Annapolis holiday rentals

We found 710 holiday rentals — enter your dates for availability
Select from 381 houses, 46 apartments and other holiday rentals to find the perfect place for your stay in Annapolis. Whether you’re travelling with friends, family or even pets, holiday rentals have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a washer and dryer. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Annapolis

Showing deals for:1 Jan - 8 Jan

Interior
Private kitchen
Room
Dining
Exceptional
(21 reviews)

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

Annapolis

15% off
S$5,421
for 7 nights, 1 home
S$774 per night
includes taxes & fees
Captain's Retreat! Newly Renovated - few steps from the beach!
KI Beach House has many Great Rooms for Mingling or just being by yourself.
The owners enjoy the local wildlife. Local osprey  & herons are always fishing.
Seat 4 at the high table, 6 at the bar, and 7 or 8 more at the dining table.
Please put the umbrellas down to secure them. Volleyball in deck toy box.
Exceptional
(75 reviews)

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Stevensville

8% off
S$9,383
for 7 nights, 1 home
S$1,340 per night
includes taxes & fees
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Kitchen
Porch Dining Table
Upstairs Hall
Swimming Pool
Exceptional
(35 reviews)

Waterfront Home near Annapolis, MD

Harwood

8% off
S$17,559
for 7 nights, 1 home
S$2,508 per night
includes taxes & fees
Waterfront Home near Annapolis, MD
POOL TABLE, TENNIS/PICKLE BALL RACKETS, BEACH SUPPLIES, BOARD GAMES, MOVIES
FAMILY ROOM W/FIREPLACE & FLAT SCREEN TV
LARGE OPEN KITCHEN
SCREENED PORCH
Exceptional
(48 reviews)

Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

Annapolis

12% off
S$7,953
for 7 nights, 1 home
S$1,136 per night
includes taxes & fees
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
Great Room
Terrace/patio
Kitchen - Granite Island
The Green Bedroom View
Exceptional
(16 reviews)

Waterfront Architectural Masterpiece with private dockage available.

Annapolis

7% off
S$13,245
for 7 nights, 1 home
S$1,892 per night
includes taxes & fees
Waterfront Architectural Masterpiece with private dockage available.
Interior
New Kitchen 2022
Property grounds
Exterior
Exceptional
(66 reviews)

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville

8% off
S$4,276
for 7 nights, 1 home
S$611 per night
includes taxes & fees
Circa 1700 Chesapeake Colonial home on the National Register.
Marina
Terrace/patio
Living room with wood fireplace and second TV with basic channels
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

7% off
S$5,094
for 7 nights, 1 home
S$728 per night
includes taxes & fees
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Cozy, queen size bedroom on the second floor complete with a large, flatscreen TV
Large, beautifully updated kitchen area is perfect for meal times.
Dining
Patio located off of the living room is perfect for sitting out and enjoying the natural settings.
Exceptional
(39 reviews)

West Annapolis Cottage- 6BR Walk to Navy Stadium

Annapolis

7% off
S$8,695
for 7 nights, 1 home
S$1,242 per night
includes taxes & fees
West Annapolis Cottage- 6BR Walk to Navy Stadium
Inquire on both homes: togetherness without everyone being under the same roof!
In Stevensville MD 5 miles to Chesapeake Bay Bridge. 20 miles o Annapolis.
Ready for some friendly competition? Enjoy our reversible tabletop shuffleboard.
Attention all "Foodies" Check out the galley! Open water views.
Exceptional
(43 reviews)

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

Stevensville

8% off
S$9,383
for 7 nights, 1 home
S$1,340 per night
includes taxes & fees
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Exterior
Kitchen
Kitchen
Kitchen
Exceptional
(32 reviews)

Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate

Stevensville

11% off
S$2,889
for 7 nights, 1 room
S$413 per night
includes taxes & fees
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
Interior
Private kitchen
Living area
Living area
Exceptional
(14 reviews)

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

Annapolis

7% off
S$6,767
for 7 nights, 1 home
S$967 per night
includes taxes & fees
The General's House-Spacious Home w/Pool & Hot Tub
Interior
Living area
Living area
Dining
Exceptional
(11 reviews)

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

Riva

8% off
S$5,362
for 7 nights, 1 home
S$766 per night
includes taxes & fees
Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!
Private kitchen
Living area
Dining
Interior
Exceptional
(52 reviews)

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Stevensville

8% off
S$8,649
for 7 nights, 1 home
S$1,236 per night
includes taxes & fees
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Exterior
Private kitchen
Dining
Dining
Excellent
(12 reviews)

