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Featured Cottages in Trappe

Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland

Wittman
With a stay at this cottage in Wittman, you'll be on the waterfront, and 7.7 mi (12.4 km) from Phillips Wharf Environmental Center and 8.1 mi (13.1 km) from ...
Relaxing Waterfront Cottage Near St Michaels, Maryland
"Point of View" Waterfront cottage with panoramic views on Tilghman Island

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

Tilghman Island
When you stay at this cottage in Tilghman, you'll be 12 minutes by foot from Tilghman Watermen’s Museum.
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Saint Michaels
With a stay at this cottage in St. Michaels, you'll be a 5-minute walk from St. Michaels Museum and 7 minutes by foot from St. Michaels Winery.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
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Premier St. Michaels Cottage - T. Blades House -  Walk to Everything in Town

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St Michaels
With a stay at this cottage in St. Michaels, you'll be within a 10-minute walk of Chesapeake Bay Maritime Museum and St. Michaels Museum.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

St Michaels
With a stay at this cottage in St. Michaels, you'll be within a 10-minute walk of St. Michaels Museum and Chesapeake Bay Maritime Museum.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Saint Michaels
With a stay at this cottage in St. Michaels, you'll be a 5-minute walk from Chesapeake Bay Maritime Museum and 6 minutes by foot from St. Michaels Museum.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
The Middle Point Cabin in Saint Michaels

The Middle Point Cabin in Saint Michaels

Neavitt
With a stay at this cottage in Neavitt, you'll be 9.8 mi (15.8 km) from Chesapeake Bay Maritime Museum and 10 mi (16.1 km) from St. Michaels Museum.
The Middle Point Cabin in Saint Michaels
Waterfront, cozy cottage with private pool on 27 acres

Waterfront, cozy cottage with private pool on 27 acres

Cambridge
Located in Cambridge, this cottage is on the waterfront, within a 15-minute drive of Spocott Windmill and Richardson Maritime Museum.
Waterfront, cozy cottage with private pool on 27 acres
Eastern Shore Waterside Cottage Near St. Michaels

Eastern Shore Waterside Cottage Near St. Michaels

Neavitt
With a stay at this cottage in Neavitt, you'll be on the waterfront, and 9.9 mi (16 km) from Chesapeake Bay Maritime Museum and 10.1 mi (16.2 km) from St. Michaels ...
Eastern Shore Waterside Cottage Near St. Michaels
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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.

Trappe Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Trappe will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Trappe definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Trappe, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Trappe Cottages essential information

Accommodation
30 Cottages
Lowest Price
AU$150
Highest Price
AU$706
Popular accommodation
Relaxing Waterfront Cottage Near St Michaels, Maryland, "Point of View" Waterfront cottage with panoramic views on Tilghman Island, John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town, Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, The Middle Point Cabin in Saint Michaels, Waterfront, cozy cottage with private pool on 27 acres , Eastern Shore Waterside Cottage Near St. Michaels

Top trending 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 AU$365 per night from 13 Jan to 14 Jan
AU$365
includes taxes & fees
13 Jan - 14 Jan 2025
Located in Cambridge, Hyatt Regency Chesapeake Bay is on the waterfront, a 4-minute drive from Bay Country Shop and 6 minutes from Dorchester County Visitors ...
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 AU$706 per night from 9 Jan to 10 Jan
AU$706
includes taxes & fees
9 Jan - 10 Jan 2025
A stay at Inn at Perry Cabin places you in the heart of St. Michaels, within a 15-minute walk of Chesapeake Bay Maritime Museum and St. Michaels Museum.
Inn at Perry Cabin
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundableReserve now, pay when you stay
The price is AU$150 per night from 5 Jan to 6 Jan
AU$150
includes taxes & fees
5 Jan - 6 Jan 2025
When you stay at St Michaels Inn in St. Michaels, you'll be in the historical district, within a 5-minute drive of St. Michaels Winery and Chesapeake Bay Maritime ...
St Michaels Inn
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Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites

2.5 out of 5
8708 Alicia Drive, Easton, MD
Fully refundableReserve now, pay when you stay
The price is AU$192 per night from 1 Jan to 2 Jan
AU$192
includes taxes & fees
1 Jan - 2 Jan 2025
With a stay at Best Western Plus Easton Inn & Suites in Easton, you'll be within a 5-minute drive of Easton Cycle and Sport and Talbot Massage.
Best Western Plus Easton Inn & Suites
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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.

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^Subject to availability and chosen travel dates.