Book Holiday Homes in Sterling

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Featured Holiday Homes in Sterling

Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms

Worcester MA
The price is AU$781 per night from 16 Dec to 17 Dec
AU$781
16 Dec - 17 Dec
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
Relaxing Getaway: Entire 3-BR Home w/ Fireplace

Relaxing Getaway: Entire 3-BR Home w/ Fireplace

Marlborough MA
Located in Marlborough, this vacation home is within a 5-minute drive of Callahan State Park and Old Grist Mill Museum.
Opens in a new windowRelaxing Getaway: Entire 3-BR Home w/ Fireplace
Newly Renovated Luxury 3-Bed 2-Bath Home with Easy Airport Access

Newly Renovated Luxury 3-Bed 2-Bath Home with Easy Airport Access

Framingham MA
The price is AU$378 per night from 16 Dec to 17 Dec
AU$378
16 Dec - 17 Dec
includes taxes & fees
Located in Framingham, this vacation home is within a 5-minute drive of Josephine Kochnowicz Clock Tower and Old Danforth Street Bridge.
Opens in a new windowNewly Renovated Luxury 3-Bed 2-Bath Home with Easy Airport Access
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New renovation cozy house in Worcester

New renovation cozy house in Worcester

Worcester MA
The price is AU$731 per night from 19 Dec to 20 Dec
AU$731
19 Dec - 20 Dec
includes taxes & fees
With a stay at this vacation home in Worcester, you'll be within a 5-minute drive of Blackstone River and Union Station.
Opens in a new windowNew renovation cozy house in Worcester
Beautiful Lakefront Home with Private Beach

Beautiful Lakefront Home with Private Beach

Shrewsbury MA
Located in Boylston, this vacation home is on a lake, within a 10-minute drive of Cyprian Keyes and Quinsigamond State Park.
Opens in a new windowBeautiful Lakefront Home with Private Beach
Home Away from Home!

Home Away from Home!

Worcester MA
The price is AU$590 per night from 17 Dec to 18 Dec
AU$590
17 Dec - 18 Dec
includes taxes & fees
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!
Leicester Lake Front Home, Come Relax!

Leicester Lake Front Home, Come Relax!

Leicester MA
Located in Leicester, this vacation home is on the waterfront, within a 15-minute drive of Vibra Hospital of Western Massachusetts - Central Campus and Burnside ...
Opens in a new windowLeicester Lake Front Home, Come Relax!
Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

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

Shrewsbury MA
With a stay at this vacation home in Shrewsbury, you'll be within a 5-minute drive of Ski Ward Ski Area and Bowlero Shrewsbury.
Opens in a new windowBeautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.
totally remodeled   house with fitness room, close to Boston and Worcester

totally remodeled house with fitness room, close to Boston and Worcester

Framingham MA
With a stay at this vacation home in Framingham, you'll be a 3-minute walk from Old Danforth Street Bridge and within a 5-minute drive of Cochituate State ...
Opens in a new windowtotally remodeled house with fitness room, close to Boston and 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.

Sterling 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 Sterling vacation homes are the perfect way for you to wing it.

Holiday houses in Sterling 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 Sterling 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 Sterling adventures, obvs.

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

Sterling Holiday Homes essential information

Accommodation
86 Holiday Homes
Lowest Price
AU$104
Highest Price
AU$781
Popular accommodation
Spacious 4-bedroom with four and half bathrooms, Relaxing Getaway: Entire 3-BR Home w/ Fireplace, Newly Renovated Luxury 3-Bed 2-Bath Home with Easy Airport Access, New renovation cozy house in Worcester, Beautiful Lakefront Home with Private Beach, Home Away from Home!, Leicester Lake Front Home, Come Relax!, Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku., totally remodeled house with fitness room, close to Boston and Worcester

Top trending hotels in Sterling

Chocksett Inn and Restaurant

Chocksett Inn and Restaurant

3.5 out of 5
59 Laurelwood Road Sterling MA
Fully refundableReserve now, pay when you stay
The price is AU$267 per night from 16 Dec to 17 Dec
AU$267
16 Dec - 17 Dec
includes taxes & fees
Located in Sterling, Chocksett Inn and Restaurant is within a 10-minute drive of Davis' Farmland & Mega Maze and Museum of Russian Icons.
Opens in a new windowChocksett Inn and Restaurant
Red Roof Inn Boston - Southborough/ Worcester

Red Roof Inn Boston - Southborough/ Worcester

2 out of 5
367 Turnpike Rd Southborough MA
Fully refundableReserve now, pay when you stay
The price is AU$104 per night from 18 Dec to 19 Dec
AU$104
18 Dec - 19 Dec
includes taxes & fees
A stay at Red Roof Inn Boston - Southborough/ Worcester places you in the heart of Southborough, a 4-minute drive from Lake Chauncy Public Beach and 5 minutes ...
Opens in a new windowRed Roof Inn Boston - Southborough/ Worcester
Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 out of 5
150 Great Wolf Dr Fitchburg MA
Fully refundable
The price is AU$270 per night from 13 Jan to 14 Jan
AU$270
13 Jan - 14 Jan 2026
includes taxes & fees
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 ...
Opens in a new windowGreat Wolf Lodge Boston / Fitchburg, MA
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The Verve Hotel Boston Natick, Tapestry Collection by Hilton

The Verve Hotel Boston Natick, Tapestry Collection by Hilton

3.5 out of 5
1360 Worcester St Natick MA
Fully refundableReserve now, pay when you stay
The price is AU$164 per night from 21 Dec to 22 Dec
AU$164
21 Dec - 22 Dec
includes taxes & fees
When you stay at The Verve Hotel Boston Natick, Tapestry Collection by Hilton in Natick, you'll be in the business district, within a 5-minute drive of Natick ...
Opens in a new windowThe Verve Hotel Boston Natick, Tapestry Collection by Hilton
Don't see what you're looking for?
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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.

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^Subject to availability and chosen travel dates.