Wellesley Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in Wellesley
Price found within the past 48 hours. Click for updated prices.
Delta Hotels by Marriott Richmond Downtown
Downtown Richmond
CA $1,347
per person
Dec 17 - Dec 20
found 5 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Richmond (RIC)
9/10 Wonderful! (1,002 reviews)
The hotel was centrally located and very clean. All the staff I had interacted with were extremely friendly and helpful. We even got there around noon and they were able to check us in early. I would definitely stay here again the next time I’m in Richmond!
Reviewed on Sep 21, 2026
Eagle Inn by Hotel O Richmond Midlothian Turnpike
Midlothian
CA $1,068
per person
Dec 17 - Dec 20
found 5 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Richmond (RIC)
6/10 (24 reviews)
Booked room thru Expedia. Expedia charged my card $158. Get to hotel. They say room is booked but they only received $38. They said I have to pay the balance. I left. Still awaiting refund.
Reviewed on Jun 11, 2026
Where to stay in Wellesley
Find the best Wellesley areas and neighborhoods for the activities you enjoy most. Learn more about Wellesley
Downtown Richmond
3 out of top 10 points of interest in this area
Explore the central business district, home to Fortune 500 companies and architectural gems like the Virginia State Capitol. Discover vibrant nightlife in Shockoe Bottom and Shockoe Slip districts.
Short Pump
1 out of top 10 points of interest in this area
Boasting shopping centers like Short Pump Town Center and West Broad Village, this suburban area offers a variety of restaurants, a skating rink, and a bowling alley for entertainment.
Fan District
Boasting a long stretch of Victorian architecture, this residential area is home to VCU's Monroe Park Campus, tree-lined avenues, and numerous parks. Explore local cafes, restaurants, and the nearby Virginia Center for Architecture at Branch House.
North Chesterfield
While North Chesterfield might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Chesterfield Towne Center and River City Sportsplex.
Museum District
You'll enjoy the museums and monuments in Museum District. You might want to make time for a stop at Virginia Museum of Fine Arts or Virginia Museum of History & Culture.
Wellesley Hotel Deals
Graduate by Hilton Richmond
301 West Franklin Street Richmond VA
Fully refundableReserve now, pay when you stay
CA $205
CA $239 total
Oct 1 - Oct 2
includes taxes & fees
The Jefferson Hotel
101 West Franklin Street Richmond VA
Fully refundableReserve now, pay when you stay
CA $441
CA $512 total
Oct 4 - Oct 5
includes taxes & fees
9.8/10 Exceptional! (1,004 reviews)
"Beautiful Hotel. Great restaurant and food. Wonderful amenities and beautiful room. I even had a dressing area with table and full length mirror."
Reviewed on Sep 20, 2026
Holiday Inn Hotel and Suites Richmond West End by IHG
8008 W. Broad St Richmond VA
Fully refundable
CA $144
CA $168 total
Oct 19 - Oct 20
includes taxes & fees
8.8/10 Excellent! (658 reviews)
"One of the worst experiences I have ever had in a hotel. It started with the front desk woman that checked me out being rude and uninterested. She did not smile or great me. She answered with head nods and would not answer the most basic questions. When I asked if there was trolley carts or any bell ..."
Reviewed on Sep 20, 2026
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.
Frequently asked questions
How much does a Wellesley vacation package cost?
Discover the best of Wellesley from as little as CA $1,065. We offer a wonderful selection of rental cars, hotels and flights to suit your travel style. Land even more discounts when you add a couple of activities or tours to your vacation package.
How do I get a cheap travel package to Wellesley?
Secure flights that fit in with your schedule, add a hotel room to your booking and see how much you save with a Wellesley vacation package. It's as easy as that! From flights and hotels to tours and rental cars, Expedia makes traveling cheaply a cinch. And with over 550 airlines and 1,000,000 properties worldwide to choose from, you won't be short of choice.
Where should I stay in Wellesley?
Most people who travel to Wellesley put both Greater Richmond Convention Center and Richmond Raceway on their must-see lists. Why not consider a hotel within walking distance of these fantastic attractions?
How far in advance should I book my Wellesley vacation?
Browse Expedia to compare international airfares ASAP. You can generally purchase a ticket up to a year in advance. If you can't see your preferred carrier, or you have to book last minute, fear not. Cheap fares to Wellesley sometimes emerge within weeks of departure.
What does an Expedia Wellesley travel package include?
Expedia has all you need to plan your Wellesley escape, but what goes into your package is your call. Choose from any combination of rental cars, flights and hotels. Chasing some activities or tours to keep you on the go? Once you've made your booking, you can add them on too. No matter your style, there's a vacation package to meet your needs.
What should I know before booking a Wellesley travel package?
We already have low prices. However, you'll snap up even more bargains if you book your flights, hotels and car rentals together. With an Expedia package, you'll always get transparent pricing and a terrific range of choice.
Can I choose my airline with a Wellesley Expedia vacation package?
Yes, and with over 550 airlines to choose from worldwide, you have plenty of choice. Look through the available options and see which airline suits your needs and budget.
If I'm not able to travel, can I cancel my Wellesley vacation package?
It is possible to cancel your Wellesley booking if your travel plans have changed. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. You may be able to change or cancel free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.
Things to do
Downtown Richmond Must-See Landmarks with Self-Guided Audio Tour
CA $15
per traveller
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.