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© craigslist - Map data © OpenStreetMap
available jan 1, 2022
air conditioning
furnished
apartment
laundry on site
off-street parking
private bath
private room
LIVE IN A BIG BEAUTIFUL LOG HOME THAT'S COZY COMFY ! 999. per month plus 999.00 security deposit. ready jAN 1st, will go fast.. BEDROOM, sitting ROOM FURNISHED room has mini ...
Partial Matches Found
Partial Matches Found
We found 43 more vacation rentals for Craigslist: Chester, MD Vacation Rentals that partially match or are similar
$1,018
4 Bedroom 4.5 baths Dog-friendly 4.83 6 reviews What our guests are saying... AI-generated...
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Avg / night: $1,018. Renovated, dog-friendly home with private pool, hot tub & stunning backyard | Located in Pasadena, MD | 4.83 Stars | 4 Bed, 4.5 Bath | Pet-friendly. Dog-friendly. Max 14 guests. Whether you're planning to explore Annapolis, Baltimore, or Washington, DC, this four-bedroom home in Pasadena perfectly fits the bill. Enjoy a living space that's been renovated from top to bottom ...
Avg / night: $495. Riverfront home with multiple decks, central AC, washer/dryer - two dogs OK | Located in Arnold, MD | 4.84 Stars | 3 Bed, 3 Bath | Pet-friendly. Dog-friendly. Max 8 guests. This newly updated mid-century modern home offers a peaceful retreat from the brisk pace of everyday life. The home sits above Chase Creek on a spectacular piece of land surrounded by acres of open space, ...
Avg / night: $484. Gorgeous & bright retreat with patio, firepit, W/D, & stunning rooftop views | Located in Annapolis, MD | 5.0 Stars | 2 Bed, 1.5 Bath | No Pets. No pets. Max 6 guests. This bright and inviting vacation home provides an ideal escape for a romantic couple's getaway or a family excursion, allowing you to explore all the attractions Annapolis offers. Nearby, you'll find popular d...
Avg / night: $2,416. 3-story home near river with patio, firepit, Ping-Pong, grill and wood fireplace | Located in Annapolis, MD | 6 Bed, 6.5 Bath | No Pets. No pets. Max 12 guests. Perfect for family and group gatherings, this darling, three-story home near Severn River is calling your name! There is a beautiful paver patio with a backyard firepit surrounded by a wooded backyard and mature lan...
Avg / night: $1,927. Lakefront home with private dock, deck, hot tub, firepit, Ping-Pong, large yard | Located in Annapolis, MD | 4.86 Stars | 6 Bed, 4.5 Bath | Pet-friendly. Dog-friendly. Max 16 guests. Experience incredible and memorable indoor and outdoor spaces at this spacious waterfront home! Admire unparalleled Lake Ogleton views from your large backyard, which also is equipped with a fa...
Avg / night: $1,011. Updated historic home with parking; near Academy, college & harbor - central AC | Located in Annapolis, MD | 4.95 Stars | 4 Bed, 2.5 Bath | No Pets. No pets. Max 8 guests. Located within a block of the William Paca House and Gardens and two blocks from Annapolis Harbor, St. Johns College, and the Naval Academy, this historic home is the perfect home base for an exciting and...
Avg / night: $739. Historic downtown townhome with brick courtyard, sunroom & parking | Located in Annapolis, MD | 4.0 Stars | 3 Bed, 2.5 Bath | No Pets. No pets. Max 6 guests. Conveniently located in the Historic District of downtown Annapolis, this two-story retreat is perfect for families and friends looking for a convenient location with parking to immerse yourselves in the history of Annap...
Avg / night: $1,698. Dog-friendly riverfront home with dock, 2 balconies, waterside patio, & grill | Located in Annapolis, MD | 5.0 Stars | 4 Bed, 4.5 Bath | Pet-friendly. Dog-friendly. Max 10 guests. The Master Shipwright offers you downtown convenience, history, and charm as well as, a true Annapolis waterfront experience on Spa Creek. Four painstakingly renovated floors bring this home into ...
Avg / night: $1,384. Beautiful waterfront home on The Chesapeake Bay with private dock & beach access | Located in Annapolis, MD | 4.67 Stars | 5 Bed, 3.5 Bath | No Pets. No pets. Max 10 guests. Find gorgeous gathering spaces inside and out at this light-filled three-story waterfront home on a protected inlet of the Chesapeake Bay. Here in Bay Ridge, you'll have a private dock, access to the ba...
