Family-friendly holiday rentals in East Highland Park

The Farm House Retreat

Looking for a peaceful escape with easy access to the city? Welcome to the Farm House Retreat! Nestled in the country, yet only 20 minutes from downtown Richmond, 15 minutes from the airport, and just 8 minutes from local shops. Enjoy a cozy Queen-sized bed, sleeper sofa, fireplace, coffee bar, fridge, central air/heat, lightning-fast Wi-Fi, and streaming TV, all run on 100% renewable energy. Ideal for business travel, weekend getaways, or family and friends. Your perfect country retreat awaits!

Indoor spaces · Family · TV

Cozy Carver Accommodations

You've found a rare unicorn! This ultra-cozy row home is perfectly placed just blocks from VCU, and a short walk to the Fan, Jackson Ward & downtown. It's also less than 2 miles from "Richmond's Playground": Scott's Addition. This 540 sq. ft. home is filled with midcentury accents, local art, granite countertops, stainless steal appliances & pine floors. It has everything you need to cook and do laundry. You can also park for free with our street parking pass. We welcome your well-trained pets!

Family · Kitchen · Hiking

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!

Family · Kitchen · Location

Spacious, pet-friendly nature retreat | The Bohive

Escape to The Bohive off I-95, a charming 1200 sq ft studio, conveniently located just off the interstate & minutes from downtown. On a private “nature reserve”, this is the perfect place to unwind & recharge. Inside, you'll find a comfortable king bed & kitchenette (no stove). The cozy living area has a smart TV, great for relaxing after a long day of exploring. Enjoy coffee on the private deck or immerse yourself in nature before heading out. Great spot for road trippers! STR2024-00002

Kitchen · Family · Location

Trailside Treehouse - Riverside in Richmond, VA

Fulfill your childhood dream of camping in a treehouse! From this central spot, easily explore the trails and river. Then, relax on the deck and enjoy the magic of the trees. •Airbnb “Top 20 Places to Stay in VA” •"Best of Richmond" by Style Magazine •Featured in Airbnb article on hospitality •One of "8 Great Airbnbs" in the U.S. by Inside Hook •Comes with bathroom, kitchenette & lounge apartment in host house •Dog-friendly Social media: @trailside_treehouse City permit #BLDR-107741-2022

Family · Indoor spaces · Pets

Cozy 3-Bedroom Home - Minutes to Downtown Richmond

Your family and friends will love the convenience of this centrally located home, while also enjoying the cheerful and cozy space it offers. It's just minutes from Richmond International Raceway, the Convention Center, VCU campuses, and downtown Richmond, which offers an influx of wonderful restaurants and eateries...both indoor or patio dining. Don't delay...make your reservation today! Your host's top priority is YOU and making sure your stay is a comfortable and enjoyable experience!

Family · Indoor spaces · Cleanliness

Cozy "Blue Butterfly" Cottage w/ futon

Clean & cozy 1 bedroom cottage w/ ample parking. Cottage is located in a safe and quiet neighborhood close to shopping with a plethora of restaurants. Only minutes away from the historic City of Richmond with it's rich history, museums, & beautiful views of the James River. Enjoy the nightlife with scads of restaurants & clubs or dine at Rockets Landing & watch the sun set over the river. Being centrally located makes this cottage the perfect place for traveling nurses & professionals.

Indoor spaces · Family · TV

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.

Family · Kitchen · Check-in

The Barkin’ B & B

Just five minutes from the airport and downtown, this cozy tiny home offers rustic charm and modern comfort. Fully equipped with kitchen essentials, books, games, and even coloring books, it’s perfect for relaxing. Pet-friendly, it comes stocked with dog treats, chews, toys, and a large fenced-in backyard for furry companions to enjoy. Conveniently located for travelers, it provides a peaceful retreat while keeping you close to city attractions. A perfect home away from home!

Kitchen · Indoor spaces · Condition

Quaint Studio in Oregon Hill

This quaint studio apartment lies in the heart of historic Oregon Hill. Less than two blocks from the James River nestles this space near VCU, Hollywood Cemetery, Brown's Island and Downtown Richmond. Studio on the Hill invites you to enjoy the best of Richmond with its vibrant arts scene, deep history and unbelievable food scene. Whether you're visiting Richmond for move-in day at VCU or a concert at the Allianz Amphitheatre, we're perfectly situated for your stay!

Family · Indoor spaces · Getting around

Spacious unit in Arts District

Tucked away in the heart of The Arts District, you'll be able to walk to all the best restaurants and activities the city has to offer. A few blocks away from The National and a few minutes away from Cary Town, The Fan, Shockoe Bottom, Manchester, and Scott's Addition, you'll have easy access to anything the city has to offer! Just blocks away from the convention center, this unit is perfect for Richmond guests who are in town for work related events.

Indoor spaces · Kitchen · Access

Luxe Decor & Private Balcony in Grandiose District

Welcome to Eileen East! The new gateway to exploring Richmond, where boutique style meets 5-star hospitality. You’ll find a little bit of everything in this historic, charming neighborhood just outside downtown proper -- from award-winning restaurants to parks with scintillating views of the city’s skyline, come make yourself at home in the heart of Church Hill. Booking now for vacations, staycations, remote workers, and everything in between.

Family · Indoor spaces · Comfort