Annapolis
2 guests

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2

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0

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Annapolis

Nov 03 - Nov 04 ·
2 guests

Vacation homes in Annapolis

Annapolis
2 guests

Adults:

2

Children:

0

Child’s age:

Over 110 stays assessed to highlight the standout picks

Navigation

1. Gaia House

2. Vintage Charm: Annapolis Retreat

3. The Pool Loft At Poplar Hill

4. Private Single Family Home Close To Both Water And Downtown!

Vacation Homes in Annapolis

5. Downtown Annapolis King George 3Rd Floor Hideaway

6. Annapolis Charm Waterfront Getaway Near Usna - Fish & Crab From Your Private Pier!

7. Oasis By The Bay - Waterfront Heated Pool Hot Tub

Vacation Homes in Annapolis,Maryland with Private Pool

8. Walk To Everything Historic Arts District

9. Bay Ridge Unit By Downtown Annapolis And Quiet Waters Park

10. Golden Anchor Retreat Lux Living!

  • Guest favorite
Gaia House Gaia House

Gaia House

102 Louis Drive
2.7 km (1.7 mi) from city center
9
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Terrace

Located nearly a 5-minute walk from Capitol Church of Christ, the 2-bedroom Gaia House Villa Annapolis offers quick access to various city attractions in the vicinity. Providing guests with Wi-Fi and private parking, the villa is 2.6 km from St. Anne's Episcopal Church.

9
57 reviews
~ €123 / night

Gaia House

2.7 km (1.7 mi) from city center
9
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Terrace

Gaia House

Located nearly a 5-minute walk from Capitol Church of Christ, the 2-bedroom Gaia House Villa Annapolis offers quick access to various city attractions in the vicinity. Providing guests with Wi-Fi and private parking, the villa is 2.6 km from St. Anne's Episcopal Church.

9
57 reviews
From € 123 / night
Vintage Charm: Annapolis Retreat Vintage Charm: Annapolis Retreat

Vintage Charm: Annapolis Retreat

3 Hill Street
0.8 km (0.5 mi) from city center
204
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Ironing facilities
  • Terrace

The 3-bedroom Vintage Charm: Annapolis Retreat Villa accommodates up to 5 guests and offers proximity to Mission Escape Rooms, located nearly a 10-minute walk away.

9.7
14 reviews
~ €326 / night

Vintage Charm: Annapolis Retreat

0.8 km (0.5 mi) from city center
204
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Ironing facilities
  • Terrace

Vintage Charm: Annapolis Retreat

The 3-bedroom Vintage Charm: Annapolis Retreat Villa accommodates up to 5 guests and offers proximity to Mission Escape Rooms, located nearly a 10-minute walk away.

9.7
14 reviews
From € 326 / night
The Pool Loft At Poplar Hill The Pool Loft At Poplar Hill

The Pool Loft At Poplar Hill

700 Broadmoor Drive
7.3 km (4.5 mi) from city center
65
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Golf centre
  • Outdoor swimming pool

To enjoy your vacation in Annapolis, stay at the spacious 1-bedroom The Pool Loft At Poplar Hill Apartment Annapolis, which is just 0.8 km from Broadneck Peninsula Trail and only 9 minutes' walk from Christ Our Anchor Presbyterian Church. This 65 m² apartment offers modern facilities, such as Wi-Fi and essentials like private car parking for car travellers.

The area surrounding The Pool Loft At Poplar Hill Apartment offers a variety of activities, including cycling and fisheries.

9.8
4 reviews
~ €183 / night

The Pool Loft At Poplar Hill

7.3 km (4.5 mi) from city center
65
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Golf centre
  • Outdoor swimming pool

The Pool Loft At Poplar Hill

To enjoy your vacation in Annapolis, stay at the spacious 1-bedroom The Pool Loft At Poplar Hill Apartment Annapolis, which is just 0.8 km from Broadneck Peninsula Trail and only 9 minutes' walk from Christ Our Anchor Presbyterian Church. This 65 m² apartment offers modern facilities, such as Wi-Fi and essentials like private car parking for car travellers.

