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Vacation rentals in Lakeside

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Top-rated vacation rentals in Lakeside

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guesthouse in Richmond

4.93 out of 5 average rating, 142 reviews

Not-so-Tiny Home by Scotts Addition w/ Pvt Parking

Private, safe, & close to everything (<90 seconds to highways in all directions!), with off-street parking & a yard, my newly built 500 sqft Not-so-Tiny Home is walkable to coffee shops, bars, & restaurants, & 1 mile from Scott’s Addition, the mecca of Richmond’s brewery & restaurant scene. Ideal for long or short stays for couples & solo travelers, this well-designed home has work space & can host up to 4 in a ground-floor queen bedroom, a full bedroom loft, & a sleeper sofa in the living room!

Guest suite in Henrico

4.89 out of 5 average rating, 501 reviews

Kindness Sweet

Private suite for Max of 2 ($10 for 2) Connected to the main house, where the owner lives. Separate entrance is behind the home (yellow dr) that leads you through a laundry room into your space. Down the drive and around the house. Great for nurses & business travelers. Close to Henrico Dr, St. Mary's, & VCU. 9 mi from the city, 3 mi from Short Pump. We welcome paying guests only that are respectful & quiet. *Sometimes after a big rain harmless waterbugs sneak in. Firepit available bring wood

Home in Glen Allen

4.97 out of 5 average rating, 221 reviews

Cozy Cottage *DOG FRIENDLY* w/ fenced-in backyard

This home has been completely renovated to make you feel at home! With a king size bed in one room and a queen in the other, there’s plenty of room for couples traveling together or families with kids. Add to that, the pet-friendly yard complete with fire pit and grill, and you may never want to leave! Settled into a quiet neighborhood near I-95, I-295, I-64, with tons of restaurants in the area and only 10 minutes from Richmond, this location is ideal for travelers and longterm guests alike.

Guest suite in Richmond

4.99 out of 5 average rating, 234 reviews

Historic Meets Hip: Modern Basement Retreat

Welcome to Historic Meets Hip, a modern retreat in the basement of a fully renovated 100-year-old American Foursquare near Battery Park. This stylish 1-bed, 1-bath apartment features a cozy living room, dining area, and kitchenette with a mini fridge and coffee maker, plus a 55" 4K Smart TV. Just 5 minutes from downtown Richmond, with easy access to I-95 and I-64, you'll enjoy a private side entrance with a smart lock. Battery Park, with its pool, tennis, and basketball courts, is steps away.

Home in Richmond

4.94 out of 5 average rating, 299 reviews

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!

Home in Richmond

4.99 out of 5 average rating, 153 reviews

Strawberry Moon - Colorful cottage near Maymont

Welcome to Strawberry Moon! Our maximalist home is thoughtfully designed for a perfect vacation experience. Our unique property is full of colorful wallpaper, murals, and insta-worthy moments inside and out. The spacious backyard, featuring a pink cowboy pool, and large deck is a great place to spend time relaxing. Our convenient location provides easy access to restaurants, breweries, and shopping. We are also just a short walk away from Maymont, Byrd Park, and the James River.

Rental unit in The Fan

4.94 out of 5 average rating, 772 reviews

Private B&B in Historic Fan

We are looking for people who will enjoy the Historic Fan District of Richmond. The stand alone apartment includes a bedroom, bathroom, and renovated kitchen which has microwave, refrigerator, toaster ,and Keurig coffee machine. For our overnight guests we will provide the ingredients for a delicious breakfast: baked goods butter jams etc., 6 breakfast cereals, , fresh fruit , tea and for Keurig 10 varieties of coffee plus hot chocolate and hot apple cider.

Home in Henrico

4.87 out of 5 average rating, 107 reviews

⭐️ NEW Modern Stay w/King+Queen beds in Richmond ⭐️

Welcome to our newly renovated home where modern charm meets cozy elegance. Every detail in this home was crafted with your experience in mind and will serve as the perfect haven from which to explore Richmond, VA. Ideally located in a quiet and peaceful neighborhood of the West-End of Richmond but also conveniently minutes away from all major Highways, Downtown Richmond, local Breweries, Restaurants, Parks, Museums and Shopping.

