A historic downtown street at dusk with vintage street lamps, brick buildings, and a sign for 'FELSH POINT'.

Holiday Homes in Maryland

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Top Cities in Maryland

Our top choices for Maryland holiday homes

1. RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Downtown Frederick
9.2 out of 10, Wonderful, (149 reviews)
"Great location. Amenities were perfect for a little bit of an extended stay. Definitely will come back in the future"
United States
Dave T.
The price is €231
includes taxes & fees
15 Nov - 16 Nov
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

2. Rooftop Deck Escape! Free Parking!

Rooftop Deck Escape! Free Parking!
South Baltimore
8.6 out of 10, Excellent, (78 reviews)
"Very clean, easy check-in and nice lay out. Would recommend to any one."
United States
Frank M.
The price is €239
includes taxes & fees
17 Nov - 18 Nov
Rooftop Deck Escape! Free Parking!

3. Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.8 out of 10, Exceptional, (31 reviews)
"Great stay"
United States
Guillaume P.
The price is €183
includes taxes & fees
15 Nov - 16 Nov
Cute, Cozy 2-bedroom house near Annapolis with water access

4. 4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry

4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
Knoxville
10.0 out of 10, Exceptional, (37 reviews)
"Great stay, super nice people and wonderful house."
United States
Kenzie S.
The price is €446
includes taxes & fees
16 Nov - 17 Nov
4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry

5. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
"Super clean, well furnished and in a nice quiet neighborhood close to downtown Annapolis. Great place to stay!"
United States
Ryan C.
The price is €430
includes taxes & fees
16 Nov - 17 Nov
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

6. Spacious 5-bedroom house with AC in gorgeous Annapolis historic district capital

Spacious 5-bedroom house with AC in gorgeous Annapolis historic district capital
Historic District
Spacious 5-bedroom house with AC in gorgeous Annapolis historic district capital

7. Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!

Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!
Downtown Ocean City
10.0 out of 10, Exceptional, (39 reviews)
"Great vacation area and accommodation!"
United States
Letizia
The price is €272
includes taxes & fees
15 Dec - 16 Dec
Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!

8. Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly

Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly
Fishing Creek
9.8 out of 10, Exceptional, (60 reviews)
"We were looking for a quiet, remote place to have a relaxing week as a family. This house was perfect. Clean and comfortable and beautiful views"
United States
Natalie B.
Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly

9. Charming 2-bedroom house with fitness room and AC in Glen Burnie

Charming 2-bedroom house with fitness room and AC in Glen Burnie
Glen Burnie
9.4 out of 10, Exceptional, (16 reviews)
"Very private and cozy stay!"
United States
Anna K.
Charming 2-bedroom house with fitness room and AC in Glen Burnie

10. Spacious and Family Friendly 6-bedrooms house in delightful Silver Spring.

Spacious and Family Friendly 6-bedrooms house in delightful Silver Spring.
Silver Spring
9.8 out of 10, Exceptional, (9 reviews)
"Group of friends stayed there while in town for HS reunion - and it was lovely to have a place to lounge and enjoy each others company. Place was great!!"
United States
Penny P.
Spacious and Family Friendly 6-bedrooms house in delightful Silver Spring.

11. Charming Historic Annapolis Home With Two Off-street Parking Places!

Charming Historic Annapolis Home With Two Off-street Parking Places!
Historic District
10.0 out of 10, Exceptional, (223 reviews)
"Fabulous place. Great space. Loved the gorgeous kitchen. Location was amazing we walked everywhere even in 90 plus degree heat. The owners are great super responsive and kind!I highly recommend you stay here if visiting Annapolis!"
United States
Aliza D.
Charming Historic Annapolis Home With Two Off-street Parking Places!

12. BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!

BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!
North Ocean City
9.8 out of 10, Exceptional, (166 reviews)
"We had a great stay! The house was clean and plenty of parking. Very family friendly house, had everything we needed and close to everything. The host was great too! We felt at home and will be booking again for another family vacation."
United States
Teressa
The price is €268
includes taxes & fees
15 Nov - 16 Nov
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!

13. 3-B rooms 5 beds & 2 BR Spacious House 1 mile from downtown with 2 free parking.

3-B rooms 5 beds & 2 BR Spacious House 1 mile from downtown with 2 free parking.
Silver Spring
9.8 out of 10, Exceptional, (97 reviews)
"Property was great, comfortable beds. Hosts were terrific, would stay here again."
United States
Greg F.
3-B rooms 5 beds & 2 BR Spacious House 1 mile from downtown with 2 free parking.

14. Deep Creek Lake and Wisp just minutes away, includes pass to CARC (pool/gym)

Deep Creek Lake and Wisp just minutes away, includes pass to CARC (pool/gym)
Accident
10.0 out of 10, Exceptional, (330 reviews)
"Great location for our needs. My kids loved the game room and the swing in the front yard."
United States
Leia C.
Deep Creek Lake and Wisp just minutes away, includes pass to CARC (pool/gym)

15. 5BR Chesapeake Waterfront Estate with Private Dock

5BR Chesapeake Waterfront Estate with Private Dock
Perryville
10.0 out of 10, Exceptional, (16 reviews)
"Excellent communication with our host. Our family had a great mini vacation."
United States
Wayne W.
5BR Chesapeake Waterfront Estate with Private Dock

16. Welcome to our newly built house

Welcome to our newly built house
Marley
9.0 out of 10, Wonderful, (20 reviews)
"everything was as defined in the profile. i will def stay here again !!!"
United States
Cindy H.
Welcome to our newly built house

17. Fall Cove Mornings & Fireside Nights in St Inigoes

Fall Cove Mornings & Fireside Nights in St Inigoes
St Inigoes
9.0 out of 10, Wonderful, (21 reviews)
"The house was in a great location and very comfortable. We enjoyed the family games, fishing from the pier and drinks on the porch. We plan to return for another fun weekend."
United States
Court M.
Fall Cove Mornings & Fireside Nights in St Inigoes

18. Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Rohrersville
10.0 out of 10, Exceptional, (22 reviews)
"Our stay was so enjoyable!"
United States
Kimberly C.
The price is €393
includes taxes & fees
23 Nov - 24 Nov
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

19. Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (22 reviews)
"It was a great place to relax, sleep and come home to after busy days in Frederick area. We would definitely stay here again!"
United States
Janice M.
The price is €432
includes taxes & fees
22 Nov - 23 Nov
Newly constructed 6 bedroom home

20. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.4 out of 10, Exceptional, (26 reviews)
"Pet friendly!"
United States
Mary Beth S.
The price is €332
includes taxes & fees
15 Dec - 16 Dec
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Maryland Hotel Reviews

Find out more about Maryland

Maryland Holiday Homes information

Number of reviews
1,322
Accommodation
4806 Holiday Homes
Lowest Price
€183
Highest Price
€446

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