The area surrounding The Pool Loft At Poplar Hill Apartment offers a variety of activities, including cycling and fisheries.

9.8
4 reviews
From € 183 / night

Vacation Homes in Annapolis

  • Beach access
Private Single Family Home Close To Both Water And Downtown! Private Single Family Home Close To Both Water And Downtown!

Private Single Family Home Close To Both Water And Downtown!

1029 Harbor Dr
3.8 km (2.4 mi) from city center
  • 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 can host up to 8 guests, boasting a convenient location within 10 minutes' drive of iconic cultural attractions such as The Chesapeake Children's Interactive Museum. Located 4.1 km from the public maritime United States Naval Academy Museum, the accommodation comes with a terrace and playground for added enjoyment.

9.4
7 reviews
~ €377 / night

Private Single Family Home Close To Both Water And Downtown!

3.8 km (2.4 mi) from city center
  • 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 can host up to 8 guests, boasting a convenient location within 10 minutes' drive of iconic cultural attractions such as The Chesapeake Children's Interactive Museum. Located 4.1 km from the public maritime United States Naval Academy Museum, the accommodation comes with a terrace and playground for added enjoyment.

9.4
7 reviews
From € 377 / night
Downtown Annapolis King George 3Rd Floor Hideaway Downtown Annapolis King George 3Rd Floor Hideaway

Downtown Annapolis King George 3Rd Floor Hideaway

165 King George Street
0.5 km (0.3 mi) from city center
65
  • BBQ facilities
  • Car park
    Charges may apply
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Garden area

The spacious 1-bedroom Downtown Annapolis King George 3Rd Floor Hideaway Apartment is located 46 km from Union Marc Washington train station and about 5 minutes' walk from the Harwood Big Brice House. The apartment features Wi-Fi, along with parking for guests travelling by car.

8.6
9 reviews
~ €222 / night

Downtown Annapolis King George 3Rd Floor Hideaway

0.5 km (0.3 mi) from city center
65
  • 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 1-bedroom Downtown Annapolis King George 3Rd Floor Hideaway Apartment is located 46 km from Union Marc Washington train station and about 5 minutes' walk from the Harwood Big Brice House. The apartment features Wi-Fi, along with parking for guests travelling by car.

8.6
9 reviews
From € 222 / night
  • Private beach
Annapolis Charm Waterfront Getaway Near Usna - Fish & Crab From Your Private Pier! Annapolis Charm Waterfront Getaway Near Usna - Fish & Crab From Your Private Pier!

Annapolis Charm Waterfront Getaway Near Usna - Fish & Crab From Your Private Pier!

1709 River Road
7.6 km (4.7 mi) from city center
125
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Live entertainment
  • Sun terrace

The 3-bedroom Annapolis Charm Waterfront Getaway Near Usna - Fish & Crab From Your Private Pier! villa is located in a business area, around 6 km from Bay Head Park and offers guests to take advantage of a sundeck and a picnic area. Along with a vending machine and an outdoor fireplace, this accommodation also features a car park.

Activities such as canyoning and fisheries can be organised on site.

9.4
10 reviews
~ €499 / night

Annapolis Charm Waterfront Getaway Near Usna - Fish & Crab From Your Private Pier!

7.6 km (4.7 mi) from city center
125
  • 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!

The 3-bedroom Annapolis Charm Waterfront Getaway Near Usna - Fish & Crab From Your Private Pier! villa is located in a business area, around 6 km from Bay Head Park and offers guests to take advantage of a sundeck and a picnic area. Along with a vending machine and an outdoor fireplace, this accommodation also features a car park.

Activities such as canyoning and fisheries can be organised on site.

