Cottages in Maryland at the best prices

1669 available cottage rental offers

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Maryland cottages
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1669 Best cottages in Maryland

Serene Spot, West River Dock, Sunsets, The Bay, Only 40 Min From Alexandria, Dc. - Maryland
9.6 49 reviews
Maryland
22/09 – 25/09
$292/nighttotal: $876 (3 )

Serene Spot, West River Dock, Sunsets, The Bay, Only 40 Min From Alexandria, Dc.

1 3
cottage, Shady Side
This waterfront cottage in Shady Side, Maryland, is situated on a peninsula on the West River, approximately 32 kilometres from Annapolis and close to Galesville.
The one-bedroom, one-bathroom property sleeps three, offering a private dock, kitchen with fridge and microwave, air conditioning, a terrace, garden, parking, internet access, and proximity to Thanksgiving Farm Wines and South River Golf Links.
Charming 2-bedroom 1 Bath Cottage With Ac, Wifi In Peaceful North Beach, Md. - Maryland
9.4 6 reviews
Maryland
04/09 – 07/09
$356/nighttotal: $1068 (3 )

Charming 2-bedroom 1 Bath Cottage With Ac, Wifi In Peaceful North Beach, Md.

2 2
cottage, North Beach
This holiday let in North Beach is located 800 metres from the Chesapeake Bay and 800 metres from the Bayside History Museum.
This holiday let offers Wi-Fi, air conditioning, a dishwasher, and a microwave oven, with parking and laundry facilities available on site.
Chesapeake City Pool Retreat  Waterfront Stay In The Woods - Maryland
8.8 15 reviews
Maryland
15/10 – 18/10
$512/nighttotal: $1536 (3 )

Chesapeake City Pool Retreat Waterfront Stay In The Woods

2 6
cottage, Elkton
This charming cottage is located just 10 kilometres from Chesapeake Inn, nestled in a peaceful wooded setting on the water in Elkton. It has received very good ratings from previous guests.
The property has two bedrooms and two bathrooms, comfortably accommodating up to seven guests. It features a private waterfront location, a spacious open floor plan, a swimming pool, and a large deck overlooking the water.
Sunrise Landing: Waterfront Cottage In Avenue! - Maryland
Maryland
17/07 – 16/10
$250/nighttotal: $22750 (91 )

Sunrise Landing: Waterfront Cottage In Avenue!

1 3
cottage, Cobb Island
This Cobb Island waterfront holiday home is situated a short drive (approximately 21km) from St Clement's Island State Park and 40km from the Port of Leonardtown Winery, offering convenient access to boating.
The two-bedroom, one-bathroom property sleeps four, features a fully equipped kitchen with appliances including a fridge, microwave, stove, coffee maker and ice maker, in-unit laundry, air conditioning, a terrace, garden, internet access, and on-site parking.
Beautiful Waterfront 2-bedroom Cottage In Tranquil Piney Point With Wifi, Ac - Maryland
10 5 reviews
Maryland
15/10 – 18/10
$351/nighttotal: $1053 (3 )

Beautiful Waterfront 2-bedroom Cottage In Tranquil Piney Point With Wifi, Ac

2 6
cottage, Piney Point
This Piney Point waterfront holiday home is situated near St Mary's River State Park and the Piney Point Lighthouse, offering tranquil river views.
Sleeping up to six guests, the two-bedroom property boasts a fully equipped kitchen, air conditioning, Wi-Fi, smart TVs, and on-site barbecue facilities, making it ideal for families exploring the local area's attractions including the Patuxent River Naval Air Museum.
Private Home In Garrett County, Surrounded By Trees,\n Fields \N And Farmland. - Maryland
10 47 reviews
Maryland
15/10 – 18/10
$289/nighttotal: $867 (3 )

Private Home In Garrett County, Surrounded By Trees,\n Fields \N And Farmland.

