
Holiday rentals in Oakham
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Top-rated holiday rentals in Oakham
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Other great holiday rentals in Oakham
Guest favourite

Flat in Leicester
4.87 out of 5 average rating, 15 reviewsSunny & Spacious 3BR, close to Worcester!
KirakiraRating, 5 stars2 days ago
Jeremiah & Kasie were helpful and accommodating! Great stay - spacious apartment for myself and my daughters. Great communication and helpful tips.

Guest suite in Worcester
5 out of 5 average rating, 4 reviewsQuietRelaxing,Pvt Bath+Kit,nr480acrePark WPI UMass
ChaitanyaRating, 5 stars2 weeks ago
Julia's place is good, and Jamie helped us enjoy our visit. While the room is small, there is place outside and nearby park is gorgeous.

Flat in Barre
4.84 out of 5 average rating, 69 reviewsLovely 3-bedroom City Escape
AnnRating, 5 stars2 weeks ago
Great place! Super clean and beautiful interior space. Loved staying there and would DEFINITELY stay again!
Top guest favourite

Farm stay in Rutland
4.96 out of 5 average rating, 372 reviewsFarm Living
JenniferRating, 5 stars5 days ago
It's a beautiful back yard and working farm. It's peaceful & fun to hear the animals ( peacock & donkey). There is lots to do for kids. The place was clean with roomy main bedroom & livingroom. The kitchen had everything needed but lacked ample counter space or room to store unrefrigerated food. The dehumidifier ran all the time & had to be emptied every day. The patio has couch & chairs looked comfy but got wet in rain. The picnic table was nice & coukd be dried off. My grandkids had a blast using the pool, trampoline, hammock, see-saw & climbing structures. It's a very peaceful place. We hiked on 2 different Mass Rail Trails near by.
Guest favourite

Home in West Brookfield
4.89 out of 5 average rating, 66 reviewsHillside Hideaway
JoannaRating, 5 stars1 week ago
What a gem of a place! Perfectly located to our daughter’s boarding school. We spent both parent’s weekends and graduation here, staying with multi-generations of our family. It has enough space in the great room for a small gathering. Just a wonderful spot that we highly recommend.

Flat in Worcester
4.77 out of 5 average rating, 170 reviewsSpacious/private studio steps to restaurants/bars
CherylRating, 5 stars2 weeks ago
Went for a long weekend. It got me closer to Mount Wachusette than my house is without breaking the bank. Great place to just exist and relax. Neighborhood can be a bit lively, but over all good.

Flat in West Brookfield
4.55 out of 5 average rating, 65 reviewsSpacious Massachusetts Apartment
JamesRating, 5 stars3 weeks ago
Friends and I had no issues at all. Place was clean and very cheap. Small for 4 but we didn’t need a huge place and it worked well. The floors are a little uneven and easy to trip over but everything else was great.
Guest favourite

Home in Paxton
5 out of 5 average rating, 8 reviewsMCM Vibe•Workspace•Arcade•Firepit•BBQ•Dogs OK•Yard
AnnRating, 5 stars5 days ago
We had travelled from Wales in the UK not sure what to expect - we had a lovely surprise. Such a beautiful place to stay,a guarantee home from home feel. The whole house is beautifully furnished and decorated. The kitchen is fully equipped with high quality utensils and crockery. The bathroom is also very clean and well stocked with toiletries etc. The bedrooms are tastefully decorated with lovely comfortable bedding. The welcome pack in the kitchen was full of goodies - brilliant. For those travelling with dogs this is an ideal place to stay - fully provided are mess towels,bowls,poo bags etc. There is an outdoor fenced area ideal for the dogs to play an exercise. The house is situated in a leafy green area lovely and quiet to relax , it was just the place for us. Would love to come back sometime. Greg is an exceptional helpful and friendly host. Cannot fault this place 10/10 Thank you very much Greg
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- Fenway Park
- Harvard University
- Brown University
- Six Flags New England
- Monadnock State Park
- Prudential Center
- MIT Museum
- Museum of Fine Arts, Boston
- Isabella Stewart Gardner Museum
- Boston Public Library
- Symphony Hall
- Pawtucket Country Club
- Berkshire East Mountain Resort
- Brimfield State Forest
- Nashoba Valley Winery, Distillery, Brewery and Restaurant
- Cochituate State Park
- Franklin Park Zoo
- Middlesex Fells Reservation
- Bigelow Hollow State Park
- Bright Nights at Forest Park
- Douglas State Forest
- Ashland State Park
- Trinity Church
- John Hancock Tower