Oakham Holiday Rentals

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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Oakham holiday rentals

Exterior

Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (28 reviews)
"So calm, clean and relaxing, and beautiful! Wonderful stay! "
United States
Sarah G.
The price is HK$1,374
HK$2,015 total
includes taxes & fees
10 May - 11 May
Dove Cabin up in the Trees
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, (33 reviews)
"Cutest home! My family loved it! "
United States
Shanna D.
The price is HK$783
HK$2,912 total
includes taxes & fees
12 May - 13 May
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Interior

Trainmaster's Inn - Caboose

Trainmaster's Inn - Caboose
Palmer
9.4 out of 10, Exceptional, (10 reviews)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
United States
Edward L.
The price is HK$1,174
HK$2,694 total
includes taxes & fees
10 May - 11 May
Trainmaster's Inn - Caboose
Front of property

Lakefront Cottage 2 Mi to Palladium in Worcester!

Lakefront Cottage 2 Mi to Palladium in Worcester!
3.0 star property
Worcester
The price is HK$1,417
HK$3,403 total
includes taxes & fees
12 May - 13 May
Lakefront Cottage 2 Mi to Palladium in Worcester!
Dining

Beautiful Worcester Downtown King Bd/Office World Cup Boston

Beautiful Worcester Downtown King Bd/Office World Cup Boston
Worcester
The price is HK$1,057
HK$2,545 total
includes taxes & fees
20 May - 21 May
Beautiful Worcester Downtown King Bd/Office World Cup Boston
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, (13 reviews)
"Enjoyed our stay while visiting Amherst. Thoughtful hosts with welcome touches. Provided details for finding, easy checkin and checkout, ample supplies for our needs. Thanks "
United States
Grace
The price is HK$1,292
HK$1,556 total
includes taxes & fees
26 May - 27 May
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Exterior

Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Westminster
10.0 out of 10, Exceptional, (34 reviews)
"We had a wonderful stay at this lake-front cottage looking up at the nearby ski resort. The cottage was cozy and quiet in a great location. The check-in process was easy, and the owner was very accessible. Terrific rental!"
United States
Lane D.
The price is HK$1,762
HK$4,114 total
includes taxes & fees
20 May - 21 May
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Interior

Angel Sky Challenge

Angel Sky Challenge
Worcester
The price is HK$1,253
HK$2,025 total
includes taxes & fees
10 May - 11 May
Angel Sky Challenge
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, (28 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
The price is HK$2,748
HK$5,239 total
includes taxes & fees
10 May - 11 May
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
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
8.0 out of 10, Very good, (2 reviews)
"Welcoming, cute."
United States
Trinity M.
The price is HK$1,465
HK$1,846 total
includes taxes & fees
10 May - 11 May
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Terrace/patio

Lovely & Spacious 2 Br, W/King/Queen beds 2 Bath.

Lovely & Spacious 2 Br, W/King/Queen beds 2 Bath.
Shrewsbury
9.2 out of 10, Wonderful, (17 reviews)
"The place was perfect for my stay. Ebenezer was an awesome host. He was very responsive and accommodating. I will stay here again. "
United States
Lori S.
Lovely & Spacious 2 Br, W/King/Queen beds 2 Bath.
Interior

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$1,485
HK$3,447 total
includes taxes & fees
25 May - 26 May
Cozy Adventure Filled Escape Free Parking 2 Bedroom Apts
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, (26 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$1,233
HK$1,659 total
includes taxes & fees
10 May - 11 May
Newly Built Barn Loft in Pioneer Valley
Smart TV, books

Heart of Shrewsbury St – 2BR Stay

Heart of Shrewsbury St – 2BR Stay
Shrewsbury Street
The price is HK$1,691
HK$2,213 total
includes taxes & fees
20 May - 21 May
Heart of Shrewsbury St – 2BR Stay
Interior

Fitchburg quiet side modern 2BD.

Fitchburg quiet side modern 2BD.
Fitchburg
10.0 out of 10, Exceptional, (4 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$1,102
HK$2,287 total
includes taxes & fees
14 May - 15 May
Fitchburg quiet side modern 2BD.
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, (11 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$2,153
HK$3,997 total
includes taxes & fees
11 May - 12 May
Spacious 4-bedroom with four and half bathrooms
4 bedrooms, iron/ironing board, free WiFi, bed sheets

Spacious 4BR Family Home in Worcester near Parks 16/2

Spacious 4BR Family Home in Worcester near Parks 16/2
Worcester
10.0 out of 10, Exceptional, (3 reviews)
"Clean, perfect, had everything we needed for a quick stay "
United States
Sierra M.
The price is HK$965
HK$2,968 total
includes taxes & fees
10 May - 11 May
Spacious 4BR Family Home in Worcester near Parks 16/2
Interior

Cozy 3-bedroom house in serene Worcester with fitness room and office

Cozy 3-bedroom house in serene Worcester with fitness room and office
Worcester
The price is HK$3,523
HK$4,606 total
includes taxes & fees
10 May - 11 May
Cozy 3-bedroom house in serene Worcester with fitness room and office
Dining

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

12B-Cozy 3BR Apartment with Koi Pond in Worcester
Millbury
10.0 out of 10, Exceptional, (1 review)
"Super nice place to stay with lots of food options in the area."
United States
Roberto A G.
The price is HK$900
HK$2,474 total
includes taxes & fees
10 May - 11 May
12B-Cozy 3BR Apartment with Koi Pond in Worcester
Smart TV

Grand Worcester Getaway! Pets Welcome! Comfortable

Grand Worcester Getaway! Pets Welcome! Comfortable
Worcester
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay, it was in a convenient location, was comfortable and clean. "
United States
Juliette L.
The price is HK$1,214
HK$2,527 total
includes taxes & fees
10 May - 11 May
Grand Worcester Getaway! Pets Welcome! Comfortable
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

Beechwood Hotel

Beechwood Hotel

6/10 Okay
"Parking was fine, Sonoma restaurant was terrible"
Nicholas 2-night trip
Posted 3 hours ago
Beechwood Hotel

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?

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.