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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, 186 reviews
Flat in Barre
Lovely 3-bedroom City Escape
4.85 out of 5 average rating, 82 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
5–10 Aug
Top guest favourite
Home in Brimfield
Brookside Cabin retreat feet from Little Alum Lake
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 4 beds, 1 bathroom
8–13 Aug
Superhost
Room in Spencer
Tranquil retreat
4.63 out of 5 average rating, 81 reviews, 1 queen bed, 1.5 bathrooms
1–6 Aug
Superhost
Home in Spencer
Contemporary Lakeside Retreat
4.77 out of 5 average rating, 184 reviews, 2 bedrooms, 3 beds, 1 bathroom
25–30 Aug
Top guest favourite
Flat in Leicester
Barred Owl Retreat: Sunny 4 Bdr Apartment
4.94 out of 5 average rating, 82 reviews, 4 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
Top guest favourite
Room in Belchertown
The Lacey Rose - A Victorian Suite
5.0 out of 5 average rating, 257 reviews, 1 king bed, 1.5 bathrooms
1–6 Aug
Superhost
Townhouse in Holden
Beautifully Renovated 3 Bedroom Townhome w/parking
4.89 out of 5 average rating, 53 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
1–6 Aug
Guest favourite
Guest house in Worcester
Carriage house apartment
4.82 out of 5 average rating, 329 reviews, 1 bedroom, 2 beds, 1 bathroom
9–14 Aug
Flat in West Brookfield
Apartment in town center
4.54 out of 5 average rating, 50 reviews, 3 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Flat in Belchertown
Sunset Ridge
4.95 out of 5 average rating, 56 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Guest favourite
Flat in Barre
Townhouse on the Barre Commons
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 7 beds, 1 bathroom
2–7 Aug
Guest favourite
Townhouse in West Brookfield
Luxury By The Lake
4.86 out of 5 average rating, 186 reviews, 3 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Guest favourite
Home in West Brookfield
Sun-Dappled Retreat - Walk to Wickaboag Lake!
4.93 out of 5 average rating, 44 reviews, 2 bedrooms, 4 beds, 2.5 bathrooms
18–23 Aug
Guest favourite
Home in Barre
The Purple Rooster
4.94 out of 5 average rating, 33 reviews, 3 bedrooms, 5 beds, 3.5 bathrooms
1–6 Aug
Guest favourite
Cabin in Rutland
Farm Stay in Rustic Cabin (#2)
4.86 out of 5 average rating, 21 reviews, 1 bedroom, 6 beds, 1 bathroom
1–6 Aug
Room in Worcester
Your Luxurious Getaway in Worcester
4.71 out of 5 average rating, 17 reviews, 1 queen bed, 1 bathroom
7–12 Aug
Guest favourite
Home in Worcester
COMFORTABLE 2ND FLOOR, FULL EQUIPPED&PET FRIENDLY
4.86 out of 5 average rating, 167 reviews, 3 bedrooms, 6 beds, 1 bathroom
2–7 Aug
Flat in West Brookfield
Spacious Massachusetts Apartment
4.62 out of 5 average rating, 89 reviews, 3 bedrooms, 3 beds, 1 bathroom
16–21 Aug