Cottages in Maryland at the best prices

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Maryland cottages
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1669 Best cottages in Maryland

Best family friendly Maryland cottage rentals

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

Peaceful Suite On The Water "Osprey." Sunrise Over The River From Your Porch. - Maryland
9.0 8 reviews
Maryland
15/08 – 17/08
$365/nighttotal: $730 (2 )

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.
Chesapeake Bay Cottage - Maryland
9.9 262 reviews
Maryland
25/11 – 29/11
$538/nighttotal: $2152 (4 )

Chesapeake Bay Cottage

1 4
cottage , Deale
This charming Deale cottage is situated directly on the Chesapeake Bay, just 30 kilometres from Annapolis and a scenic 48 kilometre drive to the Eastern Shore. The cottage consistently receives excellent reviews for its location, cleanliness, and overall guest experience.
The three-bedroom property provides comfortable accommodation for families or groups. Guests can enjoy a fully equipped kitchen, a private beach, and two kayaks for exploring the bay's tranquil waters.
Pet Friendly Delightful Waterfront Cottage On Hoopers Island, Md. - Maryland
10 51 reviews
Maryland
19/06 – 21/06
$594/nighttotal: $1188 (2 )

Pet Friendly Delightful Waterfront Cottage On Hoopers Island, Md.

1 2
cottage , Chesapeake Ranch Estates
This waterfront cottage is located in Fishing Creek, Chesapeake Ranch Estates, just 9 kilometres from Middle Hooper Island and within a 32-kilometre radius of Lower Hooper Island and Blackwater National Wildlife Refuge.
The 65 square metre property offers one bedroom, one bathroom and can accommodate up to four guests, with amenities including a fully equipped kitchen, a terrace, a garden and parking.
Rodo Beach Cottage - Dog Friendly Private Beach With Pier - Tesla Charger - Maryland
9.9 68 reviews
Maryland
19/07 – 25/07
$853/nighttotal: $5118 (6 )

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

3 4
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.

Best Maryland cottages with a garden

Soul Oasis - Home On The Chesapeake Bay - Maryland
10 49 reviews
Maryland
20/07 – 23/07
$334/nighttotal: $1002 (3 )

Soul Oasis - Home On The Chesapeake Bay

2 2
cottage , Lusby
This charming cottage is situated in Lusby, just a short walk from the Chesapeake Bay beach and within easy reach of Cove Point Lighthouse and Drum Point Lighthouse. The property enjoys an excellent user rating, reflecting its peaceful setting and proximity to natural beauty.
The cottage features a unique layout with a bedroom on the main floor and a loft, accommodating up to 5 guests. Guests can enjoy a range of amenities including a trex deck with stunning bay views, a fully equipped kitchen, a washer and dryer, and beach chairs, making it perfect for families or groups seeking a relaxing getaway.
Cottage, Breakfast, & Hiking On 100 Ac Horse Farm - Maryland
10 155 reviews
Maryland
03/07 – 05/07
$459/nighttotal: $918 (2 )

Cottage, Breakfast, & Hiking On 100 Ac Horse Farm

1 2
cottage , Boonsboro
This charming cottage, situated in Middletown, Maryland, is approximately 97 kilometres from Washington, D.C., a 20-minute drive from Frederick, and offers private access to the Appalachian Trail, plus proximity to Harpers Ferry National Park and Antietam National Battlefield.
The self-catering property sleeps two guests in one bedroom and one bathroom, boasting a heated seasonal pool, tennis court, farm animals, and a daily complimentary breakfast including artisanal pastries and farm-fresh eggs.
Potomac Rvr Woodland Cottage, Polite Pets Welcomed, Central Air, Stunning Sunset - Maryland
9.8 60 reviews
Maryland
10/07 – 13/07
$606/nighttotal: $1818 (3 )

Potomac Rvr Woodland Cottage, Polite Pets Welcomed, Central Air, Stunning Sunset

3 5
cottage , Tall Timbers
This Tall Timbers holiday home enjoys a riverside location, less than 1.5 kilometres from the Potomac River and within a 10-kilometre radius of Piney Point Beach, Piney Point Lighthouse, and St. Mary's River State Park.
The 102-square-metre property offers three bedrooms, one bathroom, and sleeps eight guests, boasting a fully equipped kitchen, a terrace, a garden, a spa, free Wi-Fi, and an arcade/game room.
Block To Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr To Dc - Maryland
10 20 reviews
Maryland
22/06 – 25/06
$494/nighttotal: $1482 (3 )

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

2 4
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.

