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Oakham Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Oakham holiday rentals

1 bedroom, Internet, bed sheets

1. Clean & Cozy Private room - 3 floor_R 1

Clean & Cozy Private room - 3 floor_R 1
Union HIll
The price is HK$628
HK$899 total
includes taxes & fees
16 Aug - 17 Aug
Clean & Cozy Private room - 3 floor_R 1
Exterior

2. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (3 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is HK$1,795
HK$2,069 total
includes taxes & fees
25 Aug - 26 Aug
Cottage by the Castle – Downtown Spencer
Property grounds

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, (21 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$1,497
HK$1,815 total
includes taxes & fees
13 Aug - 14 Aug
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
TV

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

Large 3BD 1st Floor Apartment Minutes from 290
Franklin Plantation
10.0 out of 10, Exceptional, (4 reviews)
"It was a great place for my family and i"
United States
Taisha M.
The price is HK$1,177
HK$2,514 total
includes taxes & fees
28 Aug - 29 Aug
Large 3BD 1st Floor Apartment Minutes from 290
Interior

5. 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$2,056 total
includes taxes & fees
13 Aug - 14 Aug
Angel Sky Challenge
Exterior

6. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.6 out of 10, Exceptional, (34 reviews)
"So calm, clean and relaxing, and beautiful! Wonderful stay! "
United States
Sarah G.
The price is HK$1,377
HK$2,044 total
includes taxes & fees
16 Aug - 17 Aug
Dove Cabin up in the Trees
Smart TV

7. 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, (36 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
The price is HK$1,871
HK$4,214 total
includes taxes & fees
17 Aug - 18 Aug
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Interior

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

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
The price is HK$392
HK$1,043 total
includes taxes & fees
15 Aug - 16 Aug
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Smart TV, books, stereo

9. Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.6 out of 10, Exceptional, (34 reviews)
"The place was really nice! Very clean and well decorated. We had a great short stay and would definitely book it again in the future."
United States
Emily O.
The price is HK$1,236
HK$1,688 total
includes taxes & fees
24 Aug - 25 Aug
Newly Built Barn Loft in Pioneer Valley
Living area

10. Clean & Cozy Private- 3 floor_R 4

Clean & Cozy Private- 3 floor_R 4
Union HIll
The price is HK$537
HK$794 total
includes taxes & fees
13 Aug - 14 Aug
Clean & Cozy Private- 3 floor_R 4
Interior

11. 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
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,047
HK$2,707 total
includes taxes & fees
13 Aug - 14 Aug
Modern Stay 3BR Worcester Apt • FREE Parking near Clark University & I-290 4/1
Outdoor dining

12. Serene 1-bedroom suite on 75 acre horse property

Serene 1-bedroom suite on 75 acre horse property
Belchertown
10.0 out of 10, Exceptional, (33 reviews)
"We had a lovely weekend, it was quiet, private and watching the horses in the pasture was wonderful. We would definitely stay again. "
United States
Kim G.
The price is HK$947
HK$1,847 total
includes taxes & fees
18 Aug - 19 Aug
Serene 1-bedroom suite on 75 acre horse property
3 bedrooms, WiFi

13. 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
Newly Refreshed 3bd Spacious Unit Minutes from 290
Smart TV

14. 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$1,120
HK$3,006 total
includes taxes & fees
13 Aug - 14 Aug
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Exterior

15. 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, (40 reviews)
"Beautiful location and perfect for a fishing getaway! House was clean and cozy!"
United States
Julianne R.
The price is HK$1,569
HK$3,933 total
includes taxes & fees
7 Sept - 8 Sept
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Interior

16. 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$2,252
HK$3,873 total
includes taxes & fees
10 Sept - 11 Sept
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Property grounds

17. Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Brimfield
9.2 out of 10, Wonderful, (7 reviews)
"Welcoming, cute."
United States
Trinity M.
The price is HK$1,267
HK$1,608 total
includes taxes & fees
13 Aug - 14 Aug
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Living area

18. Clean & Cozy Private-3 floor_R 2

Clean & Cozy Private-3 floor_R 2
Union HIll
The price is HK$678
HK$955 total
includes taxes & fees
30 Aug - 31 Aug
Clean & Cozy Private-3 floor_R 2
Smart TV, books

19. 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$1,659
HK$2,177 total
includes taxes & fees
17 Aug - 18 Aug
Heart of Shrewsbury St – 2BR Stay
Living area

20. Clean & Cozy Private- 3 floor_R 3

Clean & Cozy Private- 3 floor_R 3
Union HIll
The price is HK$671
HK$947 total
includes taxes & fees
30 Aug - 31 Aug
Clean & Cozy Private- 3 floor_R 3
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

Holiday Inn Express & Suites Sturbridge by IHG

Holiday Inn Express & Suites Sturbridge by IHG

10/10 Excellent
"N/A"
Renata 1-night trip
Posted 7 hours ago
Holiday Inn Express & Suites Sturbridge by IHG

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:

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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?

Home Away from Home!: This holiday home rental outside of Oakham offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and 1 hot tub.

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.