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 NZ$867 per night from 19 Jan to 20 Jan
NZ$867
19 Jan - 20 Jan 2026
includes taxes & fees
Stay at this holiday home in Worcester. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Bowlero Worcester and Goddard Rocket Launching ...
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
Stay at this holiday home in Marlborough. Enjoy free Wi-Fi, patios and an in-room coffee maker. Popular attractions Ghiloni Park and Old Grist Mill Museum are ...
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
Stay at this holiday home in Framingham. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Garden in the Woods and Danforth Art School are ...
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 NZ$1,006 per night from 9 Jan to 10 Jan
NZ$1,006
9 Jan - 10 Jan 2026
includes taxes & fees
Stay at this holiday home in Worcester. Enjoy laundry facilities and air conditioning. Popular attractions Fitton Field and Hart Center are located nearby.
Opens in a new windowNew renovation cozy house in Worcester
Beautiful Lakefront Home with Private Beach

Beautiful Lakefront Home with Private Beach

Shrewsbury MA
Stay at this holiday home in Boylston. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Cyprian Keyes and Busta Rhymes Island are located ...
Opens in a new windowBeautiful Lakefront Home with Private Beach
Home Away from Home!

Home Away from Home!

Worcester MA
The price is NZ$681 per night from 21 Dec to 22 Dec
NZ$681
21 Dec - 22 Dec
includes taxes & fees
Stay at this business-friendly holiday home in Worcester. Enjoy a garden, laundry facilities and patios. Popular attractions EcoTarium and Quinsigamond State ...
Opens in a new windowHome Away from Home!
Leicester Lake Front Home, Come Relax!

Leicester Lake Front Home, Come Relax!

Leicester MA
Stay at this holiday home in Leicester. Enjoy a garden, laundry facilities and patios. Popular attractions Buck Hill Conservation Dam and John J. Binienda Memorial ...
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
Stay at this holiday home in Shrewsbury. Enjoy free Wi-Fi, laundry facilities and an in-room coffee maker. Popular attractions Ski Ward Ski Area and Northborough ...
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
Stay at this holiday home in Framingham. Enjoy a fitness centre, laundry facilities and an in-room coffee maker. Popular attractions Wayland Town Beach and Cochituate ...
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
NZ$126
Highest Price
NZ$1,006
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 NZ$307 per night from 21 Dec to 22 Dec
NZ$307
21 Dec - 22 Dec
includes taxes & fees
Stay at this hotel in Sterling. Enjoy free Wi-Fi, free parking and room service. Popular attractions Mary Had a Little Lamb Statue and Davis' Farmland & Mega ...
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 NZ$126 per night from 24 Dec to 25 Dec
NZ$126
24 Dec - 25 Dec
includes taxes & fees
Stay at this hotel in Southborough. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in their ...
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
The price is NZ$321 per night from 19 Jan to 20 Jan
NZ$321
19 Jan - 20 Jan 2026
includes taxes & fees
Stay at this family-friendly resort in Fitchburg. Enjoy 4 indoor pools, free water park access and room service. Our guests praise the helpful staff in their ...
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 NZ$191 per night from 27 Dec to 28 Dec
NZ$191
27 Dec - 28 Dec
includes taxes & fees
Stay at this business-friendly hotel in Natick. Enjoy free Wi-Fi, free parking and 2 restaurants. Our guests praise the helpful staff and the clean rooms in ...
Opens in a new windowThe Verve Hotel Boston Natick, Tapestry Collection by Hilton
Don't see what you're looking for?
See all available properties in Sterling
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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.