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
18/06 – 21/06
$514/nighttotal: $1542 (3 )

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

1 5
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.
Watrfnt Cottage @Chesapeakeparadise Kayaks/dogs Ok - Maryland
9.7 275 reviews
Maryland
25/11 – 29/11
$618/nighttotal: $2472 (4 )

Watrfnt Cottage @Chesapeakeparadise Kayaks/dogs Ok

3 4
cottage , Deale
This charming cottage is situated just 16km from Deale, on the western shore of the Chesapeake Bay, offering a peaceful retreat close to the vibrant city of Annapolis. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The cottage spans 111 square metres and comfortably accommodates up to 8 guests. It boasts a fully equipped kitchen, a private garden with a fire pit and a pier, and access to kayaks and other watercraft for exploring the nearby creek and Chesapeake Bay.
Cottage On The Bay - Maryland
9.9 89 reviews
Maryland
11/07 – 16/07
$382/nighttotal: $1910 (5 )

Cottage On The Bay

1 4
cottage , Long Beach
This Long Beach holiday home, situated in Saint Leonard, Maryland, is close to three private beaches, 24km from Solomons Island and Prince Frederick, and approximately 80km from Washington, D.C.
The two-bedroom, one-bathroom property sleeps four, boasting a fully equipped kitchen with dishwasher, Jacuzzi access, kayaks and paddleboards, smart TVs, and a washer/dryer; guests can enjoy scenic hilltop views.
New! Private Luxury Spa Hot Tub Retreat With Ping Pong - Maryland
10 1 review
Maryland
11/08 – 21/08
$1937/nighttotal: $19370 (10 )

New! Private Luxury Spa Hot Tub Retreat With Ping Pong

3 2
cottage , Severn
This Severn holiday flat is situated 12.8 kilometres from Arundel Mills Mall and 33.8 kilometres from Oriole Park at Camden Yards, offering proximity to outdoor pursuits such as hiking and biking.
This spacious 118 square metre residence accommodates up to six guests with three bedrooms and three bathrooms, featuring a hot tub, private terrace, on-site parking, Wi-Fi, air conditioning, a fireplace, a dedicated workspace, a fully equipped kitchen, and an in-unit washer and dryer.

Best pet friendly Maryland cottage rentals

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

Chesapeake Bay Vacation Rental W/ Boat Dock! - Maryland
8.0 15 reviews
Maryland
11/07 – 16/07
$565/nighttotal: $2825 (5 )

Chesapeake Bay Vacation Rental W/ Boat Dock!

3 4
cottage , Rock Point
This Rock Point waterfront holiday home is situated 5.1 km from the Potomac River and within 26 km of Aqualand Marina and the Zekiah Swamp Natural Environment Area.
The 79 square metre property sleeps five guests in four bedrooms and one bathroom, boasting a fully equipped kitchen, terrace, garden, parking, and Wi-Fi.
Potomac Riverfront! Home Near St Clements Island - Maryland
Maryland
02/10 – 04/10
$471/nighttotal: $942 (2 )

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.
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/scotland - Maryland
9.6 14 reviews
Maryland
15/08 – 17/08
$538/nighttotal: $1076 (2 )

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/scotland

2 2
cottage , Piney Point
This Piney Point waterfront holiday home boasts stunning Chesapeake Bay views, is situated in Point Lookout, Southern Maryland, and is a short 3.2km drive from Point Lookout State Park and the Smith Island Ferry.
The 95 square metre property offers two bedrooms, one bathroom, sleeps six, and includes a fully equipped kitchen, Wi-Fi, air conditioning, a garden, parking, and on-site amenities such as a fire pit, kayaks, and fishing/crabbing equipment.
Charming 1br Cottage W/ Wifi, Ac In Wonderful Wye Mills - Maryland
9.2 7 reviews
Maryland
19/07 – 25/07
$238/nighttotal: $1428 (6 )

Charming 1br Cottage W/ Wifi, Ac In Wonderful Wye Mills

2 4
cottage , Queenstown
This Queenstown cottage, near the Avalon Theatre and Third Haven Friends Meeting House, offers a convenient base for exploring local attractions such as the Hazel Miner Monument and Adkins Arboretum, although precise distances are unavailable.
The self-catering property features two bedrooms, one bathroom, sleeps four guests, and includes amenities such as Wi-Fi, air conditioning, parking, and a garden with a terrace; a washing machine and a kitchen with a fridge and microwave are also provided.
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