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Oakham Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Oakham holiday rentals

1. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (8 reviews)
"The cottage is beautiful, cozy and super comfortable! We loved it! The hosts also were super, communicative and friendly. The place was clean, we had everything we needed, is in a very safe area, and very pretty! Hight recommended! Thank you for hosting us!"
United States
Fabiola
The price is HK$1,616
HK$1,781 total
includes taxes & fees
28 Sept - 29 Sept
Cottage by the Castle – Downtown Spencer
A living room with a TV, sofa, chairs, a lamp, and a window with sheer curtains.

2. Clean & Cozy Private-3 floor_R 2

Clean & Cozy Private-3 floor_R 2
Union HIll
The price is HK$628
HK$899 total
includes taxes & fees
1 Oct - 2 Oct
Clean & Cozy Private-3 floor_R 2
A grassy outdoor area with a hammock, chairs, and a stone wall.

3. Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Ware
9.8 out of 10, Exceptional, (26 reviews)
"Nice place to stay a lot of family activities on the premises short distance to shopping and attractions"
United States
Andrew
The price is HK$1,367
HK$1,611 total
includes taxes & fees
27 Sept - 28 Sept
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
A modern kitchen with white cabinetry, a large island, and pendant lighting.

4. Modern Farmhouse Close to Mt. Wachusett

Modern Farmhouse Close to Mt. Wachusett
Holden
The price is HK$2,224
HK$4,738 total
includes taxes & fees
7 Oct - 8 Oct
Modern Farmhouse Close to Mt. Wachusett
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

5. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (3 reviews)
"The place was immaculate, very large room, great kitchen, great bath, plenty of room for a family, quiet and secluded area few minutes away from town, outstanding communication with the property owner..true home away from home...Try it for yourself.."
United States
Giora Y.
The price is HK$1,255
HK$2,453 total
includes taxes & fees
25 Oct - 26 Oct
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

6. Charming 1-bedroom apartment with AC & Breakfast in Sturbridge

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
The price is HK$745
HK$1,437 total
includes taxes & fees
5 Oct - 6 Oct
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

7. Angel Sky Challenge

Angel Sky Challenge
Worcester
2.0 out of 10, (1 review)
"The add states an entire home, this is a home with small bedrooms and a bathroom. I was under the impression by the description the entire home was ours without others on the property. I’d put that in the description I felt under comfortable with the men on the property. False advertising "
United States
Cameron R.
The price is HK$1,255
HK$1,975 total
includes taxes & fees
28 Sept - 29 Sept
Angel Sky Challenge
A modern living room with a leather sofa, a coffee table, and a dining table. There are two windows providing natural light, a ceiling light fixture, and a trash can.

8. Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (38 reviews)
"The host was so responsive and made sure everything was perfect! It was the cutest and most comfy set up! With an adorable town beach 5 min down the road! Highly recommend!"
United States
Nora M.
The price is HK$1,235
HK$1,637 total
includes taxes & fees
1 Oct - 2 Oct
Newly Built Barn Loft in Pioneer Valley
A house with a stone wall and a dock extending into a calm body of water.

9. Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Westminster
9.6 out of 10, Exceptional, (42 reviews)
"Very clean and tidy!Tyler was great - even accommodated last minute to add our dogs to the booking!Would definitely stay again!"
United States
Christina C.
The price is HK$1,255
HK$3,313 total
includes taxes & fees
28 Sept - 29 Sept
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
A living room with a gray sofa, a coffee table, and a rug. There are two windows with blinds, a door, and a wall-mounted plant.

10. Large 3BD 1st Floor Apartment Minutes from 290

Large 3BD 1st Floor Apartment Minutes from 290
Franklin Plantation
10.0 out of 10, Exceptional, (5 reviews)
"It was a great place for my family and i"
United States
Taisha M.
The price is HK$957
HK$2,128 total
includes taxes & fees
29 Sept - 30 Sept
Large 3BD 1st Floor Apartment Minutes from 290
A wooden cabin with a glass upper floor, surrounded by a forest.

11. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (36 reviews)
"The owner was pleasant and accommodating "
United States
Maryann
The price is HK$1,376
HK$1,952 total
includes taxes & fees
28 Sept - 29 Sept
Dove Cabin up in the Trees
A room with two black leather sofas, a glass-top coffee table, white walls, and a ceiling light.

12. Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1

Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
Main South
8.0 out of 10, Very good, (2 reviews)
"The host was very communicative and obviously has tried to make this unit a reasonable place to have people stay. However, the layout of the place was not ideal. They turned a front sitting room into a bedroom, but it doesn't really work well. Further, that room smelled like marijuana our whole stay (1-night). It connected to the stairwell up to the units above, and my guess is that those people just smoke weed all day/night and it's impacting this unit. Further, the outside of the house is...
United States
Jeffrey B.
The price is HK$1,000
HK$2,491 total
includes taxes & fees
27 Sept - 28 Sept
Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
A bedroom with a large mirror, a bed with floral bedding, a standing lamp, and a window with curtains.

13. Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Shrewsbury
9.6 out of 10, Exceptional, (37 reviews)
"Lovely and great location "
United States
Kimberlee K.
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
A spacious living room with a wooden ceiling, a grey sofa, a staircase, and a large window.

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

Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Westminster
10.0 out of 10, Exceptional, (37 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
The price is HK$1,765
HK$3,812 total
includes taxes & fees
28 Sept - 29 Sept
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
A living room with two sofas, a coffee table, and a bookshelf.

15. Heart of Shrewsbury St – 2BR Stay

Heart of Shrewsbury St – 2BR Stay
Shrewsbury Street
8.0 out of 10, Very good, (1 review)
"We did not receive information on how to enter the property until we arrived and called the owner. There was a lot of poison ivy growing in our parking area."
United States
Sharon
The price is HK$1,440
HK$1,828 total
includes taxes & fees
29 Sept - 30 Sept
Heart of Shrewsbury St – 2BR Stay
A modern kitchen with a marble countertop, stainless steel sink, and a dining area with a green sofa and a plant.

16. Fitchburg quiet side modern 2BD.

Fitchburg quiet side modern 2BD.
Fitchburg
9.8 out of 10, Exceptional, (7 reviews)
"The apartment was very well and thoughtfully appointed. There were four adults in our party, and there was plenty of room. There is a full kitchen and a washer and dryer furnished. Two TVs. The lounging area, fire pit, and grill area were very nice places to sit and relax, with a privacy fence all around. The owners (or managers?) were very responsive and helpful. It is an upstairs apartment, but two of our party were in our 70s and 80s, and had no problems with it. Would highly recommend!!"
United States
Roberta
The price is HK$653
HK$2,114 total
includes taxes & fees
5 Oct - 6 Oct
Fitchburg quiet side modern 2BD.
A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

17. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (21 reviews)
"Perfect location"
United States
Harmony F.
The price is HK$2,157
HK$3,788 total
includes taxes & fees
28 Sept - 29 Sept
Spacious 4-bedroom with four and half bathrooms

18. Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2

Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Worcester
10.0 out of 10, Exceptional, (6 reviews)
"Clean, perfect, had everything we needed for a quick stay "
United States
Sierra M.
The price is HK$1,000
HK$2,671 total
includes taxes & fees
27 Sept - 28 Sept
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
A neatly made bed with rolled towels, a bedside table with a lamp, and a large mirror on the wall.

19. Newly Refreshed 3bd Spacious Unit Minutes from 290

Newly Refreshed 3bd Spacious Unit Minutes from 290
Franklin Plantation
9.4 out of 10, Exceptional, (3 reviews)
"The communication was wonderful. There were some things that needed to be addressed and they were.We would definitely rent again! The space is very spacious and clean"
United States
Anonymous traveller
The price is HK$784
HK$1,930 total
includes taxes & fees
30 Sept - 1 Oct
Newly Refreshed 3bd Spacious Unit Minutes from 290
A living room with a sofa, a clock, a floor lamp, and a rug.

20. Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Shrewsbury
9.4 out of 10, Exceptional, (54 reviews)
"Amazing host and fabulous spacious property. "
United States
Kelly L.
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
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

Spark By Hilton Northborough

Spark By Hilton Northborough

10/10 Excellent
"Breakfast was a little disappointing"
Michelle 1-night trip
Posted 1 hour ago
Spark By Hilton Northborough

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-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8: This holiday home rental outside of Oakham is located in a rural location, and has a garden, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What’s there to see and do in Oakham?

Explore the area and family-friendly sights such as Great Wolf Lodge Waterpark, 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.