List your Property
Homewood, Annapolis, Maryland, United States of America

Homewood holiday rentals

We found 47 holiday rentals — enter your dates for availability

Discover a selection of 47 holiday home rentals in Homewood, Annapolis that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Stayz holiday homes have the best amenities for hanging out with the people that matter most, including pool and internet/WiFi. Prices start at AU$ 167 per night, and holiday houses and flats & apartments are popular options for a stay in Homewood. Either way, you'll find holiday accommodation for everyone's needs.
DynamicDestinationRefinements
AsyncDestinationUrgency

Find the best place to stay — Homewood

Charming Cottage Near Navy Marine Corp Stadium in Annapolis

Sleeps 4 · 1 Bedroom · 1 Bathroom
AU$ 226 avg/night
(114)

ACROSS FROM STADIUM - walk to downtown Annapolis.

Sleeps 10 · 4 Bedrooms · 3 Bathrooms
AU$ 492 avg/night
(15)

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

Sleeps 10 · 4 Bedrooms · 3 Bathrooms
AU$ 663 avg/night
(2)

Cape Cod close to Downtown Annapolis

Sleeps 5 · 3 Bedrooms · 2 Bathrooms
AU$ 726 avg/night
(1)

Perfect historic home, walk to downtown Annapolis

Sleeps 6 · 4 Bedrooms · 2 Bathrooms
AU$ 435 avg/night
(11)

Charming Annapolis Victorian

Sleeps 12 · 6 Bedrooms · 4 Bathrooms
AU$ 1,137 avg/night
(36)

Search 47 holiday rentals

Top rated rentals — Homewood
Stayed Oct 2021

Immaculate home in a perfect location

We had an absolutely wonderful weekend at this home. It was beyond pristine with every imaginable amenity. Every comfort of your own home but decorated like a museum. It’s clear the owner takes so much pride in their home & wish to share it with othe...

Niki B.
Niki B.
Stayed Oct 2021

Annapolis Sailboat Show

My family stayed at the property with two other couples and their kids while we were in town for the Annapolis sailboat show. This property was very close to the docks and was in great condition. The host was easy to get ahold of and let us in the pr...

Christi C.
Christi C.
Stayed Oct 2021

Perfect for a visit to Annapolis

Miller's cottage is in a convenient location for your visit to the Annapolis area. Owners are great and very accommodating. Cottage is comfortable and well equipped. We visited during a busy weekend in Annapolis. Traffic/parking downtown was difficul...

Trish M.
Trish M.

NY, NY

Stayed Oct 2021

Charm, comfort and location — the perfect couples stay in Annapolis

We just finished a delightful two nights in this wonderfully redone (and exceptionally clean) bungalow. It’s an easy walk to colonial-era Annapolis, and all the restaurants, music venues, museums (counting the first floor of the statehouse) shops and...

Chuck K.
Chuck K.
Stayed Sep 2021

Comfortable home close to everything.

We stayed five nights including 2 nights with our son, his wife and 2 small children. The house was very clean, comfortable and had everything we needed and then some. The location is close to Annapolis attractions in a quiet neighborhood. We would s...

howard a.
howard a.
Stayed Sep 2021

Ladies Weekend Getaway in MD

I came to the area with 4 of my girlfriends for the Seafood Festival held at Sandy Point Park. The house was perfect for our stay. It is literally around the corner from the Naval Academy. They have a nice paved walking trail that goes all the way ar...

Pam F.
Pam F.

Chester, Virginia

Stayed Sep 2021

Great Experience!!

We rented for a USNA class reunion along with 4 other classmates and their spouses. Perfect location: walking distance to Navy-Marine Corps Memorial Stadium and the Westin hotel (where the reunion HQ was). Great space: plenty of room inside and out. ...

Brad B.
Brad B.
Stayed Sep 2021

The Perfect House!

This property is even better than the beautiful pictures on the listing! The house is thoughtfully outfitted with everything you could possibly want for your stay with high end products. The entire home was also spotlessly clean and so comfortable! W...

Tara D.
Tara D.
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy

How many holiday accommodation are available around Homewood?

Our 2021 accommodation listings offer a large selection of 47 holiday rentals around Homewood. From 40 holiday houses to 6 flats & apartments, find unique holiday homes for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Homewood is on Stayz.

Can I rent Houses in Homewood?

Yes, of course. Stayz offers 40 Houses in Homewood. Our other popular types of Homewood holiday rentals include:

  • Condos/Apartments: 6 holiday houses
  • Cabins: 2 holiday houses
  • Cottages: 2 holiday houses

But you can also enjoy a great stay in one of our other holiday rentals including Studios and more.

Can I find a holiday accommodation with pool in Homewood?

Yes, you can select your preferred holiday accommodation with pool among our 3 holiday homes with pool available in Homewood. Please use our search bar to access the selection of holiday rentals available.