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

Holiday Homes in Chatham

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Chatham holiday homes

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, (48 reviews)
"Very peaceful and quiet, which was very nice. Outside was very nice to look at in the morning!"
United States
Lance S.
The price is €351
includes taxes & fees
7 Oct - 8 Oct
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, (54 reviews)
"Nice place ! "
United States
Pattie C.
The price is €301
includes taxes & fees
30 Sept - 1 Oct
Located in Historic Old West End. Minutes from the River District and Casino.
A kitchen with a stainless steel refrigerator, wooden cabinets, a sink, and a door with a 'blessed' sign.

3. The Country Estate #1 Tranquil 1BR estate perfect for a relaxing getaway.

The Country Estate #1 Tranquil 1BR estate perfect for a relaxing getaway.
Danville
The price is €148
includes taxes & fees
20 Oct - 21 Oct
The Country Estate #1 Tranquil 1BR estate perfect for a relaxing getaway.
A dining area with a dark wooden table, a chair, a wall clock, a framed picture, and a wall-mounted light fixture.

4. 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 €439
includes taxes & fees
28 Sept - 29 Sept
Walking Distance to Casino
A room with large windows, a fireplace, a coffee table, and two white armchairs.

5. Zen at Marker 10~ Lakefront Home with Hot Tub!

Zen at Marker 10~ Lakefront Home with Hot Tub!
Pittsville
10.0 out of 10, Exceptional, (1 review)
"Love this place! Such a beautiful environment and the communication was amazing!"
United States
Abigail A.
Zen at Marker 10~ Lakefront Home with Hot Tub!
A wooden dock extending into a river with a kayak on it, a covered area with outdoor seating, and a building with a porch.

6. 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, (43 reviews)
"Loved our stay. The property was perfect for our needs. As a family of cooks we LOVED the well appointed kitchen!"
United States
Elizabeth H.
The price is €712
includes taxes & fees
29 Sept - 30 Sept
Shangri-La -dogs friendly, firepit, wifi, 2 kayaks, 2 kitchens, and a Pool Table
A living room with a black leather sofa, two side chairs, a wooden coffee table, and a ceiling fan.

7. Family Friendly 3BR with hot tub and sand pit!

Family Friendly 3BR with hot tub and sand pit!
Glade Hill
The price is €423
includes taxes & fees
29 Sept - 30 Sept
Family Friendly 3BR with hot tub and sand pit!
A blue door with a window, a welcome sign, and a patterned rug.

8. Private Guesthouse w/Kitchen - Minutes from Uptown

Private Guesthouse w/Kitchen - Minutes from Uptown
Martinsville
9.8 out of 10, Exceptional, (36 reviews)
"Great place to stay!"
United States
Sherri F.
The price is €148
includes taxes & fees
27 Sept - 28 Sept
Private Guesthouse w/Kitchen - Minutes from Uptown
A cozy room with a wooden paneled wall, a red sofa, a glass coffee table with a candle, and a flat-screen TV displaying a cityscape.

9. Cozy Farm Stay-3 Bedroom House in Lynch Station

Cozy Farm Stay-3 Bedroom House in Lynch Station
Lynch Station
10.0 out of 10, Exceptional, (3 reviews)
"It was clean, Hist was responsive, and seemed to care about your stay. "
United States
Joshua C.
The price is €242
includes taxes & fees
6 Oct - 7 Oct
Cozy Farm Stay-3 Bedroom House in Lynch Station
A spacious living room with a large TV, a red sofa, and a patterned rug.

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

Iconic Church Turned Unique Stay (Casino/VIR)
Danville
10.0 out of 10, Exceptional, (13 reviews)
"We really enjoyed our stay!"
United States
Connie R.
The price is €570
includes taxes & fees
27 Sept - 28 Sept
Iconic Church Turned Unique Stay (Casino/VIR)
A two-story house with a balcony, a flag, and a staircase leading to the entrance.

11. Hudson Haven Lakefront w Private Dock + Firepit Sleeps 8 Quiet Cove

Hudson Haven Lakefront w Private Dock + Firepit Sleeps 8 Quiet Cove
Huddleston
9.8 out of 10, Exceptional, (36 reviews)
"Loved this place! So peaceful and relaxing! "
United States
Anonymous traveller
The price is €538
includes taxes & fees
30 Sept - 1 Oct
Hudson Haven Lakefront w Private Dock + Firepit Sleeps 8 Quiet Cove
A lakeside residential area with multiple houses and a boat dock.

