Book Holiday Homes in Oakham

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Featured Holiday Homes in Oakham

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

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

Worcester MA
With a stay at this vacation home in Worcester, you'll be within a 5-minute drive of UMass Memorial Medical Center - Hahnemann Campus and Central Rock Climbing ...
Opens in a new windowSpacious 4-bedroom house in charming Worcester with AC, WiFi
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

Ware MA
The price is AU$279 per night from 19 May to 20 May
AU$279
19 May - 20 May
includes taxes & fees
Located in Ware, this vacation home is in a rural location, within a 15-minute drive of Wilton s Children Store and Rock House Reservation.
Opens in a new windowLittle House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms

Worcester MA
The price is AU$714 per night from 18 May to 19 May
AU$714
18 May - 19 May
includes taxes & fees
With a stay at this vacation home in Worcester, you'll be within a 5-minute drive of Bowlero Worcester and College of the Holy Cross.
Opens in a new windowSpacious 4-bedroom with four and half bathrooms
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Beautiful Worcester Downtown King Bd/Office World Cup Boston

Beautiful Worcester Downtown King Bd/Office World Cup Boston

Worcester MA
The price is AU$455 per night from 19 May to 20 May
AU$455
19 May - 20 May
includes taxes & fees
A stay at this vacation home places you in the heart of Worcester, within a 5-minute drive of The Hanover Theatre for the Performing Arts and Fitton Field.
Opens in a new windowBeautiful Worcester Downtown King Bd/Office World Cup Boston
Brand New Stylish & Spacious 3-BR Retreat!

Brand New Stylish & Spacious 3-BR Retreat!

Worcester MA
With a stay at this vacation home in Worcester, you'll be within a 5-minute drive of EcoTarium and Union Station.
Opens in a new windowBrand New Stylish & Spacious 3-BR Retreat!
Home Away from Home!

Home Away from Home!

Worcester MA
With a stay at this vacation home in Worcester, you'll be within a 5-minute drive of Quinsigamond State Park and EcoTarium.
Opens in a new windowHome Away from Home!
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower

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

Westminster MA
The price is AU$731 per night from 20 May to 21 May
AU$731
20 May - 21 May
includes taxes & fees
With a stay at this vacation home in Westminster, you'll be on the waterfront, within a 10-minute drive of Great Wolf Lodge Waterpark and Wachusett Mountain ...
Opens in a new windowLakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Shrewsbury MA
Located in Shrewsbury, this vacation home is within a 5-minute drive of Ski Ward Ski Area and Bowlero Shrewsbury.
Opens in a new windowBeautiful 2 Bedrooms with 2 Beds in Shrewsbury
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

Spencer MA
Located in Spencer, this vacation home is on the waterfront, within a 10-minute drive of Saint Joseph's Abbey and Buck Hill Conservation Dam.
Opens in a new windowConvenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
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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
84 Holiday Homes
Lowest Price
AU$124
Highest Price
AU$731
Popular accommodation
Spacious 4-bedroom house in charming Worcester with AC, WiFi, Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6, Spacious 4-bedroom with four and half bathrooms, Beautiful Worcester Downtown King Bd/Office World Cup Boston, Brand New Stylish & Spacious 3-BR Retreat!, Home Away from Home!, Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower, Beautiful 2 Bedrooms with 2 Beds in Shrewsbury , Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

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$277 per night from 17 May to 18 May
AU$277
17 May - 18 May
includes taxes & fees
With a stay at Great Wolf Lodge Boston / Fitchburg, MA in Fitchburg, you'll be a 1-minute drive from Great Wolf Lodge Waterpark and 6 minutes from Wachusett ...
Opens in a new windowGreat Wolf Lodge Boston / Fitchburg, MA
Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

2.5 out of 5
277 Main Street (RT 131) Sturbridge MA
Fully refundableReserve now, pay when you stay
The price is AU$124 per night from 17 May to 18 May
AU$124
17 May - 18 May
includes taxes & fees
When you stay at Publick House Historic Inn and Country Motor Lodge in Sturbridge, you'll be in the historical district, within a 5-minute drive of Old Sturbridge ...
Opens in a new windowPublick House Historic Inn and Country Motor Lodge
Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St Southbridge MA
Fully refundableReserve now, pay when you stay
The price is AU$151 per night from 21 May to 22 May
AU$151
21 May - 22 May
includes taxes & fees
A stay at Wellsworth Hotel places you in the heart of Southbridge, steps from Central Mills Historic District and Southbridge Town Common.
Opens in a new windowWellsworth Hotel
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Comfort Inn Auburn - Worcester

Comfort Inn Auburn - Worcester

2.5 out of 5
426 Southbridge St Auburn MA
Fully refundable
The price is AU$159 per night from 24 May to 25 May
AU$159
24 May - 25 May
includes taxes & fees
With a stay at Comfort Inn Auburn - Worcester in Auburn, you'll be a short 4-minute walk from Auburn Mall and within 3 minutes by car from Bowlero ...
Opens in a new windowComfort Inn Auburn - Worcester
Don't see what you're looking for?
See all available properties in Oakham
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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.

Top Picks

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