50 Best Maryland Apartments on Holiday Lettings - Vacation rentals

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Garrett County
386 properties
Vacation rentals Ocean City
302 properties
Swanton
89 properties
Apartments Baltimore
67 properties
Montgomery County
51 properties
Talbot County
28 properties
Apartments Annapolis
23 properties
Oxon Hill
15 properties
Calvert County
10 properties
Kent Island
6 properties
Rock Hall
6 properties
Sabillasville
6 properties
Capitol Heights
5 properties

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1,158 Vacation rentals

12

Vacation apartment in Maryland

Montgomery County / Bethesda

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
Luxury basement apartment in Bethesda. Two minute walk to Montgomery Mall. Right next to 270 & 495. NIH and WALTER REED is about a 5 minute drive. Separate private entrance into walk out basement. 1 bedroom, 1 full bath, large living room with fireplace, brand-new kitch …see more

from $99 / night

$693 / week

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from $99 / night

20

Preston Vacation home rental

Maryland / Preston

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our home has a beautiful fire fly show in our historical wooded back yard. Always enjoy our wildlife our humming birds are the best. Go four leaf clover hunting. The deck is comfortable with lounge chairs for basting in the summer sun. We have goats that get loose... …see more

from $87 / night

$250 / week

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from $87 / night

(18) Excellent 

25

Cottage rental in Maryland

Maryland / Annapolis

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Half a block to walk to the Naval Academy Stadium and minutes away from stunning Annapolis town center. This adorable little cottage has lots of sleeping and great outdoor space. Sun Porch & Plenty of parking. A perfect place to relax and enjoy Annapolis, the pro …see more

from $350 / night

$2,100 / week

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avg. 3 hours 33 minutes

from $350 / night

16

Vacation home in Maryland

Maryland / Capitol Heights

2 6 14 nights min

  • 2 bedrooms
  • Sleeps 6
  • 14 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
This is a nice, clean 2-bedroom detached home with great amenities located in close-in suburban Washington DC metro area. The home has a large fenced back yard suitable for kids to play or for your bring-along pets. There is off-street parking, including a driveway wi …see more

from $100 / night

$700 / week

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Responds fast!
avg. 2 hours 14 minutes

from $100 / night

(9) Excellent 

57

Vacation home in Baltimore

Maryland / Baltimore

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
Built in the 1920s, this Tudor style house retains its original charm, it is spacious and creatively painted, with hardwood floors throughout. Fully furnished and decorated with artwork, rugs and antiques from our travels around the world. Two bedrooms with comfortable …see more

from $130 / night

$750 - $1,030 / week

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avg. 2 hours 17 minutes

from $130 / night

12

Maryland Vacation townhouse rental

Maryland / Parkville

1 1 1 night min

  • 1 bedroom
  • Sleeps 1
  • 1 night min
  • Air conditioning
Near Towson University, Morgan State University, Goucher College, and University of Maryland Baltimore County. Also close to Samaritan Hospital, Towson Mall, and easy access to I-695 bound for Washington D.C., New York City, etc. Plaza in walking distance (6 blocks) (Wa …see more

from $35 / night

$245 / week

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Responds fast!
avg. 1 hour 32 minutes

from $35 / night

(1) Excellent 

18

Vacation home rental

Maryland / Annapolis

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Ask about children
  • Air conditioning
  • Private garden
A stones throw to the stadium and downtown shuttles. Walk the Poplar Trail to the Annapolis Uptown eateries on West Street. Stay here and add on 301 for your large groups or multiple families! 3 Bedrooms, 4 1/2 bath, Sleeps 6-8 Master (sleep 2) King …see more

from $550 / night

$1,995 - $2,345 / week

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Responds fast!
avg. 3 hours 33 minutes

from $550 / night

11

Vacation home in Maryland

Maryland / Parkville

1 1 1 night min

  • 1 bedroom
  • Sleeps 1
  • 1 night min
  • Air conditioning
Close to Towson University, University of Maryland Baltimore County, and Morgan State University. The airport is 45 minutes (car, shuttle, Uber ) away. You’ll love the house because the location is perfect for those who don't want heavy traffic, and it's a very quite ne …see more

from $30 / night

$210 / week

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Responds fast!
avg. 1 hour 32 minutes

from $30 / night

12

Vacation apartment in Maryland

Maryland / Frederick

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Air conditioning
  • Pet friendly
  • Private garden
This spacious one bedroom, fully furnished, 1,000 square foot, Parisian styled apartment is a 6 minute drive from downtown Frederick. Located on 3/4 acre with ample off-street parking, this delightful apartment is completely furnished with granite counter tops, tile kit …see more

