Vacation rentals with a fireplace in Annapolis

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Top-rated accommodations with a fireplace in Annapolis

Guests agree: these accommodations with a fireplace are highly rated for location, cleanliness, and more.

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Guest favourite

Home in Annapolis

4.98 out of 5 average rating, 130 reviews

Crab Cakes and Football Historic District

Soak up the vintage charm of this restored property. The house features a private master suite balcony, an open-plan living space, chic eclectic furnishings, exposed brick, a wood burning fireplace, a front garden, and an outdoor back BBQ area. STR# 143754 When we decided to convert to a short term rental I looked at other properties in the area and how they described them. I could tell you the house was built in 1901 and is located in one of the most sought after neighborhoods in historic Annapolis. That's all well and good but to be honest there's a book on the coffee table that will tell you all the history (if you really want to know). I might not know a lot about writing a great summary but after almost 3 decades of living in Annapolis I think I know what people want: 1) Great food and drink! 2) Great location for walking to everything and.. 3) An outdoor area to enjoy the mornings and evenings during any down time. Unfortunately the one thing that can really ruin the fun is PARKING! Well guess what, we've got all the things I listed above and not one parking spot, but TWO (right at your back door!). Don't be fooled when other properties offer you a parking pass. That does not mean you'll be parking near your rental! Enjoy full access to our home. We do not live there so it is not cluttered with "stuff". Consider it a hotel with all the amenities of home! We live 5-10 minutes from the property so you'll have your privacy but we are nearby if you need assistance. We are available by text or calling for any questions or help you may need. The home is in the Art District of Annapolis right in the middle of all the fun. Enjoy the hustle and bustle of the city center during the day and evening, but return to a quiet neighborhood to recharge. Free designated parking for 2 cars. Park upon arrival and you my never need your car again until your departure! No parties. Dogs welcome on a case by case basis.

Jul. 28 – Aug. 4

$737 CAD per night

Guest favourite

Condo in Annapolis

4.94 out of 5 average rating, 347 reviews

Brand New Reno in Historic Dist w 2 Parking spots

Spotless / sanitized !! Renovated upstairs unit two bedroom with TWO parking spots in the Historic District . Everything is high end ,brand new and used exclusively as a short term rental. Private entrance, cute small custom kitchen, ceiling fans, mini split A.C/ heat in every room for year round comfort. Hardwood floors, quality linens , lucid matresess, Keurig coffee bar, toiletries . Walk to town in 10 min or less or take the free trolley to Main st,USNA,Churches,AYC. No children under 10.

Nov. 26 – Dec. 3

$307 CAD per night

Guest favourite

Cottage in Edgewater

4.99 out of 5 average rating, 129 reviews

Waterfront Chesapeake Bay Getaway Firepit & Pier!

Gorgeous sunrises from your completely remodeled waterfront cottage! Experience fresh Maryland Crabs or fish caught from your private pier & enjoy the peace, serenity and bay breezes from your furnished deck and green space. Enjoy true nature and explore Selby Bay on the South River with our complimentary canoe! Super clean with water views from kitchen, dining, living room & enclosed porch! Situated in a quiet neighborhood within 45 minutes of DC & 15 minutes from Annapolis & the Naval Academy.

Aug. 16 – 23

$536 CAD per night

Guest favourite

Apartment in Stevensville

4.98 out of 5 average rating, 241 reviews

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Apr. 24 – May 1

$299 CAD per night

Guest favourite

Guest suite in Arnold

4.96 out of 5 average rating, 568 reviews

Old Bay Bungalow

This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

Jul. 24 – 31

$174 CAD per night

Guest favourite

Home in Shady Side

5.0 out of 5 average rating, 118 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silverwater is a lesson in quiet luxury, compelling architecture, unimaginable views and endless comforts. Original fine art and luxe bedding envelope you in a modern, light-filled space. Outside you will be treated to an expansive waterfront lawn that is great for games and afternoon sun. Rest on modern lounges or watch the sunset on your private waterfront bluestone patio tucked into the sea grass. As a guest favorite, your fabulous getaway is here—just read the reviews!

