Chatham Holiday Rentals

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Our top choices for Chatham holiday rentals

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
9.8 out of 10, Exceptional, (43 reviews)
"Perfect location to the casino and restaurants. We loved our stay. "
United States
Gail
The price is HK$1,269
HK$2,476 total
includes taxes & fees
26 Apr - 27 Apr
Located in Historic Old West End. Minutes from the River District and Casino.

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
The price is HK$1,079
HK$3,640 total
includes taxes & fees
28 Apr - 29 Apr
Walking Distance to Casino

Charming remodeled historic home in the small town of South Boston, Virginia.

Charming remodeled historic home in the small town of South Boston, Virginia.
South Boston
10.0 out of 10, Exceptional, (6 reviews)
"The property was not available, but the owner took great care of us and made sure that we had everything we needed. The owner was great and we were well pleased. "
United States
Ricky L.
The price is HK$1,417
HK$2,661 total
includes taxes & fees
4 May - 5 May
Charming remodeled historic home in the small town of South Boston, Virginia.

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
9.4 out of 10, Exceptional, (16 reviews)
"It was a nice location for us while in town for a funeral and visiting family in the area. It was everything we needed for our brief stay."
United States
William P.
The price is HK$656
HK$1,641 total
includes taxes & fees
27 Apr - 28 Apr
Tiny House - 6 miles from Averett University and 5.4 miles from Caesars Virginia

Amazing Views and Two Kayaks Ready to Use!

Amazing Views and Two Kayaks Ready to Use!
Moneta
10.0 out of 10, Exceptional, (101 reviews)
"Great location…plenty of amenities. A great getaway, sabbatical, or recharge. Peaceful and "
United States
John Paul J.
The price is HK$1,107
HK$1,639 total
includes taxes & fees
26 Apr - 27 Apr
Amazing Views and Two Kayaks Ready to Use!

Boat, fish, golf, swim, & dine at Mariners Landing on Smith Mountain Lake!

Boat, fish, golf, swim, & dine at Mariners Landing on Smith Mountain Lake!
Huddleston
10.0 out of 10, Exceptional, (27 reviews)
"Excellent stay. Host was very accommodating on a last minute weekend getaway booking. Love this location on SML."
United States
Amy C.
The price is HK$775
HK$2,102 total
includes taxes & fees
27 Apr - 28 Apr
Boat, fish, golf, swim, & dine at Mariners Landing on Smith Mountain Lake!

Charming Country Cottage- Long Term Stays Welcome!

Charming Country Cottage- Long Term Stays Welcome!
Eden
7.8 out of 10, Good, (6 reviews)
"Clean place. Very good communication. Only issue is parking Hard getting in and out especially with bigger vehicles when someone is parked right along house. Know that if you are tall person you may fill cramped/ claustrophobic as cealings are sloped."
United States
Craig
The price is HK$691
HK$1,563 total
includes taxes & fees
26 Apr - 27 Apr
Charming Country Cottage- Long Term Stays Welcome!

Church of the Perpetual Boogie: near VIR & Casino

Church of the Perpetual Boogie: near VIR & Casino
Danville
10.0 out of 10, Exceptional, (10 reviews)
"We really enjoyed our stay!"
United States
Connie R.
The price is HK$1,762
HK$3,837 total
includes taxes & fees
27 Apr - 28 Apr
Church of the Perpetual Boogie: near VIR & Casino

Book early for 2025 at Birds Eye View in Bernards Landing w lake access

Book early for 2025 at Birds Eye View in Bernards Landing w lake access
Moneta
10.0 out of 10, Exceptional, (132 reviews)
"Excellent location and property! Well equipped, clean, and even had some toys there for our two children to enjoy. Host was very responsive and directions were straightforward, would highly recommended and look forward to coming again!"
United States
Adam B.
The price is HK$1,245
HK$3,360 total
includes taxes & fees
27 Apr - 28 Apr
Book early for 2025 at Birds Eye View in Bernards Landing w lake access

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, (42 reviews)
"Beautiful place and super responsive host! Highly recommended!"
United States
Lauren G.
The price is HK$1,057
HK$2,331 total
includes taxes & fees
26 Apr - 27 Apr
Cozy Lakefront Condo with Kayaks at Bernard's Landing on Smith Mountain Lake

Cozy midtown 3 bedroom/1 bath

Cozy midtown 3 bedroom/1 bath
Danville
10.0 out of 10, Exceptional, (2 reviews)
"Great stay! Misty was very welcoming. Will definitely visit again!"
United States
Hope B.
The price is HK$931
HK$3,657 total
includes taxes & fees
26 Apr - 27 Apr
Cozy midtown 3 bedroom/1 bath

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, (16 reviews)
"Quiet, well appointed place with a beautiful view. "
United States
Steve V.
The price is HK$1,410
HK$2,568 total
includes taxes & fees
2 May - 3 May
One room cabin set on our farm for a peaceful getaway.