from $95 / night

$600 / week

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from $95 / night

23

Vacation home with shared pool in Preston

Maryland / Preston

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful 18 acres large deck over looks historical woods. Nature at its best... Hawks, rabbits, deer, all kinds of birds.... Our hummin birds are fabulous... WE have a complimentary canoe, bikes, we can set up a water slide for a fee also manicures and pedicures plus …see more

from $75 / night

$350 - $420 / week

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from $75 / night

60

Vacation home in Maryland

Maryland / Fort Washington

4 12 2 nights min

  • 4 bedrooms
  • Sleeps 12
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Barbie's palace very large home sits on a corner lot lots of privacy wraparound porch patio and deck four bedrooms four bathrooms formal living room and dining room large family large basement that goes throughout the whole house must-see very nicely decoratedHouse is …see more

from $425 / night

$2,975 / week

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from $425 / night

5

Vacation townhouse in Maryland

Maryland / Owings Mills

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
we have a spacious furnished room with full bath.. living room and kitchen is fully aquainted if you want to use something . Plenty of parking space ..pretty quiet place for a short stay ... Tv with chromecast service is available in the room.... its perfecrly convenie …see more

from $30 / night

$210 / week

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Responds fast!
avg. 44 minutes

from $30 / night

7

Condo rental in Maryland with shared pool

Maryland / National Harbor

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
*** Minimum 3 night stay *** Your D.C. Vacation Springboard Wyndham National Harbor places you within a quarter-mile radius of an innovative complex of shops, restaurants and attractions that borders the banks of the Potomac River. With its walkable appeal, public art, …see more

from $199 / night

$1,393 / week

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Responds fast!
avg. 1 hour 26 minutes

from $199 / night

14

Home rental in Frederick

Maryland / Frederick

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
If you like the show Fixer-Upper, you'll love the Uptown Cottage! Near Downtown Frederick, great restaurants, beautiful parks, historic sites and shopping. Less than an hour from Baltimore and Washington DC. Fully renovated, a great space for relaxing when you are not o …see more

from $135 / night

$945 / week

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from $135 / night

10

Vacation cottage in Maryland

Calvert County / Saint Leonard

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Looking for a peaceful beach getaway? Located in quiet Long Beach overlooking Flag Harbor Yacht Haven marina, this cottage is a few minutes walk to the sandy beach along cliffs famous for fossils from the Miocene. The shallow water is safe for children to swim, and a fa …see more

from $260 / night

$1,110 / week

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from $260 / night

(2) Very Good 

10

Vacation condo rental

Maryland / National Harbor

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This two bedroom condo is newly built and decorated. There is a full kitchen, and Wireless Internet for your convenience. This is a awesome place to stay with all the comfort you need. Treasured Past, Trendsetting Present - Just minutes from Washington, D.C., along t …see more

from $299 / night

$2,093 / week

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from $299 / night

(1) Excellent 

13

Maryland Vacation home rental

Maryland / Clinton

4 14 2 nights min

  • 4 bedrooms
  • Sleeps 14
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Sits on a gated 7.5 acres flat land. Makes you feel living in the country and yet so close to the city. Easy 30 minutes drive or less to Washington DC, National Harbor, MGM Casino, Tanger outlets, Old Town Alexandria, Andrews/Bolling Airforce bases, and many more. Adjac …see more

from $120 / night

$840 / week

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Responds fast!
avg. 2 hours 0 minutes

from $120 / night

24

Oakland Vacation home rental

Garrett County / Oakland

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
Let the adventure begin! Sunset Reflections is a cheerful 3 bedroom lakefront home that will allow you to experience a true Deep Creek getaway! The beautifully decorated Great Room is enhanced with cathedral style ceilings, an impressive stacked stone fireplace and floo …see more

from $308 / night

$1,295 - $2,593 / week

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from $308 / night

(7) Excellent 

Certificate of Excellence

17

Vacation condo with shared pool in Maryland

Maryland / Ocean City

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Great deal for OC!. The building's exteior, and pool had been recently remodeled with upgrades. This spacious yet simply decorated three bedroom penthouse condo has a full kitchen, 3 bedrooms and 2 baths; amenities include elevator, AC, cable TV, WI-FI internet access, …see more

