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Wayside Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Wayside vacation rentals

A grand lobby with a large Christmas tree, marble columns, and a red carpeted floor.

1. A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations

A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
Richmond
9.6 out of 10, Exceptional, (121 reviews)
"Great alternative to a house or hotel"
United States
Ashley Jo P.
$186 nightly
The price is $213
Sep 9 - Sep 10
Total with taxes and fees
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
A marina with docked boats, a covered structure, and a forested hillside in the background.

2. A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Richmond
9.4 out of 10, Exceptional, (245 reviews)
"We had a great stay! Perfect get away for our anniversary. It had everything we needed and was super quiet with a great view. Thank you Captain Ron, for an amazing experience "
United States
Allison K.
$186 nightly
The price is $213
Sep 13 - Sep 14
Total with taxes and fees
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
A calm lake with a dock and a small building, surrounded by trees.

3. MV GiaMaria

MV GiaMaria
3.5 star property
Richmond
9.2 out of 10, Wonderful, (16 reviews)
"So much fun!! Excellent host! Very informative. Loved the privacy and being on the water. The bed was super comfortable and the fireplace (electric) kept us warm and cozy. It was such a unique thing to do and we will be back!"
United States
Jane
$243 nightly
The price is $277
Sep 9 - Sep 10
Total with taxes and fees
MV GiaMaria
A modern kitchen with a built-in refrigerator, a grey wall with an air conditioning unit, and a staircase leading to a landing.

4. Adorable 2-bedroom house with AC in charming Richmond VA

Adorable 2-bedroom house with AC in charming Richmond VA
Richmond
$168 nightly
The price is $191
Sep 9 - Sep 10
Total with taxes and fees
Adorable 2-bedroom house with AC in charming Richmond VA
A living room with a brown leather sofa, a wooden coffee table with decorative items, a kitchen in the background, and a framed cityscape picture on the wall.

5. The New Amsterdam Nook: European-inspired guest suite in Mechanicsville. Features 2 bedrooms, 1 spa-like bath, full kitchen, indoor fireplace, dedicated workspace. Enjoy a large yard with pool, hot tub, playground, and BBQ. Comfortably fits 4-6.

The New Amsterdam Nook: European-inspired guest suite in Mechanicsville. Features 2 bedrooms, 1 spa-like bath, full kitchen, indoor fireplace, dedicated workspace. Enjoy a large yard with pool, hot tub, playground, and BBQ. Comfortably fits 4-6.
Mechanicsville
10.0 out of 10, Exceptional, (2 reviews)
"Everything was as great. Great for my young sons and family"
United States
Ray v.
$199 nightly
The price is $213
Sep 9 - Sep 10
Total with taxes and fees
The New Amsterdam Nook: European-inspired guest suite in Mechanicsville. Features 2 bedrooms, 1 spa-like bath, full kitchen, indoor fireplace, dedicated workspace. Enjoy a large yard with pool, hot tub, playground, and BBQ. Comfortably fits 4-6.
A dock area with boats, a covered seating area, and a sign indicating no trespassing for boat owners and guests only.

6. Cookie B

Cookie B
3.0 star property
Richmond
9.6 out of 10, Exceptional, (8 reviews)
"Was fantastic. Watching the sunrise was so memorable, captain ron was so friendly and stayed in communication well. will visit again. "
United States
Reshelle
$260 nightly
The price is $297
Sep 19 - Sep 20
Total with taxes and fees
Cookie B
A modern living room with a sofa, coffee table, and a TV on a cabinet.

7. The Farmhouse Retreat

The Farmhouse Retreat
Mechanicsville
10.0 out of 10, Exceptional, (5 reviews)
"Had a great stay while fishing the james river. "
United States
Travis D.
$139 nightly
The price is $160
Sep 9 - Sep 10
Total with taxes and fees
The Farmhouse Retreat
A modern kitchen with white cabinets, a stainless steel oven, a microwave, and a marble dining table.