Insta-worthy 2Bd/1Ba Apt Steps from Downtown!

Insta-worthy 2Bd/1Ba Apt Steps from Downtown!
Danville
10.0 out of 10, Exceptional, (3 reviews)
"Great unit, thoroughly enjoyed staying here."
United States
Joseph M.
The price is HK$784
HK$2,066 total
includes taxes & fees
27 Apr - 28 Apr
Insta-worthy 2Bd/1Ba Apt Steps from Downtown!

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, (78 reviews)
"We had great communication from host and we had a blast.got to explore the property. Found me some new rocks and the hot tub was private. Would definitely stay again. If you love the outdoors go stay here."
United States
Sherry T.
The price is HK$1,077
HK$2,344 total
includes taxes & fees
28 Apr - 29 Apr
Reagan’s Retreat~ Farmhouse Cottage on 45 acres~Hot Tub, Fire Pit

Avalon Cottage w/ hot tub

Avalon Cottage w/ hot tub
Danville
10.0 out of 10, Exceptional, (7 reviews)
"Hot tub is the #1 draw, then the affordability and location. This is my 2nd stay and I hope to stay here again next yr. Great timely response to communications"
United States
Deb Deborah W.
The price is HK$1,551
HK$4,361 total
includes taxes & fees
12 May - 13 May
Avalon Cottage w/ hot tub

#322 Pointe - 2 Bedroom Lakefront Condo at Mariners SML

#322 Pointe - 2 Bedroom Lakefront Condo at Mariners SML
Huddleston
9.6 out of 10, Exceptional, (10 reviews)
"We really enjoyed our stay!"
United States
Jill G.
The price is HK$2,089
HK$4,373 total
includes taxes & fees
26 Apr - 27 Apr
#322 Pointe - 2 Bedroom Lakefront Condo at Mariners SML

MV37 Corner Waterfront Mariners: 2 Bedroom

MV37 Corner Waterfront Mariners: 2 Bedroom
Bedford County
10.0 out of 10, Exceptional, (4 reviews)
"I would stay here again. "
United States
Zarela J.
The price is HK$1,717
HK$3,880 total
includes taxes & fees
30 Apr - 1 May
MV37 Corner Waterfront Mariners: 2 Bedroom

FULLY updated: Step-Free access 2BR2BA 2King & 1 queen. BEAUTIFUL & Pet friendly

FULLY updated: Step-Free access 2BR2BA 2King & 1 queen. BEAUTIFUL & Pet friendly
Huddleston
9.8 out of 10, Exceptional, (8 reviews)
"Lovely condo with fantastic water views. Lots of space for the family, we love this location and would definitely come back "
United States
Christie H.
The price is HK$1,008
HK$2,654 total
includes taxes & fees
11 May - 12 May
FULLY updated: Step-Free access 2BR2BA 2King & 1 queen. BEAUTIFUL & Pet friendly

10 minutes from VIR. Great bass fishing! Rustic cottage on large private pond.

10 minutes from VIR. Great bass fishing! Rustic cottage on large private pond.
Alton
10.0 out of 10, Exceptional, (1 review)
"We came down for an event at VIR. The hosts were fantastic and the home was lovely. Will be back!"
United States
Chris N.
The price is HK$3,525
HK$5,880 total
includes taxes & fees
14 May - 15 May
10 minutes from VIR. Great bass fishing! Rustic cottage on large private pond.

Heron’s Cove on Leesville Lake.

Heron’s Cove on Leesville Lake.
Gretna
8.4 out of 10, Very good, (14 reviews)
"Very nice and loved the view of the lake! "
United States
Lee W.
The price is HK$1,304
HK$2,631 total
includes taxes & fees
27 Apr - 28 Apr
Heron’s Cove on Leesville Lake.
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

Find out more about Chatham

Search for holiday rentals in Chatham on Expedia! You can easily find your home rentals, villas, holiday apartments in Chatham using one of the methods below:

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Look no further and take a look at our great range of rental properties in Chatham!

Frequently asked questions

Can I find holiday rentals in Chatham?

Yes, there are holiday rentals close to the most popular sights in Chatham, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Chatham has to offer?

Tranquil Shores Estate, Luxury Lakefront Compound w/ Heated Salt Pool, Hot Tub, Dock!: This holiday home rental outside of Chatham is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 9 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with an arcade/games room and 1 hot tub.

How many holiday rentals will I find in Chatham?

With 3 Expedia holiday rentals, you're guaranteed 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 Danville's Riverwalk Trail. In the wider area, you’ll find Tomahawk Mill Vineyard and Winery and Danville Mall.

What are holiday rentals like in Chatham?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chatham. Holiday rentals offer extras such as patios, hot tubs and fire pits so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a family getaway.