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis

8% off
S$4,698
for 7 nights, 1 home
S$671 per night
includes taxes & fees
Fabulous 5-bedroom house with AC in charming Annapolis
Master bedroom suite w/ private covered balcony
3 covered balconies, a ground floor patio, and ceramic and propane grills.
Living area
Private kitchen
Exceptional
(78 reviews)

Charming Annapolis WaterVIEW Home

Annapolis

11% off
S$4,175
for 7 nights, 1 home
S$596 per night
includes taxes & fees
Charming Annapolis WaterVIEW Home
Lawn for yard games along the waterfront, or simply relax in the shade
Enjoy screened in porch with dining table and sitting area
West-facing screened porch with bar area and café lights for night ambience
Sitting area overlooking Burley Creek
Exceptional
(64 reviews)

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

Annapolis

7% off
S$4,983
for 7 nights, 1 home
S$712 per night
includes taxes & fees
Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis
Exterior
Interior
Private kitchen
Interior
Exceptional
(15 reviews)

Charming Home located minutes from the Naval Academy and Downtown Annapolis

Annapolis

7% off
S$5,534
for 7 nights, 1 home
S$791 per night
includes taxes & fees
Charming Home located minutes from the Naval Academy and Downtown Annapolis
Marina
Interior
Interior
Exterior
Exceptional
(56 reviews)

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

West River

12% off
S$1,657
for 7 nights, 1 cottage
S$237 per night
includes taxes & fees
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Interior
Private kitchen
Living area
Interior
Exceptional
(11 reviews)

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

Annapolis

8% off
S$9,902
for 7 nights, 1 home
S$1,415 per night
includes taxes & fees
Unique Listing! Entire Downtown Triplex w/Private Parking! Sleeps 12-18. Pets ok
Dining
Terrace/patio
Living area
Exterior
Exceptional
(31 reviews)

Charming 3BDR Bungalow Near Annapolis​

Riva

9% off
S$2,947
for 7 nights, 1 home
S$421 per night
includes taxes & fees
Charming 3BDR Bungalow Near Annapolis​
Property grounds
Pool
Private kitchen
Interior
Exceptional
(218 reviews)

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Stevensville

11% off
S$4,376
for 7 nights, 1 room
S$625 per night
includes taxes & fees
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Separate entryway with electronic keypad.
Quiet, tree-filled neighborhood. The apartment is above the garage.
Local artwork is displayed and for sale, if you wish to take a memory home.
Twin size sofa/futon for a 3rd person.
Exceptional
(21 reviews)

Annapolis Tree House Apartment- luxury shower, separate space

Annapolis

7% off
S$2,250
for 7 nights, 1 apartment
S$321 per night
includes taxes & fees
Annapolis Tree House Apartment- luxury shower, separate space
Water view from the kitchen
Property grounds
Dining
Private kitchen
Exceptional
(37 reviews)

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

Annapolis

8% off
S$6,525
for 7 nights, 1 home
S$932 per night
includes taxes & fees
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Outdoor dining
Dining
Exterior
Living area
Exceptional
(34 reviews)

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

Annapolis

8% off
S$6,193
for 7 nights, 1 home
S$885 per night
includes taxes & fees
Sailor's Retreat! Perfect home for the getaway weekend. Best location!
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

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

    More space, more privacy, more amenities — more value

Historical Annapolis will entice you

The area's history and live music are just some of the reasons to come on holiday to Annapolis. Renowned for its university setting, shopping and restaurants, this city welcomes all visitors. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Annapolis

Do you want to find attractions to see in the area? Venture out of your holiday home and check out everything that makes Annapolis a fun place to get away to. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Bay Hills Golf Club (4.7 mi / 7.6 km)
  • Maryland Renaissance Festival (5.4 mi / 8.6 km)
  • Thanksgiving Farm Wines (10.4 mi / 16.8 km)
  • Renditions Golf Club (10.7 mi / 17.3 km)
  • Queenstown Harbor Golf (17.4 mi / 28 km)
  • St. Michaels Winery (19.9 mi / 32.1 km)

Exploring the natural landscape of Annapolis

Whether you're looking for adventure or just want to spend some time taking in the scenery, Annapolis is a great place to spend some time outside. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Maryland Quiet Waters Park (2.4 mi / 3.9 km)
  • Bay Ridge Beach (2.9 mi / 4.6 km)
  • Sandy Point Beach (5.7 mi / 9.2 km)
  • Northern Chesapeake Bay (8 mi / 12.8 km)
  • Fort Smallwood Park (11 mi / 17.6 km)
  • Eastern Neck National Wildlife Refuge (14.9 mi / 24 km)

Transport to and around Annapolis

Fly into Fort Meade, MD (FME-Tipton), the closest airport, located 16.2 mi (26.1 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Baltimore Washington International Airport (BWI), which is 16.8 mi (27 km) away.