8. Luxury Stay! 10 min away from Fort Lee.

Luxury Stay! 10 min away from Fort Lee.
Prince George
8.6 out of 10, Excellent, (18 reviews)
"The home was very clean and very comfortable. Communication was excellent. We would definitely stay here again!"
United States
CHRIS
$371 nightly
The price is $417
Sep 14 - Sep 15
Total with taxes and fees
Luxury Stay! 10 min away from Fort Lee.
A bedroom with a bed, a TV, and built-in shelving with decorative items.

9. Magnolias, a chill out place.

Magnolias, a chill out place.
Richmond
9.2 out of 10, Wonderful, (24 reviews)
"Would stay again!"
United States
Amir D.
$105 nightly
The price is $120
Sep 13 - Sep 14
Total with taxes and fees
Magnolias, a chill out place.
A living room with a sofa, coffee table, TV, and a door with a 'No Smoking' sign.

10. The Birdhouse - Cozy Cottage Retreat in Richmond

The Birdhouse - Cozy Cottage Retreat in Richmond
Swansboro West
10.0 out of 10, Exceptional, (6 reviews)
"The most beautifully finished cottage! Host very responsive!! Loved it."
United States
Stephanie S.
$203 nightly
The price is $206
Sep 9 - Sep 10
Total with taxes and fees
The Birdhouse - Cozy Cottage Retreat in Richmond
A hotel room with a bed, a wooden dresser, a television, a desk, and a chair.

11. 2 Queen Beds | Non-Smoking, Micfridge

2 Queen Beds | Non-Smoking, Micfridge
Petersburg VA
$72 nightly
The price is $79
Sep 9 - Sep 10
Total with taxes and fees
2 Queen Beds | Non-Smoking, Micfridge
A modern kitchen with a central island, stainless steel appliances, and bar stools.

12. The Studio@ Eanes Drug-Heart of the Historic District

The Studio@ Eanes Drug-Heart of the Historic District
Church Hill
10.0 out of 10, Exceptional, (95 reviews)
"Very clean, cozy and in an excellent location."
United States
Courtney W.
$169 nightly
The price is $193
Sep 9 - Sep 10
Total with taxes and fees
The Studio@ Eanes Drug-Heart of the Historic District
A modern kitchen with white cabinetry, a stainless steel refrigerator, a built-in oven, and a microwave.

13. Historic Haven in Church Hill in The Heart of the Historic District

Historic Haven in Church Hill in The Heart of the Historic District
Church Hill
10.0 out of 10, Exceptional, (79 reviews)
"Nice stay"
United States
Danelle B.
$164 nightly
The price is $187
Sep 20 - Sep 21
Total with taxes and fees
Historic Haven in Church Hill in The Heart of the Historic District
A patio with a wooden deck, a gray outdoor sofa with a yellow pillow, a wooden chair, a small round table, and a spiral staircase leading to a balcony.

14. Colorful private guesthouse in charming Richmond with Parking

Colorful private guesthouse in charming Richmond with Parking
Northern Barton Heights
10.0 out of 10, Exceptional, (6 reviews)
"I like this location. It is close to where I was hanging out in Richmond. The check-in was super easy, and the decorations are fun!"
United States
Jim H.
$190 nightly
The price is $217
Sep 9 - Sep 10
Total with taxes and fees
Colorful private guesthouse in charming Richmond with Parking
A corner building with large windows and a black awning.

15. Heart of RVA Arts District Walk to VCU, MCV, The National, Quirk Prime Downtown

Heart of RVA Arts District Walk to VCU, MCV, The National, Quirk Prime Downtown
Downtown Richmond
9.6 out of 10, Exceptional, (26 reviews)
"The place was clean and tidy, check-in was well organized and friendly, location super convenient."
United States
Maya S.
Heart of RVA Arts District Walk to VCU, MCV, The National, Quirk Prime Downtown
A modern kitchen with white cabinets, a central island with stools, stainless steel appliances, and a wooden countertop.

16. The Vibe: 3BR- Wedding-Ready Retreat with King Comfort & Fire Pit on 10 acres

The Vibe: 3BR- Wedding-Ready Retreat with King Comfort & Fire Pit on 10 acres
Charles City County
10.0 out of 10, Exceptional, (5 reviews)
"The property was amazing! Will definitely stay there again!"
United States
Jorge V.
$547 nightly
The price is $590
Oct 1 - Oct 2
Total with taxes and fees
The Vibe: 3BR- Wedding-Ready Retreat with King Comfort & Fire Pit on 10 acres
A modern kitchen with stainless steel appliances, white cabinetry, and a granite countertop.

