You’re driving through Central Massachusetts, specifically that beautiful, rolling stretch of Worcester County, and you start looking for hotels in Sterling MA. You check the usual apps. You scan the maps. And then you realize something kinda funny: there is basically only one actual hotel within the town lines.
Seriously. Just one.
If you’re the type of traveler who expects a row of Hilton Gardens and Marriotts right next to the town common, you're going to be surprised. Sterling is a place of apple orchards, the "Mary Had a Little Lamb" statue, and quiet winding roads. It isn't a land of sprawling hospitality chains.
But honestly? That’s part of the charm. If you’re coming for a wedding at the 228 in Sterling or visiting Davis’ Farmland with the kids, you have to be a bit strategic about where you rest your head.
The Only Game in Town: Chocksett Inn
Let’s talk about the Chocksett Inn. This is it. This is the primary option for anyone who wants to stay in Sterling without crossing a border.
It’s located at 59 Laurelwood Road. If you’ve ever been to a wedding in this part of the state, you likely know the name. It’s a 27-room property that manages to feel like a cozy New England inn while offering the amenities of a much larger hotel.
What makes it work?
- The Vibe: It’s got that "old-world" feel but it was actually built in 1989. You get the benefit of modern plumbing and HVAC with the aesthetics of a historic farmhouse.
- The Food: The Chocksett Cellar Grille is legit. It’s one of the few places in town where you can get a refined meal and a cocktail without driving ten miles.
- The Convenience: It’s literally two minutes from the town center and very close to the massive Davis’ Farmland & Mega Maze.
The rooms are surprisingly spacious. Many of them include kitchenettes, which is a lifesaver if you’re traveling with picky eaters or just want to store some local cider from Meadowbrook Orchards. Just a heads-up: it’s a massive wedding venue. If you’re booking a random weekend in June, expect to see a lot of people in tuxedos and bridesmaids’ dresses.
👉 See also: Mammoth Lakes CA 93546 United States: Why People Keep Getting the Seasons Wrong
The Elephant in the Room: The Historic Sterling Inn
If you drive down Route 12, you’ll see a massive, gorgeous, white-clapboard building that looks like the platonic ideal of a Massachusetts inn. That is the Sterling Inn.
Don’t try to book a room there.
It’s been closed since 2012. It’s a bit of a local heartbreaker, honestly. For a century, it was the place to stay, but it’s currently a preservation project. The Eastern Pennsylvania Preservation Society has been involved in trying to find an investor to bring it back to life. As of early 2026, it remains a "time capsule" of New England history—fascinating to look at, but you can’t sleep there. Yet.
When Sterling is Full: Where Do You Actually Go?
Since there are only 27 rooms at the Chocksett, they go fast. When that happens, you’re looking at a 10-to-15-minute drive in almost any direction.
Leominster is your best bet for traditional chains. The DoubleTree by Hilton Hotel Leominster is the heavyweight here. It’s about 8 miles north of Sterling. It has an indoor pool, a decent gym, and those warm cookies everyone obsessed over for a decade. It’s reliable.
If you want something a bit more "resort-style," Great Wolf Lodge in Fitchburg is roughly 10 miles away. It’s pricey. It’s loud. It has a massive indoor water park. If you have kids and you're visiting Sterling for the farm, this might actually be your best play. You do the farm during the day and the water slides at night. Good luck getting any sleep, though.
To the south, you have Worcester. The AC Hotel by Marriott Worcester is about 12 miles away and feels a lot more "city-chic" than anything in Sterling. If you want a walkable downtown area with bars and restaurants after your day in the country, head toward Worcester.
Real Talk: The "Hidden" Bed and Breakfast Options
If you’re willing to drive 15 minutes, you can find some unique spots that fit the Sterling vibe better than a highway hotel.
- The Groton Inn: A bit further out, but it’s stunning. High-end, boutique, and very "New England."
- The Colonial Hotel (Gardner): It’s got a massive ballroom and an indoor pool. It’s about 20 minutes away and offers a similar "inn" feel to the Chocksett.
- Plain View Farm: Located in Sterling, this is more of a bed and breakfast experience. It’s quiet. It’s on a hill. It’s exactly what people picture when they think of Central Mass.
Navigating Sterling (The Logistics)
Sterling isn't a "walking town" when it comes to hotels. You need a car. There is no Uber graveyard waiting at the Chocksett Inn at 2:00 AM.
If you’re staying at a hotel nearby and attending an event at The 228 in Sterling, plan your transportation ahead of time. Most people assume they can just pull up an app, but out here, you might be waiting 30 minutes for a ride—if one shows up at all.
Also, keep an eye on the seasons. Sterling is a destination for "leaf peepers." In October, the price of hotels in Sterling MA and the surrounding areas can double. The Apple Fiesta in the fall brings in crowds that fill up every room from Leominster to Worcester.
Actionable Tips for Your Stay
Don't just book the first thing you see. Central Mass is spread out, and "5 miles" on a winding back road feels a lot longer than 5 miles on a highway.
- Check the Wedding Calendar: Before booking Chocksett, call and ask if there’s a massive wedding that weekend. If you want quiet, you might prefer a chain in Leominster.
- Distance to Davis' Farmland: If the kids are the priority, staying in Leominster (DoubleTree) or even the Great Wolf Lodge saves you the stress of a long morning drive.
- Food Prep: Sterling is quiet at night. Most kitchens close early. If you’re arriving after 9:00 PM, grab food in Worcester or Leominster before heading into town.
- Historical Tours: If you're a history buff, check if the Eastern Pennsylvania Preservation Society is running one of their limited tours of the old Sterling Inn. It's a rare chance to see a massive 103-acre resort frozen in time.
The reality of staying in Sterling is that you're choosing peace and quiet over convenience. It’s a town that has fought hard to keep its rural character, and that means fewer neon signs and more stars in the sky. Whether you land a room at the Chocksett or end up at a Marriott ten miles away, you're still in one of the prettiest corners of the Commonwealth.