Hot Annapolis Cottage Rates

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Featured Cottages in Annapolis

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

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

Annapolis
Book a stay at this beach cottage in Annapolis. Enjoy free WiFi, a beach locale, and a fitness center. Popular attractions Annapolis Landing Marina and Annapolis ...
Waterfront dog-friendly home with beach just mins to Downtown Annapolis
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
Book a stay at this golf cottage in Annapolis. Enjoy free WiFi, a garden, and tennis courts. Popular attractions Annapolis Bowl and Westfield Annapolis Mall ...
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Amazing views, short walks to great dining!

Amazing views, short walks to great dining!

Annapolis
Book a stay at this family-friendly cottage in Annapolis. Enjoy free WiFi, a garden, and a picnic area. Popular attractions Helen Avalynne Tawes Garden and Navy-Marine ...
Amazing views, short walks to great dining!
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Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

Annapolis
Stay at this cottage in Annapolis. Enjoy free WiFi, a garden, and patios. Popular attractions Helen Avalynne Tawes Garden and Navy-Marine Corps Memorial Stadium ...
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break

Annapolis
Stay at this cottage in Annapolis. Enjoy free breakfast, free WiFi, and a garden. Popular attractions Sandy Point State Park and Bay Hills Golf Club are located ...
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break
Pet-friendly Annapolis Home: Walk to Beach!

Pet-friendly Annapolis Home: Walk to Beach!

3 out of 5
Annapolis
Stay at this 3-star beach cottage in Annapolis. Enjoy free parking, a marina, and a garden. Popular attractions Bay Ridge Beach and Annapolis Golf Club are located ...
Pet-friendly Annapolis Home: Walk to Beach!
6 Mi to Dtwn: Family-friendly Home in Annapolis!

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

3 out of 5
Annapolis
Stay at this 3-star cottage in Annapolis. Enjoy free parking, in-room fireplaces, and air conditioning. Popular attractions Broad Creek Marsh and Annapolis Harbour ...
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown

Annapolis
Stay at this cottage in Annapolis. Enjoy free WiFi, a garden, and patios. Popular attractions 14 Fleet Street and 48 Fleet Street are located nearby.
Secluded Cozy Cottage in Historic Downtown
The Yellow Cottage on Harness Creek

The Yellow Cottage on Harness Creek

Annapolis
Stay at this cottage in Annapolis. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Great Frogs Winery and Maryland Quiet Waters Park ...
The Yellow Cottage on Harness Creek
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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.

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

Annapolis Cottages essential information

Accommodation
18 Cottages
Lowest Price
NZ$168
Highest Price
NZ$348
Popular accommodation
Waterfront dog-friendly home with beach just mins to Downtown Annapolis, NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak, Amazing views, short walks to great dining!, Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking, , Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring break , Pet-friendly Annapolis Home: Walk to Beach!, 6 Mi to Dtwn: Family-friendly Home in Annapolis!, Secluded Cozy Cottage in Historic Downtown, The Yellow Cottage on Harness Creek

Top trending hotels in Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is NZ$348 per night from 9 Apr to 10 Apr
NZ$348
includes taxes & fees
9 Apr - 10 Apr
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
Historic Inns of Annapolis
The Westin Annapolis

The Westin Annapolis

4 out of 5
100 Westgate Cir, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is NZ$298 per night from 6 Apr to 7 Apr
NZ$298
includes taxes & fees
6 Apr - 7 Apr
Stay at this 4-star spa hotel in Annapolis. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
The Westin Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd, Annapolis, MD
Fully refundable
The price is NZ$220 per night from 14 Apr to 15 Apr
NZ$220
includes taxes & fees
14 Apr - 15 Apr
Stay at this 3.5-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Crowne Plaza Annapolis by IHG
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Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is NZ$168 per night from 20 Apr to 21 Apr
NZ$168
includes taxes & fees
20 Apr - 21 Apr
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
Hilton Garden Inn Annapolis Downtown
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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.