17. NEW Williamsburg, Long Range Lake Views, Hot Tub, Sauna, Fire Pit, Game Room

NEW Williamsburg, Long Range Lake Views, Hot Tub, Sauna, Fire Pit, Game Room
Lanexa
$560 nightly
The price is $605
Sep 14 - Sep 15
Total with taxes and fees
NEW Williamsburg, Long Range Lake Views, Hot Tub, Sauna, Fire Pit, Game Room
A wooden gazebo with a bench and string lights, surrounded by trees.

18. Private Garden Home w/ Large Fenced Yard + Gazebo

Private Garden Home w/ Large Fenced Yard + Gazebo
Broad Rock
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay here for two nights! The beds were extremely comfortable and it was quiet and peaceful sleeping there both nights. We enjoyed the backyard very much - both our pets and kids. My son thought the gazebo with twinkle lights out back was so magical. :) We appreciate the cleanliness of the place and would only have appreciated a little space with maybe kids’ books, puzzles, or blocks or something. My young kiddos go crazy for those things when we stay at vacation rentals and it...
United States
Stacie C.
$295 nightly
The price is $337
Sep 13 - Sep 14
Total with taxes and fees
Private Garden Home w/ Large Fenced Yard + Gazebo
A modern living room with a sofa, chairs, a dining table, and a fireplace.

19. The "Rhythm" Suite - Downtown Richmond - Pet Friendly - Parking Included

The "Rhythm" Suite - Downtown Richmond - Pet Friendly - Parking Included
Downtown Richmond
10.0 out of 10, Exceptional, (9 reviews)
"Great location for shows at The National and Ember Music Hall."
United States
Ryan D.
$292 nightly
The price is $334
Sep 9 - Sep 10
Total with taxes and fees
The "Rhythm" Suite - Downtown Richmond - Pet Friendly - Parking Included
A high-ceilinged interior with skylights and built-in shelving.

20. Heart of the Arts - New King Suite on West Broad Condo’s next to Quirk MCV VCU

Heart of the Arts - New King Suite on West Broad Condo’s next to Quirk MCV VCU
Downtown Richmond
9.6 out of 10, Exceptional, (54 reviews)
"Great stay."
United States
Brian D.
$153 nightly
The price is $175
Sep 9 - Sep 10
Total with taxes and fees
Heart of the Arts - New King Suite on West Broad Condo’s next to Quirk MCV VCU
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.
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Top Wayside Hotel Reviews

The Berkeley Richmond, Outset Collection by Hilton

The Berkeley Richmond, Outset Collection by Hilton

10/10 Excellent
"This hotel was wonderful!! The staff was so helpful with all the questions I had, and so friendly! They saved us money on parking, directions for the venue we were headed to during our stay, and places to eat. We would love to spend more time in Richmond and would definitely stay at this hotel again. Cannot say enough!!!! Very positive!! Thank you!!"
jennifer 1-night trip
Posted 2 hours ago
The Berkeley Richmond, Outset Collection by Hilton

Find out more about Wayside

Everything you need to know about Wayside vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wayside vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wayside vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Wayside vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wayside. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Wayside in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $175 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Wayside rentals

At Expedia, we put the best Wayside vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Wayside rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wayside vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wayside. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Wayside?

Yes, we give you a choice of vacation rentals near top local attractions in Wayside, or you can select a more secluded option if you're looking for relaxation.

What are some of the best vacation rentals in Wayside?

Fantastic 5-bedroom Luxury home in charming Richmond: Visitors like this Wayside vacation home rental. It has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Wayside?

While exploring the area, visit family-friendly sights like The Lazy Daisy, or get outside and enjoy nature at Dorey Park. Beacon Theatre and The Barns of Kanak are a couple of places you'll find in the larger area.

What are vacation rentals like in Wayside?

Vacation rentals are private accommodations you can stay in for several days or longer in Wayside. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for family gatherings.