Trappe Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Trappe

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd, Cambridge, MD
Fully refundableReserve now, pay when you stay
The price is 5.455.692 ₫ per night from 28 Sept to 29 Sept
5.455.692 ₫
7.449.390 ₫ total
28 Sept - 29 Sept
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"Great stay at the Hyatt! Beautiful location and property, staff incredible! Only lost a star because drinks/food a bit overpriced and not 5 star."

Reviewed on 18 Aug 2025

Hyatt Regency Chesapeake Bay
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is 15.062.454 ₫ per night from 17 Sept to 18 Sept
15.062.454 ₫
18.225.701 ₫ total
17 Sept - 18 Sept
includes taxes & fees
9.4/10 Exceptional! (361 reviews)
Lived up to its Reputation
"My wife and I recently stayed here to celebrate a milestone birthday. It certainly lived up to the hype and was one do the nicer places we have ever stayed."

Reviewed on 25 Aug 2025

Inn at Perry Cabin
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundable
The price is 2.650.886 ₫ per night from 8 Sept to 9 Sept
2.650.886 ₫
2.916.027 ₫ total
8 Sept - 9 Sept
includes taxes & fees
St Michaels Inn
See all 439 properties in Trappe
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Trappe holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday to Trappe costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Trappe?
To pick up cheap Trappe holiday packages, organise your getaway outside of peak times such as public holidays. You'll typically find lower prices and better availability when it's less busy.
How many days is enough for Trappe?
Typically, a handful of days is enough to see the top sights during your Trappe holiday. However, if you want to have time to chill out or go on day tours, consider extending your trip.
How to find the best Trappe package deals?
Use Expedia's filter tool to help you find some unbeatable Trappe package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Trappe package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your holiday package as soon as possible.
Is it cheaper to book a Trappe holiday as a package?
An Expedia holiday package could score you significant savings when compared to booking hotels and flights individually. Better still, you can tailor your Trappe escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a holiday package to Trappe?
If you're considering a spontaneous Trappe adventure, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Trappe?

  1. Pick your dates: The things you want to do in Trappe and your favourite season can help you decide when to travel.
  2. Budget wisely: In addition to the price of your accommodation, you should factor in other expenses too. These include flights, food and transportation. Also, put aside some extra funds for unexpected costs that may crop up during your trip to Trappe.
  3. Set the duration of your trip: Start by listing all the attractions and activities you'd like to experience in Trappe. Then, estimate how long you'll need for each, along with any travel time.
  4. Combine your accommodation and airfare: Once you've settled on your dates and duration, book the ideal Trappe holiday package for you.