Photo by Susie Edwards

Search Vacation Homes in Jamestown

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Vacation Homes in Jamestown

Fridge, microwave, oven, stovetop
Historic Union Chapel Elementary School near Cumberland River & Lake

Vacation Home in Jamestown

10.0 out of 10, Exceptional, (43)
"Great place to stay"
United States
Joseph G.
The price is AED 367
AED 486 total
includes taxes & fees
15 Dec - 16 Dec
Historic Union Chapel Elementary School near Cumberland River & Lake
Exterior
Lake house. Less than 3 miles from beautiful Lake Cumberland.

Vacation Home in Jamestown

9.4 out of 10, Exceptional, (26)
"Great little place, close to town. Very clean place and host was amazing and very accommodating "
United States
mike v.
The price is AED 397
AED 895 total
includes taxes & fees
11 Dec - 12 Dec
Lake house. Less than 3 miles from beautiful Lake Cumberland.
Fridge, microwave, oven, stovetop
Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!

Vacation Home in Jamestown

10.0 out of 10, Exceptional, (19)
"Amazing stay! House is very clean with lovely decor! Will stay here again for sure!!"
United States
Jennifer L.
The price is AED 595
AED 1,445 total
includes taxes & fees
9 Dec - 10 Dec
Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!
Fridge, microwave, oven, stovetop
The Lodge Lake Retreat – Family-Friendly with Private River Access

Vacation Home in Jamestown

2.0 star property
The price is AED 220
AED 668 total
includes taxes & fees
9 Dec - 10 Dec
The Lodge Lake Retreat – Family-Friendly with Private River Access
Fridge, microwave, oven, stovetop
Great place to gather near Lake Cumberland

Vacation Home in Jamestown

10.0 out of 10, Exceptional, (10)
"Great location, house is very nice, clean and spacious and close to the Jamestown boat ramp. Will definitely stay here again."
United States
Michael o.
The price is AED 918
AED 1,850 total
includes taxes & fees
19 Dec - 20 Dec
Great place to gather near Lake Cumberland
Fridge, microwave, oven, stovetop
Charming 5-bedroom/3-bath home with easy access to Lake Cumberland

Vacation Home in Jamestown

9.6 out of 10, Exceptional, (5)
"Everything was great"
United States
Jeremy W.
The price is AED 859
AED 1,777 total
includes taxes & fees
10 Dec - 11 Dec
Charming 5-bedroom/3-bath home with easy access to Lake Cumberland
Terrace/patio
Cumberland River School House

Vacation Home in Jamestown

The price is AED 588
AED 1,321 total
includes taxes & fees
21 Dec - 22 Dec
Cumberland River School House
Outdoor dining
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.

Vacation Home in Jamestown

10.0 out of 10, Exceptional, (156)
"Check in was very easy, beautiful home,views were pretty,overall great family time!"
United States
paige m.
The price is AED 853
AED 2,187 total
includes taxes & fees
9 Dec - 10 Dec
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.
Fridge, microwave, oven, stovetop
Historic Union Chapel School-Two Room, near Cumberland River & Lake Cumberland

Vacation Home in Jamestown

10.0 out of 10, Exceptional, (53)
"We loved staying here. We highly recommend it. It was very clean, unique and the hosts are wonderful people."
United States
Bryan B.
The price is AED 459
AED 587 total
includes taxes & fees
10 Dec - 11 Dec
Historic Union Chapel School-Two Room, near Cumberland River & Lake Cumberland
Exterior
LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups

Vacation Home in Faubush

10.0 out of 10, Exceptional, (3)
"Everglow Hollow was great! We stayed for a long weekend and it was the perfect place to relax, while not being too far away from Lake Cumberland. Host also responded to questions right away and were very helpful. "
Canada
Morgan P.
The price is AED 278
AED 707 total
includes taxes & fees
9 Dec - 10 Dec
LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups
Outdoor dining
Boating Mecca: Near Dale Hollow Lake & Golf!

