Best Annapolis Vacation Rentals
Vintage Charm: Annapolis Retreat
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Terrace
Situated within 10 minutes' walk of Mission Escape Rooms, the 3-bedroom Vintage Charm: Annapolis Retreat Villa is ideal for up to 5 guests.
Vintage Charm: Annapolis Retreat
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Terrace
Vintage Charm: Annapolis Retreat
Situated within 10 minutes' walk of Mission Escape Rooms, the 3-bedroom Vintage Charm: Annapolis Retreat Villa is ideal for up to 5 guests.
Neptune By The Water
- BBQ facilities
- Free parking
- Air conditioning
- Tea and coffee facilities
- Heating
- Patio
Situated around 10 minutes by car from the Chesapeake Bay Bridge, the 3-bedroom Neptune By The Water Annapolis villa provides access to numerous tourist attractions in the area. The accommodation accommodates up to 10 guests and invites them to enjoy a patio.
Neptune By The Water
- BBQ facilities
- Free parking
- Air conditioning
- Tea and coffee facilities
- Heating
- Patio
Neptune By The Water
Situated around 10 minutes by car from the Chesapeake Bay Bridge, the 3-bedroom Neptune By The Water Annapolis villa provides access to numerous tourist attractions in the area. The accommodation accommodates up to 10 guests and invites them to enjoy a patio.
Waterfront Annapolis Cottage: Fire Pit & Pier
- Cookware/ Kitchen utensils
- Free parking
- Flat-screen TV
Staying at the 3-bedroom Waterfront Annapolis Cottage: Fire Pit & Pier, guests can visit Broadneck Park, which is nearly a 10-minute drive away. The Annapolis holiday home is available for up to 5 guests and offers hire for rent.
Waterfront Annapolis Cottage: Fire Pit & Pier
- Cookware/ Kitchen utensils
- Free parking
- Flat-screen TV
Waterfront Annapolis Cottage: Fire Pit & Pier
Staying at the 3-bedroom Waterfront Annapolis Cottage: Fire Pit & Pier, guests can visit Broadneck Park, which is nearly a 10-minute drive away. The Annapolis holiday home is available for up to 5 guests and offers hire for rent.
Cheap Annapolis Vacation Rentals
Downtown Annapolis King George 3Rd Floor Hideaway
- BBQ facilities
-
Car park
Charges may apply
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Garden area
The spacious 65 m² Downtown Annapolis King George 3Rd Floor Hideaway Apartment is a good choice for accommodating up to 3 guests, offering a prime setting about 900 metres from Mission Escape Rooms. The 1-bedroom apartment is situated 46 km from Union Marc Washington train station and in close proximity to Saint Johns Street & College Avenue Far-side Northbound bus station.
Downtown Annapolis King George 3Rd Floor Hideaway
- BBQ facilities
-
Car park
Charges may apply
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Garden area
Downtown Annapolis King George 3Rd Floor Hideaway
The spacious 65 m² Downtown Annapolis King George 3Rd Floor Hideaway Apartment is a good choice for accommodating up to 3 guests, offering a prime setting about 900 metres from Mission Escape Rooms. The 1-bedroom apartment is situated 46 km from Union Marc Washington train station and in close proximity to Saint Johns Street & College Avenue Far-side Northbound bus station.
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Beach access
Private Single Family Home Close To Both Water And Downtown!
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Mini-bar
- Garden area
The 4-bedroom Private Single Family Home Close To Both Water And Downtown! Annapolis is located about a 25-minute stroll from Annapolis Landing Marina and has a terrace and playground to ensure a memorable stay.
Private Single Family Home Close To Both Water And Downtown!
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Mini-bar
- Garden area
Private Single Family Home Close To Both Water And Downtown!
The 4-bedroom Private Single Family Home Close To Both Water And Downtown! Annapolis is located about a 25-minute stroll from Annapolis Landing Marina and has a terrace and playground to ensure a memorable stay.
The Pool Loft At Poplar Hill
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Golf centre
- Outdoor swimming pool
To enjoy your vacation in Annapolis, stay at the spacious 65 m² The Pool Loft At Poplar Hill Apartment Annapolis, which is approximately a 10-minute ride from Chesapeake Bay Bridge and within a 7-km distance of Chase Lloyd House. Wi-Fi and private car parking are also available at the 1-bedroom apartment.
Explore the surrounding area of the property through activities like cycling and fisheries.
