A town with a prominent church, a large parking lot, and a mix of residential and commercial buildings.

Chatham Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Chatham vacation rentals

A wooden deck with a gazebo, outdoor furniture, and a grill.

1. Cozy house in private Leesville Lake community

Cozy house in private Leesville Lake community
Pittsville
10.0 out of 10, Exceptional, (47 reviews)
"Very peaceful and quiet, which was very nice. Outside was very nice to look at in the morning!"
United States
Lance S.
$355 nightly
The price is $399
Sep 6 - Sep 7
Total with taxes and fees
Cozy house in private Leesville Lake community
A dining area with a wooden table, chairs, a chandelier, and a cabinet with decorative items.

2. Located in Historic Old West End. Minutes from the River District and Casino.

Located in Historic Old West End. Minutes from the River District and Casino.
Danville
10.0 out of 10, Exceptional, (51 reviews)
"Nice place ! "
United States
Pattie C.
$295 nightly
The price is $340
Sep 6 - Sep 7
Total with taxes and fees
Located in Historic Old West End. Minutes from the River District and Casino.
A wooden deck with string lights, a bench, and a table.

3. Avalon Cottage w/ hot tub

Avalon Cottage w/ hot tub
Danville
10.0 out of 10, Exceptional, (8 reviews)
"Fantastic place and my go-to from here on out! Clean, newly upgraded and quiet and has everything you need. Great experience from beginning to end!"
United States
Adam S.
$486 nightly
The price is $559
Sep 7 - Sep 8
Total with taxes and fees
Avalon Cottage w/ hot tub
A spacious living room with a large TV, a red sofa, and a patterned rug.

4. Iconic Church Turned Unique Stay (Casino/VIR)

Iconic Church Turned Unique Stay (Casino/VIR)
Danville
10.0 out of 10, Exceptional, (11 reviews)
"We really enjoyed our stay!"
United States
Connie R.
$564 nightly
The price is $648
Sep 5 - Sep 6
Total with taxes and fees
Iconic Church Turned Unique Stay (Casino/VIR)
A modern living room with a sofa, a coffee table, a TV, and a sliding glass door leading to an outdoor area.

5. Tiny House - 6 miles from Averett University and 5.4 miles from Caesars Virginia

Tiny House - 6 miles from Averett University and 5.4 miles from Caesars Virginia
Danville
9.6 out of 10, Exceptional, (18 reviews)
"I enjoyed my stay up there this place is good for being on the outskirts but at the same time right next to everything. It was a very cute little place. It had everything you needed."
United States
Ashley L.
$210 nightly
The price is $243
Sep 13 - Sep 14
Total with taxes and fees
Tiny House - 6 miles from Averett University and 5.4 miles from Caesars Virginia
A large building with a swimming pool, tennis courts, and a parking lot.

6. Cozy Lakefront Condo with Kayaks at Bernard's Landing on Smith Mountain Lake

Cozy Lakefront Condo with Kayaks at Bernard's Landing on Smith Mountain Lake
Moneta
10.0 out of 10, Exceptional, (55 reviews)
"Great place with a great host!"
United States
Adam H.
$251 nightly
The price is $282
Sep 8 - Sep 9
Total with taxes and fees
Cozy Lakefront Condo with Kayaks at Bernard's Landing on Smith Mountain Lake
A dining area with a dark wooden table, a chair, a wall clock, a framed picture, and a wall-mounted light fixture.

7. Walking Distance to Casino

Walking Distance to Casino
Danvilel
10.0 out of 10, Exceptional, (28 reviews)
"Room where great, loved the mattress. Definitely had a great night sleep here!"
United States
Brenda
$438 nightly
The price is $503
Sep 9 - Sep 10
Total with taxes and fees
Walking Distance to Casino
A balcony with a view of a lake, a dock, and a small building.

8. Amazing Views and Two Kayaks Ready to Use!

Amazing Views and Two Kayaks Ready to Use!
Moneta
10.0 out of 10, Exceptional, (109 reviews)
"Beautiful property exactly as described. Great view of the lake, nice amenities, and use of kayaks was appreciated. Host was very responsive and friendly. Snacks and sodas provided were a nice touch, and so were the bathrobes and slippers and the hammock on the porch. Awesome property with everything you need. Will definitely recommend and stay again!!!"
United States
Terri
$172 nightly
The price is $193
Sep 8 - Sep 9
Total with taxes and fees
Amazing Views and Two Kayaks Ready to Use!
A view from a balcony overlooking a lake with a restaurant and buildings in the background.

