Roseland Vacations from $452

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Your Roseland Vacation

Say bye-bye to the worries of planning and hello to a Roseland vacation package. With everything organized before you leave, you can focus on discovering this city, starting with Laurel Ridge, which is good for skiing, adventure sports and mountain biking. Every trip to Roseland needs a well-planned itinerary. Fill yours with leading attractions like Lovingston Winery, Blue Mountain Barrel House and Virginia Blue Ridge Railway Trail. No matter your travel plans or the size of your budget, putting together a tailored Roseland vacation is a breeze with Expedia.

The Latest Roseland vacation packages

Price found within the past 48 hours. Click for updated prices.
The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Starr Hill
Price was $625, price is now $452 per person
$452
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Charlottesville (CHO)
8.6/10 Excellent! (926 reviews)
The property was a very cute boutique style hotel. Loved the lobby and the artwork and style aesthetic. Nice rooftop fire pit setup. Beds were very comfortable. Very quiet stay.

Reviewed on Oct 17, 2025

Graduate by Hilton Charlottesville

Graduate by Hilton Charlottesville

4 out of 5
Venable
Price was $638, price is now $454 per person
$454
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Charlottesville (CHO)
8.2/10 Very Good! (1,002 reviews)
Close to the college. Room was barely clean.

Reviewed on Oct 20, 2025

Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Venable
Price was $640, price is now $461 per person
$461
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Charlottesville (CHO)
9.6/10 Exceptional! (313 reviews)
Hospitality was awesome. Very relaxing. Great choice

Reviewed on Oct 13, 2025

Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was $676, price is now $492 per person
$492
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Charlottesville (CHO)
9.2/10 Wonderful! (496 reviews)
Very nice stay and staff

Reviewed on Oct 24, 2025

Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Venable
Price was $631, price is now $465 per person
$465
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Charlottesville (CHO)
9.2/10 Wonderful! (269 reviews)
The place looked really cute, but nothing in the room seemed to actually work! The TV wouldn’t connect to the hotel’s WIFI, and there was no one at the front desk to ask for help. The shower also wasn’t draining properly, so we had to stand in a pool of water while we showered. The record player also didn’t work properly. Any time we needed front staff beyond checking in, no one was there despite being told there would be. Oh yeah, and we woke up in the middle of the night to the loudest train noises!! It literally sounded like we were on top of the train. The place was very cute it just wasn’t very functional and there was no one to go to for help.

Reviewed on Oct 21, 2025

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Discover the most popular places to visit in Roseland

Reids Gap Trailhead

You can take time to visit Reids Gap Trailhead during your travels to Roseland. Discover the mountain views in this relaxing area.

Reids Gap Trailhead

Woodson's Mill

You can spend an afternoon studying the exhibits at Woodson's Mill during your trip to Lowesville. Take in the museums while you're in the area.

Woodson's Mill

What to do in Roseland

Blue Ridge Parkway Bundle

Blue Ridge Parkway Self-Guided Audio Tour Bundle

$24
per traveler
Blue Ridge Parkway Self-Guided Audio Tour Bundle
See all activities in Roseland

Roseland Hotel Deals

Piedmont Grove

Piedmont Grove

2 out of 5
236 Beech Grove Road, Roseland, VA
$242 nightly
The price is $271 total per night from Nov 2 to Nov 3
$271 total
Nov 2 - Nov 3
Total with taxes and fees
9.2/10 Wonderful! (30 reviews)
Enjoyed our stay

Reviewed on Sep 1, 2025

Piedmont Grove
Luxury Wintergreen 5BR • Hot Tub • Sleeps 16+ • Dog Friendly

Luxury Wintergreen 5BR • Hot Tub • Sleeps 16+ • Dog Friendly

Wintergreen Resort
10/10 Exceptional! (14 reviews)
Good Stay
Nice place with great amenities.

Reviewed on Jul 4, 2025

Get rates
Luxury Wintergreen 5BR • Hot Tub • Sleeps 16+ • Dog Friendly
Sleep Inn Staunton

Sleep Inn Staunton

2.5 out of 5
222 Jefferson Hwy, Staunton, VA
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $97 total per night from Nov 16 to Nov 17
$97 total
Nov 16 - Nov 17
Total with taxes and fees
9.2/10 Wonderful! (1,323 reviews)
good breakfast..nice shower. nice bed

Reviewed on Oct 20, 2025

Sleep Inn Staunton
See all 1,445 properties in Roseland
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 Roseland Vacation Packages

Roseland Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
45ºF
Max Temp Summer
85ºF
Top Sights
Bold Rock Hard Cider Nellysford Cidery, Crabtree Falls and Blue Mountain Barrel House

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Frequently asked questions

How much does a Roseland vacation package cost?
You can grab a vacation package to this destination from $452 on Expedia. But how much your vacation to Roseland costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Roseland?
You can typically find reduced prices and greater availability in July, September and December. Explore our cheap Roseland vacation packages and you could score some great off-season deals.
How many days is enough for Roseland?
Generally, a handful of days is enough to tick off the major attractions during your Roseland vacation. But if you'd like to have time to rest or go on day trips, think about extending your trip.
How to find the best Roseland package deals?
Use Expedia's handy filters to help you find some terrific Roseland 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 escape for midweek, or search for Roseland package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Roseland vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still get the freedom to create a tailored Roseland vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Roseland?
Score incredible discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment Roseland escape.
How to plan a trip to Roseland?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Roseland.
  2. Work out your budget: Make sure you have enough money to pay for everything from dining out and transportation to airfares and activities. Your hotel will probably be the largest expense during your trip to Roseland.
  3. Use Expedia's trip planning tool to explore Roseland: Research every aspect of your trip to Roseland with this handy planner. Invite family or friends to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Work out your trip length: Consider how much time you'd like to spend exploring Roseland. Plan your itinerary so you can get to all the activities and attractions you're interested in at a comfortable pace.
  5. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a personalized Roseland vacation package.
  6. Add on experiences and excursions: Have a look at our travel guide to find some exciting things to do in Roseland. Book tickets or make reservations before you go to save time and skip the hassle of searching for activities when you arrive.

Does Expedia offer Book Now, Pay Later Roseland vacation packages?
If you're anything like us, you love exploring new places but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Roseland trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.

Explore a world of travel with Expedia

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