Holiday Houses in Maryland

Updating

age 0-16
114 Results

Relevance

Price low to high

Price high to low

Reviews

114 Holiday homes

Best kept secret by the bay (Entire House)

Fishing Creek house

3 bedrooms / 2 bathrooms / sleeps 4

4

Responds fast! avg. 2 hours 54 minutes

Match: Cycling holidays

All filters match

from £152 / night

£913 / week

Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

Wittman log cabin

5 bedrooms / 5 bathrooms / sleeps 10

3

Match: Cycling holidays

All filters match

from £870 / night

£5,573 - £6,510 / week

Cambridge Colonial Home, Walk to Town & Waterfront

Cambridge house

3 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 30 minutes

Match: Cycling holidays

All filters match

from £214 / night

£1,498 / week

Annapolis Crows Nest Cottage: Chesapeake Bay View

Annapolis villa

5 bedrooms / 3 bathrooms / sleeps 20

Match: Cycling holidays

All filters match

from £620 / night

£2,675 - £3,424 / week

Townhouse in Historic Downtown Cumberland

Cumberland house

3 bedrooms / 1 bathroom / sleeps 7

5

Responds fast! avg. 1 hour 40 minutes

Match: Cycling holidays

All filters match

from £108 / night

£627 / week

NEW! Annapolis Home w/ Deck & Whitehall Bay Access

Cape Saint Claire house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 30 minutes

Match: Cycling holidays

All filters match

from £196 / night

£1,367 / week

Chesapeake Beach Apt. Walk to Bay, Beach & Marina!

Chesapeake Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 30 minutes

Match: Cycling holidays

All filters match

from £63 / night

£437 / week

Huge Stevensville House Overlooking Eastern Shore!

Stevensville house

3 bedrooms / 5 bathrooms / sleeps 10

1

Responds fast! avg. 30 minutes

Match: Cycling holidays

All filters match

from £357 / night

£2,497 / week

Old World Charm, Immaculate Potomac River Woodland Cottage, Polite Pets OK

Piney Point house

3 bedrooms / 1 bathroom / sleeps 8

2

Responds fast! avg. 3 hours 49 minutes

Match: Cycling holidays

All filters match

from £89 / night

£895 - £1,818 / week

5 BR - AWESOME lake views, pool, billiards, tennis & hot tub on Wisp Mountain!

McHenry house

5 bedrooms / 5 bathrooms / sleeps 14

3

Match: Cycling holidays

All filters match

from £223 / night

£1,561 - £2,631 / week

Ocean City Condo w/Patio + Indoor & Outdoor Pools!

Ocean City apartment

2 bedrooms / 2 bathrooms / sleeps 8

2

Responds fast! avg. 19 minutes

Match: Cycling holidays

All filters match

from £112 / night

£781 / week

Water water everywhere in this gorgeous home

Chance house

3 bedrooms / 2 bathrooms / sleeps 8

3

Match: Cycling holidays

All filters match

from £223 / night

£1,427 / week

Cozy Ocean City Condo w/Patio Steps from Beach!

Ocean City apartment

2 bedrooms / 2 bathrooms / sleeps 4

1

Responds fast! avg. 30 minutes

Match: Cycling holidays

All filters match

from £112 / night

£781 / week

Cozy condo w/amazing lake view in great location & dog friendly!

McHenry house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 24 minutes

Match: Cycling holidays

All filters match

from £77 / night

£537 / week

St. Michaels Waterfront Retreat with pier, pool, kayaks, gas fire pit and bikes

Royal Oak house

5 bedrooms / 4 bathrooms / sleeps 10

Match: Cycling holidays

All filters match

from £445 / night

£5,618 / week

14 Hickory Way

Ocean Pines house

3 bedrooms / 2 bathrooms / sleeps 10

2

Match: Cycling holidays

All filters match

from £165 / night

£1,070 / week

Barbara's Villa on the Pocomoke River - A Splendid Riverfront Single Family Home

Rehobeth house

3 bedrooms / 3 bathrooms / sleeps 10

11

Responds fast! avg. 17 minutes

Match: Cycling holidays

All filters match

from £161 / night

£1,070 - £1,873 / week

Lovely Condo - Ocean View - Steps to the Ocean

Ocean City apartment

1 bedroom / 1 bathroom / sleeps 4

5

Match: Cycling holidays

All filters match

from £130 / night

£909 / week

Child-friendly, luxurious lodge close to lake and skiing

McHenry house

5 bedrooms / 4 bathrooms / sleeps 18

1

Match: Cycling holidays

All filters match

from £251 / night

£1,389 / week

Gorgeous Country Cottage On Scenic Monocacy River

Emmitsburg cottage

2 bedrooms / 2 bathrooms / sleeps 7

3

Match: Cycling holidays

All filters match

from £175 / night

£1,209 - £1,523 / week

Dog-friendly lakefront cottage w/dock, firepit & lovely views

Swanton house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 24 minutes

Match: Cycling holidays

All filters match

from £137 / night

£955 / week

Stillwater Haven

Friendsville chalet

7 bedrooms / 6 bathrooms / sleeps 20

2

Match: Cycling holidays

All filters match

from £986 / night

£6,897 / week

'Captain's Cottage' - Walk to Ocean City Beach!