The Pool Loft At Poplar Hill
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Golf centre
- Outdoor swimming pool
The Pool Loft At Poplar Hill
To enjoy your vacation in Annapolis, stay at the spacious 65 m² The Pool Loft At Poplar Hill Apartment Annapolis, which is approximately a 10-minute ride from Chesapeake Bay Bridge and within a 7-km distance of Chase Lloyd House. Wi-Fi and private car parking are also available at the 1-bedroom apartment.
Explore the surrounding area of the property through activities like cycling and fisheries.
Pet Friendly Vacation Rentals Annapolis Maryland
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Private beach
Annapolis Charm Waterfront Getaway Near Usna - Fish & Crab From Your Private Pier!
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Live entertainment
- Sun terrace
Situated around 10 minutes' drive from Broadneck Peninsula Trail, the 3-bedroom Annapolis Charm Waterfront Getaway Near Usna - Fish & Crab From Your Private Pier! villa offers guests to enjoy a sunbathing terrace and a picnic area. This Annapolis villa features opportunities for canyoning and fisheries in the area, 3.5 km from the local beach "Sandy Point State Park".
Annapolis Charm Waterfront Getaway Near Usna - Fish & Crab From Your Private Pier!
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Live entertainment
- Sun terrace
Annapolis Charm Waterfront Getaway Near Usna - Fish & Crab From Your Private Pier!
Situated around 10 minutes' drive from Broadneck Peninsula Trail, the 3-bedroom Annapolis Charm Waterfront Getaway Near Usna - Fish & Crab From Your Private Pier! villa offers guests to enjoy a sunbathing terrace and a picnic area. This Annapolis villa features opportunities for canyoning and fisheries in the area, 3.5 km from the local beach "Sandy Point State Park".
Annapolis Escape Steps To Harbor Backs To Gate 1
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Located nearly 5 minutes' walk from the preserved 1774 Hammond-Harwood House, the 1-bedroom Annapolis Escape Steps To Harbor Backs To Gate 1 Villa offers quick access to various city attractions in the vicinity. Providing guests with Wi-Fi and parking, this Annapolis holiday home is a few steps from Chase Lloyd House.
Annapolis Escape Steps To Harbor Backs To Gate 1
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Annapolis Escape Steps To Harbor Backs To Gate 1
Located nearly 5 minutes' walk from the preserved 1774 Hammond-Harwood House, the 1-bedroom Annapolis Escape Steps To Harbor Backs To Gate 1 Villa offers quick access to various city attractions in the vicinity. Providing guests with Wi-Fi and parking, this Annapolis holiday home is a few steps from Chase Lloyd House.
Walk To Everything Historic Arts District
- Cookware/ Kitchen utensils
- Free parking
- Tours/Ticket assistance
- Air conditioning
- Flat-screen TV
- Live entertainment
The 2-bedroom Walk To Everything Historic Arts District Annapolis villa, located approximately a 5-minute walk from First Baptist Church, can host up to 6 guests. Offering a treatment room and a foot bath, the property is merely 1.7 km from the American United States Naval Academy Museum.
This property offers beauty services, spa therapy, and a golf course, along with yoga instruction for sport enthusiasts. On-site treatments include body wraps, body scrub, and pedicure. The bicycles are available for rent and guests can explore the area, while a fitness room is there to keep fit.
Walk To Everything Historic Arts District
- Cookware/ Kitchen utensils
- Free parking
- Tours/Ticket assistance
- Air conditioning
- Flat-screen TV
- Live entertainment
Walk To Everything Historic Arts District
The 2-bedroom Walk To Everything Historic Arts District Annapolis villa, located approximately a 5-minute walk from First Baptist Church, can host up to 6 guests. Offering a treatment room and a foot bath, the property is merely 1.7 km from the American United States Naval Academy Museum.
This property offers beauty services, spa therapy, and a golf course, along with yoga instruction for sport enthusiasts. On-site treatments include body wraps, body scrub, and pedicure. The bicycles are available for rent and guests can explore the area, while a fitness room is there to keep fit.
Annapolis Vacation Rentals Oceanfront
Fisher House - Downtown Annapolis!
- BBQ facilities
- Air conditioning
- Tea and coffee facilities
- Heating
- Patio
Situated merely 5 minutes' walk from Main Street, Fisher House - Downtown Annapolis! villa is ideal for up to 9 guests. Located in the vicinity of the Harwood Big Brice House, this 3-bedroom holiday home provides Wi-Fi and parking.
Fisher House - Downtown Annapolis!
- BBQ facilities
- Air conditioning
- Tea and coffee facilities
- Heating
- Patio
Fisher House - Downtown Annapolis!
Situated merely 5 minutes' walk from Main Street, Fisher House - Downtown Annapolis! villa is ideal for up to 9 guests. Located in the vicinity of the Harwood Big Brice House, this 3-bedroom holiday home provides Wi-Fi and parking.
Oasis By The Bay - Waterfront Heated Pool Hot Tub
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Sauna
- Outdoor swimming pool
Situated around a 15-minute ride from Chesapeake Harbour, the 6-bedroom Oasis By The Bay - Waterfront Heated Pool Hot Tub Villa Annapolis includes an outdoor swimming pool, as well as a sauna to relax in. Featuring lake views, the Annapolis holiday home invites guests to visit Thomas Point Park, located 4.2 km away.
Oasis By The Bay - Waterfront Heated Pool Hot Tub
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Sauna
- Outdoor swimming pool
Oasis By The Bay - Waterfront Heated Pool Hot Tub
Situated around a 15-minute ride from Chesapeake Harbour, the 6-bedroom Oasis By The Bay - Waterfront Heated Pool Hot Tub Villa Annapolis includes an outdoor swimming pool, as well as a sauna to relax in. Featuring lake views, the Annapolis holiday home invites guests to visit Thomas Point Park, located 4.2 km away.
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Guest favorite
Annapolis Vacation Home: 2 Mi To Quiet Waters Park
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Ironing facilities
Offering access to entertainment venues such as Annapolis Landing Marina, situated 20 minutes' walk away, the welcoming Annapolis Vacation Home: 2 Mi To Quiet Waters Park can host up to 8 guests. Located 2.6 km from Main Street, the 4-bedroom holiday home provides Wi-Fi and a car park.
Annapolis Vacation Home: 2 Mi To Quiet Waters Park
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Ironing facilities
Annapolis Vacation Home: 2 Mi To Quiet Waters Park
Offering access to entertainment venues such as Annapolis Landing Marina, situated 20 minutes' walk away, the welcoming Annapolis Vacation Home: 2 Mi To Quiet Waters Park can host up to 8 guests. Located 2.6 km from Main Street, the 4-bedroom holiday home provides Wi-Fi and a car park.
Annapolis Vacation Rentals with Private Pool
Bayridge House By Quiet Waters, Thomas Point Parks
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Patio
To enjoy your vacation in Annapolis, stay at the spacious 2-bedroom Bayridge House By Quiet Waters, Thomas Point Parks Apartment Annapolis, which is 3.6 km from the blooming William Paca Garden and within 25 minutes' walk of Paddle or Pedal. Wi-Fi and parking are also available at this 93 m² apartment.
Bayridge House By Quiet Waters, Thomas Point Parks
- Free parking
- Security
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Patio
Bayridge House By Quiet Waters, Thomas Point Parks
To enjoy your vacation in Annapolis, stay at the spacious 2-bedroom Bayridge House By Quiet Waters, Thomas Point Parks Apartment Annapolis, which is 3.6 km from the blooming William Paca Garden and within 25 minutes' walk of Paddle or Pedal. Wi-Fi and parking are also available at this 93 m² apartment.
Annapolis @Gate 1 Steps To The Harbor Free Parking
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Up to 5 guests can stay at 1-bedroom Annapolis @Gate 1 Steps To The Harbor Free Parking Villa and enjoy the preserved 1774 Hammond-Harwood House, located approximately a 5-minute walk away. Providing guests with Wi-Fi and a private parking lot, the property is 2.1 km from Truxton City Park.
Annapolis @Gate 1 Steps To The Harbor Free Parking
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Annapolis @Gate 1 Steps To The Harbor Free Parking
Up to 5 guests can stay at 1-bedroom Annapolis @Gate 1 Steps To The Harbor Free Parking Villa and enjoy the preserved 1774 Hammond-Harwood House, located approximately a 5-minute walk away. Providing guests with Wi-Fi and a private parking lot, the property is 2.1 km from Truxton City Park.
Luxury Rooftop Pool & Dock Steps To Downtown
- Free parking
- Air conditioning
- Heating
- Rooftop pool
- Pool with view
- Outdoor swimming pool
Luxury Rooftop Pool & Dock Steps To Downtown Annapolis villa is located 13 minutes' walk from Annapolis Historic District and provides an outdoor swimming pool, ensuring a relaxing stay. The 2-bedroom holiday home hosts up to 6 guests and provides them with a private parking lot.
