Trappe Vacation Rentals from CA $396: Short-Term Rentals for 2026

Q: What's the top vacation rental in Trappe?

Private 2 Acre Waterfront Family Retreat with Pool & Pier : Visitors like this Trappe vacation home rental. It is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

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Our top choices for Trappe vacation rentals

A living room with two grey sofas, a coffee table, and a ceiling fan.

1. Cambridge Apt in Walkable Neighborhood

Cambridge

LOIS

CA $455 total

includes taxes & fees

Oct 23 - Oct 24

2. Cambridge Apt in Walkable Neighborhood

Cambridge

Anonymous traveller

CA $467 total

includes taxes & fees

Oct 22 - Oct 23

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

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

Cambridge

Mary Beth S.

CA $556 total

includes taxes & fees

Nov 19 - Nov 20

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

4. Sailwinds Loft at Cambridge Creek

Cambridge

Sharon D.

CA $359 total

includes taxes & fees

Oct 27 - Oct 28

5. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Downtown Cambridge

Kristen S.

CA $531 total

includes taxes & fees

Nov 1 - Nov 2

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

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

Cambridge

CA $565 total

includes taxes & fees

Oct 22 - Oct 23

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

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

Cambridge

Anonymous traveller

CA $798 total

includes taxes & fees

Oct 21 - Oct 22

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

8. Waterfront Getaway with Dock

Woolford

Meagan G.

CA $354 total

includes taxes & fees

Nov 3 - Nov 4

A covered porch with wicker furniture, a small table, and a view of a lake.

9. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

Cambridge

CA $384 total

includes taxes & fees

Oct 27 - Oct 28

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

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

Cambridge

Jill C.

CA $746 total

includes taxes & fees

Oct 21 - Oct 22

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

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

Woolford

Joyce F.

CA $955 total

includes taxes & fees

Oct 21 - Oct 22

A covered outdoor dining area with a table and chairs, overlooking a body of water and trees.

12. Sunset Breezes - quiet waterfront retreat

Dorchester County

John C.

CA $442 total

includes taxes & fees

Nov 18 - Nov 19

A kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a dining table with chairs.

13. Plum Point Cottage #1

Calvert County

CA $720 total

includes taxes & fees

Oct 24 - Oct 25

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.

14. Turnbridge Manor

Denton

Jessica H.

CA $872 total

includes taxes & fees

Oct 28 - Oct 29

Three Adirondack chairs facing a beach with a clear view of the ocean.

15. Plum Point Cottage #14

Huntingtown

Yonnick H.

CA $772 total

includes taxes & fees

Oct 26 - Oct 27

A compact kitchen with a built-in sink, wooden countertop, and a ceiling fan.

16. Plum Point Cottage #17

Huntingtown

CA $655 total

includes taxes & fees

Oct 23 - Oct 24

An outdoor dining area with a wooden table and chairs, a bottle of wine, and a vase of flowers.

17. Plum Point Cottage #15

Maryland

CA $816 total

includes taxes & fees

Oct 23 - Oct 24

A two-story house with a red roof, a brick chimney, and a small porch.

18. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

Stevensville

"The house was clean. It is clear someone lives there full time and vacated the house for our stay. Their food and clothes remained in the property. It did not bother us, but not something we expected. The AC worked well. The owner communicated there were issues before we arrived that they were working to fix and left the number of the contractor in case we experienced issues. We were there the hottest weekend so far this year and did not have any issues. It does look like they are still...

Michele F.

CA $1,486 total

includes taxes & fees

Oct 23 - Oct 24

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Top Trappe Hotel Reviews

Wylder Tilghman Island

8/10 Good

"Beautiful setting. The hotel is a bit dated. Staff is very efficient and friendly."

Comfort Inn & Suites Cambridge

8/10 Good

"The property was very convenient for our trip to the area for my wife’s class reunion. The first room we were given smelled like cigarette smoke, we went to the receptionist she apologized and found us another room which was great. The floor above us was not sound proof therefore we were able to hear all footsteps and other movements of the quests above us. They were up at 6:00 am and sounded like they were having bedroom exercises but that soon stopped and things were fine. We will stay again for our next trip to town. Nice place to stay."

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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Trappe. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Trappe?

Yes, we give you a choice of vacation rentals near popular attractions in Trappe, or you can choose a more remote option if you're looking for a relaxing stay. Trappe is known for its waterfront and parks.

What's the top vacation rental in Trappe?

Private 2 Acre Waterfront Family Retreat with Pool & Pier: Visitors like this Trappe vacation home rental. It is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

How many vacation rentals will I find in Trappe?

With 4 Expedia vacation rentals, you're sure to find just the right place for your Trappe stay.

What’s there to see and do in Trappe?

While exploring the area, visit family-friendly sights like Chesapeake Bay Maritime Museum, or get outside and enjoy nature at Gerry Boyle Park at Great Marsh. In the larger area, you’ll find Bill Burton Fishing Pier State Park and Choptank River Lighthouse.

What’s a vacation rental in Trappe like?

Vacation rentals are privately owned properties you can book for a couple of days or more in Trappe. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for small groups.

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Check prices for these dates

Our top choices for Trappe vacation rentals

1. Cambridge Apt in Walkable Neighborhood

2. Cambridge Apt in Walkable Neighborhood