Avg / night: $746. Waterfront home with scenic porches, yard, grill, jetted tub, central AC, & W/D | Located in Annapolis, MD | 4.89 Stars | 3 Bed, 3.5 Bath | No Pets. No pets. Max 10 guests. Overlooking Chesapeake Bay, this charming Annapolis home is nestled in the serene Bay Ridge community, just steps away from a private beach. Bring the whole family together and relish watching gorgeous sun...
Avg / night: $1,560. 3-story, dog-friendly home near beaches with home theatre, grill & gaming tables | Located in Annapolis, MD | 4.91 Stars | 6 Bed, 5.5 Bath | Pet-friendly. Dog-friendly. Max 15 guests. Located just a block away from the Chesapeake Bay and Bay Ridge community beaches and a few miles from Annapolis' historic downtown area, this roomy home will be perfect for a memorable family...
Avg / night: $840. Dog-friendly house with yard, deck, firepit, washer/dryer & AC - near golf | Located in Annapolis, MD | 4.9 Stars | 4 Bed, 2 Bath | Pet-friendly. Dog-friendly. Max 10 guests. Located in the highly-desirable Murray Hill neighborhood in Annapolis, find this well-appointed house. Boasting great walkability to the area's restaurants, art galleries, shops, parks, and water taxi - ...
Avg / night: $858. Sprawling Waterfront Home with views, Dock and In-Home Theatre | Located in Grasonville, MD | 3.25 Stars | 4 Bed, 4.5 Bath | No Pets. No pets. Max 8 guests. The vacation of your dreams awaits at this bayfront beauty. Large enough for the whole family to enjoy and boasting a dazzling list of amenities, this home is truly a gem! The epitome of life on the water, enjoy swimming,...
Avg / night: $1,749. Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D | Located in Annapolis, MD | 4.82 Stars | 6 Bed, 4.5 Bath | No Pets. No pets. Max 12 guests. On the quiet Lake Ogleton off of the Chesapeake, this waterfront home with a gorgeous new pool, hot tub, and private pier will be a place for you and yours to relax and make memories. This beautiful Frank Ll...
Avg / night: $776. 2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace | Located in Annapolis, MD | 4.93 Stars | 4 Bed, 3 Bath | No Pets. No pets. Max 8 guests. Looking for the perfect retreat for a memorable stay-cation with your beloved groups? Then, look no further than this two-story, family-friendly home located just a mile from the heart of the forever charming ...
Avg / night: $316. Charming brick home with patio, WiFi, AC, & W/D - walk to everything | Located in Annapolis, MD | 4.69 Stars | 2 Bed, 2 Bath | No Pets. No pets. Max 4 guests. Historical charm meets modern convenience at this darling brick home, within easy walking distance of all Annapolis charms. Situated directly across from historic St. Johns College and a few blocks from the U.S. Naval A...
Avg / night: $948. Spacious home with an outdoor pool, screened porch, washer/dryer & central AC | Located in Annapolis, MD | 4.89 Stars | 4 Bed, 3 Bath | No Pets. No pets. Max 10 guests. Nestled in a family neighborhood between Fishing Creek and the South River, this Annapolis vacation home is great for groups with children, thanks to the various children's sleeping options. It offers a large ...
Avg / night: $203. Calloway Drive Retreat | House in Shady Side | Located in Shady Side, MD | 4.62 Stars | 3 Bed, 2 Bath | No Pets. No pets. Max 6 guests. Steps from the bay, curate all of your favorite vacation memories at the Calloway Drive Retreat! Spacious, tastefully decorated, and ready to host - this lovely home boasts comfortable furnishings and modern amenities. Hang out inside amongst...
Avg / night: $937. Spacious beachfront home with decks, gas grill, wet bar, gas fireplace, and W/D | Located in Annapolis, MD | 4.93 Stars | 4 Bed, 3.5 Bath | No Pets. No pets. Max 10 guests. Featuring the most sought-after Chesapeake Bay view, this luxurious newly built waterfront Annapolis retreat is ready for you and your family and friends! The porch and balcony are where you will spend mos...
Avg / night: $327. Gorgeous dog-friendly retreat w/ fireplace, patio, & firepit | Located in Annapolis, MD | 4.86 Stars | 3 Bed, 2.5 Bath | Pet-friendly. Dog-friendly. Max 8 guests. Located just minutes from downtown nightlife, this delightful two-story vacation home is ideal for large groups or family gatherings in the heart of the city. You ll enjoy being within walking distance of local shop...
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