Search Vacation Homes in Monticello

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

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Nov 28 - Nov 30
In two weeks
Dec 5 - Dec 7
In one month
Dec 19 - Dec 21
In two months
Jan 16 - Jan 18

Vacation Homes in Monticello

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.
$174 nightly
The price is $191
Nov 23 - Nov 24
Total with taxes and fees
The Cozy Cabell Cottage
Exterior
Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!

Vacation Home in Monticello

10.0 out of 10, Exceptional, (31)
"This was a great house! Super clean, spacious and had everything we needed. We enjoyed the hot tub, firepit, and the grill. It was 30 mins to Conley Bottom marina and 15 mins to a grocery store. We would stay here again next time we're back!!"
United States
Elizabeth B.
$429 nightly
The price is $461
Nov 30 - Dec 1
Total with taxes and fees
Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!
Interior
Cozy 2-bedroom house in Jamestown with AC, WiFi

Vacation Home in Jamestown

9.8 out of 10, Exceptional, (6)
"We had an amazing stay. Host was quick to respond, although we didn't really need anything. For the most part we had a great stay. I was surprised that it was duplex not a house,but it didnt effect our stay. Would definitely stay again!!"
United States
Leslie J.
$184 nightly
The price is $207
Nov 23 - Nov 24
Total with taxes and fees
Cozy 2-bedroom house in Jamestown with AC, WiFi
Dining
Cozy 1-bedroom house in charming Allardt with AC, WiFi

Vacation Home in Allardt

10.0 out of 10, Exceptional, (12)
"Clean, comfortable, well located, with a great host who made everything easy start to finish. Would definitely stay here again."
United States
Robert M.
$110 nightly
The price is $123
Nov 23 - Nov 24
Total with taxes and fees
Cozy 1-bedroom house in charming Allardt with AC, WiFi
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.
$179 nightly
The price is $197
Dec 15 - Dec 16
Total with taxes and fees
LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups
Terrace/patio
Charming 1-bedroom fish shack in Somerset with WiFi and AC

Vacation Home in Somerset

2.0 star property
10.0 out of 10, Exceptional, (9)
"Perfect for the evening we stayed! Private, clean, safe, and centrally located."
United States
Madalyn
$133 nightly
The price is $146
Nov 23 - Nov 24
Total with taxes and fees
Charming 1-bedroom fish shack in Somerset with WiFi and AC
Fridge, microwave, oven, stovetop
Cozy 1-bedroom Tiny House with WiFi, AC in beautiful Somerset

Vacation Home in Somerset

2.0 star property
9.6 out of 10, Exceptional, (4)
"House is super cute. Great location for the weekend car activities."
United States
Penny H.
$139 nightly
The price is $159
Nov 24 - Nov 25
Total with taxes and fees
Cozy 1-bedroom Tiny House with WiFi, AC in beautiful Somerset
Outdoor dining
Boating Mecca: Near Dale Hollow Lake & Golf!

Vacation Home in Burkesville

10.0 out of 10, Exceptional, (87)
"Beautiful place, everything you need is there. had great time here. Beautiful deck. Homemade cookies that was there when we arrive was delicious. Love watching birds and squirrels. I would stay here again."
United States
Arwilda V.
$163 nightly
The price is $175
Nov 24 - Nov 25
Total with taxes and fees
Boating Mecca: Near Dale Hollow Lake & Golf!
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.
$145 nightly
The price is $160
Nov 25 - Nov 26
Total with taxes and fees
Historic Union Chapel School-Two Room, near Cumberland River & Lake Cumberland
3 bedrooms, desk, iron/ironing board, free WiFi
Hideaway 27

Vacation Home in Helenwood

10.0 out of 10, Exceptional, (37)
"Excellent place to stay. Family enjoyed it. "
United States
Aaron W.
$215 nightly
The price is $243
Nov 25 - Nov 26
Total with taxes and fees
Hideaway 27
Outdoor dining
Captivating 2-bedroom, garage door house with WiFi, AC in welcoming Somerset