Certificate of Excellence

from $98 / night

$650 - $1,350 / week

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Responds fast!
avg. 2 hours 43 minutes

from $98 / night

16

Maryland Vacation home rental

Maryland / Swanton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
If you and your family are ready to experience a true authentic Deep Creek getaway then the delightful 3 bedroom lakefront home Ski Shore is your ticket! Glistening hardwood floors and dark wooden walls create the perfect cabin style ambience throughout the main floor. …see more

from $297 / night

$1,292 - $2,074 / week

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from $297 / night

32

Vacation home with shared pool in Maryland

Garrett County / McHenry

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
Check out this updated, larger Ski Harbor end unit. Situated perfectly on a peninsula and lakefront, right by the tennis court and the indoor pool, hot tub and sauna! Best location in the development. This 4 Bedroom home has been updated and has 2 living areas with flat …see more

from $262 / night

$1,124 - $1,594 / week

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from $262 / night

(4) Excellent 

Certificate of Excellence

26

Maryland Vacation condo rental

Maryland / Oxon Hill

2 8 2 nights min

  • 2 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
We have MORE of these condos available - Perfect resort and condos for business travellers, family vacations, friends getaways and large groups! Located close to Washington D.C. Steps away from National Harbor, these 2 Bedroom vacation rental condos have all the comfort …see more

Certificate of Excellence

from $165 / night

$1,155 / week

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from $165 / night

4

Maryland Vacation barn rental

Maryland / Baltimore

10 6 1 night min

  • 10 bedrooms
  • Sleeps 6
  • 1 night min
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from $123 / night

$1,000 / week

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from $123 / night

20

Vacation cottage in Maryland

Garrett County / Oakland

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Pet friendly
Do you find yourself daydreaming about a romantic getaway in a charming lakefront home? Golden Retreat is perfect for a couple but is large enough for a small family. You’ll adore the comfortable furnishings and alluring appeal of the interior. Conveniently located a m …see more

from $314 / night

$1,408 - $2,792 / week

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from $314 / night

29

Vacation home in Maryland

Garrett County / McHenry

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
Gather the family and head to the mountains for a refreshing and unforgettable vacation at Deep Creek Village #44. This fabulous lakefront townhome has something to offer everyone all year around. For those that want to take advantage of some of Wisp's winter activities …see more

from $198 / night

$808 - $1,364 / week

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from $198 / night

14

Apartment rental in Maryland

Maryland / Ocean City

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • Child friendly
Great unit, Total update this year. New Kitchen. One block walk to the beach with a traffic light crossing. Two pools on site. Large balcony for relaxing or meals. Fishing off the pier. Transient docking available for your boat. Great location, walk to grocery st …see more

from $275 / night

$1,400 - $4,900 / week

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Responds fast!
avg. 1 hour 22 minutes

from $275 / night

(1) Excellent 

15

Vacation home with swimming pool in McDaniel

St. Michaels / McDaniel

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Halo's Haven is a true piece of Heaven!! Bring your boat and your bathing suit. Twenty picturesque acres on a beautiful point of land off of the Chesapeake Bay near historic St. Michael's, Maryland. This property is beautifully landscaped, has a waterfront pool, pool ho …see more

from $700 / night

$4,200 / week

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from $700 / night

16

Vacation home rental

Garrett County / McHenry

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Ask about children
  • Air conditioning
Create unforgettable moments with family and friends when you stay in the delightful 4 bedroom lake access home Sunrise Cove. This stunning home, with its stylish décor and open floor plan, boasts the ultimate in comfort and relaxation. Fall in the love with the gleamin …see more

from $288 / night

$1,144 - $1,715 / week

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from $288 / night

11

Vacation home in Maryland

Maryland / Annapolis

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Car not necessary
  • Air conditioning
  • Private garden
Location, location, location! Literally walk out the front door to the hustle and bustle of downtown Annapolis with the City Dock just steps away. 2 blocks to Naval Academy Gate 1. Pubs, shops and cafes just steps away! Small patio for some outdoor relaxation, wifi t …see more

from $300 / night

$2,100 - $2,800 / week

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from $300 / night

47

Home rental in Maryland

Maryland / Taneytown

3 10 1 night min

  • 3 bedrooms
  • Sleeps 10
  • 1 night min
  • Child friendly
  • Air conditioning
River House Retreat features 3 bedrooms 2 full Baths with panoramic view of the Monocacy River. Spacious home has plenty of room for all. Well equipped gourmet kitchen with large center island. Take a week and get away from everything! Relax and unwind at this scenic se …see more

