Oakham Holiday Rentals

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Check prices for these dates

Tonight
13 Oct - 14 Oct
Tomorrow
14 Oct - 15 Oct
This weekend
17 Oct - 19 Oct
Next weekend
24 Oct - 26 Oct

Holiday Rentals in Oakham

Beautiful Lakefront Home with Private Beach
Lake
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. "
Beautiful Lakefront Home with Private Beach
Dove Cabin up in the Trees
Exterior
Dove Cabin up in the Trees
9.8 out of 10, Exceptional, (25)
"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. "
The price is HK$1,365
HK$2,002 total
includes taxes & fees
21 Oct - 22 Oct
Dove Cabin up in the Trees
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Fridge, microwave, oven, stovetop
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
9.8 out of 10, Exceptional, (39)
"WE enjoyed our stay."
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
Property grounds
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
10.0 out of 10, Exceptional, (198)
"The property was exactly as described and the Owner was very helpful throughout the process. Definitely will return to this house!"
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
Waterfront Home with Stunning Views .. Dog friendly , and great fishing !!!
Property grounds
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."
Waterfront Home with Stunning Views .. Dog friendly , and great fishing !!!
Brimfield Waterfront cottage
Property grounds
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@"
Brimfield Waterfront cottage
One Bedroom Apartment with Separate Bunk Bed Area
Interior
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! "
One Bedroom Apartment with Separate Bunk Bed Area
Spacious 4-bedroom house in charming Worcester with AC, WiFi
Fridge, microwave, oven, stovetop
Spacious 4-bedroom house in charming Worcester with AC, WiFi
2.0 star property
10.0 out of 10, Exceptional, (20)
"Great space to hang out with family while in town. "
Spacious 4-bedroom house in charming Worcester with AC, WiFi
Home Away from Home!
Smart TV, fireplace
Home Away from Home!
9.4 out of 10, Exceptional, (13)
"The property was nice and accommodating for my family! "
The price is HK$1,447
HK$3,099 total
includes taxes & fees
19 Oct - 20 Oct
Home Away from Home!
Lakefront: Fish, Kayak, Canoe, Near Treehouse Brewery, Sturbridge Village!
Outdoor dining
Lakefront: Fish, Kayak, Canoe, Near Treehouse Brewery, Sturbridge Village!
10.0 out of 10, Exceptional, (4)
"Great little cottage at a lake. Super well appointed with pots, pans, gas grill, etc.... great hosts very attentive! "
Lakefront: Fish, Kayak, Canoe, Near Treehouse Brewery, Sturbridge Village!
Newly Built Barn Loft in Pioneer Valley
Smart TV, books, stereo
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"
The price is HK$1,226
HK$1,633 total
includes taxes & fees
15 Oct - 16 Oct
Newly Built Barn Loft in Pioneer Valley
Cottage on Partridge Pond
Interior
Cottage on Partridge Pond
10.0 out of 10, Exceptional, (24)
"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."
Cottage on Partridge Pond
Charming 3-bedroom apartment with WiFi, AC in lovely Leominster
Interior
Charming 3-bedroom apartment with WiFi, AC in lovely Leominster
10.0 out of 10, Exceptional, (1)
"Well equipped "
Charming 3-bedroom apartment with WiFi, AC in lovely Leominster
Modern Mid-Century in Fitchburg
Fridge, microwave, oven, stovetop
Modern Mid-Century in Fitchburg
9.4 out of 10, Exceptional, (8)
"Great property close to where we needed to be."
Modern Mid-Century in Fitchburg
Apartment in town center #1
Terrace/patio
Apartment in town center #1
8.6 out of 10, Excellent, (24)
"Clean place and was well suited for what we needed"
The price is HK$560
HK$2,259 total
includes taxes & fees
21 Oct - 22 Oct
Apartment in town center #1
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
Exterior
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."
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.
Dining
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"
Large relaxing house in 25 acres of private woods with lake access.
Spacious Massachusetts Apartment #2
Exterior
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!"
The price is HK$622
HK$2,338 total
includes taxes & fees
20 Oct - 21 Oct
Spacious Massachusetts Apartment #2
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Children’s area
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."
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
LAKE FRONT: Cozy 4-bedroom lake CAMP with WiFi and an outdoor firepit!
Terrace/patio
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. "
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

Wellsworth Hotel

Wellsworth Hotel

10/10 Excellent
"Nice hotel with well appointed room in a quiet area."
David 1-night trip
Posted 14 hours ago
Wellsworth Hotel

Find out more about Oakham

Search for holiday rentals in Oakham on Expedia! You can easily find your home rentals, villas, holiday apartments in Oakham using one of the methods below:

  • View our selection of featured holiday rentals in Oakham
  • Use the map to find apartments and other holiday homes in the Oakham neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oakham while they last

Look no further and take a look at our great range of rental properties in Oakham!

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?

Waterfront Home with Stunning Views .. Dog friendly , and great fishing !!!: This holiday home rental outside of Oakham is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a private garden and a selection of games.

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.