Holiday rentals in Chester

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chester

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

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Guest favourite

Guest house in Church Road

5.0 out of 5 average rating, 132 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.

20–27 Sep

$181 SGD 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!

26 Feb – 5 Mar

$182 SGD per night

Guest favourite

Flat 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.

22–29 Oct

$116 SGD per night

Guest favourite

Guest suite in Richmond

4.94 out of 5 average rating, 149 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.

23–30 May

$156 SGD per night

Guest favourite

Home in Colonial Heights

4.94 out of 5 average rating, 109 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

1–8 Jul

$168 SGD per night

Guest favourite

Cottage in Quinton

4.98 out of 5 average rating, 174 reviews

Luxury countryside cottage, IVY, near Richmond, 1

Two peaceful luxury cottages on a farm. Book one or both (Separate listings). Tranquility close to downtown Richmond and Richmond Int. Airport (15 min). Wineries, craft breweries, wedding venues, Busch Gardens, and more! We are 30mins from Williamsburg and 25min from downtown Richmond. Cities not your thing? We are less than an hour from beaches, national parks, golf courses, and fishing spots. So come and relax on your private deck overlooking a horse farm and enjoy the sunset.

25 Jun – 2 Jul

$179 SGD 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.

11–18 Mar

$161 SGD per night

Guest favourite

Guest house 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.

11–18 Aug

$122 SGD per night

Guest favourite

Guest house in Petersburg

4.94 out of 5 average rating, 141 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.

6–13 Dec

$159 SGD per night

Guest favourite

Treehouse in Richmond

4.88 out of 5 average rating, 119 reviews

Romantic Treehouse for 2 (No Kids) in Little Farm

Surrounded by trees and peace in our small farm in a neighborhood, this cozy little cabin is made for secluded romantic stays and to enjoy a relaxing and restful night. Not suitable for children. Only adults allowed. Cabin is 10 X 12" of cuteness with all the amenities you might need to feel comfortable, electricity, Smart TV, wifi, coffee maker, memory foam bed, and an awesome outdoor bathroom to shower under the stars!

18–25 Jan

$152 SGD per night

Guest favourite

Guest house in Richmond

4.94 out of 5 average rating, 172 reviews

Funky & colorful private guesthouse with parking!

This unique place has a style all its own with carefully curated touches of yellow! A private guesthouse tucked away and at the top of a spiral staircase. This space is a five minute drive from Richmond's most popular neighborhoods. Fully equipped with a mid-century modern kitchenette, private patio, and A/C! This space is an experience in itself. Explore Richmond's best kept secret; the Yellow Tiger's Den.

18–25 Feb

$147 SGD per night

Guest favourite

Guest house 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!

13–20 Dec

$119 SGD per night