9. AUGUST DISCOUNT DAYS BERNARDS LANDING NEXT2POOL &BEST VIEWS NEW REMODEL-BOOK NOW

AUGUST DISCOUNT DAYS BERNARDS LANDING NEXT2POOL &BEST VIEWS NEW REMODEL-BOOK NOW
Moneta
9.6 out of 10, Exceptional, (57 reviews)
"This stay was amazing. The place was clean, beautiful property with lots of amenities and relatively close to fun things to do. The property was exactly as described and I was able to cook some meals. Hot tub and indoor pool were great as well. "
United States
Jennifer H.
$228 nightly
The price is $255
Oct 4 - Oct 5
Total with taxes and fees
AUGUST DISCOUNT DAYS BERNARDS LANDING NEXT2POOL &BEST VIEWS NEW REMODEL-BOOK NOW
A cozy room with a leather sofa, a large bed with white bedding, and a wooden ceiling.

10. One room cabin set on our farm for a peaceful getaway.

One room cabin set on our farm for a peaceful getaway.
Union Hall
10.0 out of 10, Exceptional, (20 reviews)
"We loved this for a little getaway. Peaceful with beautiful little touches. Very comfortable bed and relaxing hot tub with beautiful farm and hill views. "
United States
Annie B.
$292 nightly
The price is $328
Sep 10 - Sep 11
Total with taxes and fees
One room cabin set on our farm for a peaceful getaway.
A modern kitchen with a wooden table, two stools, a stainless steel refrigerator, a microwave, and a washing machine.

11. Reagan’s Retreat~ Farmhouse Cottage on 45 acres~Hot Tub, Fire Pit

Reagan’s Retreat~ Farmhouse Cottage on 45 acres~Hot Tub, Fire Pit
Glade Hill
10.0 out of 10, Exceptional, (83 reviews)
"We had a great time staying here. The host was very responsive and accommodating. The next time we need a place in this area we will rebook it. "
United States
Kenneth H.
$264 nightly
The price is $297
Sep 7 - Sep 8
Total with taxes and fees
Reagan’s Retreat~ Farmhouse Cottage on 45 acres~Hot Tub, Fire Pit
A modern living room with a grey sofa, blue ottoman, and two armchairs. There is a TV on a wooden stand, a round mirror, and a lamp on a side table.

12. Walk to Caesars Casino | 3BR Home w/King Bed

Walk to Caesars Casino | 3BR Home w/King Bed
Danville
10.0 out of 10, Exceptional, (2 reviews)
"The house was clean and closely located to the casino"
United States
Nefertiti H.
$474 nightly
The price is $545
Sep 7 - Sep 8
Total with taxes and fees
Walk to Caesars Casino | 3BR Home w/King Bed
A hot tub with a bottle and glasses, surrounded by a wooden fence and a rural landscape.

13. Private Farm Cottage surrounded fields, farm animals, mountain views & hot tub!

Private Farm Cottage surrounded fields, farm animals, mountain views & hot tub!
Glade Hill
10.0 out of 10, Exceptional, (18 reviews)
"Really nice farm, house is clean and nicely set up, and we loved the animals!"
United States
Janet W.
$457 nightly
The price is $513
Sep 6 - Sep 7
Total with taxes and fees
Private Farm Cottage surrounded fields, farm animals, mountain views & hot tub!
A balcony with a view of a lake, grassy areas, and distant mountains.

14. Sailors Landing~ Lake/Beach front condo with ample amenities!

Sailors Landing~ Lake/Beach front condo with ample amenities!
Moneta
10.0 out of 10, Exceptional, (2 reviews)
"The condo was exceptionally charming! Everything was clean and comfortable. The morning and afternoon views were amazing. So close and convenient to Napoli's for dinner. "
United States
Eugene J.
$320 nightly
The price is $359
Sep 14 - Sep 15
Total with taxes and fees
Sailors Landing~ Lake/Beach front condo with ample amenities!
A living room with a sofa, a coffee table, and a potted plant.

15. Insta-worthy 2Bd/1Ba Apt | Minutes from Downtown!

Insta-worthy 2Bd/1Ba Apt | Minutes from Downtown!
Danville
10.0 out of 10, Exceptional, (7 reviews)
"Great unit, thoroughly enjoyed staying here."
United States
Joseph M.
$264 nightly
The price is $307
Sep 30 - Oct 1
Total with taxes and fees
Insta-worthy 2Bd/1Ba Apt | Minutes from Downtown!
A wooden dock extending into a river with a kayak on it, a covered area with outdoor seating, and a building with a porch.

