Holiday Homes in Sterling

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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Sterling holiday homes

A modern kitchen with a marble island, white cabinetry, and pendant lighting.

1. Entire home in Sterling, Massachusetts, United States

Entire home in Sterling, Massachusetts, United States
Sterling
The price is AU$1,051
includes taxes & fees
18 Nov - 19 Nov
Entire home in Sterling, Massachusetts, United States
A staircase with dark wooden steps and white handrails, leading to a door at the top.

2. Cozy & Stylish 2-bedroom Home in Leominster

Cozy & Stylish 2-bedroom Home in Leominster
Leominster
The price is AU$329
includes taxes & fees
22 Nov - 23 Nov
Cozy & Stylish 2-bedroom Home in Leominster
A compact, modern laundry room with a built-in washer and dryer, a small storage cabinet, and a tiled floor.

3. 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 AU$361
includes taxes & fees
5 Dec - 6 Dec
Angel Sky Challenge
Two Adirondack chairs on a wooden deck with a view of a lake and trees.

4. Worcester Lakefront Cottage Apt w/ Shared Dock!

Worcester Lakefront Cottage Apt w/ Shared Dock!
Worcester
9.4 out of 10, Exceptional, (20 reviews)
"The host was very accommodating and responsive. Great property in a great location, would stay again!"
United States
Michaela H.
The price is AU$633
includes taxes & fees
22 Nov - 23 Nov
Worcester Lakefront Cottage Apt w/ Shared Dock!
A wooden cabin bedroom with a bed, a nightstand, a lamp, and a bunk bed.

5. The Christmas Cottage, 4BR New England Escape

The Christmas Cottage, 4BR New England Escape
Rutland
The price is AU$1,050
includes taxes & fees
18 Nov - 19 Nov
The Christmas Cottage, 4BR New England Escape
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, (3 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 AU$924
includes taxes & fees
22 Nov - 23 Nov
4-bedroom house in nice Holden with WiFi, AC
A living room with a round table, two armchairs, a TV mounted on the wall, and a potted plant.

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

Beautiful two-story home close to downtown worcester 5beds-4bedroom
Worcester
9.0 out of 10, Wonderful, (20 reviews)
"Great house-clean, great location."
United States
Kathleen R.
The price is AU$603
includes taxes & fees
10 Dec - 11 Dec
Beautiful two-story home close to downtown worcester 5beds-4bedroom
A spacious living room with a high ceiling, a wooden floor, a black sofa, a white armchair, a small round table, and a window with curtains.

8. Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston

Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
Worcester
8.0 out of 10, Very good, (1 review)
"The house was fine overall. There were just a few things that stood out - only 3 towels but we were 4, no baking sheet for the oven, lighting in the kitchen wasn’t great, couldn’t find the house or unit number and the lock box was hard to find. The main bed was very comfortable but the pillows were not."
United States
Laura P.
The price is AU$453
includes taxes & fees
12 Nov - 13 Nov
Quiet Dead-End St, PS5 Pro Lounge, 35 Min to Boston
The Cottage is nestled next to the historic Sagendorph Mansion.

9. Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (9 reviews)
"Nice, clean and well maintained. Would stay here again."
United States
Sarah S.
The price is AU$323
includes taxes & fees
12 Nov - 13 Nov
Cottage by the Castle – Downtown Spencer
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
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean location to stay."
United States
Mike O.
The price is AU$698
includes taxes & fees
16 Nov - 17 Nov
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, (36 reviews)
"We had a great stay."
United States
Jessica D.
The price is AU$531
includes taxes & fees
16 Nov - 17 Nov
Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
A modern kitchen with white cabinets, a central island with bar stools, a large window, and a dark ceiling beam.

12. 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 AU$888
includes taxes & fees
14 Nov - 15 Nov
Spacious 5 Bedroom Retreat • Free Parking • Pet Friendly• Greater Boston
A spacious living room with wooden beams, a sliding glass door to a patio, and a cozy seating area with a sofa and chairs.

13. Retreat Near Boston with Roku, Deck, BBQ , Piano + Fenced in Yard for Pets!

Retreat Near Boston with Roku, Deck, BBQ , Piano + Fenced in Yard for Pets!
Framingham
10.0 out of 10, Exceptional, (3 reviews)
"Clean, pet friendly"
United States
Rebecca M.
The price is AU$1,077
includes taxes & fees
23 Nov - 24 Nov
Retreat Near Boston with Roku, Deck, BBQ , Piano + Fenced in Yard for Pets!
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, (10 reviews)
"An outstanding property filled with history, beautiful furniture and highly recommended"
United States
Eileen L.
The price is AU$528
includes taxes & fees
17 Nov - 18 Nov
Enjoy your stay in an antique home in an antique toy museum!
A bedroom with a wooden bed, a nightstand, a lamp, and a painting on the wall.

15. A Quintessential New England Historical Guesthouse

A Quintessential New England Historical Guesthouse
Groton
9.8 out of 10, Exceptional, (8 reviews)
"Lovely place to stay while attending a wedding. So nice to have a place to have the whole family together."
United States
Corrine B.
The price is AU$2,195
includes taxes & fees
29 Nov - 30 Nov
A Quintessential New England Historical Guesthouse
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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Learn more about Sterling

Families flock to Davis' Farmland & Mega Maze where children can pet farm animals and parents can navigate the challenging corn labyrinth. History buffs shouldn't miss the charming Mary Had a Little Lamb Statue, while nature lovers can explore nearby Tower Hill Botanic Garden's stunning seasonal displays.

See all hotels in Sterling
A white church with a steeple and clock tower, surrounded by trees and a well-maintained lawn.

Top reviews in Sterling

A modern restaurant with a central bar, wooden paneling, and a high ceiling with skylights.
Embassy Suites by Hilton Boston Marlborough

Embassy Suites by Hilton Boston Marlborough

Embassy Suites by Hilton Boston Marlborough
Marlborough

10/10 Excellent

Location was great for our needs: within walking distance to restaurants and stores. Would stay again.
Australia
Murray
Reviewed July 26, 2026
Embassy Suites by Hilton Boston Marlborough