Frequently asked questions

What is the best area to stay in Annapolis when booking a holiday rental?
Historic District is one of the more popular neighbourhoods to secure a holiday property in Annapolis. During your stay, don't miss big-hitting attractions like Maryland State House and William Paca House.
What is the most popular type of holiday rental accommodation in Annapolis?
Houses are the most popular kind of holiday rental in Annapolis, according to our data. Even if you have something different in mind, Vrbo has holiday homes in all sizes and shapes. Take a look at our options to find your perfect match.
How much does it cost to rent a holiday rental in Annapolis?
Property type, length of stay and season are some things that can influence the price of a holiday home. Simply enter your travel dates to find your perfect escape. From cosy country cottages to sprawling villas, all Vrbo holiday rentals offer unbeatable value.
How much does it cost to rent a beach house in Annapolis?
The average price for a holiday rental near the beach in Annapolis depends on when you're going and the style and size of property you're searching for. Find prices easily and quickly on Vrbo by entering your dates of travel. Then use our filters to choose the number of bedrooms and amenities that you prefer, such as WiFi, a pool and air conditioning.
Are there pet-friendly holiday rentals in Annapolis?
Pack a squeezy toy and a bone for your pup because Annapolis has 256 stays that roll out the welcome mat to doggie guests. Let your four-legged buddy join in with the family fun at one of our pet-friendly holiday rentals on Vrbo. Simply enter your travel dates then check the "Pets allowed" filter box.
Can I rent a house with a pool in Annapolis?
Pack your swimwear and swim ring, because there are 27 houses with a private pool in Annapolis. Stay at one of these terrific holiday homes and every day will be a pool day. Simply enter your travel dates into Vrbo, then use the "pool" filter to find the perfect place to make a splash!
What are popular rental amenities in Annapolis?
An electric car charging station, a firepit and an ocean view head the list of most popular rental amenities in Annapolis. Whether you're taking to the road by yourself, with your sweetheart or a bunch of friends, Vrbo will help you find a holiday home that suits your style with a load of extras you'll love.
Are there large group holiday rentals in Annapolis?
Choose from 49 properties in Annapolis that can host a group of 10 or more guests. Whether you're organising a family trip or some kind of special event, there's plenty of space to get your favourite people together under the same roof.
Are there holiday rentals in Annapolis that welcome kids?
Bring the entire family together for fun-filled adventures in Annapolis at one of our 254 family-friendly holiday homes. These stays provide conveniences that are suitable for getaways with the little ones, like laundries, multiple bedrooms and outdoor spaces. Simply check the "Properties good for families" filter and book your favourite.
What are the top attractions for families in Annapolis?
Keeping the kids happy during your holiday in Annapolis is a cinch with these family-friendly attractions:
  • Annapolis Maritime Museum
  • Sandy Point Beach
  • Triton Beach
Are there one-bedroom holiday rentals in Annapolis?
Yes, you can pick from 38 one-bedroom rentals in Annapolis. Whether you'd like a comfy cottage or a cabin, Vrbo's one-bedroom rentals are just right if you don't need lots of room. One of the major perks of having your own place? You won't ever have to share your trip with strangers.
Can I find two-bedroom holiday rentals in Annapolis?
Pick from 56 two-bedroom rentals in Annapolis. Put the kids in the second room or maybe fill it with a couple of your best buddies. There's a comfy spot for whoever's fortunate enough to be coming along.
Are there holiday rentals with WiFi in Annapolis?
You can choose from 106 holiday rentals with WiFi in Annapolis. If you'd like to disconnect from daily life during your escape, but still need to be connected to the web, these getaways have what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Annapolis?
Pick your dates and then make use of our filters to search for holiday rentals with ac in Annapolis on Vrbo. With 246 air-conditioned properties on offer here, you can enjoy a comfortable and cool stay.
How old do you have to be to rent a holiday rental in Annapolis?
We recommend you check with the Annapolis holiday rental you'd like on Vrbo as age restrictions differ. However, it's typically 16, 18 or 21.
How long can I rent a holiday rental in Annapolis for?
It all depends on the Annapolis property. To browse a list of options offering extended stays, just type your travel dates and guest number into Vrbo's search page. Look forward to having the property to yourself, along with amenities such as a fully-equipped kitchen and outdoor spaces where the kids can play. Keep an eye out for long-term stays that offer weekly or monthly discounts.

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