Oakham Holiday Rentals from €186: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Oakham has to offer?

Spacious 4-bedroom with four and half bathrooms : This holiday home rental outside of Oakham is equipped with a garden, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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Holiday Rentals in Oakham

Escape to a serene forest retreat with a cozy cabin featuring a gabled roof and inviting front porch.

"This is the sweetest property to stay in when visiting Brimfield market. I highly suggest any of the cabins on the property "

includes taxes & fees

19 Aug - 20 Aug

Compact kitchen with appliances, sink, and window.

"Had such a wonderful stay at this space. Brent was very communicative about the check in/check out process which was greatly appreciated. The main living room area is very spacious and the bedroom was comfortable. I would definitely stay here again in the future!"

includes taxes & fees

13 Aug - 14 Aug

Enjoy meals in the kitchen with a dining area featuring a table and chairs.

"We stayed for a guys hunting trip and the place was what we needed after a long day"

Enjoy a view of the surrounding area from the large window in this kitchen, featuring a double sink and sleek appliances.

"We had room for each of the adults, which included adult children. At these ages they no longer want to share a bed or bathroom with anyone. Perfect that we could come together, but have our own separate spaces. Very clean and comfortable with everything you need."

includes taxes & fees

31 Aug - 1 Sept

Situated in a wooded area, this single-story house features a front porch and a stone retaining wall.

"Matressess were outdated but otherwise great!"

"Great little cottage at a lake. Super well appointed with pots, pans, gas grill, etc.... great hosts very attentive! "

Step out onto the covered porch, flanked by a railing and street view, and enjoy the serene atmosphere.

"Great communication, assistance with maintenance, and receptive to feedback. Would stay again . "

Enjoy meals in the well-lit kitchen with stainless steel appliances, white cabinetry, and a dining area.

"You will hear a little road noice but other then that it was perfect! Extremely clean and a great location. Highly recommend "

Enjoy cooking in this well-equipped kitchen with an oven, microwave, and refrigerator.

"Nice place."

includes taxes & fees

21 Aug - 22 Aug

Decorative table features a variety of plants, a globe, and a golden sculpture.

"This was a great spot for myself and my coaches when we had to travel to the area for a cheerleading competition."

Compact kitchen with stainless steel appliances, oven, and gas stove, featuring white cabinetry and a tiled backsplash.

"We appreciated the communication and space we had! Neighborhood was quiet and host gave amazing recommendations. "

Enjoy cooking in this well-equipped kitchen with stainless steel appliances and a central island.

"House was new, bright, and clean. "

Surrounded by vibrant autumn colors, this serene lakeside setting offers a peaceful escape.

"Beautiful house and grounds! Very private with lots of room along with homey touches. Kids loved the toy cabinet and the pool table. Easy access to Boston. We thoroughly enjoyed our Easter weekend there! "

Hammock suspended between trees, offering a serene spot to relax by the water.

"This was our third time staying, and definately won’t be our last!"

"My family stayed here while in town for a family wedding. The house was very spacious and well stocked. Location was convenient for our events in Westminster. "

Relax in this cozy cabin-style room with a comfortable sofa, coffee table, and large window offering a view of the outdoors.

"Kathleen was an amazing host and the property exceeded our expectations. The kids loved the bunk room and loft and the surrounding area provided something for all interests. We will definitely be planning another stay. "

includes taxes & fees

26 Aug - 27 Aug

Enjoy al fresco dining on the deck overlooking the water, where a barbecue grill and comfortable seating await.

"Great family time and comfortable house to spend time with family during a visit to see our daughter at Holy Cross! "

Relax on the covered porch, surrounded by a peaceful lawn and mature trees.

"Property is in excellent condition and well appointed. We enjoyed our stay."

includes taxes & fees

9 Sept - 10 Sept

Relax in this inviting living area with a high ceiling, ceiling fan, and comfortable seating for two.

"Lots of bedrooms with a great family gathering space. Quiet neighborhood. Would stay again at this property. Nicely decorated. "

includes taxes & fees

10 Aug - 11 Aug

Relax in this spacious living area with a kitchen, dining, and seating space, featuring a large mirror and a TV.

"This was a sweet place to stay while we were in the area for a graduation. It is a beautiful little apartment with everything we needed, cozy and quiet, and Lucienne’s communications were clear and welcoming!"

includes taxes & fees

10 Aug - 11 Aug

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Top Oakham Hotel Reviews

La Quinta Inn by Wyndham Auburn Worcester

10/10 Excellent

"This hotel was good! It was such an easy check in and the front desk staff was super friendly and welcoming. They are currently renovating the hotel but even with that there’s no mess. The renovated rooms are extremely nice and very modern. The breakfast was small but still a good morning meal! The bed was comfortable and you could tell it was fairly new which was a huge bonus! Overall it was a great stay "

Find out more about Oakham

Everything you need to know about Oakham holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oakham holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oakham holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oakham holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakham. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oakham holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakham holiday rentals we have selected for you start as low as €186 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oakham rentals

At Expedia, we put the best Oakham holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Oakham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oakham holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oakham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there holiday rentals in Oakham?

Yes, there are holiday rentals close to the most popular sights in Oakham, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Oakham has to offer?

Spacious 4-bedroom with four and half bathrooms: This holiday home rental outside of Oakham is equipped with a garden, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What’s there to see and do in Oakham?

Explore the area and family-friendly sights such as Green Hill Park, or get out into nature at a spot like Rock House Reservation. In the wider area, you’ll find Hardwick Vineyard and Winery and Wachusett Mountain State Reservation.

What’s a holiday rental in Oakham like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakham. Holiday rentals feature extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for family gatherings.

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Holiday Rentals in Oakham

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Holiday Rentals in Oakham

Dove Cabin up in the Trees

Serene 1-bedroom suite on 65 acre horse property

Spacious Private Retreat Near Holyoke State Park!

Spacious 4-bedroom with four and half bathrooms

Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

Lakefront: Fish, Kayak, Canoe, Near Treehouse Brewery, Sturbridge Village!

Beautiful Renovated Townhome w/parking

3 Bed / 1.5 Bath Townhome

Beautiful two-story home close to downtown worcester 5beds-4bedroom

New renovation cozy house in Worcester

Charming 3-bedroom apartment in historic Grafton with WiFi

Brand new 3 bedroom house in welcoming Worcester with WiFi and AC

Beautiful Lakefront Home with Private Beach

Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

Wachusett Mountain Getaway, Lake Adjacent Home! Near 1761 Old Mill and Trails!

Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn

Leicester Lake Front Home, Come Relax!

Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!

Home Away from Home!

Newly Built Barn Loft in Pioneer Valley

Top Oakham Hotel Reviews

La Quinta Inn by Wyndham Auburn Worcester

Hampton Inn & Suites Worcester

Wellsworth Hotel

Motel 6 Leominster, MA

The Colonial Hotel

Scottish Inn Sturbridge

Comfort Inn Auburn - Worcester

Publick House Historic Inn and Country Motor Lodge

Super 8 by Wyndham Sturbridge

Find out more about Oakham

Frequently asked questions