
Holiday rentals in Pasadena
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Top-rated holiday rentals in Pasadena
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

Rachel's BnB
A well outfitted home away from home! A fully stocked kitchen with everything you need to cook for yourselves and your guests. Close to historic downtown Annapolis, the US Naval Academy, St. John's College and MD Statehouse are less than 10 minutes away There are king and queen beds in the rooms, and the 3rd bed is a comfortable pullout couch in the living room. All linens are Egyptian cotton and the beds have real down duvets. Additional cot beds and linens (up to 4) can be provided ($20 each)

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!

Waterfront Cheerful 5 home
Welcome to this brand-new relaxing home with an 80ft pier by the water for your getaway. It is perfect for vacations, retreats, meetings, family reunion and business travelers’. Create memories and beautiful experiences while enjoying the beautiful 5 Bedrooms, 4 Bathroom .one bedroom on the first floor and four beds on the second floor. House has a large custom kitchen. It is located 11 miles from BWI airport,11.8 miles from downtown Baltimore,17 miles Naval academy and 40 miles to the DC .

Secluded acre near BWI and Baltimore
Secluded suburban acre 8 minutes from BWI Airport, 15 minutes from Baltimore's Inner Harbor and from Fort Meade, and 45 minutes from Washington DC. Private house attached to host house has 1220 square feet of cozy comfort--4 times the size of a hotel room! House includes 2 bedrooms (one queen, one double), 1.5 baths, living room, foyer, dining room, full kitchen, and washer/dryer. The one-acre lot has hundreds of trees and is great for pets. Level 2 charging station is good for all EVs.

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.

Ft. Smallwood Overlook. Waterfront with Kayaks!
Delightful cottage at the confluence of Rock Creek, Patapsco River (Baltimore Inner Harbor) and the Chesapeake Bay. Adjoins Ft. Smallwood Park with its private coves and beaches. Secluded setting features water on 3 sides with beautiful relaxing views. Teeming with wildlife: ducks, geese, egrets, osprey, eagles, deer, foxes and other. Convenient to Annapolis, BWI Airport, Baltimore & Washington, D.C. Walk to the park. Cast a line, catch what you may! Total renovation 2018-2019.

Waterfront-View of Bay from your Bed-Steamy Sauna
Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Sea Dreamer
Tranquil TIDAL, riverfront, split-level home. Rent the spacious lower level with 2 bedrooms, full custom kitchen, large living room (TVs, sleeper sofas, massage chair), dining/office space, and full bath with luxury shower. Includes soaps, towels, hairdryer. Kitchen equipped for cooking, includes full fridge. Patio with grill/fire-pit, lounging and kayaks. Convenient: 25 min to BWI, 45min to Annapolis, 60min to DC. Ideal for relaxing and exploring!

The Crab House - a Private, Waterfront Guest House
Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190

Beautiful Waterfront Home With Theater Room
This beautiful Pasadena Beach House(Chesapeake Bay waterfront with Pier) private beach access and is in close proximity to Celebrations At the Bay, Fort Smallwood Park, a Golf Course, Mike’s Crab House, BWI Airport, Baltimore, Live Casino, Arundel Mills, Naval Academy, and more. **Swim at your own risk** Every Winter!!! Price Drop!!!!! Enjoy the Same Space at a Lower Rate!!!!! October to March!!!!!!!!

Coastal Waterfront 1 Bedroom Cottage
This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.
Popular amenities for Pasadena holiday rentals
Other great holiday rentals in Pasadena

The Smiths Inn

Waterfront 5 Bedroom Home Close to Annapolis

Wonderful BWI Studio "Serenity"

The Maryland House | Deck, Grill, & Marina

Waterfront Romantic Studio

Waterfront Home, Amazing Views near Annapolis

The Charming Cozy 4-Bedroom Getaway in Glen Burnie

2 bedroom Apt, private entry
When is the best time to visit Pasadena?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $163 SGD | $159 SGD | $199 SGD | $203 SGD | $214 SGD | $214 SGD | $204 SGD | $203 SGD | $177 SGD | $214 SGD | $199 SGD | $231 SGD |
| Avg. temp | 1°C | 3°C | 7°C | 13°C | 18°C | 23°C | 26°C | 25°C | 21°C | 14°C | 8°C | 4°C |
Frequently Asked Questions
Are there pet-friendly vacation rentals in Pasadena?
Four-legged friends are welcome in Pasadena. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Pasadena?
Yes! Work meets play with ease at over 50 vacation rentals in Pasadena featuring dedicated workspaces. Stay connected and productive in your home away from home.
Where should I stay in Pasadena?
Make yourself at home in Pasadena by choosing from our most frequently booked neighborhoods. We have over 190 vacation rentals in Green Haven, and over 40 vacation rentals in Sunset Beach.
Are there Pasadena vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Pasadena, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly house rentals in Pasadena?
Pasadena has more than 30 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in townhouse rentals in Pasadena?
Experience the best of Pasadena with our townhouse rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do townhouse rentals in Pasadena have air conditioning?
Absolutely! We offer over 10 townhouse rentals with air conditioning in Pasadena. Enjoy a tailored experience with all the comforts you desire.
Do townhouse rentals in Pasadena have wifi?
Absolutely! We offer over 10 townhouse rentals with wifi in Pasadena. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Pasadena

Total holiday rentals
Explore 70 holiday rentals in Pasadena

Nightly prices starting at
Pasadena holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 3,140 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
70 of Pasadena holiday rentals include wifi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Pasadena rentals

4.8 Average rating
Pasadena stays are highly rated by guests – averaging 4.8 out of 5!
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- Georgetown University
- Walter E Washington Convention Center
- National Mall
- Nationals Park
- M&T Bank Stadium
- The White House
- District Wharf
- National Museum of Natural History
- Capital One Arena
- Baltimore Convention Center
- Oriole Park at Camden Yards
- National Museum of African American History and Culture
- Arlington National Cemetery
- Howard University
- Sandy Point State Park
- Washington Monument
- Betterton Beach
- Georgetown Waterfront Park
- Patterson Park
- National Harbor
- Smithsonian American Art Museum
- Johns Hopkins University
- Codorus State Park
- Great Falls Park




