Cottage vacation rentals in Rosedale

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Top-rated cottage rentals in Rosedale

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Guest favorite

Cottage in Annapolis

4.96 out of 5 average rating, 340 reviews

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

Apr 5 – 12

ﺩ.ﺇ779 per night

Guest favorite

Cottage in Essex

5.0 out of 5 average rating, 27 reviews

The Little House of Rockaway Beach, Maryland

Unwind at this new home in a quiet, safe neighborhood on the Chesapeake Bay. Designed by the host, the house is decorated with a mix of vintage and new items lovingly chosen to create an eclectic coastal cottage. Four adults (no pets) will sleep comfortably on a queen bed and a sleep sofa w/queen mattress. The clean and modern kitchen is fully equipped. Enjoy water views from the attached deck or walk a short distance to the waterfront where a designated deck offers seating and water sport gear.

Oct 24 – 31

ﺩ.ﺇ631 per night

Guest favorite

Cottage in Pasadena

4.95 out of 5 average rating, 21 reviews

House w/Water Views of Rock Creek 2BA 2BA Cottage

Come experience a water community getaway in Pasadena Maryland. Renovated cottage in a waterfront neighborhood with full kitchen, 2 bedrooms, 2 bathrooms with laundry. Stainless steel appliances and all kitchen essentials if you wish to stay in and cook, or walk to Mike's North Crab House to pick & eat crabs. Great walkable neighborhood. Short drive to Fort Smallwood Park, the Rumor Reel waterfront restaurant and Compass Pointe Golf Course. 20 min drive to Annapolis and Baltimore. Great location

Mar 15 – 22

ﺩ.ﺇ1,038 per night

Guest favorite

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!

Dec 18 – 25

ﺩ.ﺇ1,284 per night

Guest favorite

Cottage in Chestertown

4.93 out of 5 average rating, 27 reviews

Chesapeake East Shore Chestertown, Pool & Dock

A bright, airy, newly-refurnished cottage set in the grounds of an 18th century farm on the eastern shore of Chesapeake Bay, shared pool (with your own use 6 hours a day, to Oct 1) & dock. Bring your watercraft, rods & nets Layout open kitchen, dining and living area. Master & bath on ground; upstairs 2 bed suite with bath and bedroom 5G fiber & smart TVs Gas fireplace, central heat and AC Linens, kitchen utensils & Keurig coffee maker. Washer and dryer. BBQ, deck chairs, picnic table Parking

Apr 18 – 25

ﺩ.ﺇ1,319 per night

Guest favorite

Cottage in Annapolis

4.93 out of 5 average rating, 149 reviews

Charming Cottage 2 parking spot easy walk downtown

Discover this charming, fully furnished cottage ideally accommodating up to six guests. Nestled on a serene street within walking distance of downtown, the United States Naval Academy, and the Navy and Marine Corps Stadium, this delightful space features a tranquil screened front porch, inviting living areas, and two bedrooms (one queen, two twin beds) with all bedding and linens provided. The lower level offers a full-size futon and a designated office area for added comfort and convenience.

Apr 5 – 12

ﺩ.ﺇ1,046 per night

Guest favorite

Cottage in Rock Hall

4.99 out of 5 average rating, 102 reviews

Cottage by the Bay in Rock Hall, MD

Sunny cottage in quiet waterside town of Rock Hall. Easy walk into downtown: grocery store, cafe, gift shop with beautiful housewares, gifts and jewelry, styling salon, quilt shop, ice cream shop, and local produce market. Gas fireplace, screened porch, stone patio, deck, several bicycles, tv for dvd's. Restaurants, crabs, Eastern Neck Wildlife Refuge, and nearby Tolchester and downtown Chestertown. Public pool, small beach (& picnic gazebos), bike around town...come to relax year round!

Nov 22 – 29

ﺩ.ﺇ827 per night

Guest favorite

Cottage in Annapolis

4.97 out of 5 average rating, 118 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.

Feb 13 – 20

ﺩ.ﺇ1,159 per night

Guest favorite

Cottage in Annapolis

4.94 out of 5 average rating, 316 reviews

Wright’s Cottage, Pets Welcome!

We offer a very tiny, mostly original, cottage built in the 1940’s. Located in the community of Bon Haven, large properties and big trees gives one a cozy, country feel, yet so close to bustling Annapolis! There is RV/EV hookup, an outdoor woodstove, and a propane grill for your use. The yard in the back of the cottage is fully fenced so your dog, cat, or maybe, pig or rabbit 🤔can freely play. Everything is very laid back at Wright’s cottage. Come stay and take the time to enjoy being you!

Aug 15 – 22

ﺩ.ﺇ603 per night

Guest favorite

Cottage in Pasadena

5.0 out of 5 average rating, 7 reviews

Sunset Lagoon Home

Have fun with the whole family at this stylish place! Our cozy cottage sits at the edge of a beautiful creek. Peaceful and tranquil, yet close to shops and restaurants, this waterfront property is perfect for serene getaways and family gatherings! Everyone will enjoy a unique and private space to relax. From peaceful mornings lounging on the balconies, to afternoons filled with fishing and kayaking, to magical sunsets on the 110-foot pier, this setting will quickly become a family favorite!

Apr 18 – 25

ﺩ.ﺇ1,372 per night

Guest favorite

Cottage in Glen Burnie

4.92 out of 5 average rating, 143 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.

Feb 19 – 26

ﺩ.ﺇ295 per night

Guest favorite

Cottage in Aberdeen

4.95 out of 5 average rating, 149 reviews

Tranquil Carriage House*MCM *Country *Wildlife

Pet, and Chemical Free. The Aberdeen Carriage House is in a country setting with a country road. We are not far from city limits and have most of your needs right here. In five minutes, you have a grocery store, dollar store, Target, Walgreens, Planet Fitness, and restaurants. Historic Havre de Grace, Ripken Stadium, Vineyards, Boating, and Golfing, only ten minutes. Baltimore and Stadiums are only 35 minutes down I95. The house is spotless and fully loaded with all the comforts of home.

Jul 6 – 13

ﺩ.ﺇ527 per night