9.4
10 reviews
From € 499 / night

Vacation Homes in Annapolis,Maryland with Private Pool

Oasis By The Bay - Waterfront Heated Pool Hot Tub Oasis By The Bay - Waterfront Heated Pool Hot Tub

Oasis By The Bay - Waterfront Heated Pool Hot Tub

34 East Lake Drive
4.7 km (2.9 mi) from city center
520
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Sauna
  • Outdoor swimming pool

Located approximately 10 minutes' drive from St. Anne's Episcopal Church, the 6-bedroom Oasis By The Bay - Waterfront Heated Pool Hot Tub Villa Annapolis has an outdoor swimming pool and is ideal for up to 18 guests. The accommodation offers guests a relaxing experience with a sauna.

10
3 reviews
~ €485 / night

Oasis By The Bay - Waterfront Heated Pool Hot Tub

4.7 km (2.9 mi) from city center
520
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Sauna
  • Outdoor swimming pool

Oasis By The Bay - Waterfront Heated Pool Hot Tub

Located approximately 10 minutes' drive from St. Anne's Episcopal Church, the 6-bedroom Oasis By The Bay - Waterfront Heated Pool Hot Tub Villa Annapolis has an outdoor swimming pool and is ideal for up to 18 guests. The accommodation offers guests a relaxing experience with a sauna.

10
3 reviews
From € 485 / night
Walk To Everything Historic Arts District Walk To Everything Historic Arts District

Walk To Everything Historic Arts District

52 Madison Place
0.8 km (0.5 mi) from city center
139
  • Cookware/ Kitchen utensils
  • Free parking
  • Tours/Ticket assistance
  • Air conditioning
  • Flat-screen TV
  • Live entertainment

Nestled 18 minutes' walk from the blooming William Paca Garden, Walk To Everything Historic Arts District Annapolis villa is boasting beauty services, spa therapy, and a golf course for guests' enjoyment. Located a mere 1.7 km from the undergraduate college "United States Naval Academy Museum", this 2-bedroom holiday home provides Wi-Fi and a private parking lot.

Offering a treatment room and a foot bath, this Annapolis accommodation also has yoga instruction. There is a nightclub provided for guests' enjoyment, along with a fitness room for guests to stay fit. Treatment facilities feature body scrub, pedicure, and manicure.

9
12 reviews

Walk To Everything Historic Arts District

0.8 km (0.5 mi) from city center
139
  • Cookware/ Kitchen utensils
  • Free parking
  • Tours/Ticket assistance
  • Air conditioning
  • Flat-screen TV
  • Live entertainment

Walk To Everything Historic Arts District

Nestled 18 minutes' walk from the blooming William Paca Garden, Walk To Everything Historic Arts District Annapolis villa is boasting beauty services, spa therapy, and a golf course for guests' enjoyment. Located a mere 1.7 km from the undergraduate college "United States Naval Academy Museum", this 2-bedroom holiday home provides Wi-Fi and a private parking lot.

Offering a treatment room and a foot bath, this Annapolis accommodation also has yoga instruction. There is a nightclub provided for guests' enjoyment, along with a fitness room for guests to stay fit. Treatment facilities feature body scrub, pedicure, and manicure.

9
12 reviews
Bay Ridge Unit By Downtown Annapolis And Quiet Waters Park Bay Ridge Unit By Downtown Annapolis And Quiet Waters Park

Bay Ridge Unit By Downtown Annapolis And Quiet Waters Park

907 Old Annapolis Neck Road C
3.5 km (2.2 mi) from city center
111
  • Cookware/ Kitchen utensils
  • Free parking
  • Security
  • Air conditioning
  • Flat-screen TV
  • Patio

The 111 m² Bay Ridge Unit By Downtown Annapolis And Quiet Waters Park Apartment is located 10 minutes' drive from The Kunta Kinte Alex Haley Memorial and 2.8 km from Annapolis Maritime Museum. Wi-Fi and a car park are provided for guests' business or leisure needs.

