Annapolis Holiday Rentals
Check In Check Out
Any Bedrooms
Any Guests
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Max per night
£100
100
100
400
£200
200
200
800
£300
300
300
1200
£400
400
400
1600
£500
500
500
2000
£600
600
600
2400
£700
700
700
2800
£800
800
800
3200
£900
900
900
3600
£1,000+
+1000
+1000
+4000
Studio +
0,30
1 Bedroom +
1,30
2 Bedrooms +
2,30
3 Bedrooms +
3,30
4 Bedrooms +
4,30
5 Bedrooms +
5,30
6 Bedrooms +
6,30
7 Bedrooms +
7,30
8 Bedrooms +
8,30
Filters
clear all Bedrooms
Price
Neighbourhoods
Amenities
Filters
clear all Check In Check Out
There are no pins in your viewport. Try moving the map or changing your filters.
- {providername} {price}
{sold_out_text}
We can't find prices for this accommodation
From {rate_price} {rate_periodicity}
View Map
Location
Any Distance
from
Suitability
Bathrooms
Any
More filters
Amenities
More
Property type
More
Distinctive Features
More
All 17 Rentals in Annapolis
Sort by:
Default
3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
Check in Check out
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
Check in Check out
Payment Protection
6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
Check in Check out
Payment Protection
4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Wi-Fi
- Air Conditioning
- Washer
- Grill
- DVD Player
- Cable/satellite TV
Suitability
Pet friendly
Kid friendly
Smoking allowed
Reviewed 21 June 2015
Owner has everything imaginable in the home that you would ever need for a vacation getaway. The house has lots of room so you have your privacy when needed. Beautiful...
About this property
Our beautifully-appointed home pays homage to the Colonial Period. It comfortably sleeps eight guests with four bedrooms and 2.5 baths. It boasts elegant dining and living rooms. Enjoy the quiet street and an easy stroll to downtown Annapolis.
We have taken great care and paid pain-staking...
View all property information Location Information
Annapolis, Maryland 21401
Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Cable/satellite TV
- Grill
- DVD Player
- Housekeeping Included
- Patio
- Wi-Fi
- Washer
- Air Conditioning
Suitability
Pet friendly
Kid friendly
Smoking allowed
Reviewed 19 August 2017
We stayed at the cottage for an extended period of time and it was very enjoyable. The house itself was well put together and had everything that we could have needed. The...
About this property
This City-inspected vintage cottage in Upper Eastport, located on a cul de sac, is a short walk to the Historic Harbor & just blocks from Spa Creek. History, waterfront, rooftop restaurants, wine bars, sailing, kayaking and more. We have everything here in Annapolis - USNA, sailing, culture,...
View all property information Location Information
Annapolis, Maryland 21403
Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Patio
- Wi-Fi
- Grill
- Porch
- Air Conditioning
- Washer
- Cable/satellite TV
- DVD Player
Suitability
Pet friendly
Kid friendly
Smoking allowed
Reviewed 19 October 2017
This is a great house to rent with another couple or with a family. The house is Within easy walking distance to all the fun in downtown And the waterfront. It has all the...
Reviewed 20 August 2017
We had a lovely stay in this spacious and tastefully furnished house. It was perfect for my husband and I and our three boys (8, 14 and 16). The rooms were larger than I...
About this property
A Charming detached one-family home located in one of the most vibrant neighborhoods of Annapolis. Perfectly located in a quiet residential street, only 0.8 miles from the United States Naval Academy and a short walk from Main street. The home is situated only a few steps away from West street and...
View all property information Location Information
Annapolis, Maryland 21401
Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Waterfront
- Patio
- Washer
- Grill
- Cable/satellite TV
- Parking
- Wi-Fi
- Air Conditioning
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Your family will thank you for choosing this Severn River Waterfront Retreat for Vacation! From the moment you enter this 5 bedroom home you will appreciate the spectacular views of the Severn River. Four of the five bedrooms view the Severn River, so your family will love waking up to views of...
View all property information Location Information
Annapolis, Maryland 21032
Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
Amenities & Details
- Cable/satellite TV
- Parking
- Wi-Fi
- Air Conditioning
Suitability
Pet friendly
Kid friendly
Smoking allowed
Reviewed 5 March 2018
Accommodating hostess. Thank you for your hospitality. The room was neat and clean. Close to inner city, Annapolis.
Reviewed 19 June 2017
Very nice, clean, comfortable. Hostess was very accomodating. Would plan on staying there again if another trip to the area is warranted
About this property
Our home is a 5 bedroom quality built home. This room is an office converted in to an extra bedroom space for guests to enjoy. It is located on the main level just inside the main entrance. It had double french doors which lock for privacy. Its a clean and cozy space and an expensive way to travel....
