Homewood vacation rentals

We found 98 vacation rentals — enter your dates for availability

Immerse yourself in the enchanting charm of Homewood, where the stunning landscapes of Chesapeake Bay meet a vibrant downtown brimming with history and outdoor adventures. Enjoy days filled with family-friendly attractions, from swimming at Sherwood Forest to exploring the architectural treasures of the Historic District. With diverse accommodations ranging from cozy cottages to stylish apartments, your group will find the perfect home base for unforgettable memories, all while enjoying the space and amenities that only a vacation rental can provide.

Holiday rentals with weekly discounts - Homewood

Showing deals for:Dec 4 - Dec 11

Living area
Private kitchen
Exterior
Dining
Excellent
(9 reviews)

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis

9% off
$458
$3,209 for 7 nights
All fees included
Fabulous 5-bedroom house with AC in charming Annapolis
Gourmet Kitchen with seating at the counter for 5
Open floor plan
Bright stairway to second floor where 3 bedrooms and 2 full baths await
Exterior
Exceptional
(58 reviews)

Brand New.1.5 blocks to Westin. 1st floor bed & bath. Walkable Convenience

Annapolis

7% off
$636
$4,452 for 7 nights
All fees included
Brand New.1.5 blocks to Westin. 1st floor bed & bath. Walkable Convenience
Living area
Private kitchen
Living area
Interior
Exceptional
(11 reviews)

Unique Listing! Entire Downtown Triplex w/Private Parking! Sleeps 12-18. Pets ok

Annapolis

13% off
$889
$6,220 for 7 nights
All fees included
Unique Listing! Entire Downtown Triplex w/Private Parking! Sleeps 12-18. Pets ok
Living area
Exterior
enjoy the rockers on the porch while sipping on a cup of coffee
Property grounds
Exceptional
(12 reviews)

Dog friendly! Next to Navy Stadium and DTA Shuttle!

Annapolis

8% off
$393
$2,749 for 7 nights
All fees included
Dog friendly! Next to Navy Stadium and DTA Shuttle!
Stylish half-bathroom with heated floors
Renovated kitchen with all major appliances and supplies
Guest bedroom with queen bed
Dining room with seating for 6 and electric fireplace
Exceptional
(21 reviews)

Newly renovated in DTA w parking

Annapolis

8% off
$404
$2,831 for 7 nights
All fees included
Newly renovated in DTA w parking
Terrace/patio
Private kitchen
Interior
Exterior
Exceptional
(126 reviews)

Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District

Annapolis

13% off
$150
$1,052 for 7 nights
All fees included
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District

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Find out more about Homewood

Why visit Homewood

  • Family-friendly activities: Homewood offers a variety of attractions perfect for families, including urban parks and marinas.
  • Rich history: Explore the charming historical sites in and around Homewood, adding cultural depth to your visit.
  • Vibrant downtown: Just a short trip away, downtown Annapolis features friendly locals, quaint shops, and lively atmosphere.
  • Relaxing environment: Enjoy the serene surroundings, making it an ideal spot for relaxation or a business getaway.
  • Diverse accommodations: Choose from a wide range of vacation rentals, including private homes, cottages, and cozy apartments.

Popular types of accommodation around Homewood

If you're looking for the perfect getaway in Homewood, you're in the right place. Discover our most popular vacation rental options, including houses, charming cottages, and cozy apartments. With a wide selection of Homewood properties, you can choose the ideal vacation rental that suits your needs. Enjoy more amenities and the reassurance of a seamless travel experience with our transparent information and savings.

  • Houses: The top choice for visitors in Homewood, these spacious homes offer comfort and privacy for families or groups.
  • Cottages: Charming and cozy, cottages provide a quaint retreat for those seeking a peaceful getaway.
  • Apartments: Ideal for solo travelers or couples, apartments offer convenience and easy access to local attractions.
  • Condos: Combining luxury and amenities, condos are perfect for those looking for a more upscale experience.
  • House Boats: For a unique stay, house boats allow you to enjoy waterfront living while exploring the area.**

Top attractions near Homewood

Homewood, Annapolis, is perfect for family, business, and city-themed vacations. Visitors can explore a variety of attractions, such as urban parks, marinas, and historic houses, catering to those seeking outdoor activities, cultural experiences, and family fun. Whether traveling solo or with loved ones, there's something for everyone to enjoy in and around this charming area.

