Hot St. Michaels Cottage Rates

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Featured Cottages in St. Michaels

Amazing views, short walks to great dining!

Amazing views, short walks to great dining!

Annapolis
With a stay at this cottage in Annapolis (West Annapolis), you'll be within a 5-minute drive of U.S. Naval Academy and Navy-Marine Corps Memorial Stadium.
Amazing views, short walks to great dining!
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
Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,

Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,

Annapolis
With a stay at this cottage in Annapolis (Cape Saint Claire), you'll be within a 15-minute drive of U.S. Naval Academy and Sandy Point State Park.
Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,
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Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

West River
This cottage is 19.1 mi (30.8 km) from U.S. Naval Academy and 3.3 mi (5.2 km) from Franklin Point State Park.
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
"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
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Edgewater
With a stay at this cottage, you'll be centrally located in Edgewater, within a 15-minute drive of Sand Point Marsh and South River Golf Links.
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
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!
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
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

annapolis
With a stay at this cottage, you'll be centrally located in Annapolis, within a 15-minute drive of U.S. Naval Academy and Annapolis Bowl.
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
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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.

St. Michaels 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 St. Michaels 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 St. Michaels 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 St. Michaels, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

St. Michaels Cottages essential information

Accommodation
71 Cottages
Lowest Price
AU$150
Highest Price
AU$706
Popular accommodation
Amazing views, short walks to great dining!, Relaxing Waterfront Cottage Near St Michaels, Maryland, Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays, , Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC., "Point of View" Waterfront cottage with panoramic views on Tilghman Island, Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA, 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, NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

Top trending hotels in St. Michaels

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
The Wildset

The Wildset

2.5 out of 5
209 N Talbot St, St. Michaels, MD
Fully refundableReserve now, pay when you stay
The price is AU$403 per night from 23 Dec to 24 Dec
AU$403
includes taxes & fees
23 Dec - 24 Dec
With a stay at The Wildset in St. Michaels, you'll be within a 10-minute walk of Chesapeake Bay Maritime Museum and St. Michaels Museum.
The Wildset
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Parsonage Inn

Parsonage Inn

3.5 out of 5
210 North Talbot Street, St. Michaels, MD
The price is AU$317 per night from 6 Jan to 7 Jan
AU$317
includes taxes & fees
6 Jan - 7 Jan 2025
With a stay at Parsonage Inn in St. Michaels, you'll be in the historical district, within a 15-minute walk of Chesapeake Bay Maritime Museum and St. Michaels ...
Parsonage Inn
Don't see what you're looking for?
See all available properties in 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.

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^Subject to availability and chosen travel dates.