Oakham Holiday Rentals

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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Oakham holiday rentals

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$1,455
HK$3,089 total
includes taxes & fees
9 Mar - 10 Mar
Home Away from Home!
Exterior

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, (30 reviews)
"Cutest home! My family loved it! "
United States
Shanna D.
The price is HK$1,173
HK$3,390 total
includes taxes & fees
15 Mar - 16 Mar
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
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, (25 reviews)
"Great family spot. Very clean and comfortable. Convenient to local attractions and shopping. "
United States
Dennyse M.
The price is HK$1,956
HK$4,256 total
includes taxes & fees
22 Mar - 23 Mar
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
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)
"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$1,097
HK$1,325 total
includes taxes & fees
11 Mar - 12 Mar
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Smart TV, books

Heart of Shrewsbury St – 2BR Stay

Heart of Shrewsbury St – 2BR Stay
Shrewsbury Street
The price is HK$1,021
HK$1,938 total
includes taxes & fees
9 Mar - 10 Mar
Heart of Shrewsbury St – 2BR Stay
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$3,485
HK$6,916 total
includes taxes & fees
9 Mar - 10 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$626
HK$2,350 total
includes taxes & fees
9 Mar - 10 Mar
Spacious Massachusetts Apartment #2
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, (8 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$2,151
HK$3,993 total
includes taxes & fees
9 Mar - 10 Mar
Spacious 4-bedroom with four and half bathrooms
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, (23 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$1,232
HK$1,633 total
includes taxes & fees
12 Mar - 13 Mar
Newly Built Barn Loft in Pioneer Valley
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$1,021
HK$1,750 total
includes taxes & fees
10 Mar - 11 Mar
Spacious & Clean 3BR APT near Clark University
Living area

Cozy Adventure Filled Escape Free Parking 2 Bedroom Apts

Cozy Adventure Filled Escape Free Parking 2 Bedroom Apts
3.0 star property
Worcester
The price is HK$1,372
HK$3,280 total
includes taxes & fees
9 Mar - 10 Mar
Cozy Adventure Filled Escape Free Parking 2 Bedroom Apts
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$1,164
HK$1,475 total
includes taxes & fees
11 Mar - 12 Mar
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
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$1,408
HK$2,919 total
includes taxes & fees
29 Mar - 30 Mar
4/1 - 3BR Worcester - Cozy Apartment Near Clark Uni
2 bedrooms, iron/ironing board, Internet, bed sheets

Beautiful 2-story Downtown Worcester king bed with Office

Beautiful 2-story Downtown Worcester king bed with Office
Worcester
The price is HK$915
HK$2,426 total
includes taxes & fees
9 Mar - 10 Mar
Beautiful 2-story Downtown Worcester king bed with Office
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$1,333
HK$3,003 total
includes taxes & fees
16 Mar - 17 Mar
16/3 - Spacious 4BR Worcester Home Near Parks
Smart TV

Beautiful two-story home close to downtown worcester 5beds-4bedroom

Beautiful two-story home close to downtown worcester 5beds-4bedroom
Worcester
9.0 out of 10, Wonderful, (20 reviews)
"Great house-clean, great location."
United States
Kathleen R.
The price is HK$1,721
HK$3,393 total
includes taxes & fees
2 Apr - 3 Apr
Beautiful two-story home close to downtown worcester 5beds-4bedroom
Dining

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

12B-Cozy 3BR Apartment with Koi Pond in Worcester
Millbury
The price is HK$986
HK$2,547 total
includes taxes & fees
18 Mar - 19 Mar
12B-Cozy 3BR Apartment with Koi Pond in Worcester
Dining

Warm & Cozy 4BR Near Airport + Winter-Ready Comfort• Fast WiFi

Warm & Cozy 4BR Near Airport + Winter-Ready Comfort• Fast WiFi
Webster Square
8.0 out of 10, Very good, (4 reviews)
"Great house. Excellent back yard and privacy. "
United States
michael C.
Warm & Cozy 4BR Near Airport + Winter-Ready Comfort• Fast WiFi
Interior

Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
The price is HK$1,838
HK$3,303 total
includes taxes & fees
24 Mar - 25 Mar
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Interior

Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (20 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.
Lake House in Sturbridge w/All the Views!
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

Motel 6 Leominster, MA

Motel 6 Leominster, MA

10/10 Excellent
"Good "
Steven 1-night trip
Posted 3 hours ago
Motel 6 Leominster, MA

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
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  • 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?

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 Wachusett Meadow Wildlife Sanctuary 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.