Holiday rentals in Lakeside

Stylish 2BR w/Huge Deck Walk to Botanical Gardens

Step into this immaculate, Northside cottage with designer touches, a tranquil Zen garden, and a spacious deck overlooking a fully fenced backyard. Newly renovated with bright interiors, it's perfect for relaxing after exploring Lewis Ginter Botanical Gardens (1 block away), Scott's Addition (8 min), or downtown (9 min). Walk to Hob Nob for brunch, Final Gravity Brewery, and Lakeside Farmers Market. Dog-friendly and thoughtfully decorated, consider this your home away from home in every sense!

Family · Location · Accuracy

Luxurious Spacious Retreat Close to Everything

This spacious 4-bedroom retreat is the perfect getaway for families or groups looking for comfort and convenience. Located in a quiet neighborhood close 295 and 95, this home offers everything you need for a relaxing stay. - Baby & Pet Friendly with packnplay, high chair, fully-fenced yard. - Stocked Kitchen. Nespresso, Keurig, and essentials for meal prep. -15min to Downtown Richmond or Kings Dominion. -Office with wireless printing and paper. - Dyson and Drybar Hair Dryers -Toiletries galore!

Location · Value · Amenities

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.

Value · Location · TV

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!

Location · Family · Back garden

A clean, safe, house full of steel balls and games

I'm a blue collar guy in a blue collar neighborhood in a blue collar house. House was built in 1959 and I have kept everything that works from that era. It's like going back in time. Oven, Dishwasher, some light switches, bath tub, and vanity are original. Plenty of vintage, workable pinball machines and vintage game consoles throughout the house. The place is yours to use. Also has a patio for outdoor grilling. Located near the lakeside community with local restaurants, shops, and breweries.

Family · Location · Hospitality

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.

Family · Location · TV

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.

Family · Value · Cleanliness

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!

Family · Value · Laundry

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.

Family · Location · Parks

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

Location · Family · Kitchen

Modern Glen Allen Home w/Game Room & Screened deck

Welcome to your modern family retreat in Glen Allen! This spacious 4BR, 2.5BA home offers room for everyone—with cozy living & dining areas, a 3rd-floor game room for movie or game nights, and a screened-in deck to relax after the day’s activities. Just minutes from the Henrico County Sports & Events Center, it’s perfect for families attending tournaments. Conveniently close to shopping (Short Pump Town Center), dining, and downtown Richmond!

Family · Value · Nearby

Waterfront Escape | Hot Tub, Canoe & SUP

Welcome to Rushes Reservoir—a waterfront retreat with treetop views hidden in the heart of Richmond. Perched above the reservoir, the home's main living spaces feel suspended in the canopy, with sweeping views of the woods and water. Relax in the hot tub, gather around the fire pit, paddle the reservoir by canoe or SUP, fish from the dock, or unwind on the expansive deck—all just minutes from Richmond's restaurants, breweries, and attractions.

Location · Family · Amenities