3 6
cottage, Grantsville
This Grantsville holiday home sits on over 3 acres bordering farmland, approximately 11-27km from attractions including Wisp Resort, Deep Creek Lake, and Savage River State Park, and 6km from New Germany Park.
The three-bedroom property, sleeping six, offers a fully equipped kitchen, two bathrooms (one en-suite), a gas fireplace, patio, firepit, Wi-Fi, and is close to hiking, kayaking, and golf at the Winnfield Golf course.
Walk To Beach: Pet-friendly Gem In Scotland! - Maryland
9.8 7 reviews
Maryland
22/09 – 25/09
$323/nighttotal: $969 (3 )

Walk To Beach: Pet-friendly Gem In Scotland!

1 3
cottage, Piney Point
This Piney Point holiday home is situated near Point Lookout State Park (1.6 km), Buzz's and Drury's Marinas (6.4 km), and Piney Point Lighthouse (43.5 km), offering easy access to Chesapeake Bay beaches.
The 39 square metre self-catering property sleeps three, features a sunroom, fully equipped kitchen with a Keurig coffee machine, a furnished deck with charcoal grill, driveway parking for three vehicles, and allows one pet for a fee.
Cottage Located On The Patuxent River! - Maryland
9.8 62 reviews
Maryland
03/07 – 04/07
$560/nightfor 1 night

Cottage Located On The Patuxent River!

1 2
cottage, Golden Beach
This charming cottage is situated just a short distance from the Patuxent River, offering a peaceful retreat close to Running Hare Vineyard and Battle Creek Cypress Swamp Sanctuary. The cottage boasts excellent ratings for location, cleanliness, and overall user experience, ensuring a comfortable and enjoyable stay.
The cottage comprises one bedroom and one bathroom, providing a cosy space for two guests. It features a private garden, a fireplace for cosy evenings, and modern amenities such as a coffee maker and a TV, making it ideal for a relaxing getaway.
Waterfront Maryland Retreat W/ Dock & Bay View! - Maryland
9.8 10 reviews
Maryland
15/10 – 18/10
$506/nighttotal: $1518 (3 )

Waterfront Maryland Retreat W/ Dock & Bay View!

3 6
cottage, Chance
This Chance waterfront holiday home is situated 2.6km from Shark Fin Shoal and 3.9km from Rock Island, within a 32km radius of Whitehaven Historic District and Mount Vernon Park.
The 201 square metre property boasts four bedrooms, two bathrooms, sleeps nine, and includes a fully equipped kitchen, laundry facilities, patio, barbecue, and parking.
Peaceful Suite On The Water "Osprey." Sunrise Over The River From Your Porch. - Maryland
9.2 9 reviews
Maryland
08/08 – 15/08
$300/nighttotal: $2100 (7 )

Peaceful Suite On The Water "Osprey." Sunrise Over The River From Your Porch.

1 2
cottage, Benedict
This Benedict beach house is situated near the Dr Samuel A Mudd House Museum and Drum Point Lighthouse, offering private beach access with over 150 metres of shoreline and a 120-metre pier, and is a 15-minute drive (approx. 24km) from local amenities.
Sleeping six, this self-catering property boasts a queen bed, bunk beds, and a sofa bed, plus a fully equipped kitchen, air conditioning, a terrace, garden, spa, and a gas grill; enjoy birdwatching at Walter's Walk sandbar and explore nearby attractions.
Waterfront Cottage At Hudson Creek - Cozy Year-round Retreat - Maryland
9.4 18 reviews
Maryland
22/09 – 25/09
$413/nighttotal: $1239 (3 )

Waterfront Cottage At Hudson Creek - Cozy Year-round Retreat

3 3
cottage, Madison
This Cambridge cottage, situated 7.2 kilometres from Ragged Island and 19.3 kilometres from Spocott Windmill and several maritime museums, offers convenient access to Madison's attractions.
Sleeping six guests, this three-bedroom, two-bathroom holiday home includes a washing machine, sofa bed, hairdryer, iron and ironing board, and is perfectly located for exploring the local area.
Block To Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr To Dc - Maryland
10 20 reviews
Maryland
04/09 – 07/09
$738/nighttotal: $2214 (3 )

Block To Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr To Dc

2 2
cottage, Long Beach
This St. Leonard's cottage, near Long Beach, offers easy access to Flag Ponds Nature Park and Flag Harbour Marina, both within 1.6km, and is less than 1.6km from Long Beach and Matoaka Beach.
This 74 square metre holiday home sleeps five, boasting two bedrooms, two bathrooms, a fully equipped kitchen, swimming pool, jacuzzi, and terrace, plus free Wi-Fi and on-site parking.