12. 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.
The price is €594
includes taxes & fees
26 Oct - 27 Oct
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 swimming pool with stone walls and a covered patio area.

13. Oasis Pool OPEN YEAR ROUND Private Fire Pit Modern Views

Oasis Pool OPEN YEAR ROUND Private Fire Pit Modern Views
Martinsville
9.8 out of 10, Exceptional, (26 reviews)
"Everything was fantastic "
United States
Erica B.
The price is €245
includes taxes & fees
27 Sept - 28 Sept
Oasis Pool OPEN YEAR ROUND Private Fire Pit Modern Views
A fire pit with chairs and lanterns in a nighttime outdoor setting.

14. Orchard Acres Farm Barnhouse

Orchard Acres Farm Barnhouse
Bassett
10.0 out of 10, Exceptional, (41 reviews)
"Beautiful property and home. I wish we could’ve stayed longer but this was just a short trip. The hosts were very helpful and communicative. Would definitely stay here again. "
United States
Jody P.
The price is €252
includes taxes & fees
4 Oct - 5 Oct
Orchard Acres Farm Barnhouse
A cozy living room with a brown leather sofa, a tan armchair, and a round coffee table.

15. Giggling Creek Cottage: 45 Acres of Rural Bliss, BedJet, Arcades + Pet Friendly

Giggling Creek Cottage: 45 Acres of Rural Bliss, BedJet, Arcades + Pet Friendly
Bassett
9.8 out of 10, Exceptional, (34 reviews)
"Great place to stay with a very responsive host"
United States
Jeremy A.
The price is €226
includes taxes & fees
4 Oct - 5 Oct
Giggling Creek Cottage: 45 Acres of Rural Bliss, BedJet, Arcades + Pet Friendly
A balcony with a glass table, a bottle of wine, and a chair.

16. Lakefront Retreat at Smith Mountain Lake. Covered Boat Slip + Kayaks

Lakefront Retreat at Smith Mountain Lake. Covered Boat Slip + Kayaks
Moneta
9.8 out of 10, Exceptional, (58 reviews)
"Great Stay!"
United States
Owen B.
The price is €556
includes taxes & fees
16 Oct - 17 Oct
Lakefront Retreat at Smith Mountain Lake. Covered Boat Slip + Kayaks

17. Lakefront |Deck |Fire Pit | Dock| Charcoal Grill

Lakefront |Deck |Fire Pit | Dock| Charcoal Grill
Union Hall
The price is €433
includes taxes & fees
4 Oct - 5 Oct
Lakefront |Deck |Fire Pit | Dock| Charcoal Grill
A two-story house with a porch, a staircase, and a small garden.

18. The Humble House-2-bedroom, 2 Bath house in Uptown Martinsville

The Humble House-2-bedroom, 2 Bath house in Uptown Martinsville
Martinsville
The price is €224
includes taxes & fees
26 Oct - 27 Oct
The Humble House-2-bedroom, 2 Bath house in Uptown Martinsville
A covered patio with wicker furniture, a fire pit, and a view of a green landscape.

19. Clean, Convenient and Comfortable 3BR home

Clean, Convenient and Comfortable 3BR home
Collinsville
10.0 out of 10, Exceptional, (11 reviews)
"Had everything we needed and more! "
United States
Kristen F.
The price is €268
includes taxes & fees
26 Oct - 27 Oct
Clean, Convenient and Comfortable 3BR home
An outdoor patio with a sofa, chairs, and a table, overlooking a lake and surrounded by trees.

20. Luxury Lakefront, Hot Tub, Fire Table and Theatre

Luxury Lakefront, Hot Tub, Fire Table and Theatre
Huddleston
9.8 out of 10, Exceptional, (15 reviews)
"Great location and beautiful house. Would stay again!"
United States
Catherine K.
Luxury Lakefront, Hot Tub, Fire Table and Theatre
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chatham Hotel Reviews

Sleep Inn & Suites Danville Hwy 58

Sleep Inn & Suites Danville Hwy 58

8/10 Good
"The room was very clean. The staff was friendly and helpful."
Carl 1-night trip
Posted 8 hours ago
Sleep Inn & Suites Danville Hwy 58

Find out more about Chatham

Chatham Holiday Homes information

Number of reviews
436
Accommodation
610 Holiday Homes
Lowest Price
€148
Highest Price
€712