Vacation rentals with a pool in Chesterfield County

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Top-rated rentals with a pool in Chesterfield County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Richmond

5.0 out of 5 average rating, 96 reviews

Strawberry Moon - Colorful Cottage

Welcome to Strawberry Moon! Our maximalist home is thoughtfully designed for a perfect vacation experience. Our unique property is full of colorful wallpaper, murals, and insta-worthy moments inside and out. The spacious backyard, featuring a pink cowboy pool and large deck, is a great place to spend time relaxing. Our convenient location provides easy access to the best restaurants, breweries, and shopping in town. We are also just a short walk away from Maymont, Byrd Park, and the James River.

Superhost

Place to stay in Moseley

4.75 out of 5 average rating, 4 reviews

“WaterView" The Pool Pavilion, waterfront property

This unique and elegant Family friendly partial wheelchair access property offers a beautiful waterfront view, a pool, a pier, 4 king rooms, and a futon. Offering a large entertainment area also with indoor games. This home with its hand-milled elegant woodwork, spiral staircase, and custom bar overlooks the beautiful swift creek reservoir. It resides on a 100-acre private estate with walking trails along the water. Enjoy our newly renovated fully stocked kitchen! Found in the Midlothian area.

Nov 6 – 13

€ 638 per night

Guest favorite

Apartment in Chesterfield

4.92 out of 5 average rating, 12 reviews

Chesterfield's Eclectic Comfort 1bdrm + 2bth Aprmt

This spacious, comfortable space is perfect for an extended stay in the Brandermill/Chesterfield area. With subtle elements of zen, and bits of global design you will enjoy every moment. You will be less than 15 minutes from Saint Mary's Hospital, and every major retailer, but if you prefer to walk you're across the street from Publix, local pizza & restaurants. Be sure to take full advantage of all the building's modern amenities, then retreat back to your top floor apartment for a great sleep.

Jul 11 – 18

€ 181 per night

Apartment in Richmond

4.63 out of 5 average rating, 8 reviews

Retreat: Your Own Cozy Suite

This hidden gem of a suite is conveniently located just a short drive from restaurants, popular parks, recreational areas, landmarks, and tourist attractions. It caters perfectly to couples, solo adventurers, college students, and travelers. Moreover, its close proximity to several hospitals makes it an excellent choice for those in the medical field, broadening its appeal to a diverse range of guests. Lengthy stays are welcomed, ensuring a comfortable and accommodating experience for all.

Aug 9 – 16

€ 91 per night

Guest favorite

Apartment in Moseley

4.97 out of 5 average rating, 32 reviews

Charming Virginia Getaway

Discover the charm of historic Moseley, VA in our cozy 2 bedroom apartment. Tranquility and modern comfort await you in this oasis. Enjoy scenic views and a serene atmosphere in the rich history of Moseley. This welcoming retreat is conveniently located near Richmond, Ft. Gregg-Adams, River City Sportsplex, and Richmond Speedway. In a short 10 min drive, you'll find dining options such as Texas Roadhouse, Bonefish Grill, and the Boathouse at Sunday Park. EV chargers are also on site.

Guest favorite

Apartment in Richmond

4.89 out of 5 average rating, 61 reviews

Lovely 1 BR Apartment with Riverfront Balcony

Looking for a calm space to relax while taking in the expansive views of the wild & wonderful James River? Then, look no further! Furnished with a mix of period pieces that provide a personal touch, this bright 1 BR space with private balcony & sweeping views of the city is just for you! Amenities include: garage, fitness & yoga rooms, rooftop lounge & adjoining terraces with fire pit & barbecue. Shiplock Views sits between historic Church Hill and a riverside bike & walking trail.

Sep 10 – 17

€ 125 per night

Superhost

Apartment in Midlothian

5.0 out of 5 average rating, 4 reviews

Extended Stays for Work, Insurance, Relocations

Welcome to our stylish 1 bed, 1 bath private apt in a secured access building. Perfect for traveling professionals, insurance displacements, relocations and other temporary stays. Fully furnished with a full kitchen, cozy seating, TV's in living room & bedroom, queen bed, walk-in closet. Enjoy community pool, fitness center, basketball courts, fire pit, grills, and events. Conveniently located near highways and shopping for added ease. Experience comfort and luxury during your stay!

May 13 – 20

€ 178 per night

Guest favorite

Farm stay in Chesterfield

4.99 out of 5 average rating, 74 reviews

Keystone Acres Farm **Enclosed Heated Pool**

Keystone Acres is located in Chesterfield, VA at a beautiful 1000 acre horse farm. On property we have roughly 60 horses owned by different tenants. The brick farm house in which you will be staying in overlooks one of our ponds & multiple horse barns. We have many "internal" roads here and hope you enjoy the farm views. Our 5 bedroom house is perfect for families or friends who want to have a getaway to "unplug" and experience the country life and each other's time.

Dec 5 – 12

€ 740 per night

Guest favorite

Home in Chesterfield

5.0 out of 5 average rating, 9 reviews

Lakefront Resort

Spectacular, resort style home looking onto a beautiful lake. This home is over 5,000 sqft of one of a kind living space. Guests enjoy the courtyard style backyard with mezmerizing swimming pools, hot tub, and grilling space. Inside features movie theatre, spa like master bath, gym, 4 bedrooms, 1 add'l. room w/sleep accommodations via pull out sofa and futon, 3 full baths and 2 half baths. Delight in this beautiful oasis for relaxation and a comfortable stay.

May 1 – 8

€ 560 per night

Guest favorite

Apartment in Richmond

5.0 out of 5 average rating, 22 reviews

River City Den

Come relax in this cozy nest in the city, which about 5 minutes from Brown's Island, as well as approximately 10 minutes away from Maymont and Forest Hill Park, McGuire Veterans Medical Center, MCV Hospital, and Shockoe Bottom restaurants. High speed internet is available, as well as access to pool and 24 hour gym. The living and dining area has a lot of natural light during the day, making it a very peaceful atmosphere.

Jul 31 – Aug 7

€ 117 per night

Superhost

Home in Richmond

4.84 out of 5 average rating, 348 reviews

No cleaning fee/Hot tub/Entire House 2100 Sq ft

3 miles from downtown Richmond. Large (2,000+ Square ft), beautiful house with a driveway that can fit a boat or RV. The back deck, pool, hot tub,charcoal grill and yard are great for outdoor outings. This house is located directly off HWY 64 and one exit from the shops at White Oak Village. Two miles from a new Eastgate Town Center Walmart, along with many other new stores nearby.

Oct 6 – 13

€ 209 per night

Superhost

Apartment in Richmond

4.89 out of 5 average rating, 18 reviews

Entire rental unit w 1BR/BA downtown richmond

Stay for a weekend or a while. You’ll be in the center of the city with easy access to all the attractions. It’s a college town so there’s always activities on the weekend. 2 mins from VCU 2 mins from Shockoe Bottom 15 mins from Airport Complimentary bathroom, laundry supplies for both men/women Anything else you need reach out and we’ll get to you soon as possible

Aug 7 – 14

€ 85 per night