Oakham, Massachusetts holiday accommodation: short-term house rentals & properties

Discover a selection of holiday rentals in Oakham that are perfect for your trip. Whether you're staying in a holiday rental with friends, family or even just your pets, you'll find the best amenities for hanging out with the people that matter most, such as parking and air conditioning. You're sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

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Find the best place to stay - Oakham

Private Resort Like Getaway - Close to Wachusett Mountain Ski Resort!

Sleeps 13 · 5 bedrooms · 5+ bathrooms

completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

Sleeps 6 · 3 bedrooms · 2 bathrooms

Peace of mind
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More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Choose a holiday rental for your Oakham getaway

Learn about the unique charm of Oakham with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around Oakham

Are you hoping to find attractions to visit while you're in the area? Venture out of your holiday home and experience everything that makes Oakham a one-of-a-kind holiday spot. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

Hardwick Vineyard and Winery (10.4 mi / 16.7 km)
Wachusett Mountain Ski Area (12.8 mi / 20.6 km)
Palmer Motorsports Park (13 mi / 20.9 km)
Green Hill Park (14.6 mi / 23.4 km)
Cyprian Keyes (15 mi / 24.1 km)
1761 Old Mill Gift Shop (15.2 mi / 24.5 km)

Exploring the natural features in Oakham

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Oakham is a great place to get out in nature. These are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

Rock House Reservation (9.6 mi / 15.4 km)
Wachusett Mountain State Reservation (12.4 mi / 20 km)
Quabbin Reservoir Watershed Reservation (14 mi / 22.5 km)
Regatta Point Park (15.6 mi / 25 km)
Tower Hill Botanic Garden (16.2 mi / 26.1 km)
Buffumville Lake (17.5 mi / 28.2 km)

Travelling to and around Oakham

Fly into Worcester, MA (ORH-Worcester Regional), the closest airport, located 10.6 mi (17.1 km) from the city centre.

Frequently asked questions

How much does it cost to rent a holiday home in Oakham?

The average price for a holiday home in Oakham is determined by several factors, including time of year, length of stay and property type. Whether you’re searching for a sprawling villa with space for extended family or a quaint cottage just enough for two, just add your travel dates to find stays with amazing value.

How much does it cost to rent a beach house in Oakham?

When you travel and the style and size of the property will influence how much you’ll pay for your beachside holiday home. Type in your Oakham travel dates to view your available options on Stayz. Did someone just say “private pool”? Use our filters to choose the features and amenities you want in your home.

What are the top attractions for families in Oakham?

Keeping the kids happy during your holiday in Oakham is child’s play with these awesome family-friendly attractions:

Rutland Brook Wildlife Sanctuary
Moore State Park
Rutland State Park

How old do you have to be to rent a holiday home in Oakham?

We recommend you check with the Oakham holiday home you want on Stayz as age restrictions differ. However, typically it’s 16, 18 or 21.

How long can I rent a holiday home in Oakham for?

It’s up to the Oakham property. To see all available options offering extended stays, simply enter your travel dates and guest number into Stayz. Look forward to having the entire property to yourself, as well as amenities such as air conditioning, a kitchen and outdoor spaces where the kids can play. Be on the lookout for long-term stays that offer weekly or monthly discounts.