Oakham Holiday Rentals

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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Oakham holiday rentals

Fridge, microwave, oven, stovetop

Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (6 reviews)
"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$2,149
HK$4,042 total
includes taxes & fees
11 Feb - 12 Feb
Spacious 4-bedroom with four and half bathrooms
Fridge, microwave, oven, stovetop

Spacious & Clean 3BR APT near Clark University

Spacious & Clean 3BR APT near Clark University
Main South
10.0 out of 10, Exceptional, (1 review)
"Perfect apartment with lots of room; comfortable beds. Decorated with a personal touch (some VRBO's feel too impersonal) which made it very welcoming. Could not be better located for visiting Clark University campus!"
United States
Barb S.
The price is HK$1,020
HK$1,757 total
includes taxes & fees
11 Feb - 12 Feb
Spacious & Clean 3BR APT near Clark University
Interior

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, (9 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$1,160
HK$1,392 total
includes taxes & fees
15 Feb - 16 Feb
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Smart TV

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, (24 reviews)
"Our family stayed at the house for 2 nights to attend a nearby wedding. The house was just as pictured - lovely, clean, and perfect for our stay. The hosts have been very thoughtful about every detail from easy check-in to a well stocked kitchen to cozy blankets for the comfy couch. We had a wonderful time and highly recommend! "
United States
Kelly G.
The price is HK$1,758
HK$4,011 total
includes taxes & fees
11 Feb - 12 Feb
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Smart TV, books, stereo

Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft in Pioneer Valley
Belchertown
9.4 out of 10, Exceptional, (22 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$1,231
HK$1,648 total
includes taxes & fees
12 Feb - 13 Feb
Newly Built Barn Loft in Pioneer Valley
Interior

Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!
Sturbridge
9.8 out of 10, Exceptional, (19 reviews)
"Thank you for a wonderful stay! Our family enjoyed the gorgeous views and the well-equipped home. There were toys, books, and games for the kids, and the beds were very comfortable. We’d definitely stay again!"
United States
Caitlin D.
The price is HK$2,422
HK$6,644 total
includes taxes & fees
11 Feb - 12 Feb
Lake House in Sturbridge w/All the Views!
Smart TV, fireplace

Home Away from Home!

Home Away from Home!
Worcester
9.4 out of 10, Exceptional, (15 reviews)
"Very clean ans spacious. Great communication "
United States
Tom K.
The price is HK$1,453
HK$3,085 total
includes taxes & fees
14 Feb - 15 Feb
Home Away from Home!
Terrace/patio

Spacious Getaway by TreeHouse Brewery & Amazon WareHouse

Spacious Getaway by TreeHouse Brewery & Amazon WareHouse
Charlton
8.6 out of 10, Excellent, (24 reviews)
"It’s very clean with lots of room for the price. The neighborhood is quiet and peaceful. The pool is well-maintained. The owner is very responsive and helpful. Highly recommend!"
United States
Jan L.
The price is HK$3,868
HK$7,367 total
includes taxes & fees
2 Mar - 3 Mar
Spacious Getaway by TreeHouse Brewery & Amazon WareHouse
Interior

Spacious Massachusetts Apartment #2

Spacious Massachusetts Apartment #2
West Brookfield
9.0 out of 10, Wonderful, (29 reviews)
"Really a cute place to stay, very clean and comfortable "
United States
Michelle J.
The price is HK$625
HK$2,348 total
includes taxes & fees
14 Feb - 15 Feb
Spacious Massachusetts Apartment #2
4 bedrooms, iron/ironing board, free WiFi, bed sheets

16/2 - 4BR Family Home in Worcester Near Parks

16/2 - 4BR Family Home in Worcester Near Parks
Worcester
The price is HK$732
HK$2,358 total
includes taxes & fees
11 Feb - 12 Feb
16/2 - 4BR Family Home in Worcester Near Parks
Interior

4/1 - 3BR Worcester - Cozy Apartment Near Clark Uni

4/1 - 3BR Worcester - Cozy Apartment Near Clark Uni
Main South
The price is HK$731
HK$2,187 total
includes taxes & fees
11 Feb - 12 Feb
4/1 - 3BR Worcester - Cozy Apartment Near Clark Uni
Interior

Electric House - Cozy Downtown stay

Electric House - Cozy Downtown stay
Canal District
4.0 out of 10, (1 review)
"It was uncomfortably cold and there was no running water. A refund would be in order."
United States
Deb P.
The price is HK$1,336
HK$3,282 total
includes taxes & fees
11 Feb - 12 Feb
Electric House - Cozy Downtown stay
Interior

Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
The price is HK$1,836
HK$3,299 total
includes taxes & fees
21 Feb - 22 Feb
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Books

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
The price is HK$1,231
HK$1,567 total
includes taxes & fees
11 Feb - 12 Feb
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Exterior

Beautifully updated home located just minutes from downtown Worcester.

Beautifully updated home located just minutes from downtown Worcester.
Worcester
10.0 out of 10, Exceptional, (1 review)
"Great clean place. Groceries and restaurants very close and convenient."
United States
Binoy K.
The price is HK$1,250
HK$2,862 total
includes taxes & fees
28 Feb - 1 Mar
Beautifully updated home located just minutes from downtown Worcester.
Dining

12B-Cozy 3BR Apartment with Koi Pond in Worcester

12B-Cozy 3BR Apartment with Koi Pond in Worcester
Millbury
The price is HK$984
HK$2,577 total
includes taxes & fees
15 Feb - 16 Feb
12B-Cozy 3BR Apartment with Koi Pond in Worcester
4 bedrooms, iron/ironing board, free WiFi, bed sheets

16/3 - Spacious 4BR Worcester Home Near Parks

16/3 - Spacious 4BR Worcester Home Near Parks
Worcester
The price is HK$731
HK$2,286 total
includes taxes & fees
11 Feb - 12 Feb
16/3 - Spacious 4BR Worcester Home Near Parks
Fridge, microwave, oven, dishwasher

NEW! Cushing Home | Family Cabin Near Wachusett Mtn

NEW! Cushing Home | Family Cabin Near Wachusett Mtn
Ashburnham
The price is HK$2,444
HK$6,536 total
includes taxes & fees
11 Feb - 12 Feb
NEW! Cushing Home | Family Cabin Near Wachusett Mtn
Fridge, microwave, stovetop, coffee/tea maker

16/1 Worcester - Family Stay Close to Parks & Eats

16/1 Worcester - Family Stay Close to Parks & Eats
Worcester
The price is HK$725
HK$2,386 total
includes taxes & fees
11 Feb - 12 Feb
16/1 Worcester - Family Stay Close to Parks & Eats
2 bedrooms, iron/ironing board, WiFi, bed sheets

Dream Inn LLC 2-bedroom apartment in fabulous Fitchburg with WiFi, fitness room

Dream Inn LLC 2-bedroom apartment in fabulous Fitchburg with WiFi, fitness room
Fitchburg
2.0 out of 10, (1 review)
"The stairs to get to the property were inadequate for one member of our party with mobility issues, so we had to cancel. The host was responsive and polite."
United States
Susannah
The price is HK$1,250
HK$1,746 total
includes taxes & fees
28 Feb - 1 Mar
Dream Inn LLC 2-bedroom apartment in fabulous Fitchburg with WiFi, fitness room
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
"Loved the place!"
Eddie 2-night trip
Posted 2 days 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 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.