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

Vacation Homes in Maryland

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sep - 27 Sep
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Top Cities in Maryland

A capitol building with a dome, surrounded by autumn foliage.
Vacation HomesVacation Homes

Washington

Washington
A city skyline with high-rise buildings, a marina with boats, and a river.
Vacation HomesVacation Homes

Baltimore

Baltimore

Our top choices for Maryland vacation homes

Terrace/patio

1. NEW KI Creek Retreat! 3BR/2bath water view, private house near KI wedding venues

NEW KI Creek Retreat! 3BR/2bath water view, private house near KI wedding venues
Stevensville
10.0 out of 10, Exceptional, (6 reviews)
"We enjoyed a wonderful weekend in this BEAUTIFUL HOME!! The incredible scenery & the wildlife were an added bonus. Clean, spacious home and attentive and efficient hosts. We wanted for nothing while visiting. Thank you for sharing your home!"
United States
Sharon T.
NEW KI Creek Retreat! 3BR/2bath water view, private house near KI wedding venues
Smart TV, fireplace, books, stereo

2. Light and airy cottage minutes to Naval Academy

Light and airy cottage minutes to Naval Academy
Severna Park
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful house with so much charm. Great location, easy to get to the train and to Annapolis. Loved having the water at the end of the road and seeing it from the upstairs bedroom. Beds, pillows and furniture were extremely comfortable. You will love sitting on couch surrounded by windows, so peaceful and relaxing! Would definitely stay again. I would highly recommend this location even if you are looking to do time in DC. So much do!"
United States
Lydia S.
Light and airy cottage minutes to Naval Academy
Smart TV, fireplace

3. Deep Creek Retreat | 5BR + Hot Tub + Game Room

Deep Creek Retreat | 5BR + Hot Tub + Game Room
Mountainside
9.4 out of 10, Exceptional, (9 reviews)
"Great space, wonderful view, lots of space, and beds were very comfortable."
United States
Mary B.
Deep Creek Retreat | 5BR + Hot Tub + Game Room
Terrace/patio

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

Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly
Fishing Creek
10.0 out of 10, Exceptional, (54 reviews)
"Great place to stay in a beautiful setting for our visit to Blackwater Wildlife Refuge. Had a small problem with the property but host was fast to communicate and we were happy with the ultimate resolution. Very comfortable, well stocked and cozy house. "
United States
melissa w.
Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly
Smart TV

5. Modern 2bd Getaway Walk to Metro Free Parking

Modern 2bd Getaway Walk to Metro Free Parking
Silver Spring
9.6 out of 10, Exceptional, (35 reviews)
"Nice place to stay. On street parking wasn’t a problem. Will choose this property again if we return to Silver Spring."
United States
Eugene G.
Modern 2bd Getaway Walk to Metro Free Parking
Marina

6. 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, (151 reviews)
"Great house, location was excellent "
United States
Mike G.
The price is AED 1,634
AED 3,007 total
includes taxes & fees
5 Aug - 6 Aug
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!
Interior

7. Private Home only 500 feet from the beach Oceanside!

Private Home only 500 feet from the beach Oceanside!
North Ocean City
9.8 out of 10, Exceptional, (13 reviews)
"This house was perfect for our family of 5! Easy check in and out. Good location. House was very cute and spacious. We will definitely stay again in the future!"
United States
Tabitha P.
The price is AED 1,267
AED 2,687 total
includes taxes & fees
17 Aug - 18 Aug
Private Home only 500 feet from the beach Oceanside!
Coffee/tea maker, fridge, microwave, oven

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

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.6 out of 10, Exceptional, (17 reviews)
"Highly recommend this property! Great location. Place is clean and host was very accommodating."
United States
Abi O.
The price is AED 314
AED 852 total
includes taxes & fees
2 Aug - 3 Aug
Cute, Cozy 2-bedroom house near Annapolis with water access
Microwave, oven, stovetop, dishwasher

9. Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
Annapolis
8.6 out of 10, Excellent, (7 reviews)
"Everything was as we expected or better. Very clean well appointed property "
United States
Stuart P.
The price is AED 1,488
AED 2,152 total
includes taxes & fees
3 Aug - 4 Aug
Fabulous 5-bedroom house with AC in charming Annapolis
Coffee/tea maker, fridge, microwave, oven

10. Recently Renovated Annapolis Home - Conveniently Located

Recently Renovated Annapolis Home - Conveniently Located
Murray Hill
10.0 out of 10, Exceptional, (77 reviews)
"Very clean and family friendly in a nice location with a nice backyard. "
United States
Liliana G.
Recently Renovated Annapolis Home - Conveniently Located
Terrace/patio

11. In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
Oakland
8.0 out of 10, Very Good, (81 reviews)
"Tremendous location and value!! We loved the outdoor fire pit and the downstairs bunk room for the kids. Can't wait to stay again. "
United States
Jenny A.
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
Beach nearby, sun loungers, beach towels

12. 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, (16 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is AED 1,322
AED 2,558 total
includes taxes & fees
25 Aug - 26 Aug
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Property grounds

13. Rooftop Deck Escape! Free Parking!

Rooftop Deck Escape! Free Parking!
South Baltimore
8.6 out of 10, Excellent, (63 reviews)
"Robert was an excellent host. The home was perfect for what we needed in a one night stay."
United States
Matthew Z.
The price is AED 353
AED 1,044 total
includes taxes & fees
