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Vacation rentals in Chatham

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Top-rated vacation rentals in Chatham

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

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Top guest favorite
A small kitchen area features a black dining table surrounded by four wooden chairs. A coffee station is visible on the wall, with coffee cups and a coffee maker arranged neatly. Natural light enters through the window adorned with floral curtains.
Home in Danville
4.92 out of 5 average rating, 134 reviews

Quaint & Quiet Place 10 miles from VIR

Comfortable and relaxing, this older 3-bedroom home sits on 1.5 acres with large shade trees. Both front porch and back deck areas have peaceful views. Very safe, quiet neighborhood. The circle drive extending in front of the house adds extra paved parking for trailers, etc. VIR guests welcome! Under 10 mi to VIR. Less than 1 mi. to Danville Airport & dining, and 5 mi. to historic downtown Danville and the hospital, and 8 mi to Casino. Prime location to Danville. Very fast, high-speed WIFI.

Top guest favorite
A charming lodge exterior is framed by a large tree, showcasing a cozy structure with a sloped roof and a brick chimney. Outdoor seating is arranged near a gravel area, inviting relaxation in a serene natural setting.
Home in Sandy Level
4.97 out of 5 average rating, 239 reviews

Antler Ridge Lodge - 19 Acres of Seclusion +WiFi

Only 12-mi to the Anthony Ford Boat Launch at SML, 8-mi to Myers Creek ramp at Leesville Lake. Well-stocked and waiting for your next get-a-way! Explore acres of yard, woods & creek. Leesville Lake only a 1/2-mi walk to the end of the road. Horses/hikers/bikers are welcome along the 5-mi ridge of Smith Mt only 3-mi away. Relax around a fire enjoying the starry sky or kick back in the comfortable lodge complete with a gas log fireplace, 65" Smart TV, & Fiber WiFi, 50 MBS up & down. Pet friendly.

Top guest favorite
Apartment in Danville
4.96 out of 5 average rating, 215 reviews

The Historic Blessing House in Danville on Main

Located on historic Main Street, the home has central HVAC, is workspace friendly, w/ tv and walking distance to coffee shop/wine bar/restaurant/museum/ hospital. Averette Univ is 6 blocks. Casino 1 mi Queen bed, ceiling fan, window blinds, drapes, full floor mirror & walk-in closet. Full kitchen w/ ceiling fan, coffee, tea, Keurig, bottled water, disinfectant, sanitizer, and cooking essentials. Private Bath with shower, soap, shampoo, conditioner, hair dryer. Linens incl. W/D available.

Guest favorite
An open area is presented with wooden walls and a high ceiling, featuring a seating arrangement with a couch and a side table. A carpet enhances the space, while soft lighting fixtures contribute to the ambiance. The adjoining area includes a rustic table and shelving units.
Home in Gretna
4.98 out of 5 average rating, 41 reviews

Room to Roam

A haven for nature seekers, this home is just out of town with plenty of comfort that makes you feel a world away from stresses of life. Turn onto quiet back roads to our quaint little escape just along the edge of a timber farm where creeks and streams border this secluded property. There is plenty of land to roam as you explore and appreciate the wildlife. Absence of city lights makes the night sky a perfect backdrop for stargazing. Take time to get away from it all and enjoy some relaxation.

Top guest favorite
A charming living area features rustic wooden logs as walls, complemented by a light hardwood floor. A comfortable sofa adorned with patterned cushions invites relaxation. Natural light enters through multiple windows, and a decorative chandelier hangs above a coffee table with a small plant.
Cabin in Roanoke
4.96 out of 5 average rating, 380 reviews

The Magical Cabin on Back Creek

Magic is the word most people use when they visit this hidden gem. Built in 1939 as a fishing cabin by a gentleman who incorporated box cars as rafters and beams, dates still visible since removing the attic. By far the best place I've ever lived. I decided to share it with others who love to explore, who love listening to the voice of the creek or who come just to sit on the porch high above the creek with a spouse, friend, family, or alone. For the best sleep, open the bedroom window!

Guest favorite
The farmhouse features a welcoming front porch with black railings and comfortable seating. Large windows on either side provide ample natural light. A concrete pathway leads to the entrance, surrounded by a well-kept lawn and outdoor greenery.
Home in Gretna
4.96 out of 5 average rating, 23 reviews

Farmhouse in Gretna, Virginia

East Gretna Farmhouse is located just outside the small town of Gretna, VA. Spacious 5 bedroom/3 bath home, room for the whole family or plenty of friends. Only 2 miles from the Town of Gretna, 20 miles from Smith Mountain Lake, and 40 minutes from Caesars VA Casino. Beautiful, unobstructed view, set off the road with a pet-friendly fenced backyard, firepit, and outdoor seating. Comes equipped with a dishwasher, washer & dryer provided, linens, starter toiletries, and Wi-Fi are included.

