Book Holiday Homes in Oakham

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Featured Holiday Homes in Oakham

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

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

Shrewsbury
With a stay at this vacation home in Shrewsbury, you'll be within a 15-minute drive of DCU Center and Ski Ward Ski Area.
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
Worcester Home on Indian Lake w/ Shared Boat Dock!

Worcester Home on Indian Lake w/ Shared Boat Dock!

Worcester
With a stay at this vacation home in Worcester, you'll be on the waterfront, within a 10-minute drive of DCU Center and Worcester Polytechnic Institute.
Worcester Home on Indian Lake w/ Shared Boat Dock!
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

Dog-Friendly Fitchburg Vacation Rental, Hike & Ski

Fitchburg
When you stay at this vacation home in Fitchburg, you'll be within a 10-minute drive of Fitchburg Art Museum and Fitchburg State University.
Dog-Friendly Fitchburg Vacation Rental, Hike & Ski
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Beautiful two-story home close to downtown worcester 5beds-4bedroom

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

Worcester
The price is AU$801 per night from 2 May to 3 May
AU$801
includes taxes & fees
2 May - 3 May
With a stay at this vacation home in Worcester, you'll be within a 5-minute drive of DCU Center and Union Station.
Beautiful two-story home close to downtown worcester 5beds-4bedroom
SunnyBrook House - 5 bedroom house in wonderful West Brookfield with WiFi, AC

SunnyBrook House - 5 bedroom house in wonderful West Brookfield with WiFi, AC

West Brookfield
With a stay at this vacation home in West Brookfield, you'll be within a 15-minute drive of Quaboag River and Rock House Reservation.
SunnyBrook House - 5 bedroom house in wonderful West Brookfield with WiFi, AC
Beautiful Lakefront Home with Private Beach

Beautiful Lakefront Home with Private Beach

Shrewsbury
With a stay at this vacation home in Boylston, you'll be on a lake, within a 15-minute drive of DCU Center and Cyprian Keyes.
Beautiful Lakefront Home with Private Beach
Spacious 4-bedroom house in charming Worcester with AC, WiFi

Spacious 4-bedroom house in charming Worcester with AC, WiFi

2 out of 5
Worcester
With a stay at this vacation home in Worcester, you'll be within a 5-minute drive of DCU Center and UMass Memorial Medical Center - Hahnemann Campus.
Spacious 4-bedroom house in charming Worcester with AC, WiFi
Spacious Oxford Home w/ Pool - 4 Mi to Lake!

Spacious Oxford Home w/ Pool - 4 Mi to Lake!

Oxford
With a stay at this vacation home in Oxford, you'll be within a 10-minute drive of Lake Chaubunagungamaug and Sutton Pond.
Spacious Oxford Home w/ Pool - 4 Mi to Lake!
Brand new house close to downtown & attractions. Fenced in- Pet/family friendly

Brand new house close to downtown & attractions. Fenced in- Pet/family friendly

Worcester
With a stay at this vacation home in Worcester, you'll be within a 10-minute drive of DCU Center and Central Rock Climbing Center.
Brand new house close to downtown & attractions. Fenced in- Pet/family friendly
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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.

Oakham Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Oakham vacation homes are the perfect way for you to wing it.

Holiday houses in Oakham let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Oakham in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Oakham adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Oakham with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Oakham vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Oakham Holiday Homes essential information

Accommodation
96 Holiday Homes
Lowest Price
AU$166
Highest Price
AU$801
Popular accommodation
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku., Worcester Home on Indian Lake w/ Shared Boat Dock!, Dog-Friendly Fitchburg Vacation Rental, Hike & Ski, Beautiful two-story home close to downtown worcester 5beds-4bedroom, SunnyBrook House - 5 bedroom house in wonderful West Brookfield with WiFi, AC, Beautiful Lakefront Home with Private Beach, Spacious 4-bedroom house in charming Worcester with AC, WiFi, Spacious Oxford Home w/ Pool - 4 Mi to Lake!, Brand new house close to downtown & attractions. Fenced in- Pet/family friendly

Top trending hotels in Oakham

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 out of 5
150 Great Wolf Dr, Fitchburg, MA
Fully refundableReserve now, pay when you stay
The price is AU$379 per night from 7 Apr to 8 Apr
AU$379
includes taxes & fees
7 Apr - 8 Apr
With a stay at Great Wolf Lodge Boston / Fitchburg, MA in Fitchburg, you'll be within a 5-minute drive of Great Wolf Lodge Waterpark and Wachusett Brewing ...
Great Wolf Lodge Boston / Fitchburg, MA
Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St, Southbridge, MA
Fully refundableReserve now, pay when you stay
The price is AU$190 per night from 16 Apr to 17 Apr
AU$190
includes taxes & fees
16 Apr - 17 Apr
A stay at Wellsworth Hotel places you in the heart of Southbridge, steps from Southbridge Town Common and 5 minutes by foot from Windsor Court Historic ...
Wellsworth Hotel
The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road, Gardner, MA
Fully refundableReserve now, pay when you stay
The price is AU$244 per night from 6 Apr to 7 Apr
AU$244
includes taxes & fees
6 Apr - 7 Apr
Located in Gardner, The Colonial Hotel is a 2-minute drive from Dunn State Park and 6 minutes from Mount Wachusett Community College.
The Colonial Hotel
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Comfort Inn Auburn - Worcester

Comfort Inn Auburn - Worcester

2.5 out of 5
426 Southbridge St, Auburn, MA
Fully refundableReserve now, pay when you stay
The price is AU$166 per night from 6 Apr to 7 Apr
AU$166
includes taxes & fees
6 Apr - 7 Apr
With a stay at Comfort Inn Auburn - Worcester in Auburn, you'll be within a 10-minute drive of DCU Center and Auburn Mall.
Comfort Inn Auburn - Worcester
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.