Updating...

Enter dates for more accurate prices

Trappe Rentals

Filter

Bedrooms

  • Any
  • 1+ Bedrooms
  • 2+ Bedrooms
  • 3+ Bedrooms
  • 4+ Bedrooms
  • 5+ Bedrooms
  • 6+ Bedrooms
  • 7+ Bedrooms
  • 8+ Bedrooms
  • 9+ Bedrooms
  • 10+ Bedrooms
  • 11+ Bedrooms
  • 12+ Bedrooms
  • 13+ Bedrooms
  • 14+ Bedrooms
  • 15+ Bedrooms

Price range

Per night

$10 - $500

Trappe Rentals

39 Houses

Waterfront Room Rentals 1 with Private Beach

Trappe room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 38 minutes

Price per night from

$149

1 / 34

Waterfront Room Rentals 2 with Private Beach

Trappe room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 38 minutes

Price per night from

$114

1 / 42

Waterfront Room Rentals 3 with Private Beach

Trappe room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 38 minutes

Price per night from

$115

1 / 44

Waterfront Vacation Home with Private Beach

Trappe house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 38 minutes

Price per night from

$377

1 / 55

Great rentals within 20 miles that match your search

Stunning, Newer Chesapeake Waterfront Estate, Pool - 6/7 Bedrms 5 Baths

Cambridge house

6 bedrooms / 5 bathrooms / sleeps 20

“Outstanding Vacation Rental” Our extended family (22 people - 13A/9K) had a great week at Saddle Beach. The house was beautiful and in very good condition. The option of being in the pool or the river during the day was wonderful. The house was cle

Price per night from

$569

1 / 31

St. Michael's Premier in Town Summer Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$325

1 / 7

Cottage 1b at Grandview Pleasure Point

Bozman cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$280

1 / 6

RESTORED WATERFRONT COTTAGE

Royal Oak cottage

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$411

1 / 24

Choptank River View House

Cambridge house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$1,140

1 / 16

Cottage 1a at Grandview Pleasure Point

Bozman house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$280

1 / 8

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

St. Michaels house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$428

1 / 22

Cottage at Heron Cove, Chesapeake Bay, Cambridge

Cambridge cottage

3 bedrooms / 1 bathroom / sleeps 5

Price per night from

$168

1 / 50

Main House at Grandview at Pleasure Point

Bozman house

5 bedrooms / 3 bathrooms / sleeps 13

“5 out of 5” I spent a long weekend at the main house, and it was easily the best weekend of the summer! The location is phenomenal. The house sits on large stretch of beautiful waterfront property. The views from the piers and the pool are exquisite.

Price per night from

$787

1 / 34

Cottage 2 at Grandview Pleasure Point

Bozman house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$440

1 / 9

Best sunrise in St. Michaels....Broadview Bay House

St. Michaels house

6 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$598

1 / 24

Harris Cove Cottages LLC

St. Michaels cottage

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$228

1 / 12

Waterfront 5 bd 2 ba colonial in Tilghman Island

Tilghman house

5 bedrooms / 2 bathrooms / sleeps 12

Responds fast! avg. 2 hours 49 minutes

Price per night from

$191

1 / 23

Historic Waterfront Property with Wi-Fi and Dock

St. Michaels house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 21 minutes

Price per night from

$857

1 / 18

Deerpond Carriage House

Woolford guest house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$206

1 / 17

Year Round Estate on Bay / Fam. Reunions / Slps 28

Cambridge house

7 bedrooms / 7 bathrooms / sleeps 28

“Unbelievable Home in an Unbelievable Setting!!!” Our family cant thank you enough for the memories made at captains quarters this summer. This was the first time getting away with the entire family (kids grandkids, grand parents, etc) and it was prop

Price per night from

$997

1 / 35

St. Michaels award-winning waterfront BayCottage, pool, docks, sundeck, grounds

St. Michaels villa

6 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 3 hours 35 minutes

Price per night from

$1,142

1 / 38

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

Royal Oak house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$570

1 / 37

Halos'Haven Vacation Rental

McDaniel house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$800

1 / 15

EASTERN SHORE MARYLAND WELCOMES YOU

Preston house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$86

1 / 23

6 Bdrm, 3.5 Bath, Cambridge Md Vacation Home

Cambridge house

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$992

1 / 8

Maryland’s Eastern Shore Welcomes You

Preston house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$100

1 / 20

Cambridge Colonial Home, Walk to Town & Waterfront

Cambridge house

3 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 11 minutes

Price per night from

$274

1 / 36

Premier Cottage in St. Michaels- In Town Location!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 48 minutes

Price per night from

$206

1 / 24

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 48 minutes

Price per night from

$206

1 / 27

Large Historic Thomas Harrison House on Harbor in St. Michaels Town

St. Michaels house

7 bedrooms / 4 bathrooms / sleeps 9

“Perfect in every way!” I stayed at the Thomas Harrison house a few weeks ago and all I can say is..."if you are planning on coming to St. Michael's you need to stay at this house." This house is perfect in every way. It has all the accommodations that

Responds fast! avg. 2 hours 48 minutes

Price per night from

$400

1 / 30

Tranquil Easton Waterfront Property

Easton house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$685

1 / 15

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

Wittman log cabin

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,113

1 / 36

St. Michaels Waterfront Home W/Dock for 2 boats

Neavitt house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 2 hours 3 minutes

Price per night from

$257

1 / 18

Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX

St. Michaels house

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$262

1 / 18

Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!

St. Michaels cottage

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 48 minutes

Price per night from

$217

1 / 23

Waterview Cottage In St. Michaels!

St. Michaels cottage

2 bedrooms / 3 bathrooms / sleeps 5

Responds fast! avg. 2 hours 48 minutes

Price per night from

$217

1 / 25

Halo's Haven Guest Quarters

St. Michaels house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$371

1 / 14

Lakeside Private Apartment

Wye Mills apartment

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$159

1 / 15
Viewing 38 of 39
Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more