Holiday rentals in Parole

4.95 out of 5 average rating, 120 reviews

Loft in Riva

New Loft w/South River view from treehouse deck!

Enjoy the quiet Sylvan Shores neighborhood and a view of the South River and bridges in this new modern apartment that has a treehouse style deck for relaxing and enjoying the outside. The unit is served by a separate entrance and free street parking. Bring your kayak or stand-up-paddleboard, or try your luck at fishing! The TV is upgraded to a 55". Downtown Annapolis is just 6 miles away and offers cultural attractions, bars and restaurants, historical tours and access to the Naval Academy.

4.98 out of 5 average rating, 110 reviews

Cottage in Annapolis

Miller Cottage - near Navy Stadium

Miller Cottage is a charming 1920s style cottage in the quiet neighborhood of Homewood and 1 mile to Church Circle/West Street and the state capital of Maryland, and 1 ½ miles to the City Dock. One bedroom with queen bed with an en suite bathroom with shower. Pull out couch for additional sleeping in the living room. Open plan living room, dining room and kitchen. Nautical furnishings, in a warm, bright home. Within walking distance of the Navy Marine Corp Stadium (about 6 tenths of a mile)

4.96 out of 5 average rating, 671 reviews

Guest suite in Arnold

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!

4.94 out of 5 average rating, 176 reviews

Guest suite in Arnold

Coastal Comfort Suite Near Annapolis, Hottub, EV

Hot tub is open for the season. Pool will be open May 12 through Labor Day weekend. Ideal for a couple's retreat, this king suite guest room has a massive bedroom with a seating area, mounted TV, and coffee bar with microwave/mini-fridge. An ensuite bathroom provides a luxurious shower with dual shower heads and a spacious closet. The pool and hot tub are seasonal. Please don’t hesitate to reach out with any questions, concerns, or expectations so that we can address them prior to your stay.

4.92 out of 5 average rating, 101 reviews

Flat in Annapolis

Dazzling day/night water views,1st class amemities

TREAT YOURSELF! YOU DESERVE THE VERY BEST! HUGE DISCOUNTS FOR WEEK AND MONTH LONG STAYS! Treat yourself to the good life while in Annapolis! Gorgeous 14yr. old custom designed & furnished 1470sq.ft. waterfront apartment, 9ft. ceilings, fantastic water views day & night! Private pier, firepit and 40ft. waterfront covered patio for guests use. Guest parking for 4 cars. Few minutes to US Naval Academy, Annapolis Harbor, restaurants, shopping. Pet-friendly, must be cleared with host. *see below*

4.9 out of 5 average rating, 290 reviews

Calico Cottage Guest House, king bed, free parking

Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

5 out of 5 average rating, 28 reviews

Guest suite in Annapolis

Pristine, Private 1 Bed/1 Bath Guest Apartment

Welcome to Fox Haven, where you'll enjoy a private, peaceful and pristine 1 Bed/1 Bath apartment. Able to accommodate 3 people (4 if close), we're situated on a quiet, dead-end street outside of the Annapolis Arts District. Enjoy a wooded setting, plenty of free parking and quick walking access to town, Navy stadium and loads of restaurants. Take a short shuttle ride from the nearby Westin Hotel to the heart of downtown to enjoy shopping, the historic district, and our famous waterfront.

4.96 out of 5 average rating, 183 reviews

Lil’ House - A Serene Tiny Home Experience

Newly renovated, immaculate two room tiny home. A stand-alone gem nestled against a wooded backdrop - well back from the main home - and wrapped in a huge, teak-furnished, blue stone patio with fire pit situated in a sunny opening in the mature tree canopy. Super comfy queen Murphy bed offers easy conversion of the well lit and modern main living space from living room & kitchen by day to main sleeping quarters at night. The adjoining room is a well appointed full bath and dressing area.

Superhost

Cottage in Edgewater

4.73 out of 5 average rating, 183 reviews

Waterview Studio on a sunset corner

Book more than 2 days and get up to 15% off. Last painted in June 2021, new toilet and Tempurpedic mattress top. New wood floor installed in 2024. Private and comfortable studio in a centenary house with independent entrance in a quiet neighborhood surrounded by the waters of the South River. The house is divided in two independent and private units. Great for outdoor lovers. Ideal for gate away, temporary stays for work, vacation or relaxing from the stressful life.

4.99 out of 5 average rating, 136 reviews

Garden View, a spacious 1 bedroom with loft.

