Find Chalets in Maryland from $149

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In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Top Cities in Maryland

United States Capitol showing an administrative buidling, heritage architecture and autumn leaves
ChaletsChalets

Washington

Washington

Our top choices for Maryland chalets

Exterior
4-bedroom chalet in lovely Ocean Pines with WiFi, AC

Chalet in Ocean Pines

10.0 out of 10, Exceptional, (2)
"House way bigger than it looks in pictures. Host was quick to respond to any questions! Perfect location for our weekend friends getaway."
United States
Jen H.
4-bedroom chalet in lovely Ocean Pines with WiFi, AC
Terrace/patio
Lake-view home with hot tub, dock, decks, firepit, & AC - near slopes, dogs OK

Chalet in McHenry

8.8 out of 10, Excellent, (19)
"Very comfortable stay. "
United States
Angela
Lake-view home with hot tub, dock, decks, firepit, & AC - near slopes, dogs OK
Exterior
Lake View Chalet with Hot Tub and Fire Pit

Chalet in Oakland

Lake View Chalet with Hot Tub and Fire Pit
Fridge, microwave, oven, stovetop
Luxury cabin with mountain views

Chalet in Flintstone

$237 nightly
The price is $239
Dec 10 - Dec 11
Total with taxes and fees
Luxury cabin with mountain views
Smart TV, fireplace, DVD player, books
Timroc II, FIVE STAR REVIEWS! LAKE ACCESS, GREAT SWIMMING, PRIVATE 2 ACRES!

Chalet in Oakland

10.0 out of 10, Exceptional, (110)
"We had an amazing stay at this beautiful property!! Its proximity to parks, the lake etc is ideal. We are considering another stay here in the winter months!"
United States
Keri T.
Timroc II, FIVE STAR REVIEWS! LAKE ACCESS, GREAT SWIMMING, PRIVATE 2 ACRES!
Exterior
Bearly Believable By The Lake & WISP hot-tub/pets

Chalet in McHenry

9.4 out of 10, Exceptional, (6)
"Great house, great location "
United States
Cy B.
Bearly Believable By The Lake & WISP hot-tub/pets
Exterior
1/2 double cabin with king bed and single child sized pull-out sleep sofa (sleeps 2 adults & 1 child

Chalet in Flintstone

9.0 out of 10, Wonderful, (4)
"Beautiful, calming environment to relax and unwind for the weekend. Excellent communication with property owner. Couldn’t recommend more!"
United States
Drew S.
$148 nightly
The price is $149
Dec 10 - Dec 11
Total with taxes and fees
1/2 double cabin with king bed and single child sized pull-out sleep sofa (sleeps 2 adults & 1 child
Exterior
Private cabin with two full beds. ADA accessible.

Chalet in Flintstone

10.0 out of 10, Exceptional, (7)
"This cabin has all the necessities, is in a great location and is clean and well maintained. Absolutely perfect for a couple and close to lots of outdoor activities! Will absolutely stay here in the future."
United States
Leah I.
$148 nightly
The price is $149
Dec 10 - Dec 11
Total with taxes and fees
Private cabin with two full beds. ADA accessible.
Terrace/patio
Spacious family-friendly chalet w/fenced dog run & large deck near the lake/Wisp

Chalet in Oakland

9.6 out of 10, Exceptional, (32)
"Beautiful house and great location. Loved that they had 3 queen or larger beds for the adult families and pet friendly! Check in and check out was a breeze. Highly recommend!!"
United States
Judy C.
Spacious family-friendly chalet w/fenced dog run & large deck near the lake/Wisp
Exterior
✔ Lakefront paradise & lake toys included! Hot Tub~Dock~Game room & Fire-pit!

Chalet in McHenry

10.0 out of 10, Exceptional, (6)
"We were very happy with everything about our stay. We will be likely trying to rent this house again for a future trip. We would highly recommend it."
United States
Scott R.
✔ Lakefront paradise & lake toys included! Hot Tub~Dock~Game room & Fire-pit!
Exterior
Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.

