Holiday houses in Chester

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Top-rated holiday rentals in Chester

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

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Top Guest favourite
A comfortable living area features a brown leather sectional couch with a matching armchair and ottoman. A round table sits on a patterned rug, while soft natural light filters through the window blinds. Two framed animal prints adorn the light-colored wall.
Home in Richmond
4.91 out of 5 average rating, 247 reviews

Luxury BOHO upper unit

Relax in this calm, stylish 3 bedroom/2 full bath upper level unit. Another Airbnb is in the finished basement unit. The space is completely yours and no access to the other basement unit. Only shared area is the back deck. Unit has a completely updated kitchen with stainless steal and granite. Master bedroom has a super comfy queen bed and a master bath that has a beautiful walk in shower. Guest room has another queen bed and office area has a futon. Elegance and romantic boho style throughout!

Guest favourite
A light-colored room features a dark wooden dresser with gold hardware and a framed artwork above it. The view extends toward an adjacent workspace featuring a desk and an ergonomic chair. Soft carpeting covers the floor, enhancing the room's comfort.
Guest suite in Chesterfield
4.81 out of 5 average rating, 68 reviews

the winter clover.

Forget your worries in this spacious non smoking and serene space. This cozy nest is 1.5hr away from the virginia beach, 9min from Pocahontas state park and 30min from downtown Richmond. Guess have access to a coffee machine, toaster, microwave, refrigerator and oven. A queen size bed in the room with queen size air mattress available per request if guess travels with family. Nice walking trail in the community for morning promenade. we require no more than 2 people at all time on the property.

Top Guest favourite
A modern kitchen features light-colored cabinetry and a spacious island with a marbled countertop. Stainless steel appliances are integrated, including a microwave and a coffee maker. Natural light is provided by a window above the sink, enhancing the functional layout of the space.
Home in Richmond
4.98 out of 5 average rating, 157 reviews

Open 2 acre, Huge yard/drive, K, K, Q bed, 2 bath

Private and spacious 3 bedroom, 2 full bath home on 2 acres. Less than 10 mins to Airport, Winery, Food and Shops Fully equipped kitchen for your cooking needs. Huge driveway and yard to turn around large vehicles, or boat trailers. Plenty of space to unwind and relax while enjoying Deer and other animals passing by. 10 minutes from Richmond Airport (RIC), VA Capital Bike Trail, River Dog Winery, local recreation park and shopping. 15 minutes to Downtown Richmond. 45 minutes to Williamsburg.

Top Guest favourite
Guesthouse in Chesterfield
4.99 out of 5 average rating, 96 reviews

Lulu's Peaceful Cottage

Enjoy a relaxing stay at this great located cottage. Lulu's Peaceful cottage is brand new, stylishly decorated for comfort. Private little cottage in a park like setting amongst trees & nature. Inside is an equipped kitchenette, coffee/tea bar, & is meal prep friendly. Relax in the soaking tub, or shower if you prefer. Lulu's is close to everything. Shopping, gyms, parks, & recs, hospitals, museums, & airport, and just a few miles from all major highways. Easy driveway parking & keyless entry.

Superhost
A cozy living area features a light-colored sofa with decorative pillows, positioned next to a stone fireplace. A wooden dining table is visible, along with a lush green plant. Wall art and decorative plates add character to the space, illuminated by natural light from the window.
Apartment in Chesterfield
4.82 out of 5 average rating, 386 reviews

Private guest apt on creek w/ patio & fire feature

“The Nest” is a private, ground level “basement” apartment. 15 min from downtown Richmond & 18 min to Pocahontas State Park, this space offers a peaceful, conveniently located, retreat. Private entrance, cozy patio, & large yard- all creek side. Laundry, high speed internet, Smart TV. Yard is wooded and private. Restaurants and tons of shopping within 5 min of the house, and 2.5 miles from highway access. A friend rents the upstairs of the home, which is completely separate- no shared space.