Best family friendly Maryland cottage rentals

Among the 1669 accommodations in Maryland, here are the 4 best family friendly cottage rentals

Luxurious 4br, Private Pool, Heated Spa-open Year-round, Near Downtown! - Maryland
10 153 reviews
Maryland
15/10 – 18/10
$350/nighttotal: $1050 (3 )

Luxurious 4br, Private Pool, Heated Spa-open Year-round, Near Downtown!

4 2
cottage, Ballenger Creek
This charming cottage is located in Ballenger Creek, just 10 kilometres from the historic centre of Frederick, offering a peaceful retreat in a quiet, secluded area. It has received excellent user ratings, reflecting its high standard of comfort and service.
The cottage spans 186 square metres and comfortably accommodates up to eight guests, with four bedrooms and a bathroom. It offers a range of amenities, including a swimming pool, a spa, a terrace, a garden, and a gourmet kitchen, providing everything you need for a relaxing and enjoyable stay.
Waterfront Cottage In Beautiful Hoopers Island - Maryland
10 84 reviews
Maryland
04/09 – 07/09
$456/nighttotal: $1368 (3 )

Waterfront Cottage In Beautiful Hoopers Island

2 2
cottage, Chesapeake Ranch Estates
This waterfront cottage is located in Chesapeake Ranch Estates, just 5km from Middle Hooper Island and 8km from Lower Hooper Island, offering a peaceful escape in a picturesque setting. It has received excellent user reviews, making it a popular choice for travellers.
The cottage spans 54 square metres and comfortably accommodates up to 5 guests in its two bedrooms and one bathroom. It includes a fully equipped kitchen, a garden, a terrace, and free Wi-Fi, allowing you to enjoy both indoor and outdoor relaxation, as well as easy access to the surrounding natural beauty.
Relaxing, Peaceful House In Calvert County, Md Close To Beach Towns And Dc. - Maryland
10 52 reviews
Maryland
27/06 – 04/07
$441/nighttotal: $3087 (7 )

Relaxing, Peaceful House In Calvert County, Md Close To Beach Towns And Dc.

2 2
cottage, Dunkirk
This charming cottage is situated just a short distance from Fridays Creek Winery and the Patuxent River, offering a peaceful escape in the heart of Dunkirk, Maryland. It has received excellent reviews from previous guests, making it a popular choice for travellers seeking a relaxing getaway.
The cottage spans 84 square metres and comfortably accommodates up to four guests in its two bedrooms and one bathroom. Guests can enjoy a range of amenities, including a private outdoor pool, barbecue grills, and a spacious garden, as well as the convenience of a fully equipped kitchen, free Wi-Fi and a private patio.
3b/1fb/kitchen, Center Of Town, The Cottage @ The Manor - Maryland
9.6 45 reviews
Maryland
22/09 – 25/09
$444/nighttotal: $1332 (3 )

3b/1fb/kitchen, Center Of Town, The Cottage @ The Manor

3 3
cottage, Port Deposit
This charming cottage is located just nine miles from Hollywood Casino, Garrett Island Beach, and Perry Point VA Medical Center, offering a peaceful retreat in a scenic riverside location. It has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The three-bedroom property spans 177 square metres and is ideal for families or groups of friends. It comes equipped with a modern kitchen, a private fenced garden, a fitness centre, a spa tub, and a barbecue grill, providing everything you need for a comfortable and enjoyable stay.

