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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
8–13 Aug
4.85 out of 5 average rating, 82 reviews
Cabin in Wilbraham
4BR Lakefront Cabin with Private Dock & Beach
4 bedrooms, 4 beds, 1 bathroom
8–13 Oct
New place to stay
Home in Shutesbury
Cute A-frame near Lake Wyola!
2 bedrooms, 4 beds, 1 bathroom
13–18 Sept
New place to stay
Top guest favourite
Cabin in New Salem
Rustic cabin with A/C at historic orchard & cidery
1 bedroom, 2 beds, 1 bathroom
5–10 Sept
4.95 out of 5 average rating, 19 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, 28 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, 9 reviews
Guest favourite
Guest house in Worcester
Carriage house apartment
1 bedroom, 2 beds, 1 bathroom
10–15 Aug
4.82 out of 5 average rating, 329 reviews
Home in Barre
Spacious New England Escape - Barre Common
3 bedrooms, 5 beds, 2.5 bathrooms
11–16 Aug
5.0 out of 5 average rating, 4 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
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, 87 reviews
Top guest favourite
Cottage in Petersham
Cider House Cottage
1 bedroom, 1 queen bed, 1 bathroom
24–29 Aug
4.98 out of 5 average rating, 254 reviews
Room in Worcester
Cozy Room in the City of Worcester
1 queen bed, 1 bathroom
23–28 Aug
4.73 out of 5 average rating, 22 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
Guest house in Spencer
Nantucket Cottage
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.91 out of 5 average rating, 94 reviews
Guest favourite
Home in West Brookfield
Peaceful Cottage Retreat
2 bedrooms, 3 beds, 1 bathroom
12–17 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Guest suite in Warren
Craig's Cove
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.95 out of 5 average rating, 340 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, 117 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