Holiday rentals in Chesterfield

Guest house in Church Road

5 out of 5 average rating, 209 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.

4.91 out of 5 average rating, 197 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!

Guest house in Chesterfield

4.98 out of 5 average rating, 52 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.

4.93 out of 5 average rating, 44 reviews

Nala's Place

Bring the whole family or a group of friends to this great place with lots of room for fun, located between Richmond, VA and Washington, DC: Spacious retreat in prime location. This roomy home offers comfort and convenience, featuring: • Fully equipped kitchen • Multiple bedrooms to accommodate large groups • Less than hour from attractions Busch Gardens, Richmond Convention Center, DC Area Perfect for families, friends, or business travelers seeking a comfortable base to explore the city.

4.86 out of 5 average rating, 7 reviews

Home in Chesterfield

Charming Retreat w/ Pool Table in Chesterfield!

Escape to this spacious home in Chesterfield, VA! Relax in a cozy living room with Roku TV, or cook in the fully equipped kitchen with island seating and a coffee corner. Enjoy the rec room with a pool table, laundry nook, and extra TV. The master suite features a king bed, plush seating, and attached bathroom, while two additional bedrooms offer comfort and storage. A second bathroom, roomy deck with grill, and large backyard complete the perfect retreat. Book your stay today!

4.89 out of 5 average rating, 488 reviews

Boat in Richmond

Warm, Cozy and Comfortable Houseboat, Gated Marina

Note: Dates taken? I have one other boat online-- The Cookie B with beautiful 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.

4.85 out of 5 average rating, 323 reviews

Flat in Chesterfield

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.

Guest house in Chesterfield

4.95 out of 5 average rating, 252 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, creek 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.

4.76 out of 5 average rating, 34 reviews

Wood Fireplace & Private Master

Comfort and charm in one space! The living room has a cozy fireplace, perfect for relaxing evenings. The master suite has a king-size bed and a private bathroom with a luxurious double-headed shower. With additional bedrooms for privacy, our house is perfect for families or friends. Situated in a peaceful neighborhood, you'll enjoy tranquility and be just minutes away from local attractions. Experience the ideal combination of relaxation and adventure!

4.89 out of 5 average rating, 186 reviews

Treehouse in Richmond

Romantic Treehouse for 2 (No Kids) in 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!

4.84 out of 5 average rating, 124 reviews

Cozy Cape Close to the City!

Enjoy a relaxing experience in a quiet neighborhood conveniently located less than a 10 minute drive to the city! This location is perfect for any traveling nurses who are going to McGuire VA hospital or anyone looking to experience all that the city of Richmond has to offer! Located right outside of the city and close to several highways it is a great location for everyone looking to stay in the area!

4.93 out of 5 average rating, 125 reviews

Bus in Chesterfield

The Creekside Cool Bus

Experience the ultimate glamping adventure in our converted school bus! Nestled on 5 acres of land, the campsite features lush woods and a creek. Enjoy the peace and quiet of nature with the comfort of a home away from home. Our skoolie is the perfect basecamp for outdoor adventures-just 30 minutes to Richmond and 5 minutes from the nearest trailhead at Pocahontas State Park with pass included.

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Popular amenities for Chesterfield holiday rentals

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Other great holiday rentals in Chesterfield

Private room in Midlothian

4.92 out of 5 average rating, 13 reviews

A comfy space shared with family

SaraRating, 5 stars1 month ago

Pleasant stay in an lovely neighborhood, extremely convenient for where I was spending my time. Easy and flexible checkin, perfect since I was driving from several states away and couldn't pinpoint my arrival time and came pretty late. The hostess was gracious and responsive thoughout my stay.

4.9 out of 5 average rating, 29 reviews

Private room in Richmond

• Private Room in Charming Cottage 5 mins from RVA

SebastianRating, 5 stars1 month ago

Flexible hosts. Thank you for the accommodation and being considerate of the schedule I had during my stay.

Private room in Colonial Heights

4.99 out of 5 average rating, 363 reviews

Travel and Explore, enjoy this home with Heart

DeborahRating, 5 stars1 week ago

My mom and I stayed with Don and Jane, and we cannot express enough how great the experience was. This was the first time traveling and staying in an Airbnb with my mom, so I made this selection with my mom in mind, and it was the best decision! Don and Jane were welcoming and kind, while simultaneously providing a space that was beautiful, comfortable, and felt totally private. Having the extra bedroom was a bonus. Don and Jane take care to provide EVERYTHING you could possibly need for your stay. The morning muffins were very much appreciated. My mom and I THOROUGHLY enjoyed our stay and hope to have the opportunity to return in the future. Thank you, Don and Jane! You were a blessing to Mom and me.

4.98 out of 5 average rating, 201 reviews

Private room in Richmond

“Captain’s Quarters” in 1920’s Craftsman Home

RuiwenRating, 5 stars2 weeks ago

The place is so beautiful and clean and all the furniture are very unique and have the vintage vibe. It is also close to everything. I highly recommend!

4.9 out of 5 average rating, 10 reviews

Private room in Chester

Private Room #2 with Queen Bed + 55" Smart TV

JulieRating, 5 stars6 months ago

My husband said the mattress was very comfortable (firm and not saggy). He enjoyed the ambience. Daniel was VERY responsive on text, but more than responsive -- he processed 2 changes I made with competence, without delay, and with no hint of it being a hassle. He was kind. I really appreciated his communication skills.

Private room in Glen Allen

4.94 out of 5 average rating, 174 reviews

Charming Upstairs Retreat with Workspace

JeremyRating, 5 stars1 week ago

My stay at Justina's place was absolutely charming! Every detail was thoughtfully curated, making the space feel incredibly welcoming and cozy. The apartment was spotless, beautifully decorated, and had everything we needed for a comfortable and relaxing getaway. Justina was a fantastic host – communication was seamless, and she was so friendly and helpful, providing great local recommendations. We truly enjoyed our time and would highly recommend Justina's place to anyone looking for a delightful and memorable stay!

5 out of 5 average rating, 187 reviews

Private room in Powhatan

Luxury and Private Entrance Suite-No Shared Spaces

KylieRating, 5 stars3 days ago

Our stay at Karen’s was amazing. She was very responsive and generous throughout our stay. Her Airbnb gave us everything we needed. I highly recommend Karen’s place!