Feb. 3 – 10

$720 CAD per night

Guest favourite

Cottage in Annapolis

4.94 out of 5 average rating, 172 reviews

Secluded Cozy Cottage in Historic Downtown

Beautifully restored 1928 cottage w/ open floor plan & vaulted ceilings provide a homey vibe Enjoy Historic Annapolis Towncenter in your backyard Jack & Jill bath separates queen bedrooms. Comfortable full-size daybed = 3beds Hardwood floors adorn common areas Gourmet kitchen w/ extensive granite countertops, breakfast bar & amenities Dining table & chairs, extra-large comfy couch nestled between 2 chaise lounge chairs, 55" Roku tv, electric FP, towels, linens, pvt laundry, and more!

Nov. 6 – 13

$568 CAD per night

Guest favourite

Cottage in Annapolis

4.97 out of 5 average rating, 117 reviews

Waterfront farm retreat for vacation & telework

Stay on 125-acre Hollywood Farm in a beautiful and quiet home surrounded by water and woods. Our airy, mid-century renovated cottage feels like a sanctuary, tucked away on a peninsula on one of the largest tracts of conservation land in Maryland. This cozy, light-filled space is small but spacious, allowing you to work peacefully from home with a full desk and excellent high-speed internet access. Plus, there's a dock, kayaks, and lots of outdoor space for children and pets to run around in.

Nov. 27 – Dec. 4

$518 CAD per night

Guest favourite

Cottage in Glen Burnie

4.92 out of 5 average rating, 142 reviews

Home away from home

This is a small house with private parking close to Baltimore and Annapolis. I have one queen size Murphy bed, one single pull out couch. It has an updated kitchen, updated bathroom, walk-in closet, Internet and heating and cooling. I also have a pellet stove. my kitchen is fully stocked with dishes, knives, forks, pots and pans. The bathroom has towels and rugs. I tried to add all the amenities to make it as comfortable as home. Look at pet rules under the other things to note section.

Jan. 7 – 14

$141 CAD per night

Guest favourite

Guest suite in Annapolis

4.97 out of 5 average rating, 117 reviews

Great reviews! Pool, DT, stadium, goats, and more!

Welcome to our private guest suite in walking distance to the Navy-Marine Corps Memorial Stadium. Enjoy the indoor pool (June-September), furnished deck and patio, wood-burning stove and more. Have access to community piers, waterfront parks, and soft launches on the Severn River. The sights and sounds of downtown Annapolis are minutes away. All while being centrally located between Washington DC, Baltimore, and the Eastern Shore.

Jul. 9 – 16

$358 CAD per night

Guest favourite

Home in Annapolis

4.95 out of 5 average rating, 105 reviews

The Navy House-Walk or Shuttle Downtown! 3 bd

Your family will be close to everything when you stay at this centrally-located home. 3 blocks from the Navy stadium and walking distance to amazing restaurants! Here is your Annapolis home away from home. Our 3 bedroom 2.5 bath bungalow retreat is perfect for 6-7 people wanting to relax and see all that beautiful Annapolis has to offer. There’s also a free shuttle that takes you downtown to the water. Come, enjoy!

Nov. 2 – 9

$677 CAD per night

Guest favourite

Cabin in Gambrills

4.89 out of 5 average rating, 141 reviews

Relaxing Cabin Get Away Near Annapolis & DC

This is a 1,000 sq foot open concept rustic cabin. There are 4 "rooms" including a fully equipped kitchen, a dining room, a family room with a TV for movies and streaming, and a bedroom full of windows. It is located down a 1/3 mile gravel driveway in the woods on 72 acres of land that has been dedicated in perpetuity to not being developed.

Aug. 10 – 17

$248 CAD per night