Vacation Home in Burkesville

10.0 out of 10, Exceptional, (87)
"It’s so nice and clean and convenient that we will be back! "
United States
Kim M.
The price is AED 257
AED 604 total
includes taxes & fees
9 Dec - 10 Dec
Boating Mecca: Near Dale Hollow Lake & Golf!
Interior
Comfortable & Elegant Home

Vacation Home in Columbia

10.0 out of 10, Exceptional, (8)
"Very clean just as listed would stay again."
United States
David W.
The price is AED 410
AED 840 total
includes taxes & fees
9 Dec - 10 Dec
Comfortable & Elegant Home
Microwave, dishwasher, coffee/tea maker, toaster
The Cozy Cabell Cottage

Vacation Home in Monticello

9.8 out of 10, Exceptional, (51)
"The cottage is adorable. It is clean and well kept. It has everything you need. We only stayed two nights but it perfect for a longer stay. We enjoyed our stay completely. "
United States
Kim H.
The price is AED 281
AED 703 total
includes taxes & fees
9 Dec - 10 Dec
The Cozy Cabell Cottage
Dining
The Little Brown Cottage is a 1950's, two bedroom cottage in town with one bath.

Vacation Home in Russell Springs

10.0 out of 10, Exceptional, (1)
"We loved the Little Brown Cottage. It's not far from a grocery and places to eat. We had visited to attend a grandson's wedding. This home had all things we needed plus there are games and puzzles for families to use. "
United States
Judith H.
The price is AED 367
AED 826 total
includes taxes & fees
9 Dec - 10 Dec
The Little Brown Cottage is a 1950's, two bedroom cottage in town with one bath.
Exterior
Mema and Pa’s Place

Vacation Home in Byrdstown

10.0 out of 10, Exceptional, (14)
"Property was clean and quiet. "
United States
Jeremy F.
The price is AED 496
AED 817 total
includes taxes & fees
9 Dec - 10 Dec
Mema and Pa’s Place
Interior
Fawn Run on Lake Cumberland

Vacation Home in Nancy

10.0 out of 10, Exceptional, (10)
"We had a wonderful stay! The home had everything you would need for a comfortable stay and more. My kids loved the game room full of games. We would definitely stay here again. "
United States
Allison B.
The price is AED 367
AED 1,347 total
includes taxes & fees
9 Dec - 10 Dec
Fawn Run on Lake Cumberland
Exterior
Wolf Creek Crossing Lake House Beach & Boat Launch .5 miles at Jabez Landing

Vacation Home in Nancy

10.0 out of 10, Exceptional, (2)
"Great place, close to the water and quiet neighborhood. Would recommend. "
United States
John S.
The price is AED 413
AED 1,087 total
includes taxes & fees
9 Dec - 10 Dec
Wolf Creek Crossing Lake House Beach & Boat Launch .5 miles at Jabez Landing
Interior
Avery Acres

Vacation Home in Albany

8.0 out of 10, Very Good, (2)
"The host was awesome - excellent communication and customer service. The house was extremely clean, well equipped, and roomy. The bed was comfortable. We had everything that we needed! We will definitely stay at Avery Acres again. Recommend it!"
United States
Kandy F.
The price is AED 459
AED 915 total
includes taxes & fees
9 Dec - 10 Dec
Avery Acres
Fridge, microwave, oven, stovetop
~The Hideaway~Come stay with us @DHL! Great for families! <6mi to lake/golf

Vacation Home in Burkesville

10.0 out of 10, Exceptional, (9)
"We were in town for the weekend for the River Festivus, and needed a place to stay. We were absolutely thrilled to find this home. Plenty space for everyone, beds were comfortable, and the kids loved playing basketball in our down time. Would 100% stay again! "
United States
Shane W.
The price is AED 471
AED 1,272 total
includes taxes & fees
9 Dec - 10 Dec
~The Hideaway~Come stay with us @DHL! Great for families! <6mi to lake/golf
Fridge, microwave, oven, stovetop
Joy On The Lake · Cumberland Canvas: Lake View, Fire Pit & Game Room

Vacation Home in Somerset

10.0 out of 10, Exceptional, (15)
"It was a wonderful stay. Beautiful view!"
United States
Vanessa C.
The price is AED 573
AED 1,623 total
includes taxes & fees
16 Dec - 17 Dec
Joy On The Lake · Cumberland Canvas: Lake View, Fire Pit & Game Room
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 Jamestown Hotel Reviews

Sleep Inn & Suites

Sleep Inn & Suites

10/10 Excellent
"Clean room, polite staff, and a solid breakfast. "
Andy 1-night trip
Posted 4 days ago
Sleep Inn & Suites