Wellesley Vacations from $531

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Your Wellesley Vacation

Booking a tailor-made Wellesley vacation package is an excellent way to know the ins and outs of this neighborhood. From its must-see spots to its little-known gems, you won't be short of new adventures. Squeeze in some sightseeing on your trip to Wellesley. You can't miss popular nearby attractions such as Short Pump Town Center and Childrens Museum of Richmond. No matter what your dream Wellesley vacation may look like, you can make it a reality with Expedia.

The Latest Wellesley Vacation Packages

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

Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

$531

per person

Nov 22 - Nov 25

found 8 hours ago

Roundtrip non-stop flight included

New York (NYC) to Richmond (RIC)

9.4/10 Exceptional! (386 reviews)

We came here for a family trip on Labor Day weekend. The condo was beautifully maintained and spotless when we arrived. The pool was so much fun every evening. The condo is in an amazing location, especially if you plan on going to Busch Gardens. The staff was awesome from chec check-in to check out and we even had a brief visit with maintenance for something that was not arrogant whatsoever. 10 out of 10 would stay again.

Reviewed on Sep 9, 2026

Kingsmill Resort

Kingsmill

$800

per person

Nov 26 - Nov 30

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Richmond (RIC)

8.6/10 Excellent! (1,007 reviews)

The Berkeley Richmond, Outset Collection by Hilton

Downtown Richmond

$651

per person

Nov 20 - Nov 24

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Richmond (RIC)

8.8/10 Excellent! (1,354 reviews)

Great hotel and staff was amazing

Reviewed on Sep 14, 2026

Graduate by Hilton Richmond

Downtown Richmond

$609

per person

Nov 20 - Nov 24

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Richmond (RIC)

8.4/10 Very Good! (1,452 reviews)

A house full of steel balls and games

Dumbarton

$653

per person

Nov 25 - Nov 29

found 20 hours ago

Roundtrip flight included

New York (LGA) to Richmond (RIC)

9.6/10 Exceptional! (118 reviews)

The hospitality was amazing. And the free games was a nice addition.

Reviewed on Aug 21, 2026

Where to stay in Wellesley

Find the best Wellesley areas and neighborhoods for the activities you enjoy most. Learn more about Wellesley

A city skyline at dusk with illuminated buildings, a river, and a bridge.

Downtown Richmond

2 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.

A bridge over a river with multiple arches, surrounded by trees and a railway track.

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.

A cityscape with a sunset, featuring a mix of historic and modern buildings, a prominent dome structure, and a wide street layout.

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.

A cityscape with a prominent white building with columns, surrounded by lush green lawns and trees, under a partly cloudy sky.

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.

A white bust sculpture in a grassy area with a red-roofed building and a tower in the background.

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

$147 nightly

$171 total

Oct 1 - Oct 2

Total with taxes and fees

The Jefferson Hotel

101 West Franklin Street Richmond VA

$315 nightly

$366 total

Oct 4 - Oct 5

Total with taxes and fees

9.8/10 Exceptional! (1,006 reviews)

"The staff at this hotel is always outstanding. I stay here a few times a year and the friendliness and general warmth of everyone from the front desk staff to the valet is incomparable in the United States."

Reviewed on Sep 16, 2026

Holiday Inn Hotel and Suites Richmond West End by IHG

8008 W. Broad St Richmond VA

Fully refundable

$103 nightly

$120 total

Oct 15 - Oct 16

Total with taxes and fees

See all 946 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.