Best Maryland cottages with a garden

Rodo Beach Cottage - Dog Friendly Private Beach With Pier - Tesla Charger - Maryland
9.9 68 reviews
Maryland
19/08 – 23/08
$1035/nighttotal: $4140 (4 )

Rodo Beach Cottage - Dog Friendly Private Beach With Pier - Tesla Charger

3 3
cottage, Piney Point
This charming cottage is located in Piney Point, Maryland, just a short distance from the Chesapeake Bay. It benefits from excellent user, location and cleanliness ratings.
The cottage has three bedrooms, accommodating up to eight guests, and offers a range of amenities, including private beach access, a fishing pier, kayaks and stand-up paddle boards, a Tesla charger, and contactless check-in.
Secluded Cozy Cottage In Historic Downtown - Maryland
9.6 20 reviews
Maryland
26/06 – 28/06
$1024/nighttotal: $2048 (2 )

Secluded Cozy Cottage In Historic Downtown

2 2
cottage, Annapolis
This charming cottage is located in Annapolis' Historic District, just a short walk from the City Dock and within easy reach of the State House and other key landmarks. The cottage is situated in a quiet neighbourhood, offering a peaceful retreat from the bustling city centre.
The cottage is a spacious two-bedroom property that can comfortably accommodate up to eight guests. It features a modern kitchen, a private patio with a BBQ, and a comfortable living area with an electric fireplace, a 55" Roku TV, and a full daybed.
Check Out Our Rental Discounts! 3bd-2bath, Sleeps 6, 1st Floor Master & Bath - Maryland
10 9 reviews
Maryland
04/09 – 07/09
$353/nighttotal: $1059 (3 )

Check Out Our Rental Discounts! 3bd-2bath, Sleeps 6, 1st Floor Master & Bath

3 2
cottage, Williamsport
This Williamsport cottage, situated in the city centre, offers easy access to Whitetail Ski Resort (32km), Washington, D.C. (approx. 240km), and Shenandoah National Park, and is close to Hagerstown Suns Municipal Stadium and Antietam National Battlefield.
The 111-square-metre property sleeps six guests across three bedrooms and two bathrooms, boasting a fully equipped kitchen, garden, Wi-Fi, smart TVs, and parking, with opportunities for birdwatching nearby.
Beautiful Remodeled Downtown Frederick Cottage (Pet-friendly) - Maryland
9.9 283 reviews
Maryland
28/06 – 29/06
$487/nightfor 1 night

Beautiful Remodeled Downtown Frederick Cottage (Pet-friendly)

3 2
cottage, Frederick
This charming cottage is located in Frederick, just a short walk from Baker Park and Frederick Memorial Hospital, and within 1 kilometer of Carroll Creek Linear Park and Hood College, offering easy access to both nature and cultural attractions. The cottage consistently receives excellent ratings for its location, cleanliness, and overall experience.
The cottage has two bedrooms and one bathroom, comfortably accommodating up to four guests. It features a fully equipped kitchen, a private patio, a garden, a jetted tub, and a fitness centre, providing everything you need for a relaxing and enjoyable stay.

Frequently Asked Questions about cottages in Maryland

  • What are the top must-see attractions in Maryland, United States?

    Maryland offers a diverse range of attractions. For history buffs, the Inner Harbor in Baltimore, with the National Aquarium and the historic Fort McHenry, is a must-see. History lovers should also explore Annapolis, Maryland's charming state capital, with its historic district and the United States Naval Academy. Nature enthusiasts will enjoy Assateague Island National Seashore, known for its wild horses, and the Chesapeake Bay, offering opportunities for boating, fishing, and crabbing. The Catoctin Mountain Park provides hiking trails and scenic views.
  • What are the best cottage rentals in Maryland?

  • How can one spend a 5-day holiday in Maryland, United States?

    A five-day trip could involve spending two days exploring Baltimore's Inner Harbor, visiting the National Aquarium and Fort McHenry. Dedicate a day to Annapolis, touring the historic district and the Naval Academy. Spend another day at Assateague Island National Seashore, enjoying the beach and wildlife. The remaining day could be used to explore a specific interest, such as hiking in Catoctin Mountain Park or visiting a local museum like the Walters Art Museum in Baltimore.
  • What are the best cottage rentals with a pool in Maryland?

  • Is Maryland, United States a good destination to rent a cottage?

    Yes, Maryland is excellent for cottage rentals. The Eastern Shore offers numerous charming cottages near the Chesapeake Bay, perfect for a relaxing getaway. Ocean City also has many rental cottages, ideal for beach vacations. The mountains of Western Maryland provide a different setting with rustic cottages available for rent.
  • What are the best cottage rentals with a jacuzzi in Maryland?

  • Is Maryland, United States pedestrian and cyclist-friendly?