16. Shangri-La -dogs friendly, firepit, wifi, 2 kayaks, 2 kitchens, and a Pool Table

Shangri-La -dogs friendly, firepit, wifi, 2 kayaks, 2 kitchens, and a Pool Table
Huddleston
9.8 out of 10, Exceptional, (39 reviews)
"Was a wonderful vacation. Home was great. Dock was great. Location on the lake was great. Nothing bad at all to say."
United States
Andy S.
$730 nightly
The price is $820
Sep 30 - Oct 1
Total with taxes and fees
Shangri-La -dogs friendly, firepit, wifi, 2 kayaks, 2 kitchens, and a Pool Table
A lakeside residential area with multiple houses and a boat dock.

17. The full Smith Mountain Lakefront experience: private boat slip, 3 balconies, game room, community pool & beach, propane grill, and pets welcome. No resort fees, ever.

The full Smith Mountain Lakefront experience: private boat slip, 3 balconies, game room, community pool & beach, propane grill, and pets welcome. No resort fees, ever.
Huddleston
10.0 out of 10, Exceptional, (17 reviews)
"A wonderful experience! Every aspect of the experience was a very smooth process. Property was exceptionally clean, comfortable and well maintained. Location was perfect. Would highly recommend this property and host."
United States
DENISE L.
$613 nightly
The price is $696
Sep 13 - Sep 14
Total with taxes and fees
The full Smith Mountain Lakefront experience: private boat slip, 3 balconies, game room, community pool & beach, propane grill, and pets welcome. No resort fees, ever.
A race track with multiple cars, a Coca-Cola advertisement, and a row of houses in the background.

18. Chic Haven: 2b/1bath in the Heart of Danville

Chic Haven: 2b/1bath in the Heart of Danville
Danville
10.0 out of 10, Exceptional, (2 reviews)
"This is a beautiful apartment, it has everything you need to enjoy your business trip. I will definitely stay here again, great location!"
United States
Justin L.
$255 nightly
The price is $297
Sep 30 - Oct 1
Total with taxes and fees
Chic Haven: 2b/1bath in the Heart of Danville
A well-equipped RV interior with a dining area, kitchenette, and seating space.

19. Located in beautiful Lynch Station Va this property offers an amazing escape.

Located in beautiful Lynch Station Va this property offers an amazing escape.
Lynch Station
9.4 out of 10, Exceptional, (3 reviews)
"Wonderful! Was only here overnight but loved it! Will definitely return"
United States
michele p.
$169 nightly
The price is $189
Sep 9 - Sep 10
Total with taxes and fees
Located in beautiful Lynch Station Va this property offers an amazing escape.

20. #2100 Pointe - Studio Suite at Mariners SML

#2100 Pointe - Studio Suite at Mariners SML
Bedford County
9.4 out of 10, Exceptional, (9 reviews)
"The room was clean and cozy. Exactly what we were looking for. We will definitely stay again. "
United States
Tia
$238 nightly
The price is $266
Sep 8 - Sep 9
Total with taxes and fees
#2100 Pointe - Studio Suite at Mariners SML
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chatham Hotel Reviews

Courtyard by Marriott Danville

Courtyard by Marriott Danville

10/10 Excellent
"Ice machine was full of mold not good in my drinks. Clean them please"
Brian 1-night trip
Posted 1 hour ago
Courtyard by Marriott Danville

Find out more about Chatham

Everything you need to know about Chatham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chatham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chatham vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chatham vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chatham. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chatham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $282 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chatham rentals

At Expedia, we put the best Chatham vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chatham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chatham vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chatham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Chatham?

Yes, we have vacation rentals close to well known sights in Chatham, or you can choose a more secluded option if you want a relaxing place to stay. Chatham is known for its sporting events and shopping. Make sure you have time to check out the restaurants and wineries during your trip.

What are some of the best vacation home rentals that Chatham has to offer?

Beautiful lakeside family or corporate retreat with pool, hot tub, and more!: This vacation home near Chatham is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals will I find in Chatham?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Chatham stay.

What can I see and do in Chatham?

While exploring the area, visit family-friendly sights like Danville Science Center, or get outside and enjoy nature at Leesville Lake. In the larger area, you’ll find Tomahawk Mill Vineyard and Winery and Danville Mall.

What are vacation rentals like in Chatham?

Vacation rentals are privately owned accommodations you can stay in for a couple days or more in Chatham. Vacation rentals offer extras like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a family trip or a small group gathering.