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Holiday rentals in Chatham

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Top-rated holiday rentals in Chatham

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

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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, 253 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 favourite
Flat in Danville
4.96 out of 5 average rating, 229 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
A welcoming entryway features an archway leading to a cozy living area, illuminated softly from a nearby lamp. Framed botanical art adorns the walls, alongside decorative plants in stylish pots. A neutral rug adds warmth and texture to the wooden floor.
Home in Danville
5 out of 5 average rating, 105 reviews

BRAND NEW! Charming 2 Br home...great location!!!

Perfectly nestled in a quiet, safe neighborhood! Centrally located near the downtown River District and Riverwalk Trail, Averett Univ., SOVAH Health and great restaurants. Professionally renovated, decorated and landscaped with attention to details to make your stay comfortable and enjoyable! Screened porch for coffee and birdwatching, fresh herbs and flowers for cutting, great internet for home office and smart tvs in every room. Well supplied throughout to make the perfect home away from home

Top guest favourite
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, 399 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!

Top guest favourite
A modernized cabin is set in a serene natural environment, surrounded by green grass and trees. A covered porch is featured at the front, with rocking chairs and a porch swing positioned for relaxation. A pathway leads to the cabin, enhancing accessibility.
Cabin in Long Island
4.93 out of 5 average rating, 108 reviews

100acre Woods Cabin Retreat

No Smoking in home, No animals or pets allowed! 30 mi to Lynchburg, 11 to Altavista. This cabin boasts 100 acres of serene nature while hiking the trails, fishing and swimming in the river. Canoe from the boat slip down river to the long Island community center. Relax on the large rocking chair front porch with your honey on the porch swing, or roast marshmallows and sip drinks around the fire pit! This is not a party house, it is meant to relax and enjoy peace, quiet, and nature, enjoy!

Top guest favourite
Cabin in Vinton
4.99 out of 5 average rating, 201 reviews

Secluded Oasis•Hot Tub•Blue Ridge Mountains

You found it. A secluded oasis tucked away in Virginia’s Blue Ridge Mountains. Wake up with coffee on the covered deck, listening to birdsong and the peaceful sounds of the creek. Spend your afternoons relaxing in the hammock chairs or soaking in the hot tub, then end the day around the fire pit under the stars. If you’ve been craving a quiet escape to reconnect and unwind, you’ve found it. •15 min to the Blue Ridge Parkway •20 min to Smith Mountain Lake •25 min to Downtown Roanoke

Guest favourite
Home in Blairs
5 out of 5 average rating, 9 reviews

Levi Hall Farmhouse- Whole House

This beautifully renovated farmhouse blends rustic charm with all the modern amenities needed for a relaxing and memorable stay. Nestled in a peaceful rural setting, the home features five spacious king bedrooms and four full bathrooms, thoughtfully designed for convenience and comfort. Fresh linens, plush towels, & toiletries are provided to make your stay as comfortable as possible. The kitchenette is minimal and tidy, meant for convenience rather than full-scale cooking.

Top guest favourite
Home in Chatham
5 out of 5 average rating, 32 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 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
4.94 out of 5 average rating, 171 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 favourite
The exterior of a charming single-story home features white siding, a grey roof, and two front entrances. A well-maintained lawn with green grass surrounds the house, and trees with autumn foliage provide a colorful backdrop. A paved walkway leads to the front doors.
Home in Gretna
4.98 out of 5 average rating, 86 reviews

Nellie's Nest

This adorable three bedroom is perfect for your stay in Gretna. Hit the sidewalks for a run or walk down to the best coffee shop around, The Pod. Take a quick 15 min drive to Smith Mountain Lake or visit the wineries just outside of town. Relaxed living at it's best here in small town Virginia! *More photos coming Common Destinations: Chatham Hall and Hargrave Military Academy - 12 mins Olde Dominion Agricultural Complex - 6 mins Liberty University - 36 miles

Top guest favourite
Flat in Danville
4.96 out of 5 average rating, 103 reviews

Central 1bd/1bth | 1.8 miles from Casino

This beautifully furnished 1-bedroom, 1-bathroom apartment is a haven for for you stay. Located in the heart of the city, the space is designed for comfort, productivity, and relaxation. Enjoy all the amenities of home, including a fully equipped kitchen, a cozy living area, and a separate office space tailored to support remote work. Perfectly situated and thoughtfully furnished, it’s the ideal spot for work and relaxation alike.

Top guest favourite
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, 214 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.

Popular amenities for Chatham holiday rentals

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