Annapolis holiday rentals

We found 711 holiday rentals — enter your dates for availability
Select from 377 houses, 48 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:20 Nov - 27 Nov

Great Room
Terrace/patio
The Green Bedroom View
Exterior
Exceptional
(15 reviews)

Waterfront Architectural Masterpiece with private dockage available.

Annapolis

7% off
S$13,478
for 7 nights, 1 home
S$1,925 per night
includes taxes & fees
Waterfront Architectural Masterpiece with private dockage available.
Kitchen
Porch Dining Table
Swimming Pool
Upstairs Hall
Exceptional
(33 reviews)

Waterfront Home near Annapolis, MD

Harwood

8% off
S$17,400
for 7 nights, 1 home
S$2,486 per night
includes taxes & fees
Waterfront Home near Annapolis, MD
Sitting area overlooking Burley Creek
Enjoy screened in porch with dining table and sitting area
Lawn for yard games along the waterfront, or simply relax in the shade
Beautiful waterfront home on Burley Creek with private pier
Exceptional
(61 reviews)

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

Annapolis

8% off
S$6,981
for 7 nights, 1 home
S$997 per night
includes taxes & fees
Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis
Exterior
Interior
Exterior
Interior
Exceptional
(14 reviews)

Charming Home located minutes from the Naval Academy and Downtown Annapolis

Annapolis

7% off
S$5,524
for 7 nights, 1 home
S$789 per night
includes taxes & fees
Charming Home located minutes from the Naval Academy and Downtown Annapolis
Dining
Private kitchen
Living area
Dining
Excellent
(9 reviews)

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis

8% off
S$4,699
for 7 nights, 1 home
S$671 per night
includes taxes & fees
Fabulous 5-bedroom house with AC in charming Annapolis
Living area
Terrace/patio
Exterior
Dining
Exceptional
(31 reviews)

Charming 3BDR Bungalow Near Annapolis​

Riva

9% off
S$2,972
for 7 nights, 1 home
S$425 per night
includes taxes & fees
Charming 3BDR Bungalow Near Annapolis​
Living area
Private kitchen
Interior
Room
Exceptional
(12 reviews)

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

Annapolis

7% off
S$11,873
for 7 nights, 1 home
S$1,696 per night
includes taxes & fees
The General's House-Spacious Home w/Pool & Hot Tub
Interior
New Kitchen 2022
Property grounds
Dining room
Exceptional
(64 reviews)

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville

8% off
S$4,973
for 7 nights, 1 home
S$710 per night
includes taxes & fees
Circa 1700 Chesapeake Colonial home on the National Register.
upstairs bedroom w/ King size bed and space for queen air mattress
Terrace/patio
Marina
outdoor space
Exceptional
(91 reviews)

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Pasadena

8% off
S$4,988
for 7 nights, 1 home
S$713 per night
includes taxes & fees
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Dining
Pool
Screen porch for relaxing, eating, watching the water, working on a laptop
Living area
Exceptional
(57 reviews)

Unwind at Waterfront Annapolis w/swimming pool & pier - July specials!

Annapolis

15% off
S$4,411
for 7 nights, 1 home
S$630 per night
includes taxes & fees
Unwind at Waterfront Annapolis w/swimming pool & pier - July specials!
LARGE OPEN KITCHEN
SCREENED PORCH
FAMILY ROOM W/FIREPLACE & FLAT SCREEN TV
DINING ROOM SEATS 10-14 W/LEAFS
Exceptional
(44 reviews)

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

Annapolis

12% off
S$8,652
for 7 nights, 1 home
S$1,236 per night
includes taxes & fees
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
Marina
Pool
Exterior
Living area
Exceptional
(230 reviews)

Stunning Waterfront Cottage in the Sailing Capital of the World!