Top guest favorite
A cozy bedroom features a spacious bed adorned with decorative pillows and a red throw blanket. Warm wood paneling creates a natural ambiance. Soft lighting is provided by bedside lamps, and a wooden bench offers additional seating at the foot of the bed.
Cabin in Union Hall
4.98 out of 5 average rating, 130 reviews

Black Water Junction Cabin

Our cabin is built out of old wood and doors found on the farm. Because I am such a cold natured person, I installed heated floors and a heated towel bar in addition to the mini-split and electric fireplace! The cabin is surrounded by pastures that are the home to our cows, horses, goats, pot belly pig, and chickens. The highlight of a stay at BWJ Cabin would be to sit on the front porch in a rocking chair, day bed swing or hot tub looking out over the landscape and do nothing.

Top guest favorite
Home in Chatham
5 out of 5 average rating, 23 reviews

Hermione’s Purse

In the heart of downtown Chatham just across the creek from Chatham Hall, you will find a tiny home with room for everyone. Private and quiet with sweeping green views, Hermione’s Purse is within easy walking distance of both private schools and all downtown businesses. Built to last in 1960, the original part of the home consists of the living room and kitchen, with two bedrooms upstairs. The home’s first indoor bathroom and a bedroom downstairs were added in the 1980s.

Guest favorite
A cozy living area is highlighted by a comfortable sectional sofa and a coffee table adorned with magazines. Two mirrors reflect light from nearby windows, enhancing the openness of the space. A decorative wall accent adds a welcoming touch.
Home in Danville
4.94 out of 5 average rating, 158 reviews

Comfy 3BR w/ large basement, deck, W/D, wifi

Our family's best memories occurred here - so we're opening our doors to groups looking to make memories of their own. With 3 bedrooms, 5 beds and free parking, there's room for everyone. Our huge family room with sleeper sectional, office nook, back deck, large yard, WiFi, large TVs, and games are reasons to stay in - but if you venture out, we're 10 minutes from the riverwalk and parks. With modern farmhouse decor, Retreat on Rosemary says, "Welcome to the South, y'all!"

Guest favorite
A modern kitchen features white cabinetry and a granite countertop. Stainless steel appliances, including a microwave and dishwasher, are visible. An island with a wooden base provides additional workspace. Natural light enters through two windows, illuminated by a pendant light overhead.
Home in Danville
4.98 out of 5 average rating, 115 reviews

Walking Distance to Casino

Step back in time without sacrificing comfort in this beautifully updated 2-bedroom mill house. Originally built in the early 1900s this charming home has been thoughtfully renovated to preserve its character while offering all the modern conveniences you expect. The Danville Caesars Virginia Casino is Just 0.5 mile distance and a short 9 minute walk. This home offers a private back deck with outdoor seating, fenced in backyard and a picnic table for additional seating.

Top guest favorite
The image captures a fountain with multiple streams of water, set against a backdrop of a brick building with a vibrant awning. Outdoor seating is visible at a restaurant, surrounded by greenery and park space.
Loft in Danville
4.97 out of 5 average rating, 202 reviews

2BR Riverview Fountain Loft - Best Location!

BEST LOCATION! 2 BR River District Loft in the very heart of downtown. River and Fountain Park views. Popular local restaurant downstairs and many more within short walking distance as well as Ballad Brewery and Riverwalk access and a Bikeshare station within 50 yards. Great for VIR, Averett University, Caesar’s Casino and Corporate visits.

Top guest favorite
The cozy bedroom features a spacious bed adorned with white linens and a soft teal throw. Natural light filters through a nearby set of French doors, illuminating the room. A wooden dresser and a clothing rack are visible, adding to the functional layout.
Apartment in Danville
4.98 out of 5 average rating, 162 reviews

The Central Stay on Main 1b/1bth

Discover the perfect blend of history and comfort in this 1-bedroom, 1-bathroom apartment located in a beautifully preserved historic house on Main Street, Danville, VA. With stunning natural light, exquisite stained glass accents, and a welcoming atmosphere, this space is perfect for a relaxing getaway.

Popular amenities for Chatham vacation rentals

  1. Airbnb
  2. United States
  3. Virginia
  4. Pittsylvania County
  5. Chatham