Parole holiday rentals

We found 721 holiday rentals — enter your dates for availability
Discover a selection of 19 homes and other holiday rentals in Parole that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the best amenities for spending time at your holiday home, including air conditioning and cable TV. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Parole

Showing deals for:18 Dec - 25 Dec

Room
Private kitchen
Outdoor dining
Dining
Exceptional
(21 reviews)

Captain's Retreat! Newly Renovated - few steps from the beach!

Annapolis

16% off
AU$7,813
for 7 nights, 1 home
AU$1,116 per night
includes taxes & fees
Captain's Retreat! Newly Renovated - few steps from the beach!
Great Room
Terrace/patio
Kitchen - Granite Island
The Green Bedroom View
Exceptional
(15 reviews)

Waterfront Architectural Masterpiece with private dockage available.

Annapolis

7% off
AU$14,403
for 7 nights, 1 home
AU$2,058 per night
includes taxes & fees
Waterfront Architectural Masterpiece with private dockage available.
Upstairs Hall
Porch Dining Table
Kitchen
Swimming Pool
Exceptional
(35 reviews)

Waterfront Home near Annapolis, MD

Harwood

8% off
AU$19,076
for 7 nights, 1 home
AU$2,725 per night
includes taxes & fees
Waterfront Home near Annapolis, MD
Lawn for yard games along the waterfront, or simply relax in the shade
Enjoy screened in porch with dining table and sitting area
Beautiful waterfront home on Burley Creek with private pier
West-facing screened porch with bar area and café lights for night ambience
Exceptional
(62 reviews)

Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis

Annapolis

8% off
AU$7,258
for 7 nights, 1 home
AU$1,037 per night
includes taxes & fees
Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis
Private kitchen
Interior
Interior
Exterior
Exceptional
(14 reviews)

Charming Home located minutes from the Naval Academy and Downtown Annapolis

Annapolis

8% off
AU$5,998
for 7 nights, 1 home
AU$857 per night
includes taxes & fees
Charming Home located minutes from the Naval Academy and Downtown Annapolis
Dining
Exterior
Outdoor spa tub
Living area
Exceptional
(6 reviews)

Private Resort! 100" Home Theater, HotTub, Pool, Basketball Court, extra games

Bowie

8% off
AU$11,185
for 7 nights, 1 home
AU$1,598 per night
includes taxes & fees
Private Resort! 100" Home Theater, HotTub, Pool, Basketball Court, extra games
Living area
Private kitchen
Interior
Room
Exceptional
(14 reviews)

The General's House-Spacious Home w/Pool & Hot Tub

Annapolis

7% off
AU$12,226
for 7 nights, 1 home
AU$1,747 per night
includes taxes & fees
The General's House-Spacious Home w/Pool & Hot Tub
Living area
Private kitchen
Exterior
Dining
Excellent
(11 reviews)

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis

8% off
AU$5,091
for 7 nights, 1 home
AU$727 per night
includes taxes & fees
Fabulous 5-bedroom house with AC in charming Annapolis
Marina
Terrace/patio
outdoor space
upstairs bedroom w/ King size bed and space for queen air mattress
Exceptional
(94 reviews)

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Pasadena

8% off
AU$5,336
for 7 nights, 1 home
AU$762 per night
includes taxes & fees
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Exterior
New Kitchen 2022
Interior
Property grounds
Exceptional
(65 reviews)

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville

8% off
AU$5,168
for 7 nights, 1 home
AU$738 per night
includes taxes & fees
Circa 1700 Chesapeake Colonial home on the National Register.
Exterior
Terrace/patio
Private kitchen
Living area
Exceptional
(31 reviews)

Charming 3BDR Bungalow Near Annapolis​

Riva

9% off
AU$3,219
for 7 nights, 1 home
AU$460 per night
includes taxes & fees
Charming 3BDR Bungalow Near Annapolis​
Local artwork is displayed and for sale, if you wish to take a memory home.
Quiet, tree-filled neighborhood. The apartment is above the garage.
Separate entryway with electronic keypad.
Twin size sofa/futon for a 3rd person.
Exceptional
(21 reviews)

Annapolis Tree House Apartment- luxury shower, separate space

Annapolis

7% off
AU$2,490
for 7 nights, 1 apartment
AU$356 per night
includes taxes & fees
Annapolis Tree House Apartment- luxury shower, separate space
Exterior detail
Private kitchen
Interior
Dining
Exceptional
(13 reviews)

Riverside Retreat ~ Near Annapolis & USNA ~ Home Theatre, Bar & Beach Access

Riva

21% off
AU$4,069
for 7 nights, 1 home
AU$581 per night
includes taxes & fees
Riverside Retreat ~ Near Annapolis & USNA ~ Home Theatre, Bar & Beach Access
Living area
Pool
Dining
Screen porch for relaxing, eating, watching the water, working on a laptop
Exceptional
(58 reviews)

Unwind at Waterfront Annapolis w/swimming pool & pier - July specials!

Annapolis

16% off
AU$4,777
for 7 nights, 1 home
AU$682 per night
includes taxes & fees
Unwind at Waterfront Annapolis w/swimming pool & pier - July specials!
Dining
Living area
Living area
Living area
Exceptional
(11 reviews)

Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!

Riva

8% off
AU$5,811
for 7 nights, 1 home
AU$830 per night
includes taxes & fees
Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!
Outdoor dining
Dining
Exterior
Living area
Exceptional
(34 reviews)

Sailor's Retreat! Perfect home for the getaway weekend. Best location!

Annapolis

8% off
AU$6,823
for 7 nights, 1 home
AU$975 per night
includes taxes & fees
Sailor's Retreat! Perfect home for the getaway weekend. Best location!
Interior
Pool
Exterior
Marina
Exceptional
(233 reviews)

Stunning Waterfront Cottage in the Sailing Capital of the World!