    Maryland's pedestrian and cyclist friendliness varies by location. Cities like Annapolis and Baltimore have areas that are walkable, but car use is often necessary. Dedicated bike paths exist in some areas, particularly near the Chesapeake Bay and in parks like the Patapsco Valley State Park. However, planning your routes carefully is essential, especially when cycling on roads with traffic.
  • What are the best cottage rentals for families and kids in Maryland?

  • Are there any unusual or hidden places to explore in Maryland, United States?

    Yes, there are many. Explore the abandoned town of Boonsboro, Maryland, which has a fascinating history. Visit the unique rock formations at Cunningham Falls State Park. Discover the charming town of Ellicott City, with its historic Main Street and its unique shops and restaurants. Check out the intriguing Edgar Allan Poe House and Museum in Baltimore.
  • What are the best pet friendly cottage rentals in Maryland?

  • What are some of the best cultural experiences that allow one to meet locals in Maryland, United States?

    Attending local festivals is a great way to meet people. The Maryland Renaissance Festival offers a unique experience, while smaller town festivals throughout the state offer a chance to interact with locals. Visiting local breweries or wineries provides opportunities for social interaction. Farmer's markets are another great place to meet Marylanders and sample local produce.
  • What are the best cottage rentals with parking in Maryland?

  • What are the best authentic dishes to taste in Maryland, United States?

    Maryland's cuisine is heavily influenced by the Chesapeake Bay. Crab cakes are a must-try, along with steamed blue crabs. Smith Island Cake, a unique layer cake, is another local specialty. Try the Chesapeake Bay oysters, known for their unique flavor. Many restaurants offer fresh seafood dishes prepared in various ways.
  • What are some recommended items to pack for a stay in Maryland, United States?

    Pack comfortable walking shoes, especially if you plan on exploring cities on foot. Bring sunscreen and insect repellent, particularly during the warmer months. Layers of clothing are recommended, as Maryland weather can be unpredictable. If visiting during the colder months, pack warm clothing and waterproof outerwear. Don't forget swimwear if you plan on visiting the beach or swimming in the Chesapeake Bay.

Nearby regions

Best Maryland cottage rentals with jacuzzi

Among the 1669 accommodations in Maryland, here are the 4 best cottage rentals with a jacuzzi

Firefly Cottage At The Cape, Community Beach, Spring  Adventures, Hot Tub, Usna - Maryland
10 108 reviews
Maryland
01/08 – 30/08
$396/nighttotal: $11484 (29 )

Firefly Cottage At The Cape, Community Beach, Spring Adventures, Hot Tub, Usna

1 2
cottage, Arnold
This charming cottage is located in Cape Saint Claire, just a short drive from Arnold's attractions, including Sandy Point State Park and Sandy Point Beach. The cottage has received excellent user ratings, making it a popular choice for travellers.
This holiday home offers 61 square metres of space, comfortably accommodating up to 5 guests in its one bedroom and one bathroom. The cottage is equipped with a range of amenities, including a fully fitted kitchen, a spa, a terrace, a garden, parking and Wi-Fi, ensuring a comfortable and enjoyable stay.
Cozy Cottage - Maryland
10 1 review
Maryland
27/06 – 04/07
$986/nighttotal: $6902 (7 )

Cozy Cottage

4 2
cottage, Dundalk
This Dundalk holiday home is situated within 9.6km of Johns Hopkins Bayview Medical Center, the Baltimore Cruise Terminal, and Johns Hopkins Hospital, offering convenient access to these key locations.
Sleeping eight guests, the four-bedroom, two-bathroom property boasts a fully equipped kitchen with dishwasher, a jacuzzi, private garden, parking, and air conditioning, plus a washing machine and dryer for added convenience.
Hays Beach House - Hot Tub - Private Beach - Maryland
9.8 16 reviews
Maryland
10/07 – 18/07
$1489/nighttotal: $11912 (8 )

