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Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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

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Guesthouse in Church Road

5 out of 5 average rating, 156 reviews

Heron Rock: Lakefront Cottage on Lake Chesdin

Enjoy peaceful lakefront living at Heron Rock Cottage, where you can stroll through the woods, swim or fish off the dock, paddle the lake in kayaks, or simply relax and enjoy the wildlife and beautiful sunsets. Situated on 6 acres in Dinwiddie County, this newly renovated cottage includes 2 bedrooms, full bath, full kitchen, living room with fireplace and private patio with dining area. Your stay includes full access to the grounds and dock and you are welcome to tie up a boat if you bring one.

Home in Richmond

4.93 out of 5 average rating, 138 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!

Cottage in Powhatan

4.94 out of 5 average rating, 231 reviews

$75 (Sun-Thur) $145 (Fri-Sat) 1 nights/pets

Queen bed loft upstairs. Down stairs has a bathroom, kitchen with sink, stove, oven, microwave, and complimentary kitchen-cups . There is a twin sleeper sofa in living room. Front and back porch, wireless internet and RukuTv. 14 acre farm with walking trails and creek. Pet fee $50. All monies go toward our Horse sanctuary 501c nonprofit. Cleaning Fee is $50 included in nightly rate. Day of cancellations allowed (Mon-Thur) for flexible working in area. Pony Creek and Hobbit House other rentals

Rental unit in Chesterfield

4.85 out of 5 average rating, 257 reviews

Private guest apt on creek w/ patio & fire feature

“The Nest” is a completely private, ground level “basement” apartment. 15 minutes from downtown Richmond & 18 minutes to Pocahontas State Park, this space offers a peaceful, conveniently located, retreat. Private entrance, cozy patio, & large yard- all creek side and professionally designed. Laundry in unit, high speed internet, Smart TV. Yard is wooded and private. Many restaurants and tons of shopping within 5 min of the house, and 2.5 miles from highway access. Not pet friendly at this time.

Guest suite in Richmond

4.94 out of 5 average rating, 167 reviews

New! Cozy Bright Suite w/Patio

Welcome! This private, newly renovated, walkout basement suite was created for you to have a great stay. Enjoy a patio, driveway parking, fast wifi, a workstation, a Smart TV, and a list of fun places to visit in Richmond! Most restaurants, shopping, breweries, hiking, parks, etc. are only 14-20 mins away! Enjoy fun activities and come back to a comfy getaway. We keep your space clean and bright in natural light w/blackout curtains for sleeping! Permit: STR-092482-2021 We do not accept locals.

Cottage in Dinwiddie

4.98 out of 5 average rating, 104 reviews

Country Getaway, Entire Cottage, Modern & Private

Sitting at the forest’s edge with 12’ of glass doors, Daniel Cottage has: - Huge deck w/propane grill & fire pit, cafe table & lots of seating. - Comfy Great Room has HD tv +Netflix/Prime & fully equipped kitchen w/table for 4. - Then add two queen bedrooms - Put it all at the edge of 75 acres of beautiful, natural forest ready to be explored. Two ponds (4 & 6 acres) offer fine fishing. Hike the 3+ miles of pond & forest trails or sit back & enjoy the beauty of the Virginia countryside.

Cabin in Dinwiddie

4.95 out of 5 average rating, 110 reviews

*No Fees* Lake Cabin with Private Dock

Welcome to the Cabin Tucked Away! Whether you’re looking for a spot to make memories with your spouse and family, or need a private, beautiful spot for a romantic getaway, this little lake house offers gorgeous views and plenty of space for fun on the water. Set on a small private lake, the cabin has it's own dock, fire pit, large covered porch, and includes access to two sides of the lake. No cleaning fee and no pet fees! -hot tub -playset -high speed internet via starlink

Guest suite in Midlothian

4.95 out of 5 average rating, 105 reviews

Chateau Midlothian Retreat Suite

The perfect guest suite waiting to great you to relax in this cozy retreat. Full renovation completed in 2022, including all new furnishings. As an Airbnb traveler, I focused on a clean, comfortable space that guests enjoy, and recommend to others. The Chateau Midlothian Suite Retreat is limited to two adult guests with reservations. No other outside guests are permitted. All guests must have their identity verified through Airbnb with at least two reviews to make reservations.

Guesthouse in Chesterfield

4.95 out of 5 average rating, 206 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 and creek in 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.

Guesthouse in Petersburg

4.94 out of 5 average rating, 156 reviews

"Lofty Cottage" Adorable 1-Bedroom Guest House

Enjoy this quaint Cozy Cottage with bedroom loft! This adorable 1-bedroom unique place has a style all its own. Built in the 1960’s behind the main house, it has floor to ceiling pine paneling, pine floors and fireplace. It has been recently remodeled with new tiled bathroom , newly remodeled kitchen and stainless steel appliances. A new Heating and Air unit was installed summer 2021. The pine paneling and 16 foot high ceilings gives it that "cottagey" feel.

Guesthouse in Richmond

4.97 out of 5 average rating, 393 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!

Guest suite in Midlothian

4.87 out of 5 average rating, 421 reviews

Studio Basement

Fully private basement studio apartment. LOCATION, LOCATION, LOCATION!! This basement apartment is 5 min to lots of shopping, dining, 30 min to downtown Richmond, close to major freeways, tons of historical sights within minutes!!! Tons of upgrades like, stainless steel appliances, granite counter-tops, spa rock shower floor, just to name a few.

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Popular amenities for Chester vacation rentals

Free parking on premises

Air conditioning

Stay near Chester's top sights

Kohl's Chester3 locals recommend

Half-Way House Restaurant3 locals recommend

Ashton Creek Vineyard6 locals recommend

Other great vacation rentals in Chester

Home in Chester

4.95 out of 5 average rating, 44 reviews

Peaceful, relaxing home.

Rental unit in Chester

4.96 out of 5 average rating, 46 reviews

Relaxing Farmhouse: Basement Apartment

Rental unit in Petersburg

4.93 out of 5 average rating, 15 reviews

Cozy + Quaint Loft in Old Towne

Home in Brandermill

4.94 out of 5 average rating, 18 reviews

Elegant & Spacious Family Home

Farm stay in Chesterfield

4.99 out of 5 average rating, 81 reviews

Keystone Acres Farm **Enclosed Heated Pool**

Guesthouse in Chesterfield

4.94 out of 5 average rating, 18 reviews

Lulu's Peaceful Cottage

Townhouse in Petersburg

4.93 out of 5 average rating, 59 reviews

Historic Mill Workers Cottage

Bus in Chesterfield

4.92 out of 5 average rating, 88 reviews

The Creekside Cool Bus

Quick stats about vacation rentals in Chester

Total rentals
20 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
1.5K reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Popular amenities
Gym, BBQ grill, and Laptop-friendly workspace

Frequently Asked Questions

What are the most popular amenities for House Rentals in Chester?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wireless internet, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Chester have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Chester. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Chester?
Experience the best of Chester with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Chester?
Yes! Work meets play with ease at over 10 vacation rentals in Chester featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore