Hot St. Michaels Cottage Rates

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Featured Cottages in St. Michaels

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
Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier

Cambridge
With a stay at this cottage in Cambridge, you'll be on the waterfront, and 6.3 mi (10.1 km) from Ragged Island and 7.6 mi (12.2 km) from Spocott Windmill.
Family and Pet-Friendly, Waterfront with Pier
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
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Eastern Shore Waterside Cottage Near St. Michaels

Eastern Shore Waterside Cottage Near St. Michaels

Neavitt
When you stay at this cottage in Neavitt, you'll be on the waterfront and 3 minutes by foot from Neavitt Park.
Eastern Shore Waterside Cottage Near St. Michaels
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
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 just steps from Muskrat Park and St. Michaels Marina.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Waterfront dog-friendly home with beach just mins to Downtown Annapolis

Waterfront dog-friendly home with beach just mins to Downtown Annapolis

Annapolis
When you stay at this cottage in Annapolis, you'll be on the beach, within a 10-minute walk of Annapolis Sailing School and Annapolis Landing Marina.
Waterfront dog-friendly home with beach just mins to Downtown Annapolis
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 just steps from Muskrat Park and St. Michaels Marina.
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
97 Cottages
Lowest Price
AU$175
Highest Price
AU$823
Popular accommodation
Relaxing Waterfront Cottage Near St Michaels, Maryland, Family and Pet-Friendly, Waterfront with Pier, Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, Eastern Shore Waterside Cottage Near St. Michaels, Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA, Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, Waterfront dog-friendly home with beach just mins to Downtown Annapolis, 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$823 per night from 1 Apr to 2 Apr
AU$823
includes taxes & fees
1 Apr - 2 Apr
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$175 per night from 1 Apr to 2 Apr
AU$175
includes taxes & fees
1 Apr - 2 Apr
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$418 per night from 1 Apr to 2 Apr
AU$418
includes taxes & fees
1 Apr - 2 Apr
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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Parsonage Inn

Parsonage Inn

3.5 out of 5
210 North Talbot Street, St. Michaels, MD
The price is AU$367 per night from 14 Apr to 15 Apr
AU$367
includes taxes & fees
14 Apr - 15 Apr
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.