Top Guest favourite
A well-equipped kitchen features wooden cabinetry and a modern design. Stainless steel appliances, including a refrigerator and microwave, complement the white countertops. An island with seating offers additional space, while decorative floral backsplash adds a touch of charm. Natural light brightens the room through nearby windows.
Home in Richmond
5 out of 5 average rating, 35 reviews

Stay Awhile - Private, Large Yard, Easy Travel

Welcome to the Exurbs! Peaceful property, not quite rural, not quite the suburbs. Still close enough to jump on the interstate and get where ever you need to be fairly quicky. This property has a huge fully fenced back yard, with plenty of room to unwind and relax on the front/back porch. Bring your boats and trailers, plenty of room! Interstate 288: 3 min Interstate 95 Interchange: 5 min Defense Supply: 6 min Chester: 10 min Dutch Gap Boat: 13 min RIC Airport: 20 min Fort Gregg: 20 min

Guest favourite
A modern two-story townhome features a blend of siding and stone on the exterior. The driveway is spacious, providing access to a single-car garage on the left. Nearby, a landscaped yard enhances the entryway, with tall trees visible in the background.
Townhouse in Richmond
4.98 out of 5 average rating, 47 reviews

Top Location Cozy Stay - Near Richmond

Discover this brand-new, stylish home designed for comfort and privacy near Richmond. With 5-star guest experiences, this space offers 3 spacious bedrooms, 2.5 modern bathrooms, and a main-level master suite with a remote-controlled reclining bed. Enjoy a bright living area with a large TV, a fully equipped kitchen with island, dining space, private rear porch, garage, driveway, and in-unit laundry. Perfect for families, professionals, or extended stays. Note: Basement has no shared access.

Superhost
A spacious dining area features a large table surrounded by six elegantly designed chairs with soft cushions. A decorative plant adds a touch of greenery, while the ceiling displays a modern light fixture. The walls are painted in a soft yellow tone, enhancing the warm atmosphere.
Home in Hopewell
4.81 out of 5 average rating, 182 reviews

Refresh, cheerful home from home.

Relax with the whole family at this peaceful place to stay. A home you surely call home . Newly renovated, professionally decorated to give you the feeling of calmness and enjoyment. Located in the heart of the Tri-cities, near Fort Lee, Southpark Shopping Center, Hopewell marina, the Crossing Shopping Center, convenient store, fast food, gas stations movie theater are minutes away. The house has spacious front, back and left side views with no adjacent neighbors on these three sides.

Top Guest favourite
Guest suite in Richmond
5 out of 5 average rating, 68 reviews

The Enchanted Studio w/ Tree-Top Views

Some spaces feel different the moment you walk in. The Enchanted Studio is one of them. Perched on the second floor of a beautifully crafted Richmond home, the Enchanted Studio greets you with a wall of windows and a view that stops you — a rain garden, towering trees, and a creek threading quietly along the property's edge. Thoughtfully designed, this retreat works for however you need it: a quiet escape, a remote work base, or simply a place to decompress in a beautiful setting.

Top Guest favourite
A wooden deck offers a comfortable outdoor space, featuring two rocking chairs with floral cushions. A small table stands neatly between them, adorned with a vase of flowers. Surrounding trees showcase autumn foliage, creating a serene backdrop.
Cabin in Dinwiddie
5 out of 5 average rating, 119 reviews

Dinwiddie Couples Getaway- Wells Cabin @WeldanPond

Wells Cabin @Weldan Pond is a beautiful new space designed for couples who love to relax, enjoy the outdoors (hike, fish, trail bike, & more), & marvel over beautiful views. The Cottage has a full kitchen, a large king bedroom, a bright, window filled sitting area, and a new deck overlooking Upper Weldan Pond and acres of healthy, natural hardwood forest with nearly 4 miles of trails to explore. You'll also love just enjoying the deck and the beauty of the Virginia countryside.

Superhost
A houseboat, painted in blue and white, is docked next to a wooden marina. Surrounding greenery provides a natural backdrop, while a wooden structure with a red roof is visible in the background, showcasing a peaceful riverside setting.
Boat in Richmond
4.88 out of 5 average rating, 520 reviews

Warm, Cozy and Comfortable Houseboat, Gated Marina

Note: Dates taken? I have one other boat online-- The Cookie B with beautiful river views. We offer no contact boarding if desired and we understand the need for a clean place to stay. Therefore we go beyond the recommended guidelines concerning sanitation by fogging the entire boat after each guests departure. And for dining, you can cook aboard or enjoy the Lily Pad Cafe, an outdoor covered and heated restaurant on the river, and it is only two miles from the marina.

