Holiday rentals in Lakeside

The Maplewood Retreat | Luxurious European Living

Rejuvenate in a delightful king bed, soak up the sun on the giant living room sofa, or unwind by the fire on the patio out back. Satisfy your hunger with dinner at Hobnob, a regional favorite only a block away. Walk two more blocks to get a drink at Final Gravity or breakfast at the original location of Lakeside LoveShack. You'll leave inspired and refreshed from your stay in this spacious home nestled in the family-friendly Lakeside neighborhood with easy access to downtown, and attractions.

Bright, quirky bungalow

Take it easy at this unique and tranquil home within 3 miles of downtown Richmond, VCU and the Fan (also close to I 95/64 exits). Located in the historic Bellevue neighborhood with restaurants and shops within walking distance, this charming Arts and Crafts bungalow has an open feel with a large family room and dining room, a kitchen with a tin-plated ceiling, a butcher block island, and breakfast nook. There are 2 Bedrooms, an office and large front and back porch perfect for morning coffee!

Lakeside Vintage Retreat | Classic RVA Charm

Welcome to "Vintage Lakeside", a 1-of-a-kind stay that embraces its historic charm and vintage character. This 4BR, 1.5BA home is anything but cookie-cutter—if you love homes with personality, history, and a lived-in warmth, you’ll feel right at home. This is not your typical modern Airbnb/VRBO—this house has stories to tell. If sleek and brand-new is what you're after, this might not be your match. But if you appreciate character, nostalgia, and an authentic feel, you’ll love your stay here.

Northside Hideaway

Kick back and relax in this calm, stylish studio. Located in Bellevue and close to everything. Quiet residential neighborhood. Walk to restaurants, shops and Saturday farmer’s market. Easy highway access, 10 minutes to downtown or west end. The space is located on the back of our family’s property. In addition to the studio, you will have access to the backyard, patio and fire pit. The studio is filled with light, equipped with kitchen essentials, and comes with high speed Wi-Fi, Netflix/Hulu.

Peaceful, private, upscale apartment near U of R

1 mile from UofR & a 2 min. walk to Three Chopt & Patterson Publix/restaurants, you’ll find a home-away-from-home in this impeccable 700sf one-bedroom apt. The private tree-house-like space includes large comfy couch, queen bed, full kitchen (granite, stainless), washer-dryer, fast wifi, & 2 smart TVs. The apt is above a detached garage not used for cars, which ensures quiet/privacy + off-street parallel parking (in front of them in the alley). Access does require climbing exterior stairs.

Eclectic Designer Retreat Near UofR + Peloton Bike

Modern design, impeccable lighting, and high-end finishes with a cozy wood burning fireplace. PELOTON exercise bike here, bring your cycling shoes! This charming private home is nestled in the heart of Westhampton just one mile from the University of Richmond and Libbie and Grove AVE. Surrounded by some of Richmond’s best shopping and dining and designed specifically for Airbnb guests to have a comfortable stay. Westhampton is one of Richmond’s most sought after neighborhoods. Welcome home!

Glen Allen Mid-Century Modern Casita

Welcome to the Mid-Century Modern Casita located on the border of Henrico County and Richmond City; Situated in a safe and welcoming neighborhood with easy access to the best Richmond has to offer. Every detail has been carefully considered. This home is fully equip with a washer/dryer, cookware, fast internet, smart TVs, river towels and much more to make for an accommodating stay. Conveniently located to Virginia's top attractions, we are the perfect stopping ground for your next trip!

Near West End off Libbie Avenue

Charming house in a quiet neighborhood a few minutes from St. Mary's Hospital, Libbie and Grove shopping and restaurants, Willow Lawn shopping center, Country Club of Virginia, St. Catherine's and St. Christopher's Schools. Pet-friendly with a sunny and fully-fenced backyard and only a few blocks from Westwood Park. First floor bedroom and full bath and two more bedrooms and a second full bath upstairs. Lovely backyard terrace with fire pit and grill for leisurely afternoons or cocktails.

River City Haven: 10‑Person Richmond Home

This spacious and stylish house is a perfect place to experience Richmond. Conveniently located, less than 15 minutes away from Short Pump Mall and the heart of the city. The house can accommodate up to 10 people and is pet friendly. Have everything you could ever want in an Airbnb including a King Bed, High Speed Internet, Roku TVs, Washer & Dryer, Full Kitchen Set, Luxury Bedding and Mattresses, Central A/C and Heat, Private Backyard w/ Firepit & Grill, and a responsive & caring host.

Rally & Rest: Pickleball & Designer Home

Welcome to our modern-retro 1925 brick house 🏡 — where historic charm meets bold, designer style. Perfect for groups, families, or friends who want comfort, creativity, and FUN. 📍 Steps from Scott’s Addition breweries + restaurants 🍻 🎬 Outdoor movie projector theater under the stars 🌌 🏓 Regulation-size pickleball court for epic matches 🧘 Private yoga + fitness studio with mats, blocks, and free weights 🔥 Backyard fire pit + swings for cozy nights 🚗 Parking for up to 6–8 cars

Funky, Private Guesthouse Near Richmond Food Scene

Welcome to the Yellow Tiger’s Den, a private, tucked-away guesthouse filled with bold color, thoughtful design, and a little Richmond edge. Set above a spiral staircase for total privacy, this sunny studio blends mid-century modern style with curated yellow accents, a cozy private patio, and everything you need for a relaxed stay. Located in Richmond’s historic Battery Park neighborhood, you’re minutes from the city’s growing food scene, local attractions, and easy highway access.

RVA Retreat w/ Infrared Sauna and Work Space

Located in a quiet Northside Richmond neighborhood with free parking, you’ll be just 10–15 minutes from downtown, VCU, Scott’s Addition, Carytown, and major hospitals. Enjoy a private entrance, dedicated workspace, fast WiFi, a queen bedroom, full bath, cozy living room, kitchenette, shared laundry for extended stays, and a spacious infrared sauna. Our friendly dog, Molly, may greet you outside but never enters the guest suite. Your peaceful RVA retreat.