Ocean City house

4 bedrooms / 2 bathrooms / sleeps 13

Responds fast! avg. 30 minutes

Match: Cycling holidays

All filters match

from £201 / night

£1,405 / week

National Harbor-Close to Gaylord Convention Center, MGM, DC-Great Deal!

Oxon Hill apartment

2 bedrooms / 2 bathrooms / sleeps 8

11

Responds fast! avg. 3 hours 42 minutes

Match: Cycling holidays

All filters match

from £272 / night

£1,904 / week

NEW! Lavish Ellicott City Studio w/Pool & Hot Tub!

Ellicott City studio

Studio / 1 bathroom / sleeps 4

Responds fast! avg. 30 minutes

Match: Cycling holidays

All filters match

from £107 / night

£749 / week

Contemporary Pasadena Apt w/Fireplace -Near River!

Pasadena apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 30 minutes

Match: Cycling holidays

All filters match

from £79 / night

£550 / week

Cozy Ocean City Condo w/Balcony-Steps to Beach!

Ocean City apartment

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 30 minutes

Match: Cycling holidays

All filters match

from £134 / night

£937 / week

Diamond Bay Condominium

Ocean City apartment

2 bedrooms / 2 bathrooms / sleeps 6

20

Responds fast! avg. 37 minutes

Match: Cycling holidays

All filters match

from £90 / night

£789 - £1,102 / week

St. Leonard Cottage w/Pool Overlooking Wells Cove!

Saint Leonard cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 30 minutes

Match: Cycling holidays

All filters match

from £81 / night

£562 / week

St. Michaels Area Cottage - Walk to Water & Marina

Neavitt house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 30 minutes

Match: Cycling holidays

All filters match

from £165 / night

£1,155 / week

Ocean City Condo w/ Balcony - Walk to Beach & Bay!

Ocean City condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 30 minutes

Match: Cycling holidays

All filters match

from £116 / night

£812 / week

CENTURY 1: 2 BR 2 BA, North Ocean City, DIRECT Oceanfront, FABULOUS Views!!

Ocean City condo

2 bedrooms / 2 bathrooms / sleeps 7

2

Responds fast! avg. 1 hour 1 minutes

Match: Cycling holidays

All filters match

from £223 / night

£981 - £1,070 / week

Updated Ocean City Condo - Just 60 Steps to Beach!

Ocean City apartment

2 bedrooms / 2 bathrooms / sleeps 6

2

Responds fast! avg. 30 minutes

Match: Cycling holidays

All filters match

from £125 / night

£874 / week

Ocean City Condo

Ocean City condo

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 2 hours 0 minutes

Match: Cycling holidays

All filters match

from £182 / night

£1,138 - £1,921 / week

*BOOK NOW* Beautiful Cottage in historic Annapolis

Annapolis cottage

3 bedrooms / 2 bathrooms / sleeps 6

22

Responds fast! avg. 1 hour 32 minutes

Match: Cycling holidays

All filters match

from £287 / night

£1,612 / week

Gorgeous Home on Chester River

Chestertown house

4 bedrooms / 9 bathrooms / sleeps 8

2

Match: Cycling holidays

All filters match

from £580 / night

£3,567 / week

Roomy single family house w/4 b/r and 2 1/2 bath

Fort Washington house

4 bedrooms / 3 bathrooms / sleeps 10

7

Responds fast! avg. 2 hours 6 minutes

Match: Cycling holidays

All filters match

from £112 / night

£781 / week

Belle Rose Cottage at Victory Farm (Pet Friendly!)

Chestertown house

1 bedroom / 1 bathroom / sleeps 3

3

Responds fast! avg. 1 hour 23 minutes

Match: Cycling holidays

All filters match

from £121 / night

£717 / week

Atlantic Dunes #202

Ocean City condo

1 bedroom / 1 bathroom / sleeps 4

10

Responds fast! avg. 2 hours 41 minutes

Match: Cycling holidays

All filters match

from £94 / night

£533 / week

Love Point Waterfront

Kent Island house

3 bedrooms / 3 bathrooms / sleeps 12

14

Match: Cycling holidays

All filters match

from £228 / night

£1,274 - £2,230 / week

Viewing 40 of 114
rentals in Maryland

×