A cloudy sky over a town with power lines and a few buildings in the background.
Photo by Linda Nisbett
Open Photo by Linda Nisbett

Skippers Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Skippers Vacation

With one of our vacation packages to Skippers, you'll have infinite opportunities for fun and adventure. There's lots to experience, including its rural countryside and spectacular views. If your trip to Skippers includes a little sightseeing, visit major attractions such as Meherrin River Park, Village View Mansion House and Good Earth Peanut Company. Stop dreaming and start adventuring. Check out the range of options on Expedia today and put your Skippers vacation plans into motion!

Top Skippers vacation deals

Price found within the past 48 hours. Click for updated prices.
  • A row of two-story houses with brick and white siding, featuring front porches and chimneys.
    Dec 21 - Dec 26

    Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort + Flight

    Williamsburg
    5 nights
    3.5 star property
    9.4/10 - Exceptional (424 reviews)
    Roundtrip • Halifax (YHZ) - Richmond (RIC)
    YHZ - RIC • 1 stop RIC - YHZ • 2 stops
    CA $1,268
    CA $1,159
    per traveller
    found 1 day ago
    Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort
  • A spacious living room with a large window, a modern chandelier, and a variety of framed artwork on the walls.
    Dec 21 - Dec 26

    The Commonwealth + Flight

    Downtown Richmond
    5 nights
    4.0 star property
    8.8/10 - Excellent (1,417 reviews)
    "Good food wasn’t open"
    Reviewed November 10, 2026
    Roundtrip • Halifax (YHZ) - Richmond (RIC)
    YHZ - RIC • 1 stop RIC - YHZ • 2 stops
    CA $2,179
    CA $1,642
    per traveller
    found 0 hours ago
    The Commonwealth
  • A swimming pool with lounge chairs and umbrellas, surrounded by buildings with a clear sky.
    Dec 30 - Jan 4

    Kingsmill Resort + Flight

    Kingsmill
    5 nights
    4.0 star property
    8.6/10 - Excellent (1,000 reviews)
    "Beautifully appointed resort. Plenty of things for everyone to enjoy while relaxing on property. Close to main attractions and restaurants."
    Reviewed November 10, 2026
    Roundtrip • Toronto (YYZ) - Richmond (RIC)
    YYZ - RIC • 1 stop RIC - YYZ • 1 stop
    CA $1,464
    CA $1,186
    per traveller
    found 11 hours ago
    Kingsmill Resort
  • A hallway with a grand chandelier, a wooden console table with a clock, and a mirrored wall reflecting an elevator.
    Dec 21 - Dec 26

    The Berkeley Richmond, Outset Collection by Hilton + Flight

    Downtown Richmond
    5 nights
    4.0 star property
    8.8/10 - Excellent (1,313 reviews)
    "Only problem is getting your car back without waiting long"
    Reviewed November 9, 2026
    Roundtrip • Halifax (YHZ) - Richmond (RIC)
    YHZ - RIC • 1 stop RIC - YHZ • 2 stops
    CA $1,770
    CA $1,579
    per traveller
    found 0 hours ago
    The Berkeley Richmond, Outset Collection by Hilton
  • A hallway with a wooden ceiling, white walls, and a glass door leading to a staircase.
    Dec 21 - Dec 26

    Kings Creek Plantation by TripForth + Flight

    Williamsburg
    5 nights
    3.5 star property
    8.6/10 - Excellent (44 reviews)
    "Beautiful property!!"
    Reviewed August 2, 2026
    Roundtrip • Halifax (YHZ) - Richmond (RIC)
    YHZ - RIC • 1 stop RIC - YHZ • 2 stops
    CA $2,039
    CA $1,825
    per traveller
    found 1 day ago
    Kings Creek Plantation by TripForth

Discover the most popular places to visit in Skippers

Good Earth Peanut Company

7.0/10 (26 reviews)
You can enjoy some culture when you stop by Good Earth Peanut Company in Skippers. While in this family-friendly area, you can savor the top-notch restaurants.
See properties

Skippers Hotel Deals

A hotel entrance with a covered walkway, columns, and a large glass door.

Holiday Inn Express Hotel & Suites Emporia by IHG

Holiday Inn Express Hotel & Suites Emporia by IHG
2.5 star property
10.4 km from Skippers
8.8 out of 10, Excellent, (1,000 reviews)
"Staff and breakfast were great"
The price is CA $143
CA $167 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express Hotel & Suites Emporia by IHG
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 Skippers

Frequently Asked Questions

How much does a Skippers vacation package cost?

You'll find cheap prices from CA $1,159 on Expedia for your Skippers break. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Skippers costs.

What are the cheapest months to go to Skippers?

You can generally find lower rates and better availability in January, February and November. Browse our cheap Skippers vacation packages and you could get some excellent off-season deals.

How many days is enough for Skippers?

Generally, a handful of days is enough to visit the major sights during your Skippers vacation. But if you want to have more time to chill out or take day trips, think about extending your itinerary.

How to find the best Skippers package deals?

Use Expedia's handy filters to find some great Skippers package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Skippers package deals in the low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.

Is it cheaper to book a Skippers vacation as a package?

Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component individually. And you'll still enjoy the flexibility to create a personalized Skippers vacation by choosing your favourite accommodation type, airline and car class.

When to book a vacation package to Skippers?

Secure fantastic discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Skippers break.

How to plan a trip to Skippers?

  1. Pick your travel dates: What you'd like to do in Skippers and your preferred season can help you decide when to travel.
  2. Plan your budget wisely: Besides the price of your stay, you'll need to factor in other expenses too. These include flights, transportation and food. Also, put aside some extra funds for unexpected expenses that may arise during your trip to Skippers.
  3. Decide how many days away: Start by making a list of all the sights and activities you'd like to get to in Skippers. Then, estimate how long you'll need for each, along with any travel time.
  4. Combine your airfare and accommodations: Once you've nailed down your trip dates and duration, book the right Skippers vacation package for you.

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