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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
Top guest favourite
Home in North Brookfield
Lake Lashaway Family Retreat with Dock and Kayaks
5 bedrooms, 9 beds, 2.5 bathrooms
10–15 Jul
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Barre
Townhouse on the Barre Commons
3 bedrooms, 7 beds, 1 bathroom
9–14 Jul
5.0 out of 5 average rating, 7 reviews
Flat in Barre
Lovely 3-bedroom City Escape
3 bedrooms, 3 beds, 1.5 bathrooms
12–17 Jul
4.85 out of 5 average rating, 82 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
Room in Princeton
East Princeton Getaway - in historic home
2 beds, 1 bathroom
19–24 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, 6 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, 26 reviews
Flat in West Brookfield
Spacious Massachusetts Apartment
3 bedrooms, 3 queen beds, 1 bathroom
19–24 Jul
4.62 out of 5 average rating, 89 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, 87 reviews
Top guest favourite
Farm stay in Rutland
Farm Living
1 bedroom, 6 beds, 1 bathroom
13–18 Aug
4.95 out of 5 average rating, 417 reviews
Home in Worcester
Entire home in Worcester, MA
4 bedrooms, 4 beds, 2.5 bathrooms
18–23 Jul
New place to stay
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, 251 reviews
Guest favourite
Home in West Brookfield
Peaceful Cottage Retreat
2 bedrooms, 3 beds, 1 bathroom
9–14 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Ware
Little House Inn - Private House - Secluded
2 bedrooms, 3 beds, 1 bathroom
26–31 Jul
4.9 out of 5 average rating, 334 reviews
Guest favourite
Cabin in Rutland
Farm Stay in Rustic Cabin (#2)
1 bedroom, 6 beds, 1 bathroom
10–15 Jul
4.85 out of 5 average rating, 20 reviews
Top guest favourite
Bed and breakfast in Brimfield
New England Escape
1 bedroom, 1 queen bed, 1 bathroom
23–28 Jul
4.96 out of 5 average rating, 452 reviews
Top guest favourite
Tower in Amherst
The Silo | Architectural Retreat Near UMass
1 bedroom, 2 beds, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Hardwick
Hardwick Centerpiece
3 bedrooms, 1 bed, 4.5 bathrooms
10–15 Jul
5.0 out of 5 average rating, 13 reviews