9.5
11 reviews

Bay Ridge Unit By Downtown Annapolis And Quiet Waters Park

3.5 km (2.2 mi) from city center
111
  • Cookware/ Kitchen utensils
  • Free parking
  • Security
  • Air conditioning
  • Flat-screen TV
  • Patio

Bay Ridge Unit By Downtown Annapolis And Quiet Waters Park

The 111 m² Bay Ridge Unit By Downtown Annapolis And Quiet Waters Park Apartment is located 10 minutes' drive from The Kunta Kinte Alex Haley Memorial and 2.8 km from Annapolis Maritime Museum. Wi-Fi and a car park are provided for guests' business or leisure needs.

9.5
11 reviews

Luxury Vacation Homes in Annapolis

Golden Anchor Retreat Lux Living! Golden Anchor Retreat Lux Living!

Golden Anchor Retreat Lux Living!

704 Londontown Road
6.3 km (3.9 mi) from city center
217
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Heating

Golden Anchor Retreat Lux Living! Villa Annapolis is located about 7 km from the Harwood Big Brice House, giving access to various tourist spots nearby. This 3-bedroom villa hosts up to 7 guests and provides them with a private parking lot.

10
4 reviews
~ €705 / night

Golden Anchor Retreat Lux Living!

6.3 km (3.9 mi) from city center
217
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Heating

Golden Anchor Retreat Lux Living!

Golden Anchor Retreat Lux Living! Villa Annapolis is located about 7 km from the Harwood Big Brice House, giving access to various tourist spots nearby. This 3-bedroom villa hosts up to 7 guests and provides them with a private parking lot.

10
4 reviews
From € 705 / night
  • Top location
Fisher House - Downtown Annapolis! Fisher House - Downtown Annapolis!

Fisher House - Downtown Annapolis!

142 Market Street
0.3 km (0.2 mi) from city center
1000
  • BBQ facilities
  • Air conditioning
  • Tea and coffee facilities
  • Heating
  • Patio

The 3-bedroom Fisher House - Downtown Annapolis! villa hosts up to 9 guests and provides proximity to Mission Escape Rooms, situated just 7 minutes' stroll away. Providing guests with Wi-Fi and parking, the Annapolis holiday home is only 450 metres from Maryland State House.

9
8 reviews
~ €684 / night

Fisher House - Downtown Annapolis!

0.3 km (0.2 mi) from city center
1000
  • BBQ facilities
  • Air conditioning
  • Tea and coffee facilities
  • Heating
  • Patio

Fisher House - Downtown Annapolis!

The 3-bedroom Fisher House - Downtown Annapolis! villa hosts up to 9 guests and provides proximity to Mission Escape Rooms, situated just 7 minutes' stroll away. Providing guests with Wi-Fi and parking, the Annapolis holiday home is only 450 metres from Maryland State House.

9
8 reviews
From € 684 / night
Waterfront Annapolis Cottage: Fire Pit & Pier Waterfront Annapolis Cottage: Fire Pit & Pier

Waterfront Annapolis Cottage: Fire Pit & Pier

7.7 km (4.8 mi) from city center
130
  • Cookware/ Kitchen utensils
  • Free parking
  • Flat-screen TV

The 3-bedroom Waterfront Annapolis Cottage: Fire Pit & Pier is located within 6 km of Bay Head Park, giving access to various tourist spots nearby. This Annapolis holiday home is suitable for 5 guests and offers hire for rent.

9.4
6 reviews
~ €301 / night

Waterfront Annapolis Cottage: Fire Pit & Pier

7.7 km (4.8 mi) from city center
130
  • Cookware/ Kitchen utensils
  • Free parking
  • Flat-screen TV

Waterfront Annapolis Cottage: Fire Pit & Pier

The 3-bedroom Waterfront Annapolis Cottage: Fire Pit & Pier is located within 6 km of Bay Head Park, giving access to various tourist spots nearby. This Annapolis holiday home is suitable for 5 guests and offers hire for rent.