  • U.S. Naval Academy: Explore the rich history and stunning architecture of this prestigious institution. Witness the breathtaking scenery along the banks of the Severn River, and immerse yourself in the spirit of naval tradition.
  • Chesapeake Bay Bridge: Experience the impressive engineering of this iconic bridge that connects the eastern and western shores of Maryland. Enjoy the vibrant city vibes and panoramic views of the Chesapeake Bay as you cross.
  • Sandy Point State Park: Discover outdoor adventure with beautiful beaches, hiking trails, and picnic areas. This park offers a perfect spot for relaxation and scenic views of the bay, ideal for nature enthusiasts.

Things to do recommended for couples

Planning a romantic getaway in Homewood? Enjoy a captivating performance at the Ballet Theater of Maryland, indulge in thrilling sailing adventures at Annapolis Sailing School, or savor exquisite wines at Thanksgiving Farm Wines. Each experience promises unforgettable moments and a touch of romance.

Things to do recommended for families

Families visiting Homewood can cheer on their favorite teams at the Navy-Marine Corps Memorial Stadium, have a blast at the Annapolis Bowl arcade, and unwind at Allen Pond Park, where relaxation and wellness await just a short drive away.

Things to do recommended for groups

Groups visiting Homewood, Annapolis can enjoy shopping at the Annapolis Mall Shopping Center, just 2 miles away, catch a performance at The Colonial Players theater, only 1 mile away, or explore the unique offerings of the Wild Bird Center, located 0.9 miles from Homewood.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Homewood

When you're traveling with a group, family, pets, or planning an extended stay, be sure to prioritize your preferences while filtering options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Homewood with a group: Think about how many bedrooms you require, as well as any amenities like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Homewood with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with amenities suited for their age, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Homewood: For many families, a vacation isn't truly fulfilling without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Homewood: If you're in search of vacation rentals offering discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Homewood

Homewood, a charming neighborhood in Annapolis, offers a delightful blend of family-friendly activities and rich history. Just a short trip to downtown Annapolis, visitors can explore its vibrant atmosphere filled with friendly locals, quaint shops, and historic sites. Whether you're seeking relaxation or a business-themed getaway, Homewood serves as a perfect base to experience the best of Annapolis and its surrounding areas. Enjoy the serene environment while immersing yourself in the cultural richness of the region.

  • Annapolis: Annapolis is a charming city known for its rich history and vibrant waterfront. Situated around Homewood, it offers a delightful blend of family-friendly activities and outdoor adventures. Visitors can explore the U.S. Naval Academy, relax at local beaches, or enjoy recreational activities at scenic lakes. The city's shopping mall centers and boutique shops provide ample opportunities for retail therapy, making it a perfect destination for tourists seeking both education and leisure in a picturesque setting.
  • Murray Hill: Just 0.8 miles from Homewood, Murray Hill is a quaint neighborhood that embodies the spirit of outdoor living and family fun. With its lush parks and recreational areas, it is ideal for those looking to engage in various outdoor activities. The neighborhood also features an array of shopping areas and educational institutions, making it accessible for visitors of all ages. Attractions nearby include beautiful beaches and popular tourist precincts, ensuring a fulfilling travel experience.
  • Historic District: Located 1 mile away from Homewood, the Historic District is a captivating neighborhood steeped in history and charm. This area is perfect for families and those interested in exploring the city's past. Visitors can stroll along cobblestone streets while enjoying shopping at local boutiques and dining at quaint restaurants. Key landmarks include the historic academy, the bustling tourist precinct, and the scenic dock port, which offer a glimpse into the vibrant culture and heritage of Annapolis.