Guest suite in Forest Hill

4.97 out of 5 average rating, 660 reviews

Forest Hill Modern Guest House

Located in Richmond's charming and historic Forest Hill neighborhood just blocks from the James River Park and next door to Forest Hill Park. A modern studio space with a queen-size bed and a comfy couch in a private guest house. 1 bath with a spacious shower and simple kitchenette. A great overnight space or comfortable stay for those wanting to explore the cities great food, breweries, parks, and trails!

Guesthouse in Carytown

4.97 out of 5 average rating, 340 reviews

Carytown/Byrd Park Backyard Studio

Newly built, bright, modern garage apartment, a few blocks from Carytown, and steps away from Byrd Park/Carillon has the perfect mix of city and nature. Pick up a cup of coffee and a pastry in Carytown, explore the shops, then stroll over to Byrd Park, making your way to the Carillon and down to the James River. Central RVA location puts any of the city's vibrant neighborhoods just a 10 minute drive away.

Bungalow in Richmond

4.98 out of 5 average rating, 568 reviews

The Bungalow... an Urban Oasis!

"The Bungalow" will delight the traveler looking for an urban oasis. Eclectic with 1942 charm. Covered porch is everyones favorite and overlooks relaxed garden and pond with privacy fencing. Downtown, Carytown, VFMA, Lewis Ginter Botanical Garden, Ballpark, VCU, multiple Breweries and unlimited culinary experiences are minutes away! (Look under "Other details to note" for Dog info".

Guesthouse in Richmond

4.97 out of 5 average rating, 415 reviews

A Place of Peace

A separate cozy cottage for two. Queen sized bed with en-suite full bathroom, plus a screened-in porch and an outside deck. JD, our short-haired orange cat and Ambassador, will be happy to keep you company and share HIS porch!. We are a short drive downtown and a 5-minute walk to the James River. Richmond is a foodie town with great brew-pubs everywhere. All are welcome!

Vacation rentals for every style

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Popular amenities for Lakeside vacation rentals

Free parking on premises

Air conditioning

Stay near Lakeside's top sights

Lewis Ginter Botanical Garden171 locals recommend

Kroger140 locals recommend

Blue Bee Cider39 locals recommend

Target37 locals recommend

Mekong Restaurant32 locals recommend

Stir Crazy Cafe RVA27 locals recommend

Other great vacation rentals in Lakeside

Guest suite in Glen Allen

4.97 out of 5 average rating, 76 reviews

The BeeHive

Home in Richmond

4.88 out of 5 average rating, 33 reviews

Richmond Home Near Monument Ave

Tiny home in Ashland

4.93 out of 5 average rating, 15 reviews

King Bed and Private Patio with Hammock!

Home in Richmond

4.97 out of 5 average rating, 98 reviews

Bright, quirky bungalow

Rental unit in Mechanicsville

5 out of 5 average rating, 58 reviews

Cozy "Blue Butterfly" Cottage w/ futon

Guesthouse in Henrico

4.98 out of 5 average rating, 92 reviews

Adorable Studio Guesthouse

Rental unit in Mechanicsville

5 out of 5 average rating, 15 reviews

Modern Mechanicsville Luxury 1BR Apartment

Guesthouse in The Fan

5 out of 5 average rating, 55 reviews

Heart of the Fan, Monument Avenue Carriage House

Quick stats about vacation rentals in Lakeside

Total rentals
70 properties
Total number of reviews
1.8K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Wifi availability
70 properties include access to wifi

Frequently Asked Questions

Where should I stay in Lakeside?
Make yourself at home in Lakeside by choosing from our most frequently booked neighborhoods. We have over 1,250 vacation rentals in Hermitage Road, over 240 vacation rentals in Bellevue, and over 450 vacation rentals in Bryan Park.
What are the most popular amenities for House Rentals in Lakeside?
Enhance your stay in our House Rentals with the most popular amenities: over 60 homes with a kitchen, over 60 homes with free parking, over 60 homes with wifi, over 60 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there vacation rentals with a dedicated workspace in Lakeside?
Yes! Work meets play with ease at over 40 vacation rentals in Lakeside featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Lakeside have air conditioning?
Absolutely! We offer over 60 house rentals with air conditioning in Lakeside. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Lakeside?
Lakeside has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Lakeside have a kitchen?
Absolutely! We offer over 60 house rentals with a kitchen in Lakeside. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Lakeside have wifi?
Absolutely! We offer over 60 house rentals with wifi in Lakeside. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Lakeside have free parking?
Absolutely! We offer over 60 house rentals with free parking in Lakeside. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore