Holiday rentals in Chatham

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Top-rated holiday rentals in Chatham

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Top guest favourite
A charming two-story home with a white exterior is set against a clear blue sky. A welcoming entrance with a wooden door is flanked by decorative elements. A brick pathway leads through a manicured lawn, surrounded by lush greenery, enhancing the inviting atmosphere.
Home in Danville
4.98 out of 5 average rating, 133 reviews

Historic Gem w amenities * Midweek Stay Discounts*

Experience the best of Danville in this beautifully remodeled 1920’s gem! *MID-WEEK STAY DISCOUNT OF $30 OFF STAYS OF 3 NIGHTS OR MORE SUN-THUR* * 4 Bedrooms * 2 Full Bathrooms * 5 mins to Danville Caesars Virginia Casino * 20 mins to Virginia International Raceway * 35 mins to Martinsville Speedway * Fully Equipped Kitchen * Beautiful Deck with string lights/ yard games * Fire pit with Adirondack Chairs * Free Disney+ Streaming * Driveway & Street Parking * Walk to Averett or Downtown Danville

Top guest favourite
Flat in Danville
4.96 out of 5 average rating, 205 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.

Top guest favourite
An open living area features a stone fireplace with a mounted TV above and large windows that provide a panoramic view of the lake. A round glass dining table is set near the window, complemented by a cozy sofa and armchair, inviting relaxation and gatherings.
Apartment in Moneta
4.99 out of 5 average rating, 282 reviews

Fun Lake Getaway with Breathtaking Views

Fantastic getaway on beautiful Smith Mountain Lake! Enjoy stunning views on two sides of this top-floor, corner condo with a wrap-around deck and natural shade. It is perfect for a relaxing break or an adventure! Activities include boating (with guest docks), swimming (indoor and outdoor), pickle ball, working out, and relaxing in the hot tub, steam room or sauna! If you are working remotely, this quiet space includes a desk and high-speed wireless. The individual HVAC unit also has a UV light.

Top guest favourite
A sandy beach area is bordered by calm waters. Shade is provided by tiki umbrellas, while a volleyball net is visible in the soft sand. Kayaks are placed on the shore, and green lawns extend in the background, leading to a serene lakeside view.
Apartment in Moneta
4.98 out of 5 average rating, 115 reviews

Tranquility Cove Condo at Smith Mountain Lake

—We Welcome You— Visit and experience the ultimate respite while enjoying amazing water and mountain views, sunrises, and sunsets. This ground level condo is perfectly situated in Bernard's Landing Resort on beautiful Smith Mountain Lake! This bright, stylish & thoughtfully appointed space welcomes you to a full kitchen, spacious bdrm w/king bed, walk-in shower, and a queen sleep sofa. Amenities include restaurant & bar, tennis, pickle ball, gym, sauna, hot tub, three pools and a sandy beach.

Top guest favourite
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, 234 reviews

Antler Ridge Lodge

Only 3 miles from SMITH MOUNTAIN! Zip Code 24161. (There's another Sandy Level near NC.) It is well-stocked and waiting for your next get-a-way! Explore acres of yard, woods & creek. Leesville & SML beaches & boat launches are 9-30 miles away. Walk or ride 1/2-mi to the road's end at Leesville Lake. Horses/hikers/bikers are welcome along the 5-mi ridge of Smith Mt minutes away. Relax around a fire enjoying the starry sky or kick back in the comfortable lodge complete with a gas log fireplace.

Top guest favourite
The exterior of a two-car garage is highlighted, showcasing a combination of brick and siding. A welcoming entrance door with glass accents is positioned in the center, flanked by decorative lighting. Lush greenery surrounds the property, enhancing the tranquil setting.
Guest house in Collinsville
4.96 out of 5 average rating, 754 reviews

5 Star Apartment (1000sf) w/Garage(NoCleaningFees)

This 5 Star private guest suite located in Henry County, VA is separate from the main house. The apartment is 1000 square foot of living space. The new addition has beautiful granite countertops, ceiling fan, and a large bathroom with a ceramic walk-in shower. Great neighborhood, this in-law suite is about 40 miles from the Blue Ridge Parkway and 20 minutes from the Martinsville Speedway. Philpott Lake is 8 miles away. Industrial Park is less than 2 miles away. It is 8 minutes from SOVAH.

