Oakham Holiday Rentals

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Holiday Rentals in Oakham

Beautiful Lakefront Home with Private Beach
9.4 out of 10, Exceptional, (178)
"Great location for the family. Grandson enjoyed fishing and family swimming, cookouts and fire pit. "
PeterJanet S.
Beautiful Lakefront Home with Private Beach
Dove Cabin up in the Trees
9.8 out of 10, Exceptional, (27)
"A sweet, cozy, nostalgic little cabin in the woods. It was the perfect stop over on our road trip to Acadia. Very peaceful, and the screened in porch was wonderful to relax on before bed and during breakfast. "
Maggie G.
The price is AU$399
includes taxes & fees
21 Oct - 22 Oct
Dove Cabin up in the Trees
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
9.8 out of 10, Exceptional, (39)
"WE enjoyed our stay."
Carolyn B.
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
10.0 out of 10, Exceptional, (198)
"Water front was a perfectly serene escape. House was cute and had everything we needed for a quiet getaway. Would absolutely stay here again. "
Rich L.
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
Waterfront Home with Stunning Views .. Dog friendly , and great fishing !!!
10.0 out of 10, Exceptional, (134)
"It was our 4 lake vacation there. We absolutely love it and our dog Charlie enjoys the beautiful yard and and a swim in a little bay at this property."
Anonymous traveller
Waterfront Home with Stunning Views .. Dog friendly , and great fishing !!!
Brimfield Waterfront cottage
10.0 out of 10, Exceptional, (11)
"The cabin was definitely cozy, the treats were a nice addition, and the kitchen had most of what we needed. Would return next time we plan to be in the area. Gus was great to communicate with! Thank you@"
Debora
Brimfield Waterfront cottage
One Bedroom Apartment with Separate Bunk Bed Area
9.6 out of 10, Exceptional, (22)
"My family had a wonderful stay! We attended a weekend event at WPI and this was a great location to rest after a long day. Our kids especially enjoyed the large TV in the living room. It was clean and communication/ instructions were clear. Thanks! "
Katie M.
One Bedroom Apartment with Separate Bunk Bed Area
Spacious 4-bedroom house in charming Worcester with AC, WiFi
2.0 star property
10.0 out of 10, Exceptional, (21)
"Great space to hang out with family while in town. "
Blessing T.
Spacious 4-bedroom house in charming Worcester with AC, WiFi
Home Away from Home!
9.4 out of 10, Exceptional, (13)
"The property was nice and accommodating for my family! "
Ykeca M.
The price is AU$618
includes taxes & fees
3 Nov - 4 Nov
Home Away from Home!
Lakefront: Fish, Kayak, Canoe, Near Treehouse Brewery, Sturbridge Village!
10.0 out of 10, Exceptional, (5)
Lakefront: Fish, Kayak, Canoe, Near Treehouse Brewery, Sturbridge Village!
Newly Built Barn Loft in Pioneer Valley
2.0 star property
9.4 out of 10, Exceptional, (19)
"cute little place! host was very responsive"
zane s.
The price is AU$330
includes taxes & fees
2 Nov - 3 Nov
Newly Built Barn Loft in Pioneer Valley
Cottage on Partridge Pond
10.0 out of 10, Exceptional, (25)
"Was a little nervous with the square footage but boy they have maximized every inch of this house. Lake was glorious, rooms were comfortable and all the extras were top notch. Already booked another stay for later this year. Such a perfect place for our family."
Jessica K.
Cottage on Partridge Pond
Charming 3-bedroom apartment with WiFi, AC in lovely Leominster
10.0 out of 10, Exceptional, (1)
"Well equipped "
Matt M.
Charming 3-bedroom apartment with WiFi, AC in lovely Leominster
Modern Mid-Century in Fitchburg
9.4 out of 10, Exceptional, (8)
"Great property close to where we needed to be."
Justin
Modern Mid-Century in Fitchburg
Apartment in town center #1
8.6 out of 10, Excellent, (24)
"Clean place and was well suited for what we needed"
Chris
The price is AU$441
includes taxes & fees
26 Oct - 27 Oct
Apartment in town center #1
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
10.0 out of 10, Exceptional, (13)
"The house was beautiful. Very clean, pet friendly, very good communication with owner."
JUNE
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
Large relaxing house in 25 acres of private woods with lake access.
9.6 out of 10, Exceptional, (23)
"Beautiful place and we had a great family weekend"
William M.
Large relaxing house in 25 acres of private woods with lake access.
Spacious Massachusetts Apartment #2
9.0 out of 10, Wonderful, (27)
"The apartment was very clean. It’s cozy, but had enough room for my family of 4. The house it’s a classic older New England home. It’s in the downtown part of a small cute town. Overall it was a really good experience!"
Kathleen S.
The price is AU$457
includes taxes & fees
28 Oct - 29 Oct
Spacious Massachusetts Apartment #2
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
9.6 out of 10, Exceptional, (27)
"I stayed at this property for almost a month and thoroughly enjoyed it. It had everything I needed and is conveniently located to Route 9 and I-435. The host was very responsive, which I greatly appreciated. It's nice to know such a comfortable place is available in Shrewsbury."
Patty S.
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
LAKE FRONT: Cozy 4-bedroom lake CAMP with WiFi and an outdoor firepit!
2.0 star property
9.0 out of 10, Wonderful, (8)
"House was great and plenty of towels and such. The board games were fabulous. "
Pamela M.
LAKE FRONT: Cozy 4-bedroom lake CAMP with WiFi and an outdoor firepit!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Oakham Hotel Reviews

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, 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 favourite 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 depend 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 AU$330 per night. Entering your travel dates in the search wizard might find you 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?

Beautiful Lakefront Home with Private Beach: This holiday home rental outside of Oakham is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

What’s there to see and do in Oakham?

Explore the area and family-friendly sights such as EcoTarium, 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.