Holiday houses in Chesterfield

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Top-rated holiday rentals in Chesterfield

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

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Guest favourite

Home in Richmond

4.93 out of 5 average rating, 243 reviews

Extended Stay The Sunny ☀️ Cottage At Byrd Park

Cozy cottage in the heart of Richmond near Byrd Park & Carytown. Perfect for family & friends on vacation or extended stays. Minutes from Byrd Park- grab a paddleboat and enjoy! * Short walk to Fan district, Carytown, Maymont and Byrd Park * Whole house experience, all on one floor with 1,000 SF * Private off-street parking and great front porch for relaxing outside * Fully stocked, equipped kitchen w/ new granite & stainless appliances We love hosting in Richmond! Check out our reviews!

Guest favourite

Cottage in Powhatan

4.89 out of 5 average rating, 130 reviews

Evening breeze cottage, nestled in the woods

Experience the perfect blend of comfort, tranquility, and tradition in this beautifully maintained home, steeped in a rich heritage of faith and family. Whether you're seeking a peaceful, cozy retreat to unwind or a welcoming base during your time in the area, this home provides an inviting atmosphere where you can truly relax. With its warm, quiet ambiance and pristine cleanliness, it offers an ideal sanctuary for both short stays and longer visits, ensuring your stay is restful and memorable.

Guest favourite

Guesthouse in Chesterfield

4.97 out of 5 average rating, 33 reviews

Lulu's Peaceful Cottage

Enjoy a relaxing stay at this great located cottage. Lulu's Peaceful cottage is brand new, stylishly decorated for comfort. Private little cottage in a park like setting amongst trees & nature. Inside is an equipped kitchenette, coffee/tea bar, & is meal prep friendly. Relax in the soaking tub, or shower if you prefer. Lulu's is close to everything. Shopping, gyms, parks, & recs, hospitals, museums, & airport, and just a few miles from all major highways. Easy driveway parking & keyless entry.

Guest favourite

Home in Richmond

5 out of 5 average rating, 165 reviews

*Mid-Century Boho* 2 Primary Suites! Private Patio

Welcome to this adorable mid-century modern, boho themed home! 1940s historic charmer! There’s 2 primary suites with private baths. 4 bedrooms total: 2 king beds and 2 queens: all gel memory foam and each room has a smart tv! Come hang out in the private, shaded backyard or the breezy screened in porch! 5 min to the very popular Forest Hill Park & James River. 10 min to Downtown, Carytown, The Fan, Museum District, Church Hill, breweries - great proximity to everything Richmond has to offer!

Guest favourite

Home in Richmond

5 out of 5 average rating, 49 reviews

RVA Retreat

This renovated gem is nestled in a prime cul de sac, mere minutes away from VCU, Johnston Willis, Chippenham Hospitals, SwimRVA and downtown Richmond, offering unparalleled convenience for both work and play. Stay connected with 1GB Fios internet and enjoy the latest entertainment on the new streaming TVs in the Livingroom and two bedrooms. With off-street parking and a charming small deck, this duplex unit promises the perfect blend of comfort and style. Grab this fantastic opportunity now!

Guest favourite

Home in Richmond

5 out of 5 average rating, 11 reviews

Lake Shore Retreat Full House

Welcome to this tranquil 2-bedroom, 2.5 bathroom home, nestled on the edge of the Bon Air district. This haven invites you to connect with nature, as it sits directly on a lake teeming with wildlife (including ducks, blue herons, and bald eagles). Vaulted ceilings and skylights in the main living area of the house offer abundant natural lighting. Ideally located 15-20 min from city center/Henrico Doctors’ Hospital/VCU Hospital and 10 min from Chippenham Hospital/Johnston Willis Hospital.

Superhost

Home in Richmond

4.78 out of 5 average rating, 76 reviews

Family Retreat, walk to Lake/ Fan District, fenced

Welcome to this fully renovated home, perfect for a comfortable and convenient travel experience. Kitchen is fully stocked for all of your cooking needs & includes a drip coffee maker. Enjoy nearby parks such as Maymont and Byrd Park, perfect for outdoor activities and relaxation. Conveniently located near Carytown and the Fan, offering an eclectic mix of shops, boutiques, restaurants, and entertainment options. Parking is a breeze with three designated spaces available on the property.

Guest favourite

Home in Quinton

4.9 out of 5 average rating, 127 reviews

Light & airy home w/private hot tub on golf course

This spacious and well-appointed 4 bedroom house overlooking the Brookwoods golf course with a 7-person hot tub is the ideal place for relaxation. It is located in a safe neighborhood with 5 minutes walking distance to the Jolene family winery. The lake and golf club are also within walking distance. Bring bikes, fishing gear. Conveniently located near I-95 and I-64. 20 min to downtown Richmond, 35 min to Williamsburg attractions, King’s Dominion, Busch Garden, and Water Country.

Guest favourite

Apartment in The Fan

4.9 out of 5 average rating, 247 reviews

Start Your Richmond Adventure Here

Welcome to the Chateau Floyd, where quality rest is invited, memories are made, and adventures are sought. “A single dream is more powerful than a thousand realities.” –J.R.R. Tolkien You will LOVE Richmond in THE FAN! One of the best neighborhoods for eating, taking a stroll, and relaxing. 10 minute walk to the Virginia Museum of Fine Arts, lots of places to explore, and this apartment is PERFECT for a FUN weekend out and a relaxing time in. Don't believe me? Read the reviews.

Guest favourite

Guest suite in Midlothian

4.96 out of 5 average rating, 118 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.

Guest favourite

Home in Richmond

4.92 out of 5 average rating, 13 reviews

The Villa on Falling Creek.

Every aspect of this guest cottage home is a cozy space for you to enjoy. Large glass doors and windows set you up for a stunning panoramic view of Virginian foliage complete with access to a quaint running stream in the backyard, giving you your own slice of seclusion and privacy. Tucked comfortably into a peaceful corner of a 40 acre park, with private creek views, all within minutes of shopping, breweries, dining and a casino.

Guest favourite

Home in Midlothian

4.96 out of 5 average rating, 163 reviews

The Cottage in the City -Private Yard and Fire Pit

Your family will be close to everything when you stay at this peaceful, centrally-located home. This home is equipped with anything you may need during your stay! Enjoy the beautiful naturally lit living room throughout the day, or stargaze in the back yard while enjoying gentle heat from the firepit. The best part? We are a quick drive to anything you may be looking to do in Richmond and only 12 minutes to downtown center city.