Vacation rentals in Upper Shirley

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Top-rated vacation rentals in Upper Shirley

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Guest favorite

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.

Aug 21 – 28

G$27,758 GYD per night

Guest favorite

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

G$28,234 GYD per night

Guest favorite

Farm stay in New Kent

4.99 out of 5 average rating, 120 reviews

Charming Willow Haven Modern Farmhouse Bungalow

Welcome to Willow Haven, our 23-acre horse farm, located between historic Williamsburg and downtown Richmond. We're located on the Hampton Roads Wine Trail, ideally positioned between four wineries only minutes away. Willow Haven Cottage is a two-story 900 sf charming pied-a-terre attached to our barn. Renovated in a modern farmhouse style w/ a furnished kitchen and a cozy second floor bedroom complete with an antique 4 poster queen bed, 14 ft ceiling, exposed beams and antique chandelier.

Aug 12 – 19

G$25,396 GYD per night

Guest favorite

Cottage in Ashland

4.95 out of 5 average rating, 246 reviews

The Cottage at Walnut Shade

You won’t have to travel far outside of Richmond to find relaxation in the countryside! Convenient to I-95, the Cottage at Walnut Shade provides fully furnished privacy and a chance to escape among the farm fields and history of Hanover county. Whether you’re a biker, hiker, history nut, beer fanatic, theatre lover or just want a place to call your own for the weekend, you may be surprised to find it all in the town of Ashland and surrounding Hanover county. *Internet is now available*

Oct 3 – 10

G$24,248 GYD per night

Guest favorite

Cottage in Quinton

4.98 out of 5 average rating, 175 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.

Jul 1 – 8

G$27,385 GYD 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.

Feb 24 – Mar 3

G$24,639 GYD per night

Guest favorite

Apartment in Williamsburg

4.84 out of 5 average rating, 360 reviews

The Nook

Enjoy a getaway in this cozy 1 bedroom apartment attached to a classic 1940s Cape Cod home minutes from Colonial Williamsburg and Jamestown. You'll be within biking distance to many local attractions such as Williamsburg Winery, Jamestown Island, Jamestown Settlement, Jamestown Beach, and Billsburg Brewery. Busch Gardens & Water Country are a 15 minute drive. The Nook was completely refinished in 2020. Need more space or traveling with a group? Inquire about our other units.

Nov 23 – 30

G$20,486 GYD per night

Guest favorite

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.

Aug 2 – 9

G$21,997 GYD per night

Guest favorite

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.

Sep 9 – 16

G$24,410 GYD per night

Guest favorite

Farm stay in Toano

4.94 out of 5 average rating, 180 reviews

Farm Stay - Guest Suite w/ Private Entrance

Why not add a little adventure to your trip to the Williamsburg area? Spend your days exploring all the area has to offer and then relax in our cozy retreat. Take a break and stay with us on our homestead. Sit outside on the patio with your cup of coffee (or wine) and enjoy the sights and sounds. We have chickens, geese and some crazy goats that are sure to keep you entertained. All this and less than 15 min to Williamsburg.

Jul 13 – 20

G$18,918 GYD per night

Guest favorite

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!

Aug 26 – Sep 2

G$36,554 GYD per night

Guest favorite

Guesthouse in Richmond

4.97 out of 5 average rating, 375 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!

Mar 21 – 28

G$18,221 GYD per night