Oakham Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
29 Nov - 30 Nov
Tomorrow
30 Nov - 1 Dec
Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec

Holiday Rentals in Oakham

Terrace/patio
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

Holiday Home in Ware

2.0 star property
10.0 out of 10, Exceptional, (3)
"We had a great time the place was clean and the owner was nice. I would definitely recommend."
United States
Laura B.
The price is HK$1,028
HK$1,251 total
includes taxes & fees
4 Dec - 5 Dec
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Outdoor dining
Leicester Lake Front Home, Come Relax!

Holiday Home in Leicester

10.0 out of 10, Exceptional, (32)
"The home was lovely and the lakefront spot was beautiful! It was a very relaxing stay. "
United States
Erik S.
Leicester Lake Front Home, Come Relax!
Terrace/patio
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Holiday Home in Sturbridge

9.8 out of 10, Exceptional, (89)
"Very Clean, great location"
United States
Anonymous traveller
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
Smart TV, fireplace
Home Away from Home!

Holiday Home in Worcester

9.4 out of 10, Exceptional, (14)
"The property was nice and accommodating for my family! "
United States
Ykeca M.
The price is HK$1,447
HK$3,116 total
includes taxes & fees
1 Dec - 2 Dec
Home Away from Home!
Fridge, microwave, oven, stovetop
Newly updated/furnished 3 bedrooms house

Holiday Home in Worcester

8.8 out of 10, Excellent, (13)
"House had everything you needed. Front of house parking. Large bedrooms, great back patio ,quiet neighborhood. Very comfortable definitely would stay again."
United States
Donald S.
Newly updated/furnished 3 bedrooms house
Interior
Bungalow 19 by the lake in Brimfield

Holiday Home in Brimfield

2.0 star property
10.0 out of 10, Exceptional, (2)
"Clean, comfortable and great communication with host!"
United States
Elizabeth P.
Bungalow 19 by the lake in Brimfield
Children’s area
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

Holiday Home in Shrewsbury

9.6 out of 10, Exceptional, (31)
"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."
United States
Patty S.
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Interior
Cozy 2-Floor Apartment with Garage Access

Holiday Home in Main South

9.8 out of 10, Exceptional, (27)
"Overall great place, parking in garage was great! "
United States
Michell M.
Cozy 2-Floor Apartment with Garage Access
Exterior
SalsVista 2nd Floor Corner Apt

Apartment in Forest Grove

10.0 out of 10, Exceptional, (4)
"We very much enjoyed our weekend stay at this place. The apartment was immaculate and very comfortable."
United States
Anonymous traveller
SalsVista 2nd Floor Corner Apt
Exterior
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!

Holiday Home in West Brookfield

10.0 out of 10, Exceptional, (15)
"The house was beautiful. Very clean, pet friendly, very good communication with owner."
United States
JUNE
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
Smart TV
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn

Cabin in Westminster

10.0 out of 10, Exceptional, (23)
"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. "
United States
Michael T.
The price is HK$1,752
HK$4,023 total
includes taxes & fees
9 Dec - 10 Dec
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Fridge, microwave, oven, stovetop
Spacious 4-bedroom with four and half bathrooms

Holiday Home in Worcester

10.0 out of 10, Exceptional, (5)
"We needed a place to stay while our hardwood floors were being refinished and this was perfect. We have a dog and 2 cats and there was plenty of space. The house was clean and as advertised."
United States
Deb H.
The price is HK$2,139
HK$4,024 total
includes taxes & fees
3 Dec - 4 Dec
Spacious 4-bedroom with four and half bathrooms
Exterior
Spacious Massachusetts Apartment #2

Apartment in West Brookfield

9.0 out of 10, Wonderful, (29)
"We used both apartments for time with extended family. Nice to be in the same building."
United States
Tyler K.
The price is HK$623
HK$2,339 total
includes taxes & fees
2 Dec - 3 Dec
Spacious Massachusetts Apartment #2
Fridge, microwave, oven, stovetop
Spacious 4-bedroom house in charming Worcester with AC, WiFi

Holiday Home in Worcester

2.0 star property
10.0 out of 10, Exceptional, (23)
"Great space to hang out with family while in town. "
United States
Blessing T.
Spacious 4-bedroom house in charming Worcester with AC, WiFi
Fridge, microwave, oven, stovetop
Serene 1-bedroom suite on 65 acre horse property

Apartment in Belchertown

10.0 out of 10, Exceptional, (23)
"A great jumping off point for the Pioneer Valley and 5 colleges. Brent and Claire were wonderful hosts! Nice and quiet on the property, and it’s a neat experience to have the beautiful horses right outside your window. "
United States
Claire W.
Serene 1-bedroom suite on 65 acre horse property
Property grounds
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

Holiday Home in Spencer

10.0 out of 10, Exceptional, (199)
"Great time spent with family"
Canada
Marianne B.
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
Exterior
Relaxing, Holiday Retreat, Pool, fireplace

Holiday Home in Brimfield

10.0 out of 10, Exceptional, (32)
"A truly beautiful place with the most gorgeous pool and landscaping. We will be back for sure!"
United States
Danneel A.
Relaxing, Holiday Retreat, Pool, fireplace
Exterior detail
Beautiful Renovated Townhome w/parking

Holiday Home in Holden

9.4 out of 10, Exceptional, (18)
"Nice accommodations and host made it very easy to work with. Would recommend "
United States
Brent A.
Beautiful Renovated Townhome w/parking
Microwave, oven, stovetop, dishwasher
Brand New Stylish & Spacious 3-BR Retreat!

Holiday Home in Worcester

2.0 star property
Brand New Stylish & Spacious 3-BR Retreat!
Lake
Beautiful Lakefront Home with Private Beach

Holiday Home in Shrewsbury

9.4 out of 10, Exceptional, (181)
"Great location for the family. Grandson enjoyed fishing and family swimming, cookouts and fire pit. "
United States
PeterJanet S.
Beautiful Lakefront Home with Private Beach
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.
View all properties

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Oakham Hotel Reviews

Hilton Garden Inn Worcester

Hilton Garden Inn Worcester

10/10 Excellent
"Everything was wonderful"
Stephen 1-night trip
Posted 2 days ago
Hilton Garden Inn Worcester

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?

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6: This holiday home rental outside of Oakham is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Kick off your shoes and enjoy yourself 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 Wachusett Mountain State Reservation and Wachusett Mountain Ski Area.

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.