Southside Romantic Vacations 2026

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4 Night Romantic vacations in Southside

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

Hyatt Place Richmond/Arboretum

North Chesterfield

$460

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip non-stop flight included

New Orleans (MSY) to Richmond (RIC)

8/10 Very Good! (1,005 reviews)

Excellent location, staff and accomodations. Quick easy check in, clean room and efficient in and out.

Reviewed on Aug 20, 2026

Four Points by Sheraton Richmond

North Chesterfield

$488

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip non-stop flight included

New Orleans (MSY) to Richmond (RIC)

8.8/10 Excellent! (1,007 reviews)

Would recommend this hotel for your next stay in N. Chesterfield Va.

Reviewed on Aug 20, 2026

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How can I find the best Southside vacation packages for couples?

To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing.

How can I find cheap Southside romantic packages for two?

For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering.

How can I plan a great romantic trip to Southside?

Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two.

How much is a trip for two to Southside?

Put a price on love with stunning deals for duos starting at just $460. Prices and availability are subject to change. Additional terms may apply.

Can I book Southside spa packages for couples?

Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match.

How can I book romantic weekend getaway packages in Southside?

To book a loved-up break in Southside, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation).

Can I book a romantic trip to Southside with free cancellation and/or flexible dates?

The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options.

Why should I book my Southside romantic holiday with Expedia?

If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?

Top Romantic Southside Hotels

Four Points by Sheraton Richmond

9901 Midlothian Tpke Richmond VA

5 min drive from Chesterfield Towne Center

A garden, premium mattresses, and onsite dining await couples visiting this romantic hotel. The property also offers Egyptian cotton sheets, a bar, and a lakeside ...

8.8/10 Excellent! (1,009 reviews)

"Would recommend this hotel for your next stay in N. Chesterfield Va."

Reviewed on Aug 20, 2026

Best Western Plus Governor's Inn

9826 Midlothian Tpke Richmond VA

6 min drive from Chesterfield Towne Center

A lobby fireplace, Colonial architecture, and more await visiting couples at this romantic hotel.

8.4/10 Very Good! (1,001 reviews)

"Staff was so nice. rooms were very clean. And the breakfast staff was outstanding with keeping food stocked and clean."

Reviewed on Aug 17, 2026

Hyatt Place Richmond/Arboretum

201 Arboretum Place Richmond VA

8 min drive from Chesterfield Towne Center

Premium mattresses and onsite dining await at this romantic hotel, which also offers luxury bedding and a bar.

8/10 Very Good! (1,008 reviews)

"Excellent location, staff and accomodations. Quick easy check in, clean room and efficient in and out."

Reviewed on Aug 20, 2026

See all 1,100 properties in Southside

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.