Wellesley 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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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top Holiday Package Deals in Wellesley

Price found within the past 48 hours. Click for updated prices.
Comfort Inn Williamsburg Gateway

Comfort Inn Williamsburg Gateway

2.5 out of 5
Price was CA $1,202, price is now CA $1,051 per person
CA $1,051
per person
Dec 16 - Dec 23
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
9.2/10 Wonderful! (1,366 reviews)

The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was CA $2,179, price is now CA $1,641 per person
CA $1,641
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Richmond (RIC)
8.8/10 Excellent! (1,419 reviews)
Good food wasn’t open

Reviewed on Nov 10, 2026

Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

3 out of 5
Short Pump
Price was CA $1,825, price is now CA $1,484 per person
CA $1,484
per person
Dec 21 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Richmond (RIC)
8.4/10 Very good! (1,715 reviews)

Courtyard by Marriott Richmond Airport

Courtyard by Marriott Richmond Airport

3 out of 5
Price was CA $1,919, price is now CA $1,676 per person
CA $1,676
per person
Dec 21 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Richmond (RIC)
8.4/10 Very good! (1,000 reviews)

Linden Row Inn

Linden Row Inn

3 out of 5
Downtown Richmond
Price was CA $2,157, price is now CA $1,915 per person
CA $1,915
per person
Dec 21 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Richmond (RIC)
9.2/10 Wonderful! (1,467 reviews)
Air conditioning was terrible, no bottled water offered and there was no water during checkout for a shower.

Reviewed on Nov 12, 2026

Where to stay in Wellesley

Find the best Wellesley areas and neighborhoods for the activities you enjoy most. Learn more about Wellesley
A grand neoclassical building with a central portico, large steps leading up to the entrance, and a circular mosaic at the base.

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.

Find hotels in Downtown Richmond

Wellesley Hotel Deals

Comfort Suites At Virginia Center Commons

Comfort Suites At Virginia Center Commons

2.5 out of 5
10601 Telegraph Rd Glen Allen VA
Fully refundable
The price is CA $120 per night from Dec 3 to Dec 4
CA $120
CA $139 total
Dec 3 - Dec 4
includes taxes & fees
8.2/10 Very good! (1,690 reviews)
"Very rundown and dirty hotel. Don’t stay."

Reviewed on Nov 12, 2026

Comfort Suites At Virginia Center Commons
Holiday Inn & Suites Richmond West End

Holiday Inn & Suites Richmond West End

3 out of 5
8008 W. Broad St Richmond VA
Fully refundable
The price is CA $157 per night from Nov 16 to Nov 17
CA $157
CA $182 total
Nov 16 - Nov 17
includes taxes & fees
8.8/10 Excellent! (799 reviews)
"Pretty room"

Reviewed on Nov 13, 2026

Holiday Inn & Suites Richmond West End
The Jefferson Hotel

The Jefferson Hotel

5 out of 5
101 West Franklin Street Richmond VA
Fully refundableReserve now, pay when you stay
The price is CA $449 per night from Nov 15 to Nov 16
CA $449
CA $522 total
Nov 15 - Nov 16
includes taxes & fees
9.8/10 Exceptional! (1,011 reviews)
"Outstanding hotel and staff."

Reviewed on Nov 10, 2026

The Jefferson Hotel
See all 930 properties in Wellesley
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
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Wellesley vacation package cost?
Discover the best of Wellesley from as little as CA $1,051. 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

Historic Trolley Tour

Historic Trolley Tour

CA $64
per adult
100% of travellers recommend
Historic Trolley Tour
Down in the Shokoe Bottom, the most haunted neighborhood with 350+ years of history and hauntings!

The Haunted History of Richmond tour

CA $42
per adult
The Haunted History of Richmond tour
See all activities in Richmond
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.