bathroom
25–30 Aug
4.85 out of 5 average rating, 190 reviews
Home in Holden
2 Bedroom Townhouse! NEW Kitchen!
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
4.84 out of 5 average rating, 69 reviews
Guest favourite
Home in Westminster
Wachusett Mountain Get-Away
3 bedrooms, 5 beds, 2.5 bathrooms
23–28 Aug
4.94 out of 5 average rating, 142 reviews
Top guest favourite
Cottage in Petersham
Cider House Cottage
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 254 reviews