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175 Maryland Villa Rentals

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews.
Compare Maryland villa rentals from 11 rental sites including HomeAway, Booking.com, TripAdvisor and more, from $25 a night.
Top spots in Maryland:
Masons Beach
Chesapeake Bay

STUNNING OCEAN BLK VILLA-SLEEPS 32-POOL/HOT TUB/GOLF/CHEF- 8/11-8/18 available!!

  • 15
  • 10
$1,128
HomeAway
$1,128
VRBO
Listed on 4 Sites

Comfort & Style: Chesapeake Bay Views, Outdoor Spa, Kayaks, Gated Pier & More

  • 6
  • 3
$695
Tripz

Waterfront St. Michaels -Pier, HEATED POOL IN MAY, Bikes & Kayaks

  • 5
  • 4
$625
HomeAway
$625
VRBO
Listed on 4 Sites

"Hoopers Hill" is your secluded getaway with kayaks, campfire and trampoline

  • 3
  • 4
$275
HomeAway
$275
VRBO
Listed on 4 Sites

Spectacular! Spacious Relaxing Villa in Bay Forest near Bethany Beach

  • 3
  • 3
$200
HomeAway
$200
VRBO
Listed on 4 Sites

Bayside - New Rental-Beach/Golf 4BR/3. 5B+Enclosed Loft/Game Room - Backs to Pond

  • 4
  • 4
$275
HomeAway
$275
VRBO
Listed on 4 Sites

Mtn Retreat w/ Stone Fireplace, 20 Min to Town | A STAY Charlottesville Property

  • 2
  • 2
$195
HomeAway
$195
VRBO
Listed on 4 Sites

Crossfields | Extraordinary Keswick Estate | A STAY Charlottesville Property

  • 5
  • 7
$995
HomeAway
$995
VRBO
Listed on 4 Sites

So Close, Yet So Far Away. - Five Bedroom Villa, Sleeps 10

  • 5
  • 4
$696
HomeAway
$696
VRBO

Breathtaking views from this 6 bedroom mountain home

  • 6
  • 5
$1,250
HomeAway
$1,250
VRBO
Listed on 4 Sites

Stonewall Crossing: Historic Property on the Shenandoah River

  • 4
  • 5
$585
HomeAway
$585
VRBO
Listed on 4 Sites

Historic Keswick Estate - 12 Mins to Town | A STAY Charlottesville Property

  • 5
  • 3
$995
HomeAway
$995
VRBO
Listed on 4 Sites

Mechums Cottage; Crozet: charming & cozy getaway- wine country & Wintergreen Ski

  • 1
  • 1
$115
HomeAway
$115
VRBO
Listed on 4 Sites

Colle Vineyard Estate | Minutes to Monticello | A Stay Charlottesville Property

  • 6
  • 4
$995
HomeAway
$995
VRBO
Listed on 4 Sites

Dates still available! Beach Retreat, Walk to Outlets, Restaurants

  • 3
  • 2
$214
HomeAway
$214
VRBO
Listed on 4 Sites

Luxury Villa at The Peninsula - Now sleeps 14

  • 4
  • 4
$350
HomeAway
$350
VRBO
Listed on 4 Sites

ARTIST/Writer's DELIGHT: Mt. "Church" (on a ART-ESTATE) in the Nat. Park/sleeps 5

  • 3
  • 2
$210
HomeAway
$210
VRBO
Listed on 4 Sites

Amazing DC home with rooftop deck, and city view of Monument

  • 2
  • 3
$262
HomeAway
$262
VRBO
Listed on 4 Sites

Prime location home near Capitol Hill | walk to Union Station metro !

  • 3
  • 3
$435
HomeAway
$435
VRBO
Listed on 4 Sites

PrivacyParadise w/5 Star Rating in Historic Ellicott City. Summer sell out!

  • 4
  • 4
$350
HomeAway
$350
VRBO
Listed on 4 Sites

Perfect For Families! Beautiful Views, Waterfront, Pool And So Much More!

  • 6
  • 6
$925
HomeAway
$925
VRBO
Listed on 4 Sites

Luxury Estate with Pool, Garden, Hot Tub, separate cottage

  • 6
  • 8
$899
HomeAway
$899
VRBO
Listed on 4 Sites

Waterfront Horse Farm Estate "A Slice of Heaven on Earth" Fireplace awaits

  • 5
  • 4
$650
HomeAway
$650
VRBO
Listed on 4 Sites

Millville Villa - Close to Bethany Beach!

  • 3
  • 3
$195
HomeAway
$195
VRBO
Listed on 4 Sites

Family or Group Gathering

  • 3
  • 2
$75
HomeAway
$75
VRBO
Listed on 4 Sites

Spread out in this 3-BR haven w/2-car garage | walk to metro!

  • 3
  • 3
$365
HomeAway
$365
VRBO
Listed on 4 Sites

3BR/2. 5BA H St/Union Station home - Three Bedroom Villa, Sleeps 6

  • 3
  • 2
$477
HomeAway
$477
VRBO

A DC retreat in Dupont, w/rooftop deck & view | walk to metro

  • 2
  • 3
$114
HomeAway
$114
VRBO
Listed on 4 Sites

Villa with Majestic Views of Monocacy River. Sleeps 7, 2 Bath, Full Kitchen

  • 2
  • 2
$250
HomeAway
$250
VRBO
Listed on 4 Sites

Historic Row House with unique characteristics - Studio Villa, Sleeps 2

  • Studio
  • 1
$72
HomeAway
$72
VRBO

Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18

  • 5
  • 5
$1,014
HomeAway
$1,014
VRBO
Listed on 4 Sites

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

  • 8
  • 9
$1,500
HomeAway
$1,500
VRBO
Listed on 4 Sites

Like New Villa 7 Minutes from Bethany Beach--BOOK SUMMER 2018 NOW!

  • 3
  • 3
$125
HomeAway
$125
VRBO
Listed on 4 Sites

Quiet Peaceful Country Home With Water Front Views of Swan Creek

  • 4
  • 2
$229
HomeAway
$229
VRBO
Listed on 4 Sites

Westcott House, A Magnificent Wooded Estate

  • 8
  • 5
$999
HomeAway
$999
VRBO
Listed on 4 Sites

Estate Victorian/Sleeps 18(56 w/Farmhouse & Cottage)Hot Tub, Theater & Game Room

  • 6
  • 5
$599
HomeAway
$599
VRBO
Listed on 4 Sites

Maryland Information

Other Rentals in Maryland

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