Booking with Vrbo is a breeze

Are you hoping to cut costs on your upcoming trip? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, feel free to utilize our filters to sort by price, location, and the type of vacation rental you prefer.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board is designed to help you plan your journeys more effectively. You can create new trips, manage your existing plans, or review and organize your bookings all in one place. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Homewood?
In Homewood, vacation houses are the most popular type of rental accommodation, with about 18 available in the area. These houses typically feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable retreat. Additionally, several cozy cottages can be found, offering a quaint and charming atmosphere.
How much does it cost to rent a vacation home in Homewood?
Prices for vacation rentals in Homewood 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Homewood to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Homewood vacation house rentals?
You can find great discounts on house rentals in Homewood on Vrbo, 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.
What are popular rental amenities in Homewood?
In Homewood, popular rental amenities include fully equipped kitchens, superb for travelers who enjoy preparing their own meals. Many properties also feature decks or patios, providing outdoor spaces to relax and take in the beautiful surroundings. A cozy fireplace is a common amenity, ideal for warming up after a day of outdoor activities. Additionally, some rentals come equipped with a blender, making it easy to whip up smoothies or cocktails.
Can I find family house rentals in Homewood?
In Homewood, Maryland, there are numerous family-friendly house rentals available—about 16 options throughout the area. This charming locale, located near the beautiful Deep Creek Lake, offers plenty of activities for families to enjoy. Many of these homes come equipped with spacious living areas, full kitchens for easy meal preparation, and outdoor decks or patios great for barbecues and relaxation.Visitors can expect amenities such as game rooms, cozy fireplaces, and private yards, making them ideal for families looking to unwind after a day of exploring. Nearby points of interest include the scenic state parks, where hiking and nature walks abound, as well as opportunities for boating and fishing on the lake.
Can I rent a vacation home with a pool or hot tub in Homewood?
In Homewood, Maryland, travelers will find several vacation homes available for rent that feature both pools and hot tubs. This charming area, located near Deep Creek Lake, is superb for those looking to enjoy a relaxing getaway with easy access to outdoor activities and beautiful natural scenery. Many of the rentals come equipped with private pools, hot tubs, and spacious outdoor areas ideal for gatherings or family fun. Inside, amenities such as fully equipped kitchens and cozy living spaces provide the comforts of home.
Are there any Homewood vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Homewood with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo 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.
Can I book pet-friendly vacation rentals in Homewood?
Yes, there are several pet-friendly vacation rentals available in Homewood, Maryland, with a count of 11 options to choose from. Travelers can expect a variety of amenities in these rentals, such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can enjoy the fresh air. Many properties are designed to accommodate families and groups, providing comfortable sleeping arrangements and convenient access to local attractions.Homewood is situated near beautiful natural areas, making it an ideal choice for pet owners. Nearby points of interest include parks and trails where you can take your furry friends for walks or hikes.
Can I find long-stay vacation rentals in Homewood?
A long-stay vacation rental in Homewood is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Homewood for a vacation rental?
The peak season in Homewood typically spans from May to July, making it the ideal time for those seeking a vibrant vacation experience. During these months, visitors can revel in the beauty of the outdoors, with temperatures ranging from the mid-60s to mid-80s Fahrenheit, great for hiking, picnicking, and enjoying the stunning natural surroundings.July is particularly popular, attracting families and adventure enthusiasts alike. The warm weather invites visitors to explore the picturesque trails, engage in water sports on nearby lakes, and attend local festivals that celebrate the community's rich culture and history. The lively option during this time enhances the experience, providing ample opportunities for socializing and making lasting memories.If you're looking for a more budget-friendly option, consider planning your trip in November. This month offers a quieter atmosphere, allowing you to appreciate the serene beauty of the changing seasons without the crowds. In November, you can enjoy the crisp fall air while taking leisurely strolls through Homewood's scenic landscapes.Ultimately, whether you prefer the bustling energy of the peak season or the tranquility of the late fall, Homewood has something to offer every traveler.
Are there any remote work vacation rentals in Homewood?
In Homewood, Maryland, there are several options for remote work vacation rentals, with around 19 properties available. These rentals cater specifically to the needs of remote workers, offering amenities such as free Wi-Fi, dedicated desks, and comfortable desk chairs to create an effective workspace. Additionally, many of these properties may feature computer monitors, making it easier to set up a productive environment.Homewood itself is situated near beautiful natural landscapes, providing a tranquil setting that can enhance work-life balance. After a day of remote work, travelers can enjoy local recreational activities, including hiking and exploring nearby parks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Homewood vacation rental?
Book your Homewood vacation rental 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 Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Homewood, Maryland, United States of America?
In Homewood, Maryland, visitors can enjoy a variety of attractions that highlight the area's natural beauty and recreational opportunities. The nearby Patapsco Valley State Park offers extensive hiking trails, picnic areas, and scenic views along the Patapsco River, making it a great spot for outdoor enthusiasts.Additionally, the historic Ellicott City, just a short drive away, features charming shops, restaurants, and the Ellicott City Museum, which provides insight into the town's rich history. The area also has access to the picturesque Centennial Park, which is ideal for walking, biking, and enjoying a day outdoors.For those interested in local culture, the nearby Howard County Center for the Arts hosts various events and exhibitions throughout the year, showcasing the work of local artists.
Can I change or cancel my Homewood home rental booking on Vrbo?
To find Homewood vacation rentals with free cancellation, just use Vrbo'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". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Homewood vacation rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively. Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

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