Vacation Home in Somerset

2.0 star property
9.6 out of 10, Exceptional, (13)
"The host was great & accommodated to what we needed! The place was clean & comfortable! Would stay again! "
United States
holly v.
$155 nightly
The price is $171
Nov 24 - Nov 25
Total with taxes and fees
Captivating 2-bedroom, garage door house with WiFi, AC in welcoming Somerset
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.
$223 nightly
The price is $246
Nov 23 - Nov 24
Total with taxes and fees
Lake house. Less than 3 miles from beautiful Lake Cumberland.
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.
$200 nightly
The price is $222
Nov 23 - Nov 24
Total with taxes and fees
Mema and Pa’s Place
Smart TV, fireplace
Peaceful Days at The Barn in Alpine

Vacation Home in Alpine

10.0 out of 10, Exceptional, (10)
"Wonderful place to stay and meet up with old friends"
United States
Dewey K.
$224 nightly
The price is $253
Dec 4 - Dec 5
Total with taxes and fees
Peaceful Days at The Barn in Alpine
Interior
Fawn Run on Lake Cumberland

Vacation Home in Nancy

10.0 out of 10, Exceptional, (9)
"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.
$337 nightly
The price is $367
Nov 23 - Nov 24
Total with taxes and fees
Fawn Run on Lake Cumberland
Terrace/patio
Spacious Country Home - uniquely located for great family fun

Vacation Home in Pine Knot

10.0 out of 10, Exceptional, (4)
"Over all we loved our stay! Manager was very responsive to our calls/texts. Property was nice and clean! "
United States
William W.
$270 nightly
The price is $298
Nov 24 - Nov 25
Total with taxes and fees
Spacious Country Home - uniquely located for great family fun
Property grounds
Cozy Lakehouse – Game Room, Pet-Friendly, Near Boatramp, 3-Season room!

Vacation Home in Bronston

2.0 star property
9.8 out of 10, Exceptional, (8)
"The property was great for a group trip and we enjoyed the amenities provided."
United States
Stephen S.
$362 nightly
The price is $399
Nov 23 - Nov 24
Total with taxes and fees
Cozy Lakehouse – Game Room, Pet-Friendly, Near Boatramp, 3-Season room!
Terrace/patio
Calming 1-bedroom yellow door house close to lake with Wi-Fi, AC

Vacation Home in Somerset

2.0 star property
10.0 out of 10, Exceptional, (12)
"Great little home for our short stay. Nice and clean with great back porch area!"
United States
Kevin H.
$142 nightly
The price is $156
Nov 23 - Nov 24
Total with taxes and fees
Calming 1-bedroom yellow door house close to lake with Wi-Fi, AC
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.
$206 nightly
The price is $227
Nov 23 - Nov 24
Total with taxes and fees
The Little Brown Cottage is a 1950's, two bedroom cottage in town with one bath.
Terrace/patio
Curve Cottage located on The Rattlesnake 192 just outside of Somerset.

Vacation Home in Somerset

2.0 star property
10.0 out of 10, Exceptional, (5)
"Cozy place that met our needs"
United States
Joseph H.
$229 nightly
The price is $252
Nov 23 - Nov 24
Total with taxes and fees
Curve Cottage located on The Rattlesnake 192 just outside of Somerset.
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

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Monticello Hotel Reviews

LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.

LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.

10/10 Excellent
"The host was very welcoming and provided lots of details prior to our stay. She made sure that everything was ready. We had a wonderful time and will definitely be booking this place again when we travel down to Kentucky again."
Katie V. 2-night trip
Posted 3 days ago
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.

Find out more about Monticello

Monticello Vacation Homes information

Number of reviews
Accommodation
 Vacation Homes
Lowest Price
Highest Price

Explore a world of travel with Expedia