Oakham Vacations from $587

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Your Oakham Vacation

Planning your next epic escape is a breeze with a Oakham vacation package. The neighborhood of Webster Square, which is great for cycling, makes a good starting point to discover the delights of this city. If your trip to Oakham includes some sightseeing, visit major attractions such as Rutland State Park, Barre Common District and Barre Historical Society. Expedia will help you escape the everyday. Tailor your vacation to Oakham to suit your style of travel, whatever that may be.

The Latest Oakham Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A hotel room with a bed, a desk, a chair, a television, and a kitchenette.
    Feb 2 - Feb 7

    Candlewood Suites Windsor Locks Bradley Arpt by IHG + Flight

    Windsor Locks
    5 nights
    2.5 star property
    8.4/10 - Very good (1,248 reviews)
    Roundtrip • Dallas (DFW) - Hartford (BDL)
    DAL - BDL • 1 stop BDL - DFW • 1 stop
    $696
    $587
    per traveler
    found 2 hours ago
    Candlewood Suites Windsor Locks Bradley Arpt by IHG
  • An outdoor dining area with tables and chairs, surrounded by plants and trees.
    Feb 2 - Feb 7

    Delamar West Hartford + Flight

    West Hartford
    5 nights
    4.0 star property
    9.8/10 - Exceptional (1,000 reviews)
    "Very clean and the staff was very friendly"
    Reviewed November 10, 2026
    Roundtrip • Dallas (DFW) - Hartford (BDL)
    DAL - BDL • 1 stop BDL - DFW • 1 stop
    $1,644
    $1,200
    per traveler
    found 2 hours ago
    Delamar West Hartford
  • A buffet setup with various food items in metal containers, a sign indicating 'Cheese Omelet', and a patterned wall in the background.
    Feb 2 - Feb 7

    Holiday Inn Express Vernon - Manchester by IHG + Flight

    Vernon
    5 nights
    2.5 star property
    8.6/10 - Excellent (1,000 reviews)
    "Clean room , but there was some plumbing issues which were resolved within 20 minutes, so never became a problem Staff was great and gave us an extended checkout time to meet our needs. Breakfast was really good especially the 1 minute pancakes and egg omelette. No issues with parking , plenty of space. We’ve stayed there previously, very convenient to highway ."
    Reviewed November 12, 2026
    Roundtrip • Dallas (DFW) - Hartford (BDL)
    DAL - BDL • 1 stop BDL - DFW • 1 stop
    $798
    $641
    per traveler
    found 2 hours ago
    Holiday Inn Express Vernon - Manchester by IHG
  • A hotel room with two beds, each with a beige bedspread and white pillows. There are two bedside tables with lamps, and the walls are adorned with framed artwork.
    Feb 2 - Feb 7

    The Cromwell Inn + Flight

    Cromwell
    5 nights
    2.5 star property
    6.8/10 - (60 reviews)
    Roundtrip • Dallas (DFW) - Hartford (BDL)
    DAL - BDL • 1 stop BDL - DFW • 1 stop
    $719
    $613
    per traveler
    found 2 hours ago
    The Cromwell Inn
  • A bar area with a long counter, bar stools, and shelves stocked with bottles.
    Feb 2 - Feb 7

    Sheraton Hartford Hotel at Bradley Airport + Flight

    Windsor Locks
    5 nights
    3.5 star property
    9.2/10 - Wonderful (1,002 reviews)
    Roundtrip • Dallas (DFW) - Hartford (BDL)
    DAL - BDL • 1 stop BDL - DFW • 1 stop
    $1,140
    $976
    per traveler
    found 2 hours ago
    Sheraton Hartford Hotel at Bradley Airport

Oakham Hotel Deals

Room

La Quinta Inn by Wyndham Auburn Worcester

La Quinta Inn by Wyndham Auburn Worcester
3.0 star property
14.8 mi from Oakham
8.2 out of 10, Very good, (210 reviews)
"Breakfast was not good"
$82 nightly
The price is $92
Nov 29 - Nov 30
Total with taxes and fees
La Quinta Inn by Wyndham Auburn Worcester
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.
See all properties in Oakham

Frequently Asked Questions

How much does an Oakham vacation package cost?

You'll find cheap prices from $587 on Expedia for your Oakham getaway. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Oakham costs.

What are the cheapest months to go to Oakham?

November, December and January are great times to look for cheap Oakham vacation packages. Traveling in quieter periods means you can typically find reduced prices on flights and accommodations.

How many days is enough for Oakham?

With a well-organized travel plan, you can easily tick off the most popular Oakham sights in a few days. But if you'd like to discover hidden spots or take day trips, consider booking your Oakham vacation for longer.

How to find the best Oakham package deals?

Use Expedia's filters to find some fabulous Oakham package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Oakham package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.

Is it cheaper to book an Oakham vacation as a package?

You can enjoy significant savings on your next Oakham getaway by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to view the best hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.

When to book a vacation package to Oakham?

If you're planning an impromptu Oakham trip, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land amazing deals on your flights and hotels by booking ahead.

Does Expedia offer Book Now, Pay Later Oakham vacation packages?

Your Oakham getaway should be a relaxing escape from your daily routine, not a reason for money worries. So to give you a little more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.