Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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Guest favourite

Guesthouse in Church Road

5.0 out of 5 average rating, 133 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.

Sep. 19 – 26

$215 CAD per night

Guest favourite

Home in Richmond

4.93 out of 5 average rating, 121 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!

Feb. 23 – Mar. 2

$212 CAD per night

Guest favourite

Apartment in Chesterfield

4.85 out of 5 average rating, 248 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.

Aug. 15 – 22

$142 CAD per night

Guest favourite

Guest suite in Richmond

4.94 out of 5 average rating, 150 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.

Jun. 20 – 27

$193 CAD per night

Guest favourite

Home in Colonial Heights

4.94 out of 5 average rating, 110 reviews

Quiet Haven Near I-95 & Ft Gregg-Adams/ Petersburg

This is a fantastic place to rest and relax, rewind & rejuvenate. Registered guests only Great space for long term guests, TDY & medical professionals, small families & transit guests Comfy vibes, spacious & comfortable living room, 3 bedrooms w/ sitting areas, ceiling fans & large closets, & bathtub/shower. Desk/work station Turn Key ready: Eat-in, fully equipped kitchen, stainless steel appliances, washer & dryer Linen, cleaning supplies, water, breakfast bars, coffee & tea provided

Jul. 13 – 20

$168 CAD per night

Superhost

Boat in Richmond

4.88 out of 5 average rating, 440 reviews

Warm, Cozy and Comfortable Houseboat, Gated Marina

Note: Dates taken? I have two other boats online-- The Cookie B and also--Beautiful Yacht, 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.

Oct. 4 – 11

$193 CAD per night

Guest favourite

Guesthouse in Chesterfield

4.96 out of 5 average rating, 184 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.

Oct. 4 – 11

$155 CAD per night

Guest favourite

Guesthouse in Petersburg

4.94 out of 5 average rating, 142 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.

Dec. 28 – Jan. 4

$197 CAD per night

Guest favourite

Home in Richmond

4.98 out of 5 average rating, 114 reviews

Your Cottage in the City

Whether you're visiting for business or pleasure, our home is the perfect base for your stay in Richmond. Book now and experience the best of Southern hospitality in this historic and charming neighborhood! Our home is located in the heart of Church Hill, within walking distance to some of the best restaurants, cafes, and shops in the area. With easy access to public transportation, you can explore all that Richmond has to offer.

Aug. 13 – 20

$195 CAD per night

Guest favourite

Guest suite in Richmond

4.97 out of 5 average rating, 587 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!

Sep. 10 – 17

$254 CAD per night

Guest favourite

Guesthouse in Richmond

4.97 out of 5 average rating, 374 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!

Jan. 11 – 18

$135 CAD per night

Guest favourite

Guesthouse in North Chesterfield

4.85 out of 5 average rating, 162 reviews

Modern Studio Guesthouse w/free parking

"Tidings" is a completely private detached unit, 3 minutes from Midlothian Turnpike. This space offers a quiet, convenient, and private entrance with high-speed internet, large yard, quiet neighborhood, convenient to major stores. Many restaurants and tons of shopping within 5 miles!

Oct. 8 – 15

$140 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Popular amenities for Chester vacation rentals

Kitchen

Wifi

Pool

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

Guest favourite

Guesthouse in Richmond

4.94 out of 5 average rating, 173 reviews

Funky & colorful private guesthouse with parking!

Oct. 26 – Nov. 2

$170 CAD per night

Guest favourite

Cottage in Powhatan

4.93 out of 5 average rating, 211 reviews

Horse Farm 1 nights/pets($75 Sun-Thu$145 Fri/Sat)

Jul. 31 – Aug. 7

$204 CAD per night

Guest favourite

Home in Chester

5.0 out of 5 average rating, 28 reviews

Peaceful, relaxing home.

Nov. 19 – 26

$258 CAD per night

Guest favourite

Apartment in Chester

4.97 out of 5 average rating, 33 reviews

Relaxing Farmhouse: Basement Apartment

Jun. 4 – 11

$215 CAD per night

Guest favourite

Guest suite in Chesterfield County

5.0 out of 5 average rating, 28 reviews

Modern Downstairs Studio w/ King bed

Sep. 14 – 21

$164 CAD per night

Guest favourite

Apartment in Hopewell

5.0 out of 5 average rating, 22 reviews

$ Cozy 1BR 1BA Apartment: Near Fort Gregg-Adams $

May 16 – 23

$172 CAD per night

Guest favourite

Home in Chesterfield

4.94 out of 5 average rating, 16 reviews

Luxury Townhouse in Chesterfield

Oct. 5 – 12

$201 CAD per night

Guest favourite

Apartment in Richmond

5.0 out of 5 average rating, 53 reviews

Claw foot tub/fireplace boho apartment

Mar. 17 – 24

$155 CAD per night

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Quick stats about vacation rentals in Chester

Total rentals
10 properties
Local attractions
Lowe's Home Improvement, Sonic Drive-In, and Logan's Roadhouse
Popular amenities
Gym, BBQ grill, and Laptop-friendly workspace
Wifi availability
10 properties include access to wifi
Total number of reviews
1.4K reviews
Nightly prices starting at
$41 CAD before taxes and fees

Vacation rentals in Chester

Top-rated vacation rentals in Chester

Guesthouse in Church Road

Home in Richmond

Apartment in Chesterfield

Guest suite in Richmond

Home in Colonial Heights

Boat in Richmond

Guesthouse in Chesterfield

Guesthouse in Petersburg

Home in Richmond

Guest suite in Richmond

Guesthouse in Richmond

Guesthouse in North Chesterfield

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Chester vacation rentals

Stay near Chester's top sights

Other great vacation rentals in Chester

Guesthouse in Richmond

Cottage in Powhatan

Home in Chester

Apartment in Chester

Guest suite in Chesterfield County

Apartment in Hopewell

Home in Chesterfield

Apartment in Richmond

Quick stats about vacation rentals in Chester

Total rentals

Local attractions

Popular amenities

Wifi availability

Total number of reviews

Nightly prices starting at

Destinations to explore