Chestnut Springs 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
Price found within the past 48 hours. Click for updated prices.
  • Bar (on property)
    Jul 1 - Jul 10

    Little Mod Hotel at the University + Flight

    Venable
    9 nights
    3.0 star property
    9.2/10 - Wonderful (338 reviews)
    "This wasn't my first stay and will not be my last. I love this quaint, clean and friendly hotel. The staff is friendly, professional and goes above and beyond to ensure your stay is comfortable and every need is met. The decor is adorable, the thoughtful little items in the rooms are greatly appreciated. The beds, pillows and linens are exceptional. Plus, having a cool little food truck on the premises is a great idea. Also, the location is wonderful for exploring Charlottesville."
    Reviewed May 23, 2026
    Roundtrip • Toronto (YYZ) - Charlottesville (CHO)
    YYZ - CHO • 1 stop CHO - YYZ • 1 stop
    CA $1,944
    CA $1,458
    per traveller
    found 1 day ago
    Little Mod Hotel at the University
  • 2 bars/lounges, lobby lounge
    Jul 1 - Jul 10

    The Doyle Hotel + Flight

    Starr Hill
    9 nights
    3.5 star property
    8.4/10 - Very good (1,006 reviews)
    "Valet not helpful. Parking cost extra and two blocks away. He did not offer assistance with suitcases and we had to walk back to hotel with our luggage while valet watched."
    Reviewed May 23, 2026
    Roundtrip • Toronto (YYZ) - Charlottesville (CHO)
    YYZ - CHO • 1 stop CHO - YYZ • 1 stop
    CA $2,462
    CA $1,830
    per traveller
    found 1 day ago
    The Doyle Hotel
  • Front of property
    Jul 1 - Jul 10

    Dinsmore Boutique Inn + Flight

    Venable
    9 nights
    4.0 star property
    9.6/10 - Exceptional (389 reviews)
    "Staff excellent!"
    Reviewed May 19, 2026
    Roundtrip • Toronto (YYZ) - Charlottesville (CHO)
    YYZ - CHO • 1 stop CHO - YYZ • 1 stop
    CA $2,490
    CA $1,864
    per traveller
    found 1 day ago
    Dinsmore Boutique Inn
  • Outdoor pool, sun loungers
    Jul 1 - Jul 10

    Oakhurst Inn at the University + Flight

    Jefferson Park Avenue
    9 nights
    4.0 star property
    9.2/10 - Wonderful (564 reviews)
    "Lovely"
    Reviewed May 15, 2026
    Roundtrip • Toronto (YYZ) - Charlottesville (CHO)
    YYZ - CHO • 1 stop CHO - YYZ • 1 stop
    CA $2,248
    CA $1,766
    per traveller
    found 1 day ago
    Oakhurst Inn at the University
  • Lobby sitting area
    Jul 1 - Jul 10

    Virginia Guesthouse Hotel + Flight

    Lewis Mountain
    9 nights
    2.0 star property
    9.2/10 - Wonderful (18 reviews)
    "clean room"
    Reviewed May 21, 2026
    Roundtrip • Toronto (YYZ) - Charlottesville (CHO)
    YYZ - CHO • 1 stop CHO - YYZ • 1 stop
    CA $2,029
    CA $1,632
    per traveller
    found 1 day ago
    Virginia Guesthouse Hotel

Chestnut Springs Hotel Deals

New Build! Log Cabin with Hot Tub in Wintergreen

New Build! Log Cabin with Hot Tub in Wintergreen

Wintergreen Resort VA
Get rates
New Build! Log Cabin with Hot Tub in Wintergreen
The Bear's Den at Wintergreen- 6 Bedroom

The Bear's Den at Wintergreen- 6 Bedroom

Roseland VA
10/10 Exceptional! (25 reviews)
"The host was great and the house had plenty of space for us to spread out in."

Reviewed on Feb 9, 2026

Get rates
The Bear's Den at Wintergreen- 6 Bedroom
Hotel 24 South

Hotel 24 South

3 out of 5
24 South Market Street Staunton VA
Fully refundableReserve now, pay when you stay
The price is CA $145 per night from May 28 to May 29
CA $145
CA $162 total
May 28 - May 29
includes taxes & fees
9.6/10 Exceptional! (1,135 reviews)
"Pretty, clean, nice staff, good breakfast ($15 which I think is totally reasonable in this day and age), comfy rooms."

Reviewed on May 23, 2026

Hotel 24 South
See all 1,291 properties in Chestnut Springs
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.
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Frequently asked questions

How much does a Chestnut Springs vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Chestnut Springs from just . And the more you bundle, the more money you save. The vacation of your dreams has never been more affordable.
How do I get a cheap travel package to Chestnut Springs?
Browse and lock in everything all in one place with our Chestnut Springs vacation packages. You'll discover deals on hotels, flights, tours and more that'll keep your travel budget happy and your adventurous side busy. And, with more than 550 airlines and 1,000,000 hotel options across the globe to choose from, you'll have the flexibility to mix and match your own way.
Where should I stay in Chestnut Springs?
There's so much to explore in Chestnut Springs, so spend your evenings near its top sights and treat yourself to more time sightseeing. Wintergreen Resort is one place to put on your to-do list.
What are the top hotels in Chestnut Springs?
If it's your first time in Chestnut Springs, make a reservation at Tranquil Cabin With Deck In The Wintergreen Resort or View From The Top. Both will make you feel at home and are favorites among many travelers.
How far in advance should I book my Chestnut Springs vacation?
Smart travelers will likely want to reserve their seats early. You can usually look up international fares on Expedia up to a year before your intended flight. If you're booking last minute, there's no need to worry. Discounted prices sometimes become available just weeks before departure dates.
What does an Expedia Chestnut Springs travel package include?
Expedia has all you need to lock in Chestnut Springs trip, but how your package is structured is entirely up to you. Choose from any combination of hotels, rental cars and flights. Searching for some tours or activities to keep you entertained? Once you've made your booking, you can add them too. Whatever your style, there's a package deal to meet your needs.
What should I know before booking a Chestnut Springs travel package?
A package can be cheaper than individually booking everything you need for your trip. For example, combine your flights, hotels and rental cars and score big savings. Whatever type of vacation you have in mind, there's bound to be a package that suits your budget.
Can I choose my airline with a Chestnut Springs Expedia vacation package?
Expedia has access to more than 550 airline partners globally, so you definitely can. Just select your preferred air carrier and put together your ideal Chestnut Springs vacation.
If I'm not able to travel, can I cancel my Chestnut Springs vacation package?
Because we understand life can throw you a few curveballs, the answer is yes. For further details, visit our Customer Service Portal. But generally speaking, if you've booked your Chestnut Springs vacation package in the last 24 hours, you may be able to change or cancel it for no charge. Your hotel, airline or car rental company may charge a fee if you made your booking a while ago.

Things to do

Blue Ridge Parkway Bundle

Blue Ridge Parkway Self-Guided Audio Tour Bundle

CA $33
per traveller
Blue Ridge Parkway Self-Guided Audio Tour Bundle
Shenandoah National Park Self-Guided Driving Audio Tour

Shenandoah National Park Self-Guided Driving Audio Tour

CA $23
per traveller
100% of travellers recommend
Shenandoah National Park Self-Guided Driving Audio Tour
See all activities in Roseland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.