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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, 190 reviews
Guest favourite
Farm stay in Rutland
Farm Living
1 bedroom, 6 beds, 1 bathroom
14–19 Aug
4.95 out of 5 average rating, 421 reviews
Top guest favourite
Rooms in Hubbardston
Welcome to Plain View Farm!
2 bedrooms, 2 queen beds, 1.5 bathrooms
7–12 Sept
4.97 out of 5 average rating, 32 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
Superhost
Guest house in Worcester
Carriage house apartment
1 bedroom, 2 beds, 1 bathroom
1–6 Sept
4.82 out of 5 average rating, 331 reviews
Superhost
Room in Spencer
Private room and bath in quiet home
1 queen bed, 1 bathroom
11–16 Sept
4.93 out of 5 average rating, 46 reviews
Guest favourite
Home in Leicester
Scenic Lakehouse w/ Kayaking & Canoeing
3 bedrooms, 3 beds, 1 bathroom
10–15 Nov
4.82 out of 5 average rating, 68 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
Room in Princeton
East Princeton Getaway - in historic home
2 beds, 1 bathroom
7–12 Sept
4.98 out of 5 average rating, 88 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
Home in Leicester
Cozy 2BR Townhouse Near Worcester Airport
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
New place to stay
Top guest favourite
Guest suite in Warren
Craig's Cove
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.95 out of 5 average rating, 341 reviews
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
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
Top guest favourite
Guest house in Spencer
Nantucket Cottage
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.91 out of 5 average rating, 94 reviews
Guest favourite
Room in Barre
Dharma House
1 queen bed, 1.5 bathrooms
14–19 Aug
5.0 out of 5 average rating, 11 reviews
Flat in West Brookfield
Spacious Massachusetts Apartment
3 bedrooms, 3 queen beds, 1 bathroom
16–21 Aug
4.63 out of 5 average rating, 92 reviews
Top guest favourite
Cottage in Westminster
Cottage @ Partridge Pond
3 bedrooms, 4 beds, 1.5 bathrooms
30 Sept – 5 Oct
4.99 out of 5 average rating, 92 reviews
Top guest favourite
Tower in Amherst
The Silo | Rare Architectural Retreat Near UMass
1 bedroom, 2 beds, 1 bathroom
29 Aug – 3 Sept
5.0 out of 5 average rating, 22 reviews