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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
,
5.0 out of 5 average rating, 190 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
Top guest favourite
Guest house in New Braintree
Fern Valley Frame
1 bedroom, 1 bed, No bathroom
16–21 Aug
4.97 out of 5 average rating, 131 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
Guest favourite
Room in Northborough
Guest Bedroom with Private Bathroom @ Swan House
1 queen bed, 1 bathroom
23–28 Aug
4.93 out of 5 average rating, 258 reviews
Room in Worcester
Cozy carpeted bedroom
1 queen bed, 1 bathroom
1–6 Oct
New place to stay
Guest favourite
Yurt in Wendell
Cozy yurt in the woods.
1 bedroom, 1 bed, WC
18–23 Aug
5.0 out of 5 average rating, 32 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
Home in Gardner
Lodge at Kendall Pond
3 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
4.86 out of 5 average rating, 14 reviews
Top guest favourite
Cottage in Sturbridge
Cozy Cottage on Cedar Lake- "Cottage Cheeze"
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.92 out of 5 average rating, 184 reviews
Guest favourite
Home in West Brookfield
Peaceful Cottage Retreat
2 bedrooms, 3 beds, 1 bathroom
21–26 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Room in Belchertown
Sunny room with private bathroom
1 sofa bed, 1 bathroom
19–24 Aug
4.97 out of 5 average rating, 160 reviews
Top guest favourite
Room in Barre
Dharma House 2
1 bed, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 27 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
Home in Shrewsbury
Historical New England retreat
3 bedrooms, 3 beds, 2.5 bathrooms
20–25 Sept
4.98 out of 5 average rating, 44 reviews
Guest favourite
Barn in Holden
Farm stay in a Historic Ski Lodge turned Barn
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.9 out of 5 average rating, 535 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
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
Home in Leicester
Cozy 2BR Townhouse Near Worcester Airport
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
New place to stay