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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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Guest favorite
A charming cottage-style home features a pastel pink front door, flanked by two symmetrical windows with classic shutters. The entryway is approached by a stone pathway leading up from a landscaped front yard, enhancing the welcoming appearance of the property.
Home in Danville
4.98 out of 5 average rating, 40 reviews

Lover’s retreat, walk to casino

Enjoy a trip away from your worries and strife by relaxing in this stylish couples haven that feels like stepping into your cottage Pinterest board. What better way to spend time away from home than in a spacious, artist-endowed retreat, far away from clutter, chores, and stress? Slip into a comfy bathrobe after a warm bath to watch tv, fall asleep listening to green noise, or enjoy coffee on the front porch. Ideal for longer stays- discounts applied. Extra linens and cleaning products supplied.

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, 252 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, 227 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, 48 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 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 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
4.99 out of 5 average rating, 141 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.

Guest favorite
Home in Danville
4.83 out of 5 average rating, 18 reviews

Cozy cottage

Stay at this beautifully renovated, 1940s cottage, right on the outskirts of Danville. Perfectly placed on a calm street, you will be able to relax while only being 5-10 minutes from all stores and attractions. The space is cute and cozy with everything you need to feel right at home! **PLEASE READ** This home was built in the 1940s. The ceilings are low. Most rooms are around 7 ft. The living room is 6’ 8”. If you are a taller person, the ceiling height may be uncomfortable.

Top guest favorite
Home in Chatham
5 out of 5 average rating, 31 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
Two blue armchairs are positioned in a bright living area, centered around a modern electric fireplace. A colorful red accent pillow contrasts with the blue fabric of the chairs. Light streams through the adjacent window, showcasing warm wooden flooring.
Home in Danville
4.93 out of 5 average rating, 46 reviews

Charming Farm House Right in Town!

Beautiful pastoral setting and also a short drive to the new casino! Walking distance to the Dan River walking and biking trails and to historic River Town. Lovely green views out all windows, and you get the whole house- very private- no neighbors on either side! Laundry facilities in main level and romantic fire circle with chairs to watch the sunset. Frequent deer sightings! There is an air bed in the back bedroom closet if you need it for a child or extra guest!

Guest favorite
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, 83 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 favorite
Cabin in Union Hall
4.92 out of 5 average rating, 304 reviews

The Cabin at Pine Haven Main Channel Lots of Water

Plenty of Water on the main channel. Enjoy the sun rising over the Blackwater of Smith Mountain Lake from the spacious covered porch and then spend the day playing on the water. Finish off a perfect day at the lake by sitting around the campfire. The lake front Cabin at Pine Haven has expansive views from a bluff above the water. Ask about adding Kayak Rentals or firewood to your stay.

Guest favorite
The living room features a comfortable black leather sofa and a classic armchair with a patterned design. A coffee table sits centrally on a patterned area rug, while a TV is mounted on the wall. Natural light enters through the windows, enhancing the space.
Home in Danville
4.95 out of 5 average rating, 104 reviews

The Empty Nest

Located just 2.7 miles from Caesars Virginia and 2 miles from the NC state line, the Empty Nest is your perfect getaway. With Virginia International Raceway 20 miles away and Martinsville Speedway just 30 miles, it's an ideal base for both adventure and relaxation. Enjoy the comfort and convenience of this charming retreat!

Popular amenities for Chatham vacation rentals

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