Sterling historic town center aerial view including Conant Free Public Library, Town Hall and First Church at Town Common, Sterling, Massachusetts MA, USA.

Sterling Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Sterling vacation rentals

Smart TV, fireplace

Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham

Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
Framingham
10.0 out of 10, Exceptional, (5 reviews)
"Very nice and private. Reasonably close to commuter lines into Boston."
United States
Jenny S.
The price is SAR 522
SAR 830 total
includes taxes & fees
30 Jun - 1 Jul
Private Cozy 1-br condo w/ high ceilings, WiFi, AC in quiet N. Framingham
House (2 Bedrooms) | Front of property

Lakefront Cottage 2 Mi to Palladium in Worcester!

Lakefront Cottage 2 Mi to Palladium in Worcester!
3.0 star property
Worcester
The price is SAR 736
SAR 1,697 total
includes taxes & fees
19 Jul - 20 Jul
Lakefront Cottage 2 Mi to Palladium in Worcester!
Living area

Clean & Cozy Private- 3 floor_R 5

Clean & Cozy Private- 3 floor_R 5
Union HIll
The price is SAR 301
SAR 430 total
includes taxes & fees
27 Jul - 28 Jul
Clean & Cozy Private- 3 floor_R 5
Interior

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 SAR 601
SAR 975 total
includes taxes & fees
27 Jun - 28 Jun
Angel Sky Challenge
Private kitchen

Charming 3-bedroom house in delightful Ashland for your getaway

Charming 3-bedroom house in delightful Ashland for your getaway
Ashland
10.0 out of 10, Exceptional, (2 reviews)
"This is our second stay here and both times have been good. The house is quiet, even for it being on a well traveled road. "
United States
John W.
The price is SAR 527
SAR 1,121 total
includes taxes & fees
7 Jul - 8 Jul
Charming 3-bedroom house in delightful Ashland for your getaway
Fridge, microwave, oven, stovetop

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
9.8 out of 10, Exceptional, (25 reviews)
"Clean home, comfortable beds, host very responsive."
United States
Richard M.
The price is SAR 896
SAR 1,365 total
includes taxes & fees
1 Jul - 2 Jul
Newly Renovated beautiful 3-Bed 2-Bath Home with Easy Airport Access
Fridge, microwave, stovetop, coffee/tea maker

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

totally remodeled house with fitness room, close to Boston and Worcester
Framingham
9.0 out of 10, Wonderful, (10 reviews)
"Property was as described. It was clean and owner was very responsive. Could walk to great coffee shop. "
United States
michelle s.
The price is SAR 605
SAR 1,141 total
includes taxes & fees
27 Jun - 28 Jun
totally remodeled house with fitness room, close to Boston and Worcester
Smart TV

Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn

Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Westminster
10.0 out of 10, Exceptional, (31 reviews)
"Very pleasant stay. Would definitely stay here again. "
United States
Shreya
The price is SAR 845
SAR 1,928 total
includes taxes & fees
30 Jun - 1 Jul
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
Exterior

Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
10.0 out of 10, Exceptional, (1 review)
"Wonderful stay in the cottage. Great location, and prompt and friendly communication from the owner. Beautifully kept vintage home - such a gem!"
United States
K C.
The price is SAR 619
SAR 710 total
includes taxes & fees
29 Jun - 30 Jun
Cottage by the Castle – Downtown Spencer
TV, fireplace

Private Luxury 2 Bedroom Suite

Private Luxury 2 Bedroom Suite
Framingham
8.6 out of 10, Excellent, (8 reviews)
"Good stay! Host was extremely nice and welcoming! It snowed during the night of the stay, and they were nice enough to still shovel a path in the morning and even cleared a path around my vehicle. Thank you! There is only a microwave, but easy to make work for food options. "
United States
Logan R.
The price is SAR 469
SAR 608 total
includes taxes & fees
21 Jul - 22 Jul
Private Luxury 2 Bedroom Suite
Exterior

Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (12 reviews)
"Super cute cabin. It was winter so we didn’t get to see a lot of the lake/property but everything was very comfortable and Jim was a fantastic host. Would definitely stay again! "
United States
Rebecca
The price is SAR 1,277
SAR 1,788 total
includes taxes & fees
28 Jun - 29 Jun
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Interior

Cottage Suite "A" - Walk to Shops, Train, History

Cottage Suite "A" - Walk to Shops, Train, History
Concord
9.8 out of 10, Exceptional, (8 reviews)
"Great location. Very simple open plan. "
United States
Trevor H.
The price is SAR 533
SAR 1,145 total
includes taxes & fees
29 Jun - 30 Jun
Cottage Suite "A" - Walk to Shops, Train, History
Exterior

Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Westminster
9.6 out of 10, Exceptional, (37 reviews)
"Cutest home! My family loved it! "
United States
Shanna D.
The price is SAR 1,126
SAR 2,323 total
includes taxes & fees
7 Jul - 8 Jul
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Dining

Beautiful Worcester Downtown King Bd/Office World Cup Boston

Beautiful Worcester Downtown King Bd/Office World Cup Boston
Worcester
10.0 out of 10, Exceptional, (2 reviews)
"I had an amazing stay here and would absolutely recommend this place to anyone visiting Boston or Worcester, Massachusetts. The house was truly 100% excellent. Everything was incredibly clean, spacious, and well organized. I loved the kitchen, my room, and the bathroom, everything was spotless and very comfortable. Honestly, the entire home was sparkling clean and very welcoming.I also slept extremely well during my stay. The bed, pillows, and bedding were so comfortable, which made the...
United States
Masard T.
The price is SAR 668
SAR 1,422 total
includes taxes & fees
26 Jul - 27 Jul
Beautiful Worcester Downtown King Bd/Office World Cup Boston
Dining

Beautiful family getaway, walking distance to markets, 35 min drive to Boston

Beautiful family getaway, walking distance to markets, 35 min drive to Boston
Hopkinton
9.2 out of 10, Wonderful, (10 reviews)
"Great place to stay very nice apartment"
United States
Aaron R.
The price is SAR 537
SAR 797 total
includes taxes & fees
29 Jun - 30 Jun
Beautiful family getaway, walking distance to markets, 35 min drive to Boston
TV

Large 3BD 1st Floor Apartment Minutes from 290

Large 3BD 1st Floor Apartment Minutes from 290
Franklin Plantation
10.0 out of 10, Exceptional, (3 reviews)
"It was a great place for my family and i"
United States
Taisha M.
The price is SAR 469
SAR 1,074 total
includes taxes & fees
1 Jul - 2 Jul
Large 3BD 1st Floor Apartment Minutes from 290
Property grounds

Lakefront Cottage 2 Mi to Palladium in Worcester!

Lakefront Cottage 2 Mi to Palladium in Worcester!
Worcester
9.6 out of 10, Exceptional, (14 reviews)
"Great host! Easy to contact via text. Home was clean and perfect for my family!"
United States
Michael B.
The price is SAR 661
SAR 1,679 total
includes taxes & fees
19 Jul - 20 Jul
Lakefront Cottage 2 Mi to Palladium in Worcester!
Private kitchen

Close to Colleges: Worcester Apt w/ Lake Access!

Close to Colleges: Worcester Apt w/ Lake Access!
Worcester
10.0 out of 10, Exceptional, (15 reviews)
"The amenities were great."
United States
Missie B.
Close to Colleges: Worcester Apt w/ Lake Access!
Exterior

Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
7.6 out of 10, Good, (4 reviews)
"Hit the jackpot at this stay .Awesome area with many things to keep busy outside ,hiking all around ,lake for all kind of activities .Jim was a great host filled us in on activities in the area and was a message away for any help u may need .I will be back ."
United States
David S.
The price is SAR 1,277
SAR 1,849 total
includes taxes & fees
29 Jun - 30 Jun
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Exterior

Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
9.8 out of 10, Exceptional, (26 reviews)
"Host was incredibly friendly and accommodating and the cabin was nothing short of beautiful"
United States
Moose C.
The price is SAR 1,577
SAR 2,200 total
includes taxes & fees
28 Jun - 29 Jun
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sterling Hotel Reviews

The Verve Hotel Boston Natick, Tapestry Collection by Hilton

The Verve Hotel Boston Natick, Tapestry Collection by Hilton

10/10 Excellent
"Very clean. Good location. Friendly staff."
robert j 2-night trip
Posted 10 hours ago
The Verve Hotel Boston Natick, Tapestry Collection by Hilton

Frequently asked questions

Can I find a vacation rental in Sterling?

Yes, there are vacation rentals in Sterling near Davis' Farmland & Mega Maze, or you can choose a secluded option if you'd like a relaxing place to stay. Sterling is known for its festivals and golf courses. Make sure you have time to check out the entertainment choices and zoo during your trip.

What are some of the best vacation rentals in Sterling?

Charming 3-bedroom house in delightful Ashland for your getaway: This vacation home rental near Sterling comes with laundry facilities so you can feel at home during your trip.

How many vacation rentals will I find in Sterling?

Expedia has 3 vacation rentals for your stay in Sterling.

What’s there to see and do in Sterling?

Explore the area and family-friendly sights such as Great Wolf Lodge Waterpark, or get out into nature at a spot like Tower Hill Botanic Garden. While here, Davis' Farmland & Mega Maze and Mary Had a Little Lamb Statue are other places worth a visit.

What’s a vacation rental in Sterling like?

A vacation rental is a private property you can book for a long or short time in Sterling. Vacation rentals provide amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for family gatherings.