50 Best Maryland Apartments on Holiday Lettings - Vacation rentals

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Garrett County
565 properties
Vacation rentals Ocean City
331 properties
Swanton
131 properties
Apartments Baltimore
70 properties
Montgomery County
52 properties
Talbot County
29 properties
Apartments Annapolis
20 properties
National Harbor
17 properties
Oxon Hill
17 properties
Calvert County
9 properties
Apartments Fort Washington
9 properties
Chestertown
8 properties
Berlin
8 properties
Vacation rentals Ocean Pines
7 properties
Sabillasville
6 properties
Kent Island
6 properties
Rock Hall
6 properties
Capitol Heights
5 properties

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1,430 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 $89 / night

$623 / week

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avg. 35 minutes

from $89 / 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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avg. 1 hour 50 minutes

from $100 / 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

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. 1 hour 36 minutes

from $350 / 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 $33 / night

$231 / week

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avg. 1 hour 32 minutes

from $33 / 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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avg. 1 hour 32 minutes

from $35 / 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 $99 / night

$690 - $1,040 / week

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avg. 2 hours 7 minutes

from $99 / 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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avg. 44 minutes

from $30 / 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 $575 / night

$4,025 / week

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from $575 / 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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avg. 1 hour 26 minutes

from $550 / 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

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

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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avg. 2 hours 13 minutes

from $199 / 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 $178 / night

$1,246 / week

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from $178 / 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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avg. 3 hours 10 minutes

from $195 / night

(1) Excellent 

24

Maryland Vacation cottage rental

Calvert County / Saint Leonard

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
Escape your everyday hustle and bustle and discover a hidden treasure right on the Chesapeake Bay sands at this 4-bedroom, 1-bathroom St. Leonard vacation rental cottage. With comfortable accommodations to sleep 8, 1,200 square feet of well-appointed living space and ea …see more

from $160 / night

$1,120 - $2,310 / week

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avg. 18 minutes

from $160 / night

24

Maryland Vacation home rental

Maryland / Shady Side

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning
Escape to the bay and stay at this 2-bedroom, 1.5-bathroom vacation rental house in Shady Side Maryland! With access to a private pier and dock, this quaint cottage that comfortably sleeps 5 will provide you and your travel companions with a lifetime of memories! Built …see more

from $185 / night

$1,295 - $1,925 / week

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avg. 8 minutes

from $185 / night

29

Vacation home rental

Garrett County / McHenry

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
It's difficult to top this lake house's charm, location, and private dock slip across the road! Two stories of windows flood the living spaces with light, and the deck opens up to glimpses of the lake between the trees. Plus, you're welcome to bring the family dog along …see more

from $89 / night

$623 / week

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avg. 26 minutes

from $89 / 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

39

Vacation home in Maryland

Garrett County / McHenry

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
For your next family getaway, book a stay in this charming vacation home in the Maryland woods! Featuring a private hot tub, a game room, and incredible proximity to Wisp Mountain and Deep Creek Lake, this delightful rental is a sure bet for a family vacation for the ag …see more

from $116 / night

$812 / week

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avg. 26 minutes

from $116 / 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

$874 - $1,364 / week

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from $198 / night

34

Vacation home in Swanton

Maryland / Swanton

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Leave your worries behind and slip away for a relaxing stay at this dog-friendly Deep Creek vacation home. Equipped with a wraparound porch, a brand new hot tub, and a private boat launch right on the lake, this lovely home is perfect for the whole family. Nestled in a …see more

from $155 / night

$1,085 / week

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avg. 26 minutes

from $155 / night

31

Maryland Vacation home rental

Maryland / Ocean City

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Book your escape to this bay front Ocean City home with room for up to six people, dock access, and a shared pool. Set on one of the picturesque inlets of the Isle of Wight Bay, you'll be just two blocks from the fun-filled rides and water features of the Jolly Roger A …see more

from $54 / night

$378 / week

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avg. 26 minutes

from $54 / night

(1) Excellent 

12

Vacation apartment in Maryland

Maryland / Rock Hall

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Ask about children
  • Ask about pets
Enjoy the gentle tidal waters of the Chesapeake Bay and its tributaries from your private overlook. The Captain’s Quarters at Spring Cove is a crisp and contemporary second floor living space with great water views. An exterior stairway leads to an ample deck where you …see more

from $180 / night

$1,200 / week

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from $180 / night

(6) Excellent 

20

Tilghman Vacation cottage rental

Talbot County / Tilghman

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Enjoy the beauty and tranquility of Tilghman Island from this bright and comfortable 3 bedroom, 2 bathroom cottage known for many years as the vacation rental 'The Roost.' Available for both short and long-term rentals, the cottage is located on a quiet residential …see more

from $200 / night

$825 / week

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from $200 / night

32

Oakland Vacation home rental

Garrett County / Oakland

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Pet friendly
Experience the beauty of Deep Creek Lake at Fox Den, a charming A-frame cottage that offers a treasured chance to unwind. Both romance-seekers and those in pursuit of inner peace will relish time spent at this classic mountain getaway. Highlighted by a wall of windows, …see more

