Book Holiday Homes in Chatham

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Chatham

Waterfront home with deep water, skiing/tubing coves, firepit, pool table, SUP

Waterfront home with deep water, skiing/tubing coves, firepit, pool table, SUP

Moneta
Stay at this vacation home in Moneta. Enjoy free WiFi, a pool table, and patios. Popular attractions Smith Mountain Lake and Virginia Dare Cruises & Marina are ...
Waterfront home with deep water, skiing/tubing coves, firepit, pool table, SUP
Foothills Retreat, New Lakefront Luxury w/ Covered Decks + Hot Tub, Fire Pit Terrace, Dock & More!

Foothills Retreat, New Lakefront Luxury w/ Covered Decks + Hot Tub, Fire Pit Terrace, Dock & More!

Moneta
Stay at this vacation home in Moneta. Enjoy a pool table, balconies, and cable/satellite TV service. Popular attractions Smith Mountain Lake and Hickory Hill ...
Foothills Retreat, New Lakefront Luxury w/ Covered Decks + Hot Tub, Fire Pit Terrace, Dock & More!
Waterfront-Large Dock-Quiet Cove- Minutes to Drifters-Bridgewater Marina

Waterfront-Large Dock-Quiet Cove- Minutes to Drifters-Bridgewater Marina

Moneta
Book a stay at this family-friendly vacation home in Moneta. Enjoy free WiFi, a garden, and a pool table. Popular attractions Smith Mountain Lake and Crystal ...
Waterfront-Large Dock-Quiet Cove- Minutes to Drifters-Bridgewater Marina
Save an average of 15% on thousands of hotels when you're signed in
LAKEside Sunsets: Lakehouse w/ Private Dock

LAKEside Sunsets: Lakehouse w/ Private Dock

Moneta
Book a stay at this family-friendly vacation home in Moneta. Enjoy concierge services, a pool table, and patios. Popular attractions Waterwheel Marina and Bridgewater ...
LAKEside Sunsets: Lakehouse w/ Private Dock
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
The price is NZ$486 per night from 4 Apr to 5 Apr
NZ$486
includes taxes & fees
4 Apr - 5 Apr
Stay at this vacation home in Danville. Enjoy free WiFi and air conditioning. Popular attractions Caesars Virginia Casino and Danville Museum of Fine Arts are ...
Located in Historic Old West End. Minutes from the River District and Casino.
Sweet By and By... Your Escape to the Beauty of Smith Mountain Lake

Sweet By and By... Your Escape to the Beauty of Smith Mountain Lake

Huddleston
Stay at this vacation home in Huddleston. Enjoy free WiFi, patios, and Netflix. Popular attractions Smith Mountain Lake and Smith Mountain Lake State Park are ...
Sweet By and By... Your Escape to the Beauty of Smith Mountain Lake
Lake Paradise! Hot Tub/Pool/WIFI/Grills/Private Dock/Kayaks/SUP/Fireplaces

Lake Paradise! Hot Tub/Pool/WIFI/Grills/Private Dock/Kayaks/SUP/Fireplaces

Moneta
Book a stay at this ski vacation home in Moneta. Enjoy free WiFi, private pools, and a garden. Popular attractions Halesford Harbor Marina and Webster Marine ...
Lake Paradise! Hot Tub/Pool/WIFI/Grills/Private Dock/Kayaks/SUP/Fireplaces
Unwind & Reel 'em Inn -Lakefront House at Smith Mountain Lake, near VT & Liberty

Unwind & Reel 'em Inn -Lakefront House at Smith Mountain Lake, near VT & Liberty

Moneta
Stay at this vacation home in Moneta. Enjoy free WiFi, a garden, and a pool table. Popular attractions Webster Marine Center and Bridgewater Plaza are located ...
Unwind & Reel 'em Inn -Lakefront House at Smith Mountain Lake, near VT & Liberty
PEACEFUL LAKEFRONT TOWNHOME WITH BOAT SLIP AND DOCK

PEACEFUL LAKEFRONT TOWNHOME WITH BOAT SLIP AND DOCK

Moneta
The price is NZ$899 per night from 12 Apr to 13 Apr
NZ$899
includes taxes & fees
12 Apr - 13 Apr
Book a stay at this family-friendly vacation home in Moneta. Enjoy free WiFi, a garden, and patios. Popular attractions Smith Mountain Lake and Bayside Marina ...
PEACEFUL LAKEFRONT TOWNHOME WITH BOAT SLIP AND DOCK
Don't see what you're looking for?
See all available properties in Chatham
View all properties
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.

Chatham Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chatham vacation homes are the perfect way for you to wing it.

Holiday houses in Chatham let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chatham in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chatham adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chatham with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chatham vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Chatham Holiday Homes essential information

Accommodation
468 Holiday Homes
Lowest Price
NZ$165
Highest Price
NZ$899
Popular accommodation
Waterfront home with deep water, skiing/tubing coves, firepit, pool table, SUP, Foothills Retreat, New Lakefront Luxury w/ Covered Decks + Hot Tub, Fire Pit Terrace, Dock & More!, Waterfront-Large Dock-Quiet Cove- Minutes to Drifters-Bridgewater Marina, LAKEside Sunsets: Lakehouse w/ Private Dock, Located in Historic Old West End. Minutes from the River District and Casino., Sweet By and By... Your Escape to the Beauty of Smith Mountain Lake, Lake Paradise! Hot Tub/Pool/WIFI/Grills/Private Dock/Kayaks/SUP/Fireplaces, Unwind & Reel 'em Inn -Lakefront House at Smith Mountain Lake, near VT & Liberty, PEACEFUL LAKEFRONT TOWNHOME WITH BOAT SLIP AND DOCK

Top trending hotels in Chatham

Spacious Countryside Cabin w/Hot Tub and Firepit

Spacious Countryside Cabin w/Hot Tub and Firepit

Chatham
Stay at this vacation home in Chatham. Enjoy free WiFi and an in-room coffeemaker. Popular attraction Tomahawk Mill Vineyard and Winery is located nearby.
Spacious Countryside Cabin w/Hot Tub and Firepit
Riverside Inn & Suites by OYO Danville Ceaser Casino

Riverside Inn & Suites by OYO Danville Ceaser Casino

2.5 out of 5
2500 Riverside Dr, Danville, VA
Fully refundableReserve now, pay when you stay
The price is NZ$165 per night from 4 Apr to 5 Apr
NZ$165
includes taxes & fees
4 Apr - 5 Apr
Stay at this hotel in Danville. Enjoy free WiFi, free parking, and room service. Popular attractions Caesars Virginia Casino and Danville Mall are located ...
Riverside Inn & Suites by OYO Danville Ceaser Casino
Caesars Virginia

Caesars Virginia

3.5 out of 5
1100 W. Main Street, Danville, VA
The price is NZ$504 per night from 6 Apr to 7 Apr
NZ$504
includes taxes & fees
6 Apr - 7 Apr
Stay at this 3.5-star spa hotel in Danville. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Caesars Virginia Casino and Ballou Park ...
Caesars Virginia
Save an average of 15% on thousands of hotels when you're signed in
The Bee Hotel Danville

The Bee Hotel Danville

2.5 out of 5
420 Patton St, Danville, VA
Fully refundableReserve now, pay when you stay
The price is NZ$248 per night from 6 Apr to 7 Apr
NZ$248
includes taxes & fees
6 Apr - 7 Apr
Stay at this hotel in Danville. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions ...
The Bee Hotel Danville
Don't see what you're looking for?
See all available properties in Chatham
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.