Hays Beach House - Hot Tub - Private Beach

5 3
cottage, Piney Point
This five-bedroom cottage is located in Point Lookout, a rural beachside neighbourhood in Scotland, MD, approximately 24 kilometres from Piney Point. The property has consistently received excellent reviews from guests.
The cottage can accommodate up to 12 guests and features a fully equipped gourmet kitchen, a private hot tub with bay views, and a screened porch. Guests can enjoy direct access to a private beach for crabbing, fishing, kayaking, and stand-up paddle boarding, as well as a Tesla charger and contactless check-in.
Cottage On The Bay - Maryland
8.8 3 reviews
Maryland
22/09 – 25/09
$347/nighttotal: $1041 (3 )

Cottage On The Bay

2 3
cottage, Long Beach
This family-friendly beach lodge in St. Leonard, Maryland, offers access to three private community beaches and is situated within 160 kilometres of Washington D.C. and Joint Base Andrews, 72 kilometres from Waldorf, and 24 kilometres from Solomons Island.
This two-bedroom holiday home accommodates up to four guests, featuring two smart TVs, a bathroom with a tub, a living area with a pellet stove, a fully equipped kitchen, and on-site laundry facilities, with shared amenities including a fire pit and kayaks for exploring the bay.

Best pet friendly Maryland cottage rentals

Among the 1669 accommodations in Maryland, here are the 4 best pet friendly cottage rentals

Potomac Riverfront! Home Near St Clements Island - Maryland
Maryland
19/07 – 30/07
$337/nighttotal: $3707 (11 )

Potomac Riverfront! Home Near St Clements Island

2 2
cottage, Cobb Island
This waterfront holiday home on Cobb Island, located in Coltons Point, offers riverfront living and is conveniently situated 300 metres from the St. Clements Island Museum water taxi.
This 2-bedroom, 4-guest property spans 74 square metres and features a private pier for fishing and crabbing, a water-view balcony, and a kitchenette with essential appliances, with step-free entry to the 2-storey lock-off suite.
Pet Friendly Water View Cottage - Maryland
10 37 reviews
Maryland
29/06 – 03/07
$508/nighttotal: $2032 (4 )

Pet Friendly Water View Cottage

2 4
cottage, Riviera Beach
This charming cottage is located in Pasadena, Maryland, a picturesque waterfront neighbourhood just 20 kilometres from both Annapolis and Baltimore, offering easy access to a range of attractions. The cottage has received excellent reviews from previous guests, highlighting its comfortable and welcoming atmosphere.
The cottage spans 111 square metres and comfortably accommodates up to four guests in its two bedrooms and two bathrooms. Guests can enjoy a fully equipped kitchen, a private garden, and a host of amenities including air conditioning, laundry facilities, and free parking. The cottage is also pet-friendly, allowing guests to bring their furry companions along.
Waterfront River Cottage For 2, Dog-friendly - Maryland
9.6 27 reviews
Maryland
03/07 – 06/07
$619/nighttotal: $1857 (3 )

Waterfront River Cottage For 2, Dog-friendly

1 2
cottage, Severna Park
This charming beachside cottage is located near Severna Park, just nine miles from the B&A Trail, Severna Park Golf Center, and Bay Hills Golf Club. It has received excellent ratings for its location, cleanliness, and overall user experience.
The cottage has one bedroom and one bathroom, offering comfortable accommodation for up to two guests, and it comes equipped with a fully equipped kitchen, a terrace, a garden, a spa, and parking. Enjoy the fresh air and sunshine with the relaxing outdoor space, cook up a meal on the charcoal grill, and take advantage of the arcade/game room for entertainment.
Premier St. Michaels Cottage - T. Blades House -  Walk To Everything In Town - Maryland
9.6 286 reviews
Maryland
29/06 – 03/07
$617/nighttotal: $2468 (4 )

Premier St. Michaels Cottage - T. Blades House - Walk To Everything In Town

2 4
cottage, Easton
This charming cottage is located in St. Michaels, a short walk from the Chesapeake Bay Maritime Museum, St. Michaels Museum, and St. Michaels Winery, making it ideal for exploring this historic town. The cottage has received excellent ratings for its location, cleanliness and overall experience.
The cottage has two bedrooms and can accommodate up to five guests, making it perfect for families or groups of friends. Guests can enjoy a range of amenities including a swimming pool, terrace, garden, and a fully equipped kitchen.
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