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

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Chatham vacation 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, (46 reviews)
"You get exactly what is listed. The host was very helpful. Location is amazing. Highly recommended. Just take some lysol wipes. "
United States
Shannon W.
The price is ￥25,317
￥63,082 total
includes taxes & fees
Aug 25 - Aug 26
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.
The price is ￥25,633
￥54,551 total
includes taxes & fees
Aug 23 - Aug 24
Located in Historic Old West End. Minutes from the River District and Casino.
A modern living room with a sofa, a coffee table, a TV, and a sliding glass door leading to an outdoor area.

3. 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, (17 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.
The price is ￥14,593
￥34,962 total
includes taxes & fees
Sep 20 - Sep 21
Tiny House - 6 miles from Averett University and 5.4 miles from Caesars Virginia
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 ￥25,633
￥80,374 total
includes taxes & fees
Aug 24 - Aug 25
Walking Distance to Casino
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.

5. 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 ￥21,361
￥43,713 total
includes taxes & fees
Sep 2 - Sep 3
Cozy Farm Stay-3 Bedroom House in Lynch Station
A blue door with a window, a welcome sign, and a patterned rug.

6. Private Guesthouse w/Kitchen - Minutes from Uptown

Private Guesthouse w/Kitchen - Minutes from Uptown
Martinsville
9.8 out of 10, Exceptional, (35 reviews)
"Great place to stay!"
United States
Sherri F.
The price is ￥14,241
￥25,121 total
includes taxes & fees
Aug 23 - Aug 24
Private Guesthouse w/Kitchen - Minutes from Uptown
A wooden dock extending into a river with a kayak on it, a covered area with outdoor seating, and a building with a porch.

7. 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, (37 reviews)
"We enjoyed our stay at this home as we were in the area for our son’s graduation from Liberty! The size of the home fit our family perfectly and the layout was just great! We were so busy with graduation activities that we weren’t able to enjoy the lake much, but we know it would be the perfect spot for an SML family vacation! Thanks for a wonderful stay! "
United States
Caroline T.
The price is ￥42,919
￥136,740 total
includes taxes & fees
Sep 14 - Sep 15
Shangri-La -dogs friendly, firepit, wifi, 2 kayaks, 2 kitchens, and a Pool Table
A cozy living room with a brown leather sofa, a tan armchair, and a round coffee table.

8. 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, (33 reviews)
"Great place to stay with a very responsive host"
United States
Jeremy A.
The price is ￥14,044
￥38,985 total
includes taxes & fees
Sep 16 - Sep 17
Giggling Creek Cottage: 45 Acres of Rural Bliss, BedJet, Arcades + Pet Friendly
A fire pit with chairs and lanterns in a nighttime outdoor setting.

9. Orchard Acres Farm Barnhouse

Orchard Acres Farm Barnhouse
Bassett
10.0 out of 10, Exceptional, (38 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 ￥21,994
￥45,490 total
includes taxes & fees
Sep 1 - Sep 2
Orchard Acres Farm Barnhouse
A lakeside residential area with multiple houses and a boat dock.

10. 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 ￥33,819
￥107,260 total
includes taxes & fees
Aug 23 - Aug 24
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 spacious living room with a large TV, a red sofa, and a patterned rug.

11. 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.
The price is ￥51,569
￥92,756 total
includes taxes & fees
Aug 23 - Aug 24
Iconic Church Turned Unique Stay (Casino/VIR)
A two-story house with a balcony, a flag, and a staircase leading to the entrance.

12. 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, (35 reviews)
"Loved this place! So peaceful and relaxing! "
United States
Anonymous traveler
The price is ￥54,923
￥121,185 total
includes taxes & fees
Sep 2 - Sep 3
Hudson Haven Lakefront w Private Dock + Firepit Sleeps 8 Quiet Cove
A two-story house with a porch, a staircase, and a small garden.

13. 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 ￥21,219
￥37,156 total
includes taxes & fees
Aug 23 - Aug 24
The Humble House-2-bedroom, 2 Bath house in Uptown Martinsville
A balcony with a glass table, a bottle of wine, and a chair.

14. 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, (57 reviews)
"Great Stay!"
United States
Owen B.
The price is ￥34,890
￥82,362 total
includes taxes & fees
Sep 1 - Sep 2
Lakefront Retreat at Smith Mountain Lake. Covered Boat Slip + Kayaks
A room with a brick wall, a white door with glass panels, a small white table with a lamp, and a sofa with patterned cushions.

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

Lakefront |Deck |Fire Pit | Dock| Charcoal Grill
Union Hall
The price is ￥47,469
￥79,848 total
includes taxes & fees
Aug 23 - Aug 24
Lakefront |Deck |Fire Pit | Dock| Charcoal Grill
A swimming pool with stone walls and a covered patio area.

16. 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, (24 reviews)
"Everything was fantastic "
United States
Erica B.
The price is ￥29,757
￥45,197 total
includes taxes & fees
Sep 3 - Sep 4
Oasis Pool OPEN YEAR ROUND Private Fire Pit Modern Views
A covered patio with wicker furniture, a fire pit, and a view of a green landscape.

17. 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 ￥22,595
￥48,924 total
includes taxes & fees
Aug 30 - Aug 31
Clean, Convenient and Comfortable 3BR home
An outdoor patio with a sofa, chairs, and a table, overlooking a lake and surrounded by trees.

18. 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.
The price is ￥69,115
￥174,816 total
includes taxes & fees
Sep 2 - Sep 3
Luxury Lakefront, Hot Tub, Fire Table and Theatre
A modern interior with a wooden floor, a staircase with black railings, and a kitchen area in the background.

19. Family Lakefront Oasis - Dock, Cabana, Game Room

Family Lakefront Oasis - Dock, Cabana, Game Room
Moneta
9.0 out of 10, Wonderful, (12 reviews)
"Great stay! There was plenty of parking. The place was peaceful and had spacious bedrooms. "
United States
Katherin R.
The price is ￥42,748
￥100,131 total
includes taxes & fees
Sep 21 - Sep 22
Family Lakefront Oasis - Dock, Cabana, Game Room
A wooden dock with chairs and a table, overlooking a calm lake with trees and buildings in the background.

20. Quiet Cove-Hot Tub l Dock| Kayak| Fire Pit l Grill

Quiet Cove-Hot Tub l Dock| Kayak| Fire Pit l Grill
Goodview
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay at Smith Mountain Lake! The home was spacious and inviting, and access to the water was great! We rented a Pontoon boat for the week from Indian Point Marina. The beds were soft and cozy, and we slept really well. The kitchen was well appointed and made family meal time enjoyable. The decks and views were so relaxing. The mature trees provided shade for the outdoor space without obstructing the view. Just the right amount of privacy! We will definitely stay here...
United States
Catherine H.
The price is ￥63,292
￥124,832 total
includes taxes & fees
Aug 24 - Aug 25
Quiet Cove-Hot Tub l Dock| Kayak| Fire Pit l Grill
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

The Holbrook Hotel

The Holbrook Hotel

10/10 Excellent
"First time staying there. Will definitely stay again."
Charles 1-night trip
Posted 4 hours ago
The Holbrook Hotel

Find out more about Chatham

Chatham Vacation Homes information

Number of reviews
406
Accommodation
618 Vacation Homes
Lowest Price
￥25,121
Highest Price
￥174,816