Chalet in Oakland

10.0 out of 10, Exceptional, (4)
"The place was so clean and fully stocked. We had a wonderful stay. Five stars!! "
United States
Lori S.
$340 nightly
The price is $384
Dec 21 - Dec 22
Total with taxes and fees
Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.
Exterior
1/2 of a double cabin with one king sized bed (sleeps 2)

Chalet in Flintstone

10.0 out of 10, Exceptional, (1)
"If you’re looking for a quiet peaceful cabin to just go get lost in the world of your significant other, this is the place to go! They’re far enough from the everyday life but still close enough to enjoy all the beauty of their charming city!! The food is to die for and definitely a reason for us to return!! Nothing bad to say at all except they need larger hot water tanks bc when I’m enjoying my wife that includes sharing a shower that we would have preferred not to be rushed out of!! Otherwise...
United States
LaRon G.
$148 nightly
The price is $149
Dec 10 - Dec 11
Total with taxes and fees
1/2 of a double cabin with one king sized bed (sleeps 2)
Exterior
Double cabin with 2 queen beds, 1 king bed, common porch and each unit has a private entrance and bath.

Chalet in Flintstone

10.0 out of 10, Exceptional, (1)
"Beautiful cabin just off the interstate."
United States
Stephen L
$310 nightly
The price is $313
Dec 10 - Dec 11
Total with taxes and fees
Double cabin with 2 queen beds, 1 king bed, common porch and each unit has a private entrance and bath.
Exterior
Private cabin with two double beds (sleep 4)

Chalet in Flintstone

10.0 out of 10, Exceptional, (5)
"Only problem was coffee maker"
United States
Donna
$148 nightly
The price is $149
Dec 10 - Dec 11
Total with taxes and fees
Private cabin with two double beds (sleep 4)
Exterior
1/2 of a double cabin with two queen beds (sleeps 4)

Chalet in Flintstone

10.0 out of 10, Exceptional, (1)
"We were only able to stay for 1 night but it was a nice option to have near Rocky Gap Park. Would recommend it!"
United States
Kathryn C.
$157 nightly
The price is $158
Dec 10 - Dec 11
Total with taxes and fees
1/2 of a double cabin with two queen beds (sleeps 4)
Property grounds
Riverfront Retreat-HotTubIDock|Fenced YardINear DC

Chalet in port tobacco

10.0 out of 10, Exceptional, (9)
"Beautiful location for our family to stay to celebrate. It exceeded our expectations. "
United States
Anonymous traveler
$606 nightly
The price is $642
Dec 11 - Dec 12
Total with taxes and fees
Riverfront Retreat-HotTubIDock|Fenced YardINear DC
Terrace/patio
Wooded Retreat w Hot Tub, Loft, Game Room & Sauna

Chalet in Oakland

10.0 out of 10, Exceptional, (1)
"Wonderful place for the perfect getaway! Just like the photos definitely worth every penny. Just have in mind that you are in the woods so the bugs are inevitable but the inside of the place was very clean.Me and my family took advantage of all the amenities from the grill, hot tub, fire place. Don't think twice and book this place!"
United States
Bonny S.
Wooded Retreat w Hot Tub, Loft, Game Room & Sauna
Exterior
Private cabin with two double beds (sleeps 4)

Chalet in Flintstone

9.6 out of 10, Exceptional, (4)
"Cute, clean cabins conveniently located to highway and nearby Cumberland. Nice stay!"
United States
Amy R.
$148 nightly
The price is $149
Dec 10 - Dec 11
Total with taxes and fees
Private cabin with two double beds (sleeps 4)
Exterior
Serenity Sunsets! 2.8miles to WISP, hot-tub, pets

Chalet in McHenry

10.0 out of 10, Exceptional, (3)
"This place is great and was very clean!"
United States
Galit B.
Serenity Sunsets! 2.8miles to WISP, hot-tub, pets
Outdoor dining
Primo Vista! Spectacular views, Dock Slip, Hot Tub

Chalet in McHenry

$934 nightly
The price is $1,056
Dec 10 - Dec 11
Total with taxes and fees
Primo Vista! Spectacular views, Dock Slip, Hot Tub
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 Maryland Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Great"
stephen 3-night trip
Posted 14 hours ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Maryland

Maryland Chalets information

Number of reviews
192
Accommodation
39 Chalets
Lowest Price
$149
Highest Price
$1,056

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