Annapolis

8% off
AU$4,622
for 7 nights, 1 home
AU$660 per night
includes taxes & fees
Stunning Waterfront Cottage in the Sailing Capital of the World!
Front of House
2nd Floor Full Bath
Rear of House
Sun Room
Exceptional
(180 reviews)

Heart of Historic District!

Annapolis

26% off
AU$4,569
for 7 nights, 1 home
AU$653 per night
includes taxes & fees
Heart of Historic District!
Living area
Exterior
Outdoor dining
Room
Exceptional
(269 reviews)

Annapolis waterfront "tiny house" in garden setting

Annapolis

8% off
AU$1,681
for 7 nights, 1 cottage
AU$240 per night
includes taxes & fees
Annapolis waterfront "tiny house" in garden setting
enjoy the rockers on the porch while sipping on a cup of coffee
Exterior
Living area
Private kitchen
Exceptional
(12 reviews)

Dog friendly! Next to Navy Stadium and DTA Shuttle!

Annapolis

8% off
AU$4,362
for 7 nights, 1 home
AU$623 per night
includes taxes & fees
Dog friendly! Next to Navy Stadium and DTA Shuttle!
Living Room with Cable Television
Historic Annapolis and City Dock
Ship's Ladder Stairs to Rooftop Deck
Quaint Pinkney Street
Exceptional
(145 reviews)

Historic Downtown Charmer, Water Views and Parking!

Annapolis

12% off
AU$4,196
for 7 nights, 1 home
AU$599 per night
includes taxes & fees
Historic Downtown Charmer, Water Views and Parking!
Living area
Private kitchen
Dining
Interior
Exceptional
(7 reviews)

Historic Downtown 3BR Crabby Patty-∙Walk to USNA

Annapolis

7% off
AU$8,059
for 7 nights, 1 home
AU$1,151 per night
includes taxes & fees
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
Marina
Interior
Interior
Exterior
Exceptional
(55 reviews)

Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

West River

12% off
AU$1,803
for 7 nights, 1 cottage
AU$258 per night
includes taxes & fees
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Interior
Property grounds
Private kitchen
Dining
Exceptional
(35 reviews)

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

Annapolis

8% off
AU$7,025
for 7 nights, 1 home
AU$1,004 per night
includes taxes & fees
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

The friendly city of Parole awaits you

The gardens and surrounding scenery provide a peaceful ambience to your holiday home in Parole. Well known for its shopping, football games and university setting, this welcoming city won't disappoint. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Parole

Are you hoping to find attractions to visit while you're in town? Venture out of your cosy holiday rental and check out everything that makes Parole a fun place to get away to. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Maryland Renaissance Festival (2.4 mi / 3.9 km)
  • Renditions Golf Club (8.7 mi / 14 km)
  • Thanksgiving Farm Wines (9.2 mi / 14.8 km)
  • Laurel Park (17.5 mi / 28.1 km)
  • Severna Park Golf Center (4.3 mi / 6.9 km)
  • U.S. Naval Academy Golf Club (4.4 mi / 7.1 km)

Exploring the natural landscape of Parole

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Parole is a great place to get out in nature. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Maryland Quiet Waters Park (4 mi / 6.4 km)
  • Sandy Point Beach (8.3 mi / 13.3 km)
  • Fort Smallwood Park (10.6 mi / 17.1 km)
  • Allen Pond Park (10.8 mi / 17.3 km)
  • Northern Chesapeake Bay (10.9 mi / 17.5 km)
  • Patuxent River (17.8 mi / 28.7 km)

How to get to and around Parole

The nearest airport is in Fort Meade, MD (FME-Tipton), located 13.4 mi (21.6 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Baltimore Washington International Airport (BWI), which is 14.8 mi (23.8 km) away.

Frequently asked questions

What is the best area to stay in Parole when booking a holiday rental?
When considering a holiday rental in Parole, Maryland, a popular area to stay is near the vibrant Westfield Annapolis Mall. This area offers a variety of properties, ranging from modern apartments to charming townhouses, providing a comfortable base for your visit. The Westfield Annapolis Mall itself is a fantastic attraction, featuring a plethora of shops, dining options, and entertainment venues, making it a great spot for families and solo travellers alike.Another appealing neighbourhood is the vicinity around Broadneck Park, which is great for those who enjoy outdoor activities. This area boasts a lovely park with walking trails, sports fields, and picnic areas, ideal for a leisurely day out. Additionally, the nearby Annapolis city centre is just a short drive away, allowing you to explore its rich history, beautiful waterfront, and iconic attractions such as the United States Naval Academy and the Maryland State House.
What are the top attractions in Parole?
In Parole, Maryland, visitors can explore a variety of attractions and nearby points of interest. The area is conveniently located next to Annapolis, where one can visit the historic Maryland State House and stroll along the picturesque waterfront. Parole itself is home to the Westfield Annapolis Mall, offering a range of shopping and dining options.For outdoor enthusiasts, the nearby Broadneck Park features walking trails and sports facilities, great for a leisurely day out. Additionally, the scenic Chesapeake Bay is just a short drive away, providing opportunities for boating, fishing, and enjoying the beautiful shoreline.
Are all fees included in the Parole holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Parole holiday homes with parking?
Stayz offers a wide selection of holiday homes in Parole with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Parole holiday homes?
You can find great discounts on holiday homes in Parole on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Parole holiday home booking on Stayz?
To find Parole holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Parole?
A long-stay holiday home in Parole is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Parole holiday home?
Book your Parole holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Parole?
Prices for holiday homes in Parole vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Parole to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.