Plan your trip

Find 5 Star Hotels in Oakham, MA from $91

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices

    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

  • Check prices for these dates

    Check prices for these dates, December 15 – 16, 2026

    View in a map

    Top Oakham Hotel Reviews

    The Inn Crowd Bed and Breakfast

    A two-story house with a wrap-around porch, a gabled roof, and a front deck.

    Hampton Inn & Suites Worcester

    A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.

    Holiday Inn Express & Suites Sturbridge by IHG

    A hotel entrance with a covered walkway, columns, and a brick facade.

    Publick House Historic Inn and Country Motor Lodge

    A white colonial-style house with a symmetrical facade, a central entrance, and a well-maintained garden with colorful flowers.

    Holiday Inn Express Hotel & Suites Auburn by IHG

    A hotel with a parking lot, a covered entrance, and a brick facade.

    Comfort Inn & Suites Sturbridge - Brimfield

    A hotel with a covered patio, a stone fountain, and a brick pathway.

    Hampton Inn Auburn

    A hotel entrance with a covered walkway, a parking area, and a well-lit building facade.

    Beechwood Hotel

    A hotel with a patio area featuring outdoor seating and a garden with blue hydrangea flowers.

    The Maguire House Bed & Breakfast

    A covered porch with Adirondack chairs and a table with wine glasses, overlooking a lake and lush greenery.

    Wellsworth Hotel

    An outdoor patio area with seating, tables, and decorative lights.

    Courtyard by Marriott Worcester

    A modern lounge area with sofas, armchairs, a bar, and a fireplace.

    The Colonial Hotel

    A grand lobby with a staircase, a piano, comfortable seating, and large windows.

    Fairfield Inn & Suites by Marriott Worcester Auburn

    A Fairfield Inn & Suites by Marriott hotel with a covered entrance and landscaped surroundings.

    Chocksett Inn and Restaurant

    A room with a fireplace, a large mirror, and a window with a view of the outside.

    Howarth House B&B

    A well-lit garden area with a gazebo, a small house, and a large tree in the background.

    Trainmasters Inn

    A wooden interior with a dining table and chairs, a refrigerator, and shelves with glassware.

    Doubletree by Hilton Hotel Leominster

    A hotel lobby with a central circular skylight, a reception desk, and a seating area with sofas.

    Find out more about Oakham

    Oakham Five Star Hotel Information

    If you’re searching for the celebrity treatment, the 5 star hotels in Oakham are your dreams come true. From sprawling resorts to fancy hot spots, theseOakham 5 star hotels immerse each traveler in the most elite experience money can buy. Want to unwind with a VIP-worthy spa treatment? These hotels have the leisure you're looking for.

    Interested in sampling world-class cuisine? The on-site restaurants at the 5 stars hotels in Oakham, Massachusetts, let you do just that. You’ll even be able to book a room (or perhaps a penthouse?) at first-rate hotels near the region’s can’t-miss sights and most bustling shopping centers. Plus, many globe-trotters who visit Oakham five star hotels find incredible rates and deep discounts thanks to Expedia, so you can score a deal without sacrificing an ounce of quality.

    Everything you could possibly want (and a few things you didn’t know you needed): That’s what you’ll receive when you stay at Oakham 5 star hotels.

    Frequently Asked Questions

    How much does it cost to stay in a 5-star hotel in Oakham?

    How much you pay for a 5-star hotel in Oakham depends on factors like when you want to go and the length of your break. Our top tip for bagging the best deal? Use our pricing filters to check out all of the available options for your selected dates.

    What makes a hotel 5 stars in Oakham?

    Exemplary guest service is at the heart of every 5-star hotel in Oakham. From the second you arrive, staff cater to your every need, whether offering luggage assistance and storage or providing a turn-down service. In addition, hotels have to offer upscale conveniences to be eligible for a 5-star rating. These can include luxury toiletries, saunas or spas, pools, fine dining restaurants and knowledgeable concierge.

    Are there any 5-star all-inclusive resorts in Oakham?

    Find a luxurious getaway that includes your lodging, meals, bar and entertainment in Oakham with Expedia's filters. Search for properties rated 5 stars and click on the "All inclusive" filter. Have a look at what's included in the price. This way, you can take full advantage of the premium perks on offer as soon as you arrive.

    Are there any 5-star vacation rentals in Oakham?

    You won't find any 5-star vacation rentals in Oakham on our site, but there are some other highly rated properties worth looking into. Scan through our vacation rentals in Oakham to book the ideal place for your stay.

    Explore a world of travel with Expedia