Luxury Rooftop Pool & Dock Steps To Downtown
- Free parking
- Air conditioning
- Heating
- Rooftop pool
- Pool with view
- Outdoor swimming pool
Luxury Rooftop Pool & Dock Steps To Downtown
Luxury Rooftop Pool & Dock Steps To Downtown Annapolis villa is located 13 minutes' walk from Annapolis Historic District and provides an outdoor swimming pool, ensuring a relaxing stay. The 2-bedroom holiday home hosts up to 6 guests and provides them with a private parking lot.
4Br House Mins To Downtown Annapolis With Firepit, Basement Bar, & Sleeps 12
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Golf centre
- Sun terrace
Offering a sundeck and a golf course for guests' leisure, 4Br House Mins To Downtown Annapolis With Firepit, Basement Bar, & Sleeps 12 Villa is situated a 9-minute walk from Christ Our Anchor Presbyterian Church. The 4-bedroom holiday home hosts up to 12 guests and provides them with parking.
4Br House Mins To Downtown Annapolis With Firepit, Basement Bar, & Sleeps 12
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Golf centre
- Sun terrace
4Br House Mins To Downtown Annapolis With Firepit, Basement Bar, & Sleeps 12
Offering a sundeck and a golf course for guests' leisure, 4Br House Mins To Downtown Annapolis With Firepit, Basement Bar, & Sleeps 12 Villa is situated a 9-minute walk from Christ Our Anchor Presbyterian Church. The 4-bedroom holiday home hosts up to 12 guests and provides them with parking.
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Top location
Spectacular Location Two Bedroom State Circle Apartment
- Cookware/ Kitchen utensils
-
Car park
Charges may apply
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Garden area
Featuring a quiet location, the 2-bedroom Spectacular Location Two Bedroom State Circle Apartment Annapolis offers views of the garden, nearly a 5-minute walk from Maryland State House. The 74 m² apartment is situated 46 km from Union Marc Washington train station and just around the corner from Saint Johns Street & College Avenue Far-side Northbound bus station.
Spectacular Location Two Bedroom State Circle Apartment
- Cookware/ Kitchen utensils
-
Car park
Charges may apply
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Garden area
Spectacular Location Two Bedroom State Circle Apartment
Featuring a quiet location, the 2-bedroom Spectacular Location Two Bedroom State Circle Apartment Annapolis offers views of the garden, nearly a 5-minute walk from Maryland State House. The 74 m² apartment is situated 46 km from Union Marc Washington train station and just around the corner from Saint Johns Street & College Avenue Far-side Northbound bus station.
All Star Annapolis Retreat - Walk To Stadium
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Patio
Staying at the 3-bedroom All Star Annapolis Retreat - Walk To Stadium villa, guests can easily reach Chase Lloyd House, located about a 25-minute walk away. This Annapolis holiday home is suitable for up to 10 guests and features a car park.
All Star Annapolis Retreat - Walk To Stadium
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Patio
All Star Annapolis Retreat - Walk To Stadium
Staying at the 3-bedroom All Star Annapolis Retreat - Walk To Stadium villa, guests can easily reach Chase Lloyd House, located about a 25-minute walk away. This Annapolis holiday home is suitable for up to 10 guests and features a car park.
Modern Gem Near Historic Annapolis & Naval Academy
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Ironing facilities
- Heating
- Terrace
The 4-bedroom Modern Gem Near Historic Annapolis & Naval Academy Villa accommodates up to 8 guests and offers a prime location nearly a 10-minute ride from such places of worship as Saint Mary Catholic Church. Located 3.7 km from Maryland State House, the Annapolis holiday home provides Wi-Fi and a private parking lot.
Modern Gem Near Historic Annapolis & Naval Academy
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Ironing facilities
- Heating
- Terrace
Modern Gem Near Historic Annapolis & Naval Academy
The 4-bedroom Modern Gem Near Historic Annapolis & Naval Academy Villa accommodates up to 8 guests and offers a prime location nearly a 10-minute ride from such places of worship as Saint Mary Catholic Church. Located 3.7 km from Maryland State House, the Annapolis holiday home provides Wi-Fi and a private parking lot.
