Trappe, MD Vacation Homes from ￥38,358

A rural landscape with a dirt road leading to a red barn, surrounded by fields and a clear sky.

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Our top choices for Trappe vacation homes

A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

1. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge

Mary Beth S.

￥62,311 total

includes taxes & fees

Nov 19 - Nov 20

A bedroom with a bed, a bedside table, a window with curtains, and a view of the sea.

2. More, than just a place to sleep - welcome home!

Cambridge

￥62,932 total

includes taxes & fees

Oct 20 - Oct 21

A wooden interior with a dining area, sofas, and a table.

3. WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Cambridge

Anonymous traveler

￥88,492 total

includes taxes & fees

Oct 20 - Oct 21

A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink.

4. Waterfront Getaway with Dock

Woolford

Meagan G.

￥38,358 total

includes taxes & fees

Oct 20 - Oct 21

A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

5. WATERFRONT!! HOT TUB 3 bedroom Oasis on 2+ acres - Sleeps 8

Cambridge

Jill C.

￥82,814 total

includes taxes & fees

Oct 21 - Oct 22

A spacious living room with a large TV, blue sofa, and a ceiling fan.

6. The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford

Joyce F.

￥105,827 total

includes taxes & fees

Oct 21 - Oct 22

7. Family Beach House: Spacious Deck, Grill & Views

Chesapeak beach

Bryan P.

￥71,893 total

includes taxes & fees

Oct 27 - Oct 28

A backyard with a small waterfall, rocks, and a pond with lily pads. There are two blue chairs and a black pot near the waterfall.

8. Turnbridge Manor

Denton

Jessica H.

￥96,313 total

includes taxes & fees

Oct 27 - Oct 28

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Top Trappe Hotel Reviews

St Michaels Inn

10/10 Excellent

"Great location. Very clean."

Sandaway Suites & Beach

10/10 Excellent

"This little B&B was a complete surprise. My high school friend and I were on the Eastern Shore for our 50th high school reunion and were looking for somewhere to stay. We ended up choosing Sandaway, quite honestly, b/c it was all that was available at the time. We had no expectations. What a stunning surprise to find one of the finest accommodations I've ever stayed in, regardless of price! There was not a single thing that a traveler may require that was not thought of - from hooks in the bath, plenty of towels, brochures in the room about local attractions, two luggage racks, extra blankets and pillows. There was a carafe of hot coffee and a basket of breakfast items left quietly on the room's attached porch in the morning. There was a sweet little "goodie" bag in the room when we arrived with waters, snacks and a warm welcome note. We were informed that room around the corner from ours that had various breakfast/snack items available in the morning that we were free to help ourselves to. The host Ben was extremely helpful and kind, and had a ready solution to any questions or issue. There was a Keurig machine in our room that we couldn't get to work. When we reached out to him, he not only brought us a new machine, he also brought us two carafes of freshly brewed coffee. The room was charming & immaculate (even the tv remote was protected with a bag), with a stunning view of the Bay. I cannot recommend Sandaway highly enough. I will def be returning with my husband!"

The Wildset

10/10 Excellent

"Loved my stay at Wildset. Place is very clean, cozy & comfortable. Staff very friendly. Convenience to everything in town. Only 2 issues I had was how long it took shower water to get hot. And it wasn’t super hot. Not sure if it was cause I was in main building. Other was a knocking noise which seemed to happen primarily while restaurant was open. Not sure if it was from the dishwasher or some other equipment. I’m a light sleeper too so some people may be able to sleep thru it. Would def stay here again!!"

Find out more about Trappe

Trappe Vacation Homes information

Number of reviews	191
Accommodation	245 Vacation Homes
Lowest Price	￥38,358
Highest Price	￥166,496

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Trappe vacation homes

1. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

2. More, than just a place to sleep - welcome home!