Twin Oaks Vacation Packages

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  • Better together

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

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Top Holiday Package Deals in Twin Oaks

Price found within the past 48 hours. Click for updated prices.
Shenandoah Wilderness Traveler

Shenandoah Wilderness Traveler

2 out of 5
Price was CA $618, price is now CA $553 per person
CA $553
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottesville (CHO)
8.8/10 Excellent! (87 reviews)
I loved everything about my stay here; comfortable and clean accommodations, beautiful grounds, an on-site stables with many lovely rescued horses, wonderful restaurant inside the lodge, and a very welcoming and helpful staff. I would definitely love to stay here again one day! Thank you, Shenandoah Wilderness Traveler, for making my stay so enjoyable!

Reviewed on May 4, 2026

Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Venable
Price was CA $853, price is now CA $657 per person
CA $657
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottesville (CHO)
9.2/10 Wonderful! (326 reviews)
Free street parking was very convenient.

Reviewed on May 9, 2026

Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was CA $929, price is now CA $751 per person
CA $751
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottesville (CHO)
9.2/10 Wonderful! (559 reviews)
Clean room. Comfortable beds.

Reviewed on May 8, 2026

Sonesta ES Suites Charlottesville University

Sonesta ES Suites Charlottesville University

3 out of 5
Barracks Road
Price was CA $727, price is now CA $669 per person
CA $669
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottesville (CHO)
8.8/10 Excellent! (762 reviews)
The room was amazing and comfortable! The breakfast was very good! The lady at the front desk was friendly, funny and helpful! The gentleman in the breakfast room was very friendly. We had a few good conversations with him. Always a smile and a friendly greeting. I would definitely stay there again.

Reviewed on May 7, 2026

Boardwalk Hotel on Lake Anna by Kasa

Boardwalk Hotel on Lake Anna by Kasa

4 out of 5
Price was CA $692, price is now CA $656 per person
CA $656
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlottesville (CHO)
9/10 Wonderful! (89 reviews)
Great place! New and very clean. I would stay here again.

Reviewed on Apr 6, 2026

Twin Oaks Hotel Deals

Round Hill Inn

Round Hill Inn

2.5 out of 5
750 Round Hill Dr. Orange VA
Fully refundableReserve now, pay when you stay
The price is CA $149 per night from May 12 to May 13
CA $149
CA $164 total
May 12 - May 13
includes taxes & fees
9.6/10 Exceptional! (724 reviews)
Good location and nice place. It’s a bit dated.

Reviewed on May 7, 2026

Round Hill Inn
Boardwalk Hotel on Lake Anna by Kasa

Boardwalk Hotel on Lake Anna by Kasa

4 out of 5
200 Boardwalk Way Louisa VA
The price is CA $183 per night from May 13 to May 14
CA $183
CA $206 total
May 13 - May 14
includes taxes & fees
9/10 Wonderful! (89 reviews)
Bed only had sheets on it when I arrived. Hotel wanted me the customer to go down the hall and fix my problems

Reviewed on Apr 10, 2026

Boardwalk Hotel on Lake Anna by Kasa
Best Western Plus Crossroads Inn & Suites

Best Western Plus Crossroads Inn & Suites

2.5 out of 5
135 Wood Ridge Ter Gordonsville VA
Fully refundableReserve now, pay when you stay
The price is CA $171 per night from Jun 1 to Jun 2
CA $171
CA $192 total
Jun 1 - Jun 2
includes taxes & fees
8.8/10 Excellent! (672 reviews)
A good place to sleep while traveling

Reviewed on Apr 30, 2026

Best Western Plus Crossroads Inn & Suites
See all 608 properties in Twin Oaks
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Family Vacations
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Frequently asked questions

How much does a Twin Oaks vacation package cost?
From as little as CA $553, you can create your own Twin Oaks package the way you want. Simply combine flights, hotels and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Twin Oaks?
Book everything in one place with our Twin Oaks vacation packages. You'll discover deals on hotels, flights and more that'll keep your hip pocket happy and adventurous side satisfied. And, with more than 550 airlines and 1,000,000 properties throughout the world to pick from, you'll have the flexibility to mix and match as you want.
Where should I stay in Twin Oaks?
Choose a place within a stone's throw of Montpelier. This terrific attraction is in the thick of the action and on the must-do lists of most travelers.
How far in advance should I book my Twin Oaks vacation?
Reserving your spot early with Expedia means one less thing to have to worry about. Many air carriers advertise tickets up to a year in advance. This is generally the cheapest time to book. If circumstances have left you booking late, discount tickets to Twin Oaks sometimes occur a few weeks before departure.
What does an Expedia Twin Oaks travel package include?
It's up to you! You can select from a range of Twin Oaks packages, such as a rental car, hotel and flight. You can also book a hotel with a flight, or a rental car with a flight. Once you've made your booking, you can add on the fun stuff like activities and tours. Whatever your Twin Oaks getaway looks like, you'll save!
Can I choose my airline with a Twin Oaks Expedia vacation package?
Yes, definitely. Expedia has more than 550 airline partners to pick from worldwide. With all that choice, finding the perfect carrier to whisk you away to Twin Oaks will be a snap.
If I'm not able to travel, can I cancel my Twin Oaks vacation package?
Plans can change in the blink of an eye, so yes. You may be able to amend or cancel your Twin Oaks vacation package for free if you've booked in the last 24 hours. For bookings older than that, you can still cancel or make changes, but your car rental company, hotel or airline may charge a fee. Need more information? Take a look at our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.

Things to do

Wine and Culinary Delight Private Tour

Wine and Culinary Delight Private Tour

CA $341
per adult
Wine and Culinary Delight Private Tour
See all activities in Orange
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.