Holiday rentals in Caroline County

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Top-rated holiday rentals in Caroline County

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Superhost
A well-lit living room is presented, featuring a comfortable sectional sofa and a reclining chair. A modern black coffee table sits in the center, while a mounted TV is placed above a stylish white mantle. Large windows allow natural light to flood the space.
Home in Bowling Green
4.82 out of 5 average rating, 56 reviews

Cozy 3BR Near Golf, Kings Dominion & Meadow Event

This charming home has been recently renovated with ample natural light! Three bedrooms with queen beds. The primary suite has it's own bathroom & vanity/work area. The living room has a smart tv and space for entertaining, there are several games too. The kitchen is equipped for cooking in or ordering out featuring a little coffee station and dining area. It’s minutes away from the historic town of Bowling Green to eat, shop, or site see! Between Richmond & Fredericksburg. 15 min to Kalahari !

Guest favourite
The front porch features white railings and steps leading up to a spacious entrance. Two lantern-style light fixtures are mounted on the exterior, while the surrounding landscape includes neatly planted shrubs and a stone pathway leading up to the porch.
Home in Beaverdam
5 out of 5 average rating, 28 reviews

Wagner's Pond

Relax at the edge of the pond, or enjoy the view of the horses across the street. Have your coffee on the back porch overlooking the pond. Take a jog and enjoy the horses on the farm across the street. Fishing, kayaking and canoeing access on private lake/pond! Kings Dominion Theme Park - 17 miles Meadow Event Park/State Fair - 20 miles Lake Anna Pleasants Landing - 12 miles Ashland - 21 miles Richmond - 33 miles 15 min from I-95 4B/3.5b available across the street as well. Inquire for info.

Guest favourite
A spacious yard features a circular fire pit surrounded by multiple wooden chairs. The charming two-story farmhouse is visible in the background, framed by large trees and greenery, creating a serene outdoor setting.
Cottage in Beaverdam
5 out of 5 average rating, 16 reviews

Private Rural Retreat w/6ac Pond-Fish Kayak Relax

Want to hide away from it all but still stay close enough to enjoy great shopping and dining, recreational opportunities, and historic attractions? Our cozy, quiet and peaceful little farmhouse in Partlow, Va. is the perfect combination of both. Our almost century-old, 1,000+-square-foot getaway includes a kitchen, comfortable bedroom on the second floor, full bathroom and an adjacent open space with a trundle bed that sleeps two. 6-acre pond access with beach for relaxing, kayaking, or fishing!

Guest favourite
A charming two-story building is surrounded by lush green landscaping, featuring manicured lawns and well-maintained shrubs. A pathway leads up to the entry, which is highlighted by a welcoming porch with white railing.
Home in Ruther Glen
4.89 out of 5 average rating, 9 reviews

The Contemporary Charleston

Welcome to our home, nestled in a serene and picturesque neighborhood. Our home offers both comfort and convenience for our guest seeking a relaxing getaway. Additionally,the home features two thermostats for personalized comfort,and three inviting patios, two adult bedrooms, one children's bedroom (ideal for toddlers or school-aged kids, with space for up to two), and a convenient crib for an infant. Come relax, unwind, and enjoy! At this time, only accepting booking from guests age 25+.

Guest favourite
The farmhouse, illuminated by outdoor string lights, features a wide porch with several chairs arranged along its length. The structure showcases a two-story design with dark shutters and a red door, set against a gently sloping grassy area.
Home in Ruther Glen
4.92 out of 5 average rating, 25 reviews

Windy Hill Farmhouse

Welcome to Windy Hill Farm. Ever wanted to stay on a farm? Well look no more. This 1900's farmhouse has been totally renovated. Situated on 90 acres this home offers a relaxing and peaceful get away. Enjoy peaceful mornings and evenings on the covered porch overlooking the pond, pastures, grazing cattle and a donkey. Planting and harvesting seasons will give you the real feeling of living on a farm. Conveniently located in between Richmond and Fredericksburg Bedrooms are on 2nd floor.

Top guest favourite
An exterior view showcases a wooden staircase leading to the entrance of the accommodation. The stairs are surrounded by trees, with a pathway made of stone tiles visible in the foreground. The rustic brick wall of the building adds character to the serene natural setting.
Flat in Ashland
4.98 out of 5 average rating, 104 reviews

Ashland Aerie

Relax in this peaceful, stylish space for one, located north of Richmond. Park in the carport and go upstairs (21 steps) to enjoy privacy, convenience, and safety - with kitchenette, small washer/dryer, smart TV, desk, and exterior cameras. Ashland, less than three miles south, has restaurants (many), grocery stores, laundromats, a movie theater, a public library, churches, a post office, and Randolph Macon College. King’s Dominion and Meadow Event Park are six miles north.

