Original cottages Annapolis
Annapolis
2 guests

Adults:

2

Children:

0

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Annapolis

Nov 03 - Nov 04 ·
2 guests

Holiday Cottages in Annapolis

Annapolis
2 guests

Adults:

2

Children:

0

Child’s age:

Over 85 stays assessed to highlight the standout picks

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1. Modern Farmhouse

2. Private 2Br Home Near Apg Fast-Entire House

3. Somd Diamond House

4. Long Beach Cottage

Holiday Cottages in Annapolis

5. Spacious 5 Bedroom Stay In Westminster Perfect For Groups & Longer Stays

Cottage near Annapolis

  • Guest favorite
Modern Farmhouse Modern Farmhouse

Modern Farmhouse

2850 Saint Peters Church Road
49.1 km (30.5 mi) from Annapolis
205
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Ironing facilities
  • Terrace

Positioned 6 km from bustling shopping destinations such as Shlagel Farms, Modern Farmhouse Waldorf villa offers guests to use parking.

9.4
6 reviews

Modern Farmhouse

49.1 km (30.5 mi) from Annapolis
205
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Ironing facilities
  • Terrace

Modern Farmhouse

Positioned 6 km from bustling shopping destinations such as Shlagel Farms, Modern Farmhouse Waldorf villa offers guests to use parking.

9.4
6 reviews
  • Popular choice
Private 2Br Home Near Apg Fast-Entire House Private 2Br Home Near Apg Fast-Entire House

Private 2Br Home Near Apg Fast-Entire House

22 Liberty Street
65.1 km (40.4 mi) from Annapolis
13
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Garden area

Private 2Br Home Near Apg Fast-Entire House Aberdeen is located around 5 minutes by car from Bayanihan Food Market, giving access to various tourist spots nearby.

7.1
13 reviews
~ US$74 / night

Private 2Br Home Near Apg Fast-Entire House

65.1 km (40.4 mi) from Annapolis
13
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Flat-screen TV
  • Tea and coffee facilities
  • Garden area

Private 2Br Home Near Apg Fast-Entire House

Private 2Br Home Near Apg Fast-Entire House Aberdeen is located around 5 minutes by car from Bayanihan Food Market, giving access to various tourist spots nearby.

7.1
13 reviews
From US$ 74 / night

Holiday Cottages in Annapolis

Somd Diamond House Somd Diamond House

Somd Diamond House

28690 Amylynn Drive
62.3 km (38.7 mi) from Annapolis
  • Shared kitchen
  • Free parking
  • Express check-in/ -out
  • Air conditioning
  • Bar/ Lounge area
  • Saltwater pool

Somd Diamond House Guest House Mechanicsville villa enjoys a convenient location, an 18-minute walk from Immaculate Conception Catholic Church, and offers guests to unwind in a Jacuzzi.

There is an outdoor swimming pool, as well as a sunbathing terrace and a picnic area at the premises.

Somd Diamond House

62.3 km (38.7 mi) from Annapolis
  • Shared kitchen
  • Free parking
  • Express check-in/ -out
  • Air conditioning
  • Bar/ Lounge area
  • Saltwater pool

Somd Diamond House

Somd Diamond House Guest House Mechanicsville villa enjoys a convenient location, an 18-minute walk from Immaculate Conception Catholic Church, and offers guests to unwind in a Jacuzzi.

There is an outdoor swimming pool, as well as a sunbathing terrace and a picnic area at the premises.

  • Beach access
Long Beach Cottage Long Beach Cottage

Long Beach Cottage

15 Long Beach Road
79.0 km (49.1 mi) from Annapolis
56
  • Cookware/ Kitchen utensils
  • Air conditioning
  • Tea and coffee facilities
  • Heating
  • Jacuzzi
  • Garden area

Nestled about a 25-minute walk from Charlestown Baptist Church, Long Beach Cottage Charlestown entices guests to explore various tourist destinations nearby.

Guests can go in for canyoning and fisheries or simply indulge in a Jacuzzi.

Long Beach Cottage

79.0 km (49.1 mi) from Annapolis
56
  • Cookware/ Kitchen utensils
  • Air conditioning
  • Tea and coffee facilities
  • Heating
  • Jacuzzi
  • Garden area

Long Beach Cottage

Nestled about a 25-minute walk from Charlestown Baptist Church, Long Beach Cottage Charlestown entices guests to explore various tourist destinations nearby.

Guests can go in for canyoning and fisheries or simply indulge in a Jacuzzi.

