Homewood holiday rentals
We found 96 holiday rentals — enter your dates for availability
Discover a selection of 12 homes and other holiday rentals in Homewood that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the best amenities for spending time at your holiday home, which might include Wi-Fi and a pool. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Homewood
Historic District"Crab Cakes and Football"
Sleeps 4 · 2 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
42 reviews(42 reviews)
Cute bungalow blocks to Stadium
Sleeps 6 · 2 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Newly renovated historic Annapolis house. walking distance to navy stadium, DTA
Sleeps 14 · 5 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
Historic Annapolis Charmer <1Mile to NMC Stadium
Sleeps 20 · 6 bedrooms · 3+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Charming 3-bedroom house in Annapolis ⚓️🛥️⛵️ on the Chesapeake Bay
Sleeps 6 · 3 bedrooms · 2 bathrooms
6.06.0 out of 10
2 reviews(2 reviews)
3 bdrm close to city center, great yard & parking!
Sleeps 6 · 3 bedrooms · 2+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday home accommodation in Homewood?
According to our data, houses are the most in-demand type of holiday property in Homewood. But naturally, everyone’s idea of an epic stay can differ. Stayz has holiday homes with every shape, size and budget in mind, and we’ll help you locate your perfect match.
How much does it cost to rent a holiday home in Homewood?
Season, length of stay and property type are some of the conditions that can affect the price of a holiday home. Simply click on your dates of travel to find your ideal fit. From quaint country cottages to sprawling villas, all Stayz holiday homes offer unbeatable value.
How much does it cost to rent a beach house in Homewood?
Prices for beach houses in Homewood vary depending on the style and size of the property and time of year you’re travelling. Just enter your travel dates into Stayz and how many guests to view available options and prices. From there you can use our filter tool to refine your search results by ratings, nearby activities, amenities and more.
Are there pet-friendly holiday homes in Homewood?
With eight properties that allow pets, your furry companion can also come along on your Homewood holiday. Use our filter tool to search our pet-friendly holiday homes and find your pawfect holiday home on Stayz.
What are popular home amenities in Homewood?
A barbecue grill, a garden and a fireplace are rated the most popular home amenities in Homewood. Whether you’re travelling alone, with your spouse or a group of dear friends, Stayz will help you find a holiday home that matches your style with all the options you need.
Are there large group holiday homes in Homewood?
There are four holiday homes in Homewood that can sleep 10 or more people. Whether you’re organising a family trip or an event like an anniversary, there’s plenty of room to get your group together under one roof.
Are there holiday homes in Homewood that welcome kids?
Homewood has eight family-friendly holiday homes. And booking a stay that welcomes children is a cinch with Stayz’s “Properties good for families” filter. Besides having the entire place to yourselves, you’ll also get conveniences and perks such as living rooms, full kitchens and private pools.
What are the top attractions for families in Homewood?
Keeping the kids amused during your Homewood holiday is a snap with these awesome family-friendly attractions:
- Annapolis Maritime Museum
- Sandy Point Beach
- Annapolis Sailing School
Are there holiday homes with WiFi in Homewood?
Homewood has four holiday homes with WiFi, so you’ll be able to stay connected while you’re away. Simply check the “WiFi” box in our handy search filter for a list of properties with this feature. From streaming TV shows with the family to writing and sending emails, these Stayz homes make it a cinch to go online.
How can I find holiday homes with air conditioning in Homewood?
Homewood has eight holiday homes where you’ll be able to relax in air-conditioned comfort. To book a stay on Stayz that offers this perk, enter your desired travel dates and use the filters to select the “air conditioning” box.
How old do you have to be to rent a holiday home in Homewood?
The minimum age can vary across properties on Stayz, so double-check the rules of the holiday home in Homewood you want to book. But normally, it’s 16, 18 or 21.
How long can I rent a holiday home in Homewood for?
It all depends on the Homewood property. To look at a list of options offering extended stays, simply type your travel dates and number of people into Stayz’s search page. Look forward to having the whole property to yourself, as well as comforts such as a full kitchen, air conditioning and an outdoor space where the little ones can play. Keep your eyes peeled for any long-term stays that offer weekly or monthly discounts.