Annapolis

8% off
S$4,269
for 7 nights, 1 home
S$610 per night
includes taxes & fees
Stunning Waterfront Cottage in the Sailing Capital of the World!
Twin size sofa/futon for a 3rd person.
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.
Separate entryway with electronic keypad.
Exceptional
(21 reviews)

Annapolis Tree House Apartment- luxury shower, separate space

Annapolis

7% off
S$2,265
for 7 nights, 1 apartment
S$324 per night
includes taxes & fees
Annapolis Tree House Apartment- luxury shower, separate space
Interior
Living area
Living area
Dining
Exceptional
(10 reviews)

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

Riva

8% off
S$5,360
for 7 nights, 1 home
S$766 per night
includes taxes & fees
Waterfront 3br Cottage - Paddle, Fish, Sand, Sun!
Light and bright dining room with space for 6 (plus a high chair).
Light and bright dining room with space for 6 (plus a high chair).
Recently renovated kitchen with quartz countertops, stainless steel appliances, and all the gadgets, tools, and amenities you need to cook wonderful meals.
Light and bright dining room with space for 6 (plus a high chair).
Exceptional
(8 reviews)

Cozy Cottage with Beach Access

Annapolis

7% off
S$4,203
for 7 nights, 1 home
S$600 per night
includes taxes & fees
Cozy Cottage with Beach Access
Outdoor dining
Pool
Private kitchen
Property grounds
Exceptional
(215 reviews)

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

Stevensville

11% off
S$4,367
for 7 nights, 1 room
S$624 per night
includes taxes & fees
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Bright stairway to second floor where 3 bedrooms and 2 full baths await
Open floor plan
Gourmet Kitchen with seating at the counter for 5
Exterior
Exceptional
(58 reviews)

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

Annapolis

6% off
S$6,540
for 7 nights, 1 home
S$934 per night
includes taxes & fees
Brand New.1.5 blocks to Westin. 1st floor bed & bath. Walkable Convenience
Rear Entry and Rooftop Balcony
Historic Annapolis and City Dock
Quaint Pinkney Street
Ship's Ladder Stairs to Rooftop Deck
Exceptional
(145 reviews)

Historic Downtown Charmer, Water Views and Parking!

Annapolis

12% off
S$3,889
for 7 nights, 1 home
S$556 per night
includes taxes & fees
Historic Downtown Charmer, Water Views and Parking!
Dining
The upstairs primary suite includes a queen bed and private bath with a deep soaking tub—your own peaceful hideaway.
Fully equipped and filled with light, the kitchen opens to the backyard for easy outdoor dining.
Park with ease in the permeable gravel driveway and enjoy sustainable living with rooftop solar panels and lush native landscaping.
Exceptional
(6 reviews)

Unique and central in Eastport

Annapolis

7% off
S$5,380
for 7 nights, 1 home
S$769 per night
includes taxes & fees
Unique and central in Eastport
Main Living Area
Exterior
Dining and Work Space
Fully Loaded Kitchen with Island Seating
Exceptional
(13 reviews)

Uptown Annapolis - Peaceful, Sparkling, 1 Bed/1 Bath Apartment, Sleeps 3-4

Annapolis

11% off
S$2,488
for 7 nights, 1 home
S$355 per night
includes taxes & fees
Uptown Annapolis - Peaceful, Sparkling, 1 Bed/1 Bath Apartment, Sleeps 3-4
Outdoor dining
Exterior
Property grounds
Room
Exceptional
(267 reviews)

Annapolis waterfront "tiny house" in garden setting

Annapolis

8% off
S$1,555
for 7 nights, 1 cottage
S$222 per night
includes taxes & fees
Annapolis waterfront "tiny house" in garden setting
Interior
Interior
Exterior
Marina
Exceptional
(53 reviews)

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

West River

12% off
S$1,664
for 7 nights, 1 cottage
S$238 per night
includes taxes & fees
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Dining
Terrace/patio
Living area
Back yard and fire pit
Exceptional
(47 reviews)

Water Views - Close to Downtown Annapolis

Annapolis

5% off
S$5,882
for 7 nights, 1 home
S$840 per night
includes taxes & fees
Water Views - Close to Downtown Annapolis
Dining
Property grounds
Water view from the kitchen
Private kitchen
Exceptional
(30 reviews)

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

Annapolis

8% off
S$6,395
for 7 nights, 1 home
S$914 per night
includes taxes & fees
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
  • 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:

  • 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)
  • Chesapeake Beach Water Park (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)
  • Chesapeake Bay Environmental Center (14.3 mi / 23.1 km)
  • Rocky Point Park and Beach (19.5 mi / 31.3 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.

More holiday ideas