Cumberland Vacations from $442

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Your Cumberland Vacation

Take the hassle out of planning your next epic adventure with a Cumberland vacation package. Whether you're here for its art, food, architecture or other highlights, there's an inexhaustible array of experiences to be had. Eager to sightsee? Spend some time enjoying top attractions such as Bear Creek Lake State Park during your trip to Cumberland. Whoever you're escaping with and whatever you want to spend, your dream Cumberland vacation is only clicks away with Expedia.

The Latest Cumberland vacation packages

Price found within the past 48 hours. Click for updated prices.
Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Venable
Price was $540, price is now $442 per person
$442
per person
Feb 21 - Feb 23
found 12 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Charlottesville (CHO)
9.6/10 Exceptional! (320 reviews)
If you’re looking for a one-of-a-kind place to stay filled with history and charm, this is it. It’s right in the heart of everything UVA, yet it feels like stepping back in time—without giving up any modern comforts. Jake was incredible to work with—he was flexible with our schedule, made sure we always knew where to go, and communicated better than anyone I’ve worked with before. Thank you so much for your hospitality. We will definitely stay here again and recommend it to everyone.

Reviewed on Jan 12, 2026

Mayhurst Inn

Mayhurst Inn

3.5 out of 5
Price was $720, price is now $623 per person
$623
per person
Feb 25 - Feb 27
found 21 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Charlottesville (CHO)
9.2/10 Wonderful! (288 reviews)
A perfect spot with the delicious breakfast. Highly recommend staying here.

Reviewed on Sep 4, 2025

Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was $627, price is now $546 per person
$546
per person
Feb 14 - Feb 16
found 12 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Charlottesville (CHO)
9.2/10 Wonderful! (517 reviews)
Our room was clean and the staff was super friendly and courteous. We did hope that our room had a microwave and refrigerator. It makes sense to have that available in every room on the grounds. Guests I’m sure would appreciate it. Please consider doing this. Lastly, we could here noises above us from possibly furniture that wasn’t secure. Footsteps are understandable, but the rattle of something above room 5 was a bit annoying. This is probably an eat fix. Overall the property was safe, clean and convenient.

Reviewed on Jan 1, 2026

The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Starr Hill
Price was $616, price is now $547 per person
$547
per person
Feb 14 - Feb 16
found 12 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Charlottesville (CHO)
8.6/10 Excellent! (944 reviews)
This is a beautiful hotel. Would highly recommend.

Reviewed on Jan 11, 2026

Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Venable
Price was $590, price is now $535 per person
$535
per person
Feb 14 - Feb 16
found 12 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Charlottesville (CHO)
9.2/10 Wonderful! (281 reviews)
Room was adorable. Very unique and comfortable experience.

Reviewed on Jan 8, 2026

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Discover the most popular places to visit in Cumberland

Bear Creek Lake State Park

You can take time to visit Bear Creek Lake State Park during your travels to Cumberland. While you're in the area, wander around the natural setting.

Bear Creek Lake State Park

Cumberland Hotel Deals

Hotel Weyanoke

Hotel Weyanoke

3.5 out of 5
202 High Street Farmville VA
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $110 total per night from Jan 25 to Jan 26
$110 total
Jan 25 - Jan 26
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
Good food and service

Reviewed on Jan 3, 2026

Hotel Weyanoke
Holiday Inn Express & Suites Farmville by IHG

Holiday Inn Express & Suites Farmville by IHG

2.5 out of 5
404 Sunchase Blvd Farmville VA
Fully refundable
$89 nightly
The price is $100 total per night from Feb 1 to Feb 2
$100 total
Feb 1 - Feb 2
Total with taxes and fees
9/10 Wonderful! (623 reviews)
We had a lovely stay. The rooms were big and the beds were extremely comfortable. The staff was friendly and helpful. We would definitely stay there again.

Reviewed on Jan 11, 2026

Holiday Inn Express & Suites Farmville by IHG
Days Inn by Wyndham Farmville

Days Inn by Wyndham Farmville

2 out of 5
2015 South Main St. Farmville VA
Fully refundableReserve now, pay when you stay
$56 nightly
The price is $63 total per night from Jan 19 to Jan 20
$63 total
Jan 19 - Jan 20
Total with taxes and fees
7.4/10 Good! (324 reviews)
Staff great and friendly. Room clean. Beds comfortable. Disappointed that waffles are no longer part of complimentary breakfast.

Reviewed on Dec 29, 2025

Days Inn by Wyndham Farmville
See all 94 properties in Cumberland
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.

Find the Best Cumberland Vacation Packages

Cumberland Essential Information

Language
English
Currency
U.S dollars
Population
390
Max Temp Winter
45ºF
Max Temp Summer
90ºF

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Frequently asked questions

How much does a Cumberland vacation package cost?
You can pick up a vacation package to this top destination from $442 on Expedia. But how much your vacation to Cumberland costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Cumberland?
You can usually find reduced prices and greater availability in November, December and January. Browse our cheap Cumberland vacation packages and you could score some great off-season discounts.
How many days is enough for Cumberland?
With a well-organized itinerary, you can easily hit the top Cumberland attractions in a few days. But if you want to discover lesser-known spots or take day trips, think about booking your Cumberland vacation for longer.
How to find the best Cumberland package deals?
Start your search for a Cumberland package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Cumberland package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Cumberland adventure underway.
Is it cheaper to book a Cumberland vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and stays individually. Better still, you can customize your Cumberland trip to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Cumberland?
If you've got your Cumberland travel dates finalized, book as soon as you can to bag some awesome deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are ideal for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Cumberland vacation packages?
Your Cumberland getaway should be an escape from your busy life, not a source of money-related stress. So to allow you more flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any 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.