Hot St. Michaels Cottage Rates

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Featured Cottages in St. Michaels

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 just steps from Muskrat Park and St. Michaels Marina.
John Bruff Waterview Cottage - on Harbor and on Park - 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 just steps from Higgins Yacht Yard and Marina and St. Michaels Marina.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
"Point of View" Waterfront cottage with panoramic views on Tilghman Island

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

Tilghman Island
With a stay at this cottage in Tilghman, you'll be within a 10-minute walk of Kronsberg Park and Talbot County Library Tilghman Branch.
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
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Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland

Wittman
Located in Wittman, this cottage is on the waterfront, within a 15-minute drive of Wittman Park and CL Open Field.
Relaxing Waterfront Cottage Near St Michaels, Maryland
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
Enchanting West River Retreat

Enchanting West River Retreat

West River
This cottage is 19.3 mi (31.1 km) from U.S. Naval Academy and 3.5 mi (5.6 km) from Franklin Point State Park.
Enchanting West River Retreat
6 Mi to Dtwn: Family-friendly Home in Annapolis!

6 Mi to Dtwn: Family-friendly Home in Annapolis!

3 out of 5
Annapolis
With a stay at this cottage in Annapolis, you'll be within a 10-minute drive of U.S. Naval Academy and Broad Creek Marsh.
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb

Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb

North Beach
Located in North Beach, this cottage is on the waterfront, within a 10-minute drive of Bayside History Museum and Upper Yough River.
Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb
Pet-friendly Annapolis Home: Walk to Beach!

Pet-friendly Annapolis Home: Walk to Beach!

3 out of 5
Annapolis
With a stay at this cottage in Annapolis (Oyster Harbor), you'll be within a 15-minute drive of U.S. Naval Academy and Bay Bridge Market Place Shopping ...
Pet-friendly Annapolis Home: Walk to Beach!
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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
78 Cottages
Lowest Price
AU$137
Highest Price
AU$634
Popular accommodation
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, "Point of View" Waterfront cottage with panoramic views on Tilghman Island, Relaxing Waterfront Cottage Near St Michaels, Maryland, Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA, Enchanting West River Retreat, 6 Mi to Dtwn: Family-friendly Home in Annapolis!, Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb, Pet-friendly Annapolis Home: Walk to Beach!

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$634 per night from 26 Feb to 27 Feb
AU$634
includes taxes & fees
26 Feb - 27 Feb
A stay at Inn at Perry Cabin places you in the heart of St. Michaels, steps from Perry Cabin Park and 8 minutes by foot from Higgins Yacht Yard and Marina.
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$137 per night from 9 Mar to 10 Mar
AU$137
includes taxes & fees
9 Mar - 10 Mar
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$379 per night from 24 Feb to 25 Feb
AU$379
includes taxes & fees
24 Feb - 25 Feb
With a stay at The Wildset in St. Michaels, you'll be within a 5-minute walk of Higgins Yacht Yard and Marina and Saint Michaels Town Hall.
The Wildset
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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 just steps from Higgins Yacht Yard and Marina and St. Michaels Marina.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Don't see what you're looking for?
See all available properties in St. Michaels
View all properties
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.