Top guest favourite
Cabin in Vinton
4.99 out of 5 average rating, 140 reviews

Forest Cabin Retreat | Hot Tub & Creekside

Welcome to The Cabin! •15 min to the Blue Ridge Parkway •20 min to Smith Mountain Lake •25 min to Downtown Roanoke •40 min to Peaks of Otter Follow our IG @rambleonpines for cabin tours and photos Awaiting guests deep in the poplars that over took this holler years ago after all the green beans and potato crops were pulled from this fertile soil, is a modern chic cabin over looking a babbling creek with all the luxuries one would need for a weekend away from the grind of life.

Top guest favourite
A comfortable living area showcases a dark sofa adorned with textured pillows and a soft throw. A light wood coffee table sits centrally, accompanied by a cozy chair with a light cushion. Decorative wall art and a subtle light source create a relaxed ambience.
Guest suite in Lynchburg
4.94 out of 5 average rating, 174 reviews

Cozy, Beautiful 1br- Private entry - 10 min to LU!

Only 10 minutes from Liberty University and 20 minutes from Downtown Lynchburg! After a day of adventuring, come unwind in our cozy bungalow! With over 800sqft, this newly renovated basement unit is spacious, beautiful, clean and cozy. We are serious about coffee, so we’ve outfitted a great coffee bar. Make yourself a cup using our Nespresso, or go traditional with a Chemex and ground beans. As a courtesy, we provide some light breakfast options - cereal and oatmeal packets.

Guest favourite
The image showcases different areas of the home. A cozy living room with a smart TV and seating is visible alongside a modern kitchen with ample counter space. A dining nook features a round table with decor. A game room highlights entertainment options, including a dartboard and a mini-golf setup.
Home in Danville
4.93 out of 5 average rating, 109 reviews

Central Retreat with Gameroom Near Casino

Enjoy the comfort and convenience of our spacious home, perfect for both short getaways and extended stays. It is only 5 minutes away from Caesars Casino and 30 minutes away from VIR. Our property is equipped with modern amenities you need for a comfortable and productive stay, including: * High-speed Wi-Fi * Dedicated workspace * Smart TVs in all bedrooms * Sound system (Bluetooth) in living rooms * Game room * BBQ grill Message me about weekly or extended stay discount.

Top guest favourite
A cozy bedroom is furnished with a spacious bed covered in white linens, accented by a dark bedspread. A plush armchair and a wooden dresser are visible, with artwork adorning the walls. Natural light illuminates the room through the window, enhancing the inviting atmosphere.
Guest house in Martinsville
4.92 out of 5 average rating, 200 reviews

Private Guesthouse w/Kitchen - Minutes from Uptown

Welcome to The Blue Door on Mulberry! This private guesthouse is on a centrally-located lot at the front of Martinsville’s Mulberry neighborhood. Maintain your sense of privacy while still being close to everything Martinsville has to offer. The property is less than 5 mins from the Martinsville Uptown District, under 10 mins to the Martinsville Speedway, under 4 mins to the SOVA Hospital, and walking distance to the Virginia Museum of Natural History, Piedmont Arts, and more!

Guest favourite
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
4.95 out of 5 average rating, 151 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!"

Top guest favourite
A cozy living area features a light-colored sofa adorned with decorative pillows and a soft throw. A wooden coffee table is set with snacks and drinks, while two stylish lamps provide warm lighting. A large wall sign displays the words 'Hope Hideaway' above the sofa.
Cottage in Eden
4.99 out of 5 average rating, 125 reviews

Hope Hideaway

If you love rich history, and privacy then you will love this peaceful oasis. As soon as you pull into the main property entrance, you will naturally leave the world behind. You will take a right by the Hope sign and come upon this adorable one bedroom cottage. You will enjoy this newly remodeled home. It features a wrap around porch, deck with grill and it’s own personal lavender garden by the fire pit. It is peaceful and cozy.

Popular amenities for Chatham holiday rentals

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