from $198 / night

$1,386 / week

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from $198 / night

22

Log cabin rental in Maryland

Garrett County / Oakland

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
Get the much deserved break that you crave when you stay at Bear Paws. This charming log cabin pairs total comfort with a convenient location! Featuring an open floorplan, the spacious main level is highlighted by vaulted ceilings and polished hardwood floors. Bear the …see more

from $249 / night

$1,009 - $1,274 / week

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from $249 / night

(5) Very Good 

17

Cottage rental in North Beach

Calvert County / North Beach

1 5 2 nights min

  • 1 bedroom
  • Sleeps 5
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
The Seahorse Guest Cottage is located in North Beach, Maryland, on the western shore of the Chesapeake Bay, within an hour’s drive of Washington, Baltimore, and Annapolis. The fully furnished cottage has a living room with sofabed, bedroom with queen size bed, sunporch …see more

from $150 / night

$700 - $1,000 / week

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Responds fast!
avg. 1 hour 31 minutes

from $150 / night

41

Maryland Vacation home rental

Garrett County / McHenry

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Find peace and relaxation at this charming cabin in the woods, a two-bedroom McHenry retreat with a private deck, sweeping views of the forest, and a wonderful location for hikers, golfers, skiers, anglers, and boating enthusiasts. Tucked away in a dense grove of trees …see more

from $75 / night

$525 / week

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Responds fast!
avg. 2 hours 11 minutes

from $75 / night

(2) Excellent 

27

Vacation home in Maryland

Maryland / Saint Inigoes

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Experience luxury, peace, and tranquility when you stay at this superb 4-bedroom, 2.5-bathroom vacation rental house that sleeps 12 lucky guests on the Potomac River with unrivaled views of Potomac River. Situated on 10 acres of historic wooded land that lines the water …see more

from $355 / night

$2,485 - $3,255 / week

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Responds fast!
avg. 53 minutes

from $355 / night

26

Home rental in Ocean City

Maryland / Ocean City

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
This tropical-themed, oceanside condo with a well-appointed balcony, seasonal shared pool, and easy beach access is ideal for that seaside family getaway or trip with a group of friends. While the beach is only a short stroll from your front door, there are plenty of f …see more

from $150 / night

$1,050 / week

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Responds fast!
avg. 2 hours 11 minutes

from $150 / night

11

Vacation apartment in Maryland

Kent Island / Stevensville

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
Come to our beautiful vacation home and enjoy the scenic view while having fun on the water. Love Point Bay Vacation Home is at the mouth of the Chester River, where it connects to the Chesapeake Bay on Maryland's Eastern Shore. You will feel right at home, yet free of …see more

from $329 / night

$1,956 / week

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from $329 / night

26

Home rental in Ocean City

Maryland / Ocean City

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning
  • Pet friendly
Begin your blissful bayside getaway at this 3-bedroom, 2-bath vacation rental home in West Ocean City. This coastal cottage boasts accommodations for 8 travelers across 1,969 square feet of open and airy living space. A private waterfront oasis with a boat dock for naut …see more

from $150 / night

$1,050 - $2,695 / week

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Responds fast!
avg. 45 minutes

from $150 / night

24

Ski home to rent in McHenry

Garrett County / McHenry

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 12 mi
  • Swimming pool
  • Ski
Welcome to Magnolia! Magnolia is a beautiful 5 BR townhome with spectacular lake and mountain views. The luxurious and inviting décor flows throughout the 3 levels of living space, making this home a perfect choice for a multi-family getaway. Breathtaking lake views …see more

from $299 / night

$1,750 - $2,540 / week

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Responds fast!
avg. 2 hours 30 minutes

from $299 / night

(12) Excellent 

12

Vacation apartment in Maryland

Maryland / Ocean City

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
It's All in the Details.... Located on the top floor of an 8 unit building with parking underneath, this newly remodeled condo offers 2 beds (Queen and Full - pillowtop mattresses) in the bedroom with a brand new Queen sleeper fold out in the living room (sleeps up to 6 …see more

from $195 / night

$1,200 - $1,750 / week

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Responds fast!
avg. 3 hours 12 minutes

from $195 / night

25

McHenry Vacation home rental

Garrett County / McHenry

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
Welcome to one of Deep Creek’s most favored communities! Everyone in your group will fall in love with the location, pleasant décor throughout and the amazing level lakefront featured by Ski Harbor #26. This adorable townhome offers superb amenities both inside and out. …see more

from $221 / night

$994 - $1,344 / week

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from $221 / night