Holiday Cottages in Annapolis with Private Pool

Spacious 5 Bedroom Stay In Westminster Perfect For Groups & Longer Stays Spacious 5 Bedroom Stay In Westminster Perfect For Groups & Longer Stays

Spacious 5 Bedroom Stay In Westminster Perfect For Groups & Longer Stays

409 Manchester Road
79.3 km (49.3 mi) from Annapolis
  • Free parking
  • Housekeeping
  • Air conditioning
  • Laundry
  • Heating
  • Terrace

During the stay at Spacious 5 Bedroom Stay In Westminster Perfect For Groups & Longer Stays villa, guests can indulge in hiking and horseback riding or visit the movie theater "Carroll Arts Center", located around 25 minutes' walk away. This 3-bedroom country house hosts up to 7 guests and invites them to unwind on a patio.

Spacious 5 Bedroom Stay In Westminster Perfect For Groups & Longer Stays

79.3 km (49.3 mi) from Annapolis
  • Free parking
  • Housekeeping
  • Air conditioning
  • Laundry
  • Heating
  • Terrace

Spacious 5 Bedroom Stay In Westminster Perfect For Groups & Longer Stays

During the stay at Spacious 5 Bedroom Stay In Westminster Perfect For Groups & Longer Stays villa, guests can indulge in hiking and horseback riding or visit the movie theater "Carroll Arts Center", located around 25 minutes' walk away. This 3-bedroom country house hosts up to 7 guests and invites them to unwind on a patio.

More accommodations in Annapolis

Crowne Plaza Annapolis By Ihg Crowne Plaza Annapolis By Ihg Crowne Plaza Annapolis By Ihg
8.1
395 reviews
~ US$ 114 / night
Crowne Plaza Annapolis By Ihg
4.6 km (2.8 mi) from city center
Check Availability
Doubletree By Hilton Hotel Annapolis Doubletree By Hilton Hotel Annapolis Doubletree By Hilton Hotel Annapolis
8.2
359 reviews
~ US$ 91 / night
Doubletree By Hilton Hotel Annapolis
4.7 km (2.9 mi) from city center
Check Availability
Inn On Main Annapolis Inn On Main Annapolis Inn On Main Annapolis
8.1
259 reviews
~ US$ 118 / night
Inn On Main Annapolis
0.2 km (0.1 mi) from city center
Check Availability

Frequently Asked Questions

Which holiday cottages in Annapolis are best located near the city center?

Long Beach Cottage and Private 2Br Home Near Apg are both a short drive from Annapolis' city center. You can easily visit local attractions like the Maryland State House within minutes.

Tip:

Consider visiting downtown Annapolis during the week to avoid the crowds that gather on weekends.

Are there dog-friendly holiday cottages in Annapolis?

Both Somd Diamond House and Modern Farmhouse welcome pets without extra fees. This makes it easy to enjoy your trip with your furry friends.

Tip:

Pack a portable water bowl and snacks for your dog; some parks near your cottage have pet-friendly areas.

Which holiday cottages in Annapolis are suited for families with kids?

Spacious 5 Bedroom Stay In Westminster and Long Beach Cottage offer plenty of room and facilities for children. Families can enjoy local beaches and parks during their stay.

Tip:

Look for cottages with fenced yards-great for safely letting kids play outside.

Which Annapolis holiday cottages have scenic views?

Long Beach Cottage provides beautiful waterfront views, perfect for relaxing evenings. You can enjoy watching boats sail past from your porch.

Tip:

Book a cottage with a balcony to savor sunsets without venturing out.

Are there holiday cottages with pools in Annapolis?

While many cottages don't have pools, check for community pools nearby, or aim for properties like the Spacious 5 Bedroom Stay In Westminster that may offer similar amenities.

Tip:

Bring pool toys or floats to enhance your outdoor fun if the property does allow for pool access.

Which holiday cottages in Annapolis are ideal for longer stays?

Spacious 5 Bedroom Stay In Westminster caters well for extended stays with its full kitchen and laundry facilities. This allows you to feel more at home during longer visits.

Tip:

Look for weekly rental discounts to save money on a more extended stay.

Where can I find budget-friendly holiday cottages in Annapolis?

Private 2Br Home Near Apg offers affordable rates while being close to enjoying local attractions. This makes it a great choice for budget travelers.

Tip:

Check for mid-week availability, when prices are generally lower.

What unique local experiences should I consider during my stay in Annapolis?

Visit the U.S. Naval Academy and enjoy a guided tour to learn about its history. The stunning architecture and museums provide a unique glimpse into maritime life.

Tip:

Tours are available Monday to Saturday, so plan ahead to ensure a spot.

What seasonal events in Annapolis should I attend?

In the fall, Annapolis hosts the Annapolis Film Festival, showcasing independent films. It's a wonderful way to enjoy local culture and meet other enthusiasts.

Tip:

Book your accommodation early around the festival dates to secure good lodging.

How can I get around Annapolis while staying at a holiday cottage?

Local buses and walking paths connect many attractions easily. Renting a bike can also be a fun option to explore the waterfront area.

Tip:

Consider a bike rental from a local shop; many offer discounts for extended rentals.

Annapolis and related destinations

Location