Top guest favourite
A welcoming living area is illuminated by natural light from large windows. Two comfortable chairs and a brown couch are arranged around a central wooden coffee table, which is complemented by decorative items. A fireplace adds a cozy atmosphere to the room.
Home in Fredericksburg
4.97 out of 5 average rating, 108 reviews

Rustic Home on 5 Private Acres

Our cozy home is located in the rural area of Spotsylvania County and is nestled in 5 acres of woods with a serene creek, perfect for exploring nearby attractions. Old Town Fredericksburg, Fredericksburg Battlefield, Spotsylvania Towne Centre, Central Park, and Mary Washington University are minutes away. Lake Anna and King's Dominion are within a short drive. After a fun day, unwind in our peaceful retreat and immerse yourself in nature's tranquility.

Superhost
The sleeping area features two twin beds, each dressed in patterned white bedding with decorative pillows. A small bedside table is positioned between them, topped with a lamp providing soft light. A welcoming ambiance is created by the warm glow illuminating the space.
Flat in Ruther Glen
4.76 out of 5 average rating, 372 reviews

Small organic farm nestled in the woods near I-95

Located right off of I-95 between mile markers 104 and 98, between Fredericksburg and Richmond, VA. This is a small, practical studio apartment in the walk out basement of our organic family farm. Quiet, natural surroundings with woods to explore and seasonal vegetables and eggs available for purchase. Local attractions include Meadow Event Park, Kings Dominion, AP Hill. Close to MCDean and Carmel Church Industrial area.

Top guest favourite
A bright dining area features a round table set with decorative placemats and neatly folded napkins. Comfortable seating includes a dark sectional sofa and an armchair, positioned near a wall-mounted TV. The walls are painted a vibrant yellow, enhanced by rich orange curtains.
Home in Spotsylvania
4.93 out of 5 average rating, 247 reviews

Spotsy Spot BSMT Apt 3 Bedrooms Perfect for Pets!

The Spotsy Spot Basement Apartment: Nestled on 2 acres in the historic Spotsylvania Courthouse area. 3 bedrooms, private bath, fully equipped kitchen, cozy dining area, and convenient laundry room. 25 minutes from the University of Mary Washington and Mary Washington Hospital. Easy access to I-95. Only 40 minutes from Kings Dominion! 🏡✨ March of 2025–carpet replaced with hardwood flooring! 🏡✨

Guest favourite
A light-colored table is set for two on a screened porch, with two dark mugs and a seashell centered between them. Sunlight casts gentle shadows across the surface, and a spacious green yard is visible through the screen, bordered by trees.
Home in Doswell
4.82 out of 5 average rating, 274 reviews

Doswell Comfort

Relax from your travels in a cozy country home. Have morning coffee/tea on the porch onto the large yard & breezy tree lines. Close to local attractions; suitable for all families (pet friendly). Kings Dominion - 2 miles State Fairgrounds - 3.5 miles Randolph-Macon University - 7 miles Town of Ashland - 7 miles City of Richmond - 25 miles Central to multiple locations in Historic Hanover.

Top guest favourite
A spacious bedroom features a cozy bed with decorative pillows. A traditional area rug covers the hardwood floor. Light walls are complemented by a piece of artwork, while double doors provide storage space. The kitchen area is visible in the background.
Flat in Ashland
5 out of 5 average rating, 132 reviews

Hundred Acre Wood: basement apartment/pets welcome

Pets welcome! Cozy, comfortable, and spacious efficiency apartment with a view of pristine woods and adorable chickens and ducks. Go for a walk in the woods to Beech Creek or explore the quaint town of Ashland just 10 minutes away. A great space to unplug, rest, and get away from it all! Please note that we are not able to accommodate long-term rentals.

Top guest favourite
The cabin features a rustic log exterior with a steel roof, framed by trees displaying autumn foliage. A welcoming entrance is highlighted by a wooden door and two windows with green trim. Benches are positioned on the front porch, offering a comfortable outdoor seating area.
Cabin in Spotsylvania Courthouse
4.97 out of 5 average rating, 268 reviews

The Bedford Cabin

A gorgeous chink-style log cabin boasting a wood-burning fireplace, kitchenette, living room, and private patio. If you are looking for serenity and privacy in a rustic setting, this cabin is for you! This cabin is NOT pet-friendly. Take advantage of our walking trails that wind through hundreds of yards of Civil War earthworks!

Popular amenities for Caroline County holiday rentals