9.4
6 reviews
From € 301 / night

Cheap Vacation Homes in Annapolis,Maryland

  • Great deal
Annapolis @Gate 1 Steps To The Harbor Free Parking Annapolis @Gate 1 Steps To The Harbor Free Parking

Annapolis @Gate 1 Steps To The Harbor Free Parking

126 Prince George Street 1
0.5 km (0.3 mi) from city center
60
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities

Situated merely a 7-minute walk from Annapolis Historic District, 1-bedroom Annapolis @Gate 1 Steps To The Harbor Free Parking Villa is ideal for up to 5 guests. Located not far from Elizabeth Myers Mitchell Art Gallery, the holiday home provides Wi-Fi and private parking.

9.4
5 reviews

Annapolis @Gate 1 Steps To The Harbor Free Parking

0.5 km (0.3 mi) from city center
60
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities

Annapolis @Gate 1 Steps To The Harbor Free Parking

Situated merely a 7-minute walk from Annapolis Historic District, 1-bedroom Annapolis @Gate 1 Steps To The Harbor Free Parking Villa is ideal for up to 5 guests. Located not far from Elizabeth Myers Mitchell Art Gallery, the holiday home provides Wi-Fi and private parking.

9.4
5 reviews
Luxury Rooftop Pool & Dock Steps To Downtown Luxury Rooftop Pool & Dock Steps To Downtown

Luxury Rooftop Pool & Dock Steps To Downtown

316 Burnside St
0.9 km (0.6 mi) from city center
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Rooftop pool

Staying at the 2-bedroom Luxury Rooftop Pool & Dock Steps To Downtown Annapolis villa, guests can visit Hogshead Sign Shop, which is just 1.2 km away. The Annapolis holiday home is suitable for up to 6 guests and features a private parking lot.

10
1 reviews
~ €486 / night

Luxury Rooftop Pool & Dock Steps To Downtown

0.9 km (0.6 mi) from city center
49
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Rooftop pool

Luxury Rooftop Pool & Dock Steps To Downtown

Staying at the 2-bedroom Luxury Rooftop Pool & Dock Steps To Downtown Annapolis villa, guests can visit Hogshead Sign Shop, which is just 1.2 km away. The Annapolis holiday home is suitable for up to 6 guests and features a private parking lot.

10
1 reviews
From € 486 / night
4Br House Mins To Downtown Annapolis With Firepit, Basement Bar, & Sleeps 12 4Br House Mins To Downtown Annapolis With Firepit, Basement Bar, & Sleeps 12

4Br House Mins To Downtown Annapolis With Firepit, Basement Bar, & Sleeps 12

1228 Ramblewood Drive
7.6 km (4.7 mi) from city center
17
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Golf centre
  • Sun terrace

Staying at the 4-bedroom 4Br House Mins To Downtown Annapolis With Firepit, Basement Bar, & Sleeps 12 Villa, guests can easily reach Broadneck Peninsula Trail, located a mere 0.8 km away. This Annapolis holiday home is suitable for up to 12 guests and features parking.

9.7
3 reviews
~ €464 / night

4Br House Mins To Downtown Annapolis With Firepit, Basement Bar, & Sleeps 12

7.6 km (4.7 mi) from city center
17
  • 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

Staying at the 4-bedroom 4Br House Mins To Downtown Annapolis With Firepit, Basement Bar, & Sleeps 12 Villa, guests can easily reach Broadneck Peninsula Trail, located a mere 0.8 km away. This Annapolis holiday home is suitable for up to 12 guests and features parking.

9.7
3 reviews
From € 464 / night

Are you in a hurry?

Here is a quick list of hotels in Annapolis, selected based on their rating

Name of hotel Accommodation Rating Price, $
Gaia House

9.0 / 10

(57 Reviews)

From 137$
Vintage Charm: Annapolis Retreat

9.7 / 10

(14 Reviews)

From 365$
The Pool Loft At Poplar Hill

9.8 / 10

(4 Reviews)

From 205$
Private Single Family Home Close To Both Water And Downtown!

9.4 / 10

(7 Reviews)

From 422$
Downtown Annapolis King George 3Rd Floor Hideaway

8.6 / 10

(9 Reviews)

From 248$

Location