Relax and unwind at this peaceful and charming retreat, nestled in a quiet neighborhood. Located just minutes from Route 50, I-95, and Downtown Annapolis, Garden View is ideally situated for exploring Naval Academy sports, the Renaissance Festival, Boat Shows, and golf at The Preserve. If you prefer staying in, the fully equipped kitchen and free Wi-Fi make it easy to work or cook from the comfort of your space.

5 out of 5 average rating, 28 reviews

Home in Annapolis

CJ's Cottage

Welcome to your perfect retreat, just 8 minutes from the lively scene of downtown Annapolis! This charming cottage offers a blend of cozy, traditional charm and modern comforts. The property is situated in a peaceful and private location with amenities that make this home the ideal spot for casual gatherings or simply relaxing with a good book and a glass of wine.

4.9 out of 5 average rating, 515 reviews

Guest suite in Edgewater

South River Park Apartment

Located minutes from Annapolis, the in-law apartment offers access to Baltimore and DC in under an hour. The apartment offers its own entrance, full kitchen, one bathroom, one bedroom, tile floors, pullout sofa, Wifi, and parking. The apartment is registered with the Anne Arundel County Dept. of Inspections & Permits, #STR-15, for short term rentals.

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Popular amenities for Parole holiday rentals

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Other great holiday rentals in Parole

4.96 out of 5 average rating, 138 reviews

Blue Heron Room - Charming Private Room, Annapolis

KathleenRating, 5 stars1 week ago

I always enjoy staying here. Comfortable bed, perfect water pressure in the shower, crisp clean sheets, fridge and microwave available for our use. Great location, easy to access local roads and the highway. TV and books in the common room for entertainment, or Wi-Fi for your laptop and phone. I felt like I was home!

4.84 out of 5 average rating, 457 reviews

Cozy private room in Annapolis home

PandoraRating, 5 stars2 weeks ago

What a perfect place to get away! Cozy, artsy home and such a lovely, warm host. She volunteered use of her rain jacket when I came unprepared, left a treat for breakfast but also left me in private to recharge. The bed was comfortable, with easy access to the bathroom and kitchen, gorgeous view into the trees over the deck, great water pressure. Odin, friendly doggins, was available for petting as desired but he was also the perfect, peaceful gentleman with no barking or other intrusive antics. I can recommend highly!

4.96 out of 5 average rating, 336 reviews

Cape Cod Charm close to USNA & Annapolis - Room 2

JoeRating, 5 stars1 week ago

Beautifully decorated space, super clean, great location, and wonderful stay overall.

5 out of 5 average rating, 5 reviews

Home in Annapolis

Marymont Cottage

RangsineeRating, 5 stars3 weeks ago

It’s a warm, clean, comfortable and fell like home. There is a complete range of furniture and amenities. There is a garden behind the house, a peaceful and shady atmosphere, and a barbecue area. It is truly suitable for a family vacation. Very high speed wi-fi and completly furniture. Jennifer is a superhost, attentive and provided excellent information, was friendly and flexible without being asked. It is very worthwhile to stay here.

Home in Odenton

5 out of 5 average rating, 4 reviews

Train Tracks Getaway

Robert MerleRating, 5 stars2 weeks ago

Quiet neighborhood with a family friendly feel. Grill and outdoor games available at the house. Indoor games, books, and puzzles for all ages. Very clean. Comfortable bed and couch. Very relaxing. We were attending a wedding in Gambrill which was less than 10 minutes away. If we had the time to stay longer we would have liked to explore the area. Would book again!

4.96 out of 5 average rating, 556 reviews

Chesapeake Mornings

KathleenRating, 5 stars1 week ago

Host was waiting for me, door was open, friendly pups to help with acclimating and house tour. The bed was VERY comfortable, the shower water pressure was perfect, the room was quiet, the neighborhood was quiet. The only caution I would make is that if you are a warm person, be sure to request that the A/C be on and running. I loved everything about this home. Neat architecture, off street parking, large work desk just outside the room, strong Wi-Fi, and a VERY comfortable bed. I highly recommend this lovely home!

5 out of 5 average rating, 30 reviews

Guesthouse on The Weems Creek

ConradRating, 5 stars1 month ago

Wonderful escape in Annapolis! Private, clean, and peaceful. Host was very responsive and helpful. The guest house was fantastic and really helped us to unwind. Would definitely stay again!