An aerial view of a town surrounded by dense forests, with a mix of residential and commercial buildings, and a prominent church.

Holiday Homes in Sterling

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Sterling holiday homes

A modern kitchen with a marble island, stainless steel appliances, and bar stools.

1. Entire home in Sterling, Massachusetts, United States

Entire home in Sterling, Massachusetts, United States
Sterling
The price is €621
includes taxes & fees
5 Oct - 6 Oct
Entire home in Sterling, Massachusetts, United States
A lakeside cabin with a dock, a boat, and a second-story deck.

2. 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, (41 reviews)
"We had a great stay with our family."
United States
Sherri P.
The price is €476
includes taxes & fees
8 Oct - 9 Oct
Lakefront; view of ski mountain, firepit, dock, kayaks, laundry, outdoor shower
A living room with a sofa, a clock, a floor lamp, and a rug.

3. Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
Shrewsbury
9.4 out of 10, Exceptional, (54 reviews)
"Amazing host and fabulous spacious property. "
United States
Kelly L.
The price is €265
includes taxes & fees
13 Oct - 14 Oct
Beautiful 2 Bedrooms with 2 Beds in Shrewsbury
A modern kitchen with white cabinetry, a large island, and pendant lighting.

4. Modern Farmhouse Close to Mt. Wachusett

Modern Farmhouse Close to Mt. Wachusett
Holden
The price is €565
includes taxes & fees
25 Oct - 26 Oct
Modern Farmhouse Close to Mt. Wachusett
A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

5. Angel Sky Challenge

Angel Sky Challenge
Worcester
2.0 out of 10, (1 review)
"The add states an entire home, this is a home with small bedrooms and a bathroom. I was under the impression by the description the entire home was ours without others on the property. I’d put that in the description I felt under comfortable with the men on the property. False advertising "
United States
Cameron R.
The price is €235
includes taxes & fees
5 Oct - 6 Oct
Angel Sky Challenge
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

6. 4-bedroom house in nice Holden with WiFi, AC

4-bedroom house in nice Holden with WiFi, AC
Holden
10.0 out of 10, Exceptional, (2 reviews)
"Communication with owner was very responsive and timely. House was clean and as description. Any problems were immediately addressed by owner."
United States
larry d.
The price is €570
includes taxes & fees
20 Oct - 21 Oct
4-bedroom house in nice Holden with WiFi, AC

7. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (8 reviews)
"The cottage is beautiful, cozy and super comfortable! We loved it! The hosts also were super, communicative and friendly. The place was clean, we had everything we needed, is in a very safe area, and very pretty! Hight recommended! Thank you for hosting us!"
United States
Fabiola
The price is €214
includes taxes & fees
28 Sept - 29 Sept
Cottage by the Castle – Downtown Spencer
A bedroom with a large bed, a desk, a chair, a mirror, and a clock on the wall.

8. Game Room + Bar Lounge, 35 Min to Boston

Game Room + Bar Lounge, 35 Min to Boston
Worcester
The price is €240
includes taxes & fees
29 Sept - 30 Sept
Game Room + Bar Lounge, 35 Min to Boston
A two-story residential building with a front porch, a satellite dish, and a small front yard.

9. Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12

Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12
Worcester
The price is €642
includes taxes & fees
28 Oct - 29 Oct
Renovated Lakefront 5BR • Near Colleges • Sunsets • Sleeps 12
A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

10. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (21 reviews)
"Perfect location"
United States
Harmony F.
The price is €443
includes taxes & fees
28 Sept - 29 Sept
Spacious 4-bedroom with four and half bathrooms
A modern kitchen with white cabinetry, a built-in oven, and a dining area with a table and chairs.

11. Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access

Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
Framingham
9.6 out of 10, Exceptional, (30 reviews)
"Perfect place to stay. Clean and has everything you need. Would recommend anyone to stay here. "
United States
Michelle M.
The price is €332
includes taxes & fees
4 Oct - 5 Oct
Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
A modern kitchen with white cabinets, a central island, a microwave, and a stove.

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

totally remodeled house with fitness room, close to Boston and Worcester
Framingham
9.4 out of 10, Exceptional, (16 reviews)
"Nicely located in neighbor with easy access to highways and walking distance to coffee shop this single home is perfect for being near Boston. Space is comfortable with all the comforts of home. "
United States
Karyn V.
The price is €399
includes taxes & fees
4 Oct - 5 Oct
totally remodeled house with fitness room, close to Boston and Worcester
A modern kitchen with white cabinets, a central island with bar stools, a large window, and a dark ceiling beam.

13. Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston

Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston
Framingham
10.0 out of 10, Exceptional, (5 reviews)
"The house was nice. The beds were very comfortable. The house was close to everything. Check-in and check-out process was easy."
United States
Christina S.
The price is €465
includes taxes & fees
28 Sept - 29 Sept
Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston
A staircase with a wooden handrail and white steps, leading to a landing with a wooden table and a clock.

14. Enjoy your stay in an antique home in an antique toy museum!

Enjoy your stay in an antique home in an antique toy museum!
Winchendon
9.4 out of 10, Exceptional, (9 reviews)
"What a fun stay! Great communication with the property manager Don, cute town, lots of American history to be discovered, fun stay. 10/10 highly recommend!!!"
United States
Katja Z.
The price is €351
includes taxes & fees
28 Sept - 29 Sept
Enjoy your stay in an antique home in an antique toy museum!
A kitchen with a marble countertop, stainless steel appliances, and wooden beams.

15. A Quintessential New England Historical Guesthouse

A Quintessential New England Historical Guesthouse
Groton
9.8 out of 10, Exceptional, (7 reviews)
"Wonderful stay !!!!! Just perfect !!!"
United States
Sarah B.
The price is €1,437
includes taxes & fees
26 Oct - 27 Oct
A Quintessential New England Historical Guesthouse
A modern living room with a blue sofa, a leather armchair, and a patterned rug.

16. Luxury Boston Ranch –Sleeps 8|Pet+|Heated pool

Luxury Boston Ranch –Sleeps 8|Pet+|Heated pool
Framingham
10.0 out of 10, Exceptional, (6 reviews)
"Very nice"
United States
Tricia S.
The price is €629
includes taxes & fees
29 Sept - 30 Sept
Luxury Boston Ranch –Sleeps 8|Pet+|Heated pool
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 Sterling Hotel Reviews

La Quinta Inn by Wyndham Auburn Worcester

La Quinta Inn by Wyndham Auburn Worcester

10/10 Excellent
"I love the fact that is has a bibles"
Stephania 1-night trip
Posted 10 hours ago
La Quinta Inn by Wyndham Auburn Worcester

Find out more about Sterling

Sterling Holiday Homes information

Number of reviews
170
Accommodation
107 Holiday Homes
Lowest Price
€214
Highest Price
€1,437