Wellesley Vacation Packages

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Top Holiday Package Deals in Wellesley

Price found within the past 48 hours. Click for updated prices.
A house full of steel balls and games

A house full of steel balls and games

2.5 out of 5
Dumbarton
Price was CA $1,031, price is now CA $832 per person
CA $832
per person
Apr 16 - Apr 21
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9.6/10 Exceptional! (99 reviews)
We had a great experience staying at Pinball Pete’s place. Very clean, cozy, comfortable, with use of the kitchen and some food provided … and, of course, pinball! Our host also went above and beyond in helping us to resolve an unexpected issue. Hoping to stay there again in the future.

Reviewed on Dec 22, 2025

Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Price was CA $1,138, price is now CA $941 per person
CA $941
per person
Apr 26 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (765 reviews)
Great hotel, bathroom was was out dated

Reviewed on Feb 2, 2026

Hilton Richmond Downtown

Hilton Richmond Downtown

4 out of 5
Downtown Richmond
Price was CA $1,694, price is now CA $1,413 per person
CA $1,413
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.4/10 Very Good! (1,004 reviews)
The room was great the staff was very welcoming.

Reviewed on Feb 20, 2026

Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
Downtown Richmond
Price was CA $1,563, price is now CA $1,322 per person
CA $1,322
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.4/10 Very Good! (1,395 reviews)
Love this super cute hotel. The theme was very cool and intentional and the staff members were friendly and helpful. We will definitely stay again in the future.

Reviewed on Feb 28, 2026

The Berkeley Hotel

The Berkeley Hotel

4 out of 5
Downtown Richmond
Price was CA $1,302, price is now CA $1,105 per person
CA $1,105
per person
Apr 2 - Apr 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,540 reviews)
Most definitely the updated room was the best! Extremely well done!

Reviewed on Feb 27, 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, Virginia skyline and the James River at twilight.; Shutterstock ID 478364257

Downtown Richmond

3 out of top 10 points of interest in this area
4/5(17 area reviews)

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

Omni Richmond Hotel

Omni Richmond Hotel

4 out of 5
100 S 12th St Richmond VA
Fully refundableReserve now, pay when you stay
The price is CA $219 per night from Mar 15 to Mar 16
CA $219
CA $255 total
Mar 15 - Mar 16
includes taxes & fees
9/10 Wonderful! (1,334 reviews)
Everything was great. Room was clean and breakfast was nice

Reviewed on Mar 1, 2026

Omni Richmond Hotel
Drury Plaza Hotel Richmond

Drury Plaza Hotel Richmond

3 out of 5
11049 West Broad St Glen Allen VA
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Mar 5 to Mar 6
CA $150
CA $174 total
Mar 5 - Mar 6
includes taxes & fees
9.6/10 Exceptional! (2,891 reviews)
From a free dinner with drinks (!) to a spacious hot tub, yummy breakfast, kind and helpful staff, Drury’s was an amazing surprise! Will definitely recommend it in the future.

Reviewed on Mar 1, 2026

Drury Plaza Hotel Richmond
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 $402 per night from Mar 8 to Mar 9
CA $402
CA $468 total
Mar 8 - Mar 9
includes taxes & fees
9.8/10 Exceptional! (1,000 reviews)
Perfect room and great friendly staff.

Reviewed on Feb 20, 2026

The Jefferson Hotel
See all 882 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
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Frequently asked questions

How much does a Wellesley vacation package cost?
Discover the best of Wellesley from as little as CA $832. 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.

Discover the most popular places to visit in Wellesley

Maymont Park showing a house and heritage architecture

Maymont Park

This grand estate is a family favorite with a petting zoo, native wildlife and a preserved 19th-century mansion.

Maymont Park
Virginia Museum of Fine Arts which includes art and a city

Virginia Museum of Fine Arts

This museum houses Russian jewels, impressionist masters and ancient relics in its vast and varied collection.

Virginia Museum of Fine Arts
Lewis Ginter Botanical Garden featuring a park

Lewis Ginter Botanical Garden

Spend some time admiring the beautiful and diverse floral displays featured in this superb botanical garden, one of the finest in the country.

Lewis Ginter Botanical Garden

Things to do

Historic Trolley Tour

Historic Trolley Tour

CA $58
per adult
100% of travellers recommend
Historic Trolley Tour
Richmond: Guided Hike in James River Park

Richmond: Guided Hike in James River Park

CA $48
per adult
100% of travellers recommend
Richmond: Guided Hike in James River Park
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.