Dta Row Home Walk To City Dock & The Yard
- Air conditioning
- Heating
Situated 0.6 km from the public maritime United States Naval Academy Museum, Dta Row Home Walk To City Dock & The Yard Annapolis is ideal for up to 6 guests. Located in the vicinity of St. Anne's Episcopal Church, this 2-bedroom villa provides Wi-Fi and a car park.
Dta Row Home Walk To City Dock & The Yard
- Air conditioning
- Heating
Dta Row Home Walk To City Dock & The Yard
Situated 0.6 km from the public maritime United States Naval Academy Museum, Dta Row Home Walk To City Dock & The Yard Annapolis is ideal for up to 6 guests. Located in the vicinity of St. Anne's Episcopal Church, this 2-bedroom villa provides Wi-Fi and a car park.
Are you in a hurry?
Here is a quick list of Vacation Rentals in Annapolis, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Vintage Charm: Annapolis Retreat |
9.7 / 10 (11 Reviews) |
From 365$ | |
| Neptune By The Water |
10.0 / 10 (8 Reviews) |
From 321$ | |
| Waterfront Annapolis Cottage: Fire Pit & Pier |
9.4 / 10 (6 Reviews) |
From 259$ | |
| Downtown Annapolis King George 3Rd Floor Hideaway |
8.7 / 10 (9 Reviews) |
From 248$ | |
| Private Single Family Home Close To Both Water And Downtown! |
9.4 / 10 (7 Reviews) |
From 422$ |
Frequently Asked Questions
What are the best Annapolis vacation rentals near the historic district?
Many Annapolis vacation rentals, such as the Waterfront Annapolis Cottage and Vintage Charm: Annapolis Retreat, are just a short walk from the historic district. These rentals often have unique local character and provide a cozy stay.
To enjoy the historic charm, stroll along Main Street before 10 a.m. when shops are quieter.
Which Annapolis vacation rentals are suitable for families with kids?
Properties like the Downtown Annapolis King George 3rd Floor Hideaway and the 4Br House Mins To Downtown Annapolis are great for families, providing spacious accommodations. They are conveniently located near parks and kid-friendly attractions.
Pack a picnic and head to Quiet Waters Park on weekends; it features playgrounds and beautiful walking trails.
Are there dog-friendly Annapolis vacation rentals?
Yes, there are vacation rentals like the Annapolis @Gate 1 that welcome pets. This can make traveling with your furry friend easier.
Check local leash laws before walking your dog near any parks in the area.
Which Annapolis vacation rentals offer beautiful views?
The Oasis By The Bay - Waterfront Heated Pool Hot Tub and Neptune By The Water both provide stunning waterfront views. Relaxing by the water can make your stay even more enjoyable.
Book a waterfront rental during sunset to experience breathtaking views over the bay.
What are the best Annapolis vacation rentals with pools?
For a refreshing swim, consider the Oasis By The Bay - Waterfront Heated Pool Hot Tub or the Luxury Rooftop Pool & Dock. Both options provide excellent pool amenities.
Visit the pool area during off-peak hours, like early morning, for a quieter experience.
How can I find affordable Annapolis vacation rentals?
Look for options like The Pool Loft At Poplar Hill or Downtown Annapolis King George 3rd Floor Hideaway, which offer budget-friendly stays without sacrificing comfort. Off-season bookings can also reduce costs.
Consider visiting Annapolis in late fall for lower rental rates and fewer crowds.
Which Annapolis vacation rentals are nearby local attractions?
Accommodations like the Fisher House - Downtown Annapolis! and Spectacular Location Two Bedroom State Circle Apartment provide easy access to attractions. You'll be close to many sites like the United States Naval Academy.
Plan to explore downtown attractions early in the day to avoid afternoon crowds.
What unique events should I attend in Annapolis?
Annually, the Annapolis Boat Shows and the Maryland Renaissance Festival attract many visitors. They showcase local culture and activities.
Plan your visit in October for the Boat Show; it's a vibrant event with thousands of attendees and events around the harbor.
How can I easily get around Annapolis?
Annapolis has a convenient bus service and walkable downtown. Many attractions are close together, making walking a great way to explore.
Use the free circulator bus if staying around downtown to reach key spots without a car.
What should I know about shopping in Annapolis?
For unique local shopping, visit the boutiques on Main Street and West Street. You'll find arts, crafts, and specialty goods that reflect the local culture.
Check for seasonal sales, especially during the winter holidays, to find great deals.