View all property information Location Information
Annapolis, Maryland 21409
Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
5 Bedrooms, 3 Bathrooms, Sleeps 20 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Waterfront
- Cable/satellite TV
- Air Conditioning
- Ocean Views
- Hot Tub
- Internet Access
- Washer
- DVD Player
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Comfort & Style: Enjoy stunning Chesapeake Bay Views, Beach, Pier, Boat Slips, Park, Water Access, Fire Pit, Patio Heater and more! Charming cottage & detached studio/game room (both upgraded in 2013) offer gourmet kitchen with new stainless steel appliances, a second full kitchen in garden...
View all property information Location Information
Annapolis, Maryland 21403
Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 20
4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Grill
- Balcony
- Terrace
- Central Heating
- Patio
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Charming Annapolis home, just 150 feet from the water, with floor to ceiling windows overlooking the expansive waters of the Chesapeake Bay. Water views from almost every room. Features 4 bedrooms and 4 bathrooms with luxury upgrades, viking kitchen appliances, comfortable couches for sleeping...
View all property information Location Information
Annapolis, Maryland 21403
Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 11
1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
Check in Check out
Payment Protection
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
This is the newly renovated 780 sf studio unit that is on the ground floor of a main house that is similarly titled and on the same property. Striking and dramatic 8700 - 9000 sf contemporary, new loft style renovation of the main house with exposed structure and mechanical systems that serves as...
View all property information Location Information
Annapolis, Maryland 21401
Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Cable/satellite TV
- Private Garden
- Parking
- Wi-Fi
- Air Conditioning
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Walk to historic City Dock, waterfront restaurants, U.S. Naval Academy. Open, sunny floor plan ideal for entertaining. Craftsman style 3 BRM + den + office + front porch swing + screened back porch + game room + ample parking. Well-furnished. Sleeps 6-8 comfortably or up to 10 with available...
View all property information Location Information
Annapolis, Maryland 21403
Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Washer
- Waterfront
- Cable/satellite TV
- Wi-Fi
- Grill
- Patio
- Air Conditioning
- DVD Player
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
The Yellow House is a magnificent Waterfront Property, with interior and exterior appointments, that are truly outstanding-76 five Star reviews can be viewed on our sister site-vacation rentals by owner dot com. 230476
With its magazine worthy gardens, and spacious 6 bedrooms, designed and...
View all property information Location Information
Annapolis, Maryland 21403
Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Washer
- DVD Player
- Secure Parking
- Wi-Fi
- Cable/satellite TV
- Air Conditioning
- Balcony
- Waterfront
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Best location in Eastport ,We restored this lovely victorian house over the past sixteen years. The upstairs is modern and has all the great amenities that a renovated building provides. anderson windows to keep the place warm and toasty. Seperate heating/air conditioning controls.Wooden floors,...
View all property information Location Information
Annapolis, Maryland 21403
Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Grill
- Patio
- Terrace
- DVD Player
- Central Heating
- Balcony
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Our home is in a very nice, safe neighborhood (two blocks to firehouse and 2 blocks to police station) within walking distance to historic downtown Annapolis. It is also less than a block to the Navy football stadium and easily walkable to grocery store, pharmacy, liquor store and...
View all property information Location Information
Annapolis, Maryland 21401
Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Outdoor Dining Area
- DVD Player
- Central Heating
- Internet Access
- Grill
- Patio
- Washer
- Cable/satellite TV
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Shellback house is a three bedroom, one and 1/2 bath historic townhouse in the heart of Downtown Annapolis with a private garden. The house has views of Ego Alley (Annapolis Waterfront) from the front stoop and the master bedroom. BOOK NOW FOR 2015 LEGISLATIVE SESSION AT STIPEND RATES! Please...
View all property information Location Information
Annapolis, Maryland 21401
Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Air Conditioning
- Outdoor Dining Area
- DVD Player
- Balcony
- Washer
- Parking
- Porch
- Wi-Fi
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
HOUSE
This fully renovated, circa 1890 ,Victorian house is located in the middle of the Eastport peninsula . The house is within walking distance, or a three minute taxi ride, to downtown historic Annapolis and the US Naval Academy, as well as shopping, several marinas, theater, numerous...
View all property information Location Information
Annapolis, Maryland 21403
Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
© 2018 TripAdvisor LLC All rights reserved.
* TripAdvisor LLC is not a booking agent and does not charge any service fees to users of our site... (more)
TripAdvisor LLC is not responsible for content on external web sites. Taxes, fees not included for deals content.