from $212 / night

$994 - $1,473 / week

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from $212 / night

(4) Excellent 

13

Vacation condo in Maryland

Maryland / Oxon Hill

2 8 2 nights min

  • 2 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Inside this one-bedroom condo, enjoy all the amenities of home, including living rooms and dining areas with contemporary decor, as well as full kitchens with granite counters, appliances and bathrooms with stone tile work. The floor plan is perfect for families with pl …see more

from $185 / night

$1,295 / week

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from $185 / night

42

Vacation private room in Maryland

Talbot County / Trappe

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Great setting for a getaway relaxing weekend in a waterfront setting with a private beach. A variety of places to visit in the area, and fun outdoor activities. Two night minimum stay on weekends please. Swimming, fishing and lots of sunbathing. Amazing sunsets! This …see more

from $100 / night

$600 / week

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avg. 1 hour 32 minutes

from $100 / night

40

Vacation home in Gaithersburg

Montgomery County / Gaithersburg

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning
Spacious fully furnished private modern house in Kentlands shopping center. Walk to Shops, Restaurants, Cinema, Cafe, Grocery shops (Giant & Whole food) with activities like Art festivals, parks, gyms,...Conveniently close for business visitors to Medimmune/Novavax/Nist …see more

from $185 / night

$1,170 - $1,520 / week

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avg. 1 hour 12 minutes

from $185 / night

(1) Excellent 

50

Vacation home in Maryland

Maryland / Piney Point

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.4 mi
  • Child friendly
Fully renovated cottage with immaculate interior and view from the most rooms of the Potomac River. We are not located on the river, but across the street on a very quiet road. A water access easement runs from our door step to the Potomac River bulkhead: night lights …see more

from $99 / night

$1,200 - $1,410 / week

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from $99 / 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

(1) Excellent 

15

Maryland Vacation apartment rental

Maryland / Suitland

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Stay in our beautiful 2 bedroom 1 bath unit. We are ideal for a group of friends traveling together or meeting up, a family looking for a nice place to stay while exploring Washington, DC just a short drive, public transport, taxi or Uber ride away, or a quiet place to …see more

from $69 / night

$483 / week

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avg. 2 hours 0 minutes

from $69 / night

5

Maryland Vacation condo rental

Maryland / New Carrollton

2 7 2 nights min

  • 2 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly
  • Pet friendly
I have a 2 bedroom 2 bathroom condo for rent. It have hard wood floors through out the place. 3 plasma tv, cable, wifi, surround sound, balcony with bar and seating, Master bedroom has a king bed with 50 inch plasma. 2nd bedroom has bung bed and a twin with a 45 inch p …see more

from $200 / night

$800 - $1,150 / week

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from $200 / night

(2) Excellent 

60

Vacation chalet in Maryland

Maryland / Swanton

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 21 mi
  • Child friendly
The 3 Bedroom Rainbow Chalet is located on the Savage River in Western Maryland and about 20 minutes from Deep Creek Lake. This is a very comfortable home with spectacular views of the river and Savage River State forest from the back deck and bedroom balconies. You …see more

from $275 / night

$1,600 / week

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from $275 / night

(1) Excellent 

35

Home rental in Maryland with shared pool

Garrett County / McHenry

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Mountain Top Lodge is true to its name, situated in the premier Deep Creek Highlands, this brand new home features an amazing great room with a soaring cathedral ceiling, gas fireplace to ward off a cold winters night and a wall of windows to capture the beauty of the w …see more

from $347 / night

$1,494 - $2,538 / week

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from $347 / night

(11) Excellent 

19

Vacation apartment with shared pool in Ocean City

Maryland / Ocean City

1 6 3 nights min

  • 1 bedroom
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Harbor Breeze #63 (formerly Parrot Bay B), third floor condo at 409 St Louis Ave. One bedroom condo that sleeps 6 with two queen beds and a sleeper sofa, in addition to two full baths. Condo has two 32in HD TV's with DirecTV including HBO and Xfinity hotspots. Walkin …see more

from $60 / night

$400 - $1,400 / week

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from $60 / night

29

Vacation apartment in Ocean City

Maryland / Ocean City

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
Large Bay front condo; WiFi; Large balcony with fantastic views of the Bay, Inlet, Assateague Island, Large kitchen with GE Profile Stainless appliances, Granite Counters; Private Pier for fishing; Change over Days are Thursday or Sunday only Jun-Aug *SORRY NO UNDER 25 …see more

from $155 / night

$1,107 - $4,017 / week

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Responds fast!
avg. 2 hours 55 minutes

from $155 / night

22

Vacation home in Maryland

Montgomery County / Silver Spring

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
This stunning restored and expanded two bedroom/two bathroom mid-century modern home with ultra-gourmet kitchen and master bathroom spa suite is located in a quiet park-like setting just 6 miles to the Washington, D.C., border and 4.5 miles to the restaurants and shops …see more

from $225 / night

$1,575 / week

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from $225 / night

(1)  

12

Vacation home in Oxon Hill

Maryland / Oxon Hill

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Inside this one-bedroom condo, enjoy all the amenities of home, including living rooms and dining areas with contemporary decor, as well as full kitchens with granite counters, appliances and bathrooms with stone tile work. The floor plan is perfect for families with pl …see more

from $150 / night

$1,050 / week

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from $150 / night