Guest favourite
Guesthouse in Chesterfield
4.95 out of 5 average rating, 315 reviews

Gorgeous Creek View from your Private Eyrie

Enjoy a relaxing view of Falling Creek from the second floor apartment with a private entrance and balcony. The wall of windows overlooks a secluded backyard with visiting deer, heron, owls, and other wildlife. Sit by the pond, creek or fire pit. The property offers off street parking in a safe neighborhood which is located 20 minutes from downtown Richmond, 10 mins to Midlothian and Chesterfield, 3 mins to Swim RVA. 15 mins to the airport or train station.

Popular amenities for Chester holiday rentals

Frequently Asked Questions

  • What are the best places to stay in Chester?

    Chester has a variety of accommodations, with stays available near the downtown area and close to green spaces. Family-friendly neighborhoods and areas around parks are often recommended for convenience and a welcoming atmosphere.

  • What are the best things to do in Chester with kids?

    Children enjoy Chester's playgrounds, nature trails, and hands-on museum exhibits. Many families participate in story times at local libraries or visit community recreation centers for indoor activities.

  • What are some of the best things to do in Chester?

    Chester has scenic parks, local history exhibits, and welcoming community spaces to explore. Outdoor trails, public art, and seasonal activities are frequently suggested for visitors who enjoy relaxed, locally rooted experiences.

  • How is the weather in Chester?

    Chester has cool winters ranging from 29–48°F (-2–9°C), and summers can be warm and humid near 65–90°F (18–32°C). Rain is common throughout the year, so packing for both sun and occasional showers is advised.

  • When is the best time to visit Chester?

    Late spring and early fall are often recommended, when temperatures are milder and community events are more frequent. These seasons also bring colorful landscapes and opportunities for outdoor activities.

  • What are the best places to visit in Chester?

    Parks, local history museums, and art spaces are often recommended places to visit in Chester. The town also has scenic spots ideal for picnics and outdoor relaxation year-round.

  • What are some hiking trails in Chester?

    Nature trails in Chester’s parks are often recommended for hiking, with routes that wind through woodlands and near community ponds. Urban trails provide opportunities for birdwatching and relaxed outdoor walks.

  • What are some family activities we can do in Chester?

    Families in Chester often explore local parks, interactive museums, and playgrounds, as well as attend community events around town. Nature walks and picnics are frequently suggested for spending time together outdoors.

  • What are some of the best day trip ideas from Chester?

    Popular day trips from Chester include visiting nearby historical towns, scenic riverside parks, and regional nature preserves. Exploring museums or cultural events in surrounding areas is often suggested for variety.

  • Are there any pet friendly accommodations available in Chester?

    Chester has pet-friendly stays in several neighborhoods, especially near parks and nature areas. Many local hosts welcome pets, and community trails make outings with dogs enjoyable.

  • What are some local tips for visiting Chester?

    Locals suggest exploring the town’s public parks early in the day, engaging with community markets, and sampling locally made treats. Checking community event calendars helps you discover seasonal festivals and gatherings.

  • What is Chester known for?

    Chester is known for its community spirit, historical landmarks, and abundant green spaces. Many visitors enjoy its locally rooted traditions and welcoming neighborhoods.

  • What are the best hidden gems to explore in Chester?

    Chester has locally rooted cafes, small art galleries, and tucked-away nature trails that are frequently suggested as hidden gems. Community gardens and independent shops offer a chance to discover unique local character.

  • What are the best foods to try in Chester?

    Chester has locally rooted Southern cuisine, barbecue, and comfort dishes, with many eateries featuring seasonal ingredients. Residents frequently suggest trying pies, biscuits, and regional specialties at community markets.

  • What should I bring for a trip to Chester?

    Pack layers for changing temperatures throughout the year, as Chester's weather ranges from cool winters to warm, humid summers. Comfortable walking shoes and a light rain jacket can be helpful, especially during wetter months.

  • What is the nightlife in Chester like?

    Chester’s nightlife has casual venues, local restaurants, and spots featuring live music or trivia nights. Evenings in town tend to be relaxed, with gathering spaces for both locals and visitors.

  • What are the most popular events or festivals in Chester?

    Chester has community festivals, holiday parades, and seasonal markets that are often recommended around late spring and early fall. Local events frequently highlight regional art, food, and performances.

  • Are there family friendly vacation rentals in Chester?

    Chester has family-friendly vacation rentals in neighborhoods near parks or community centers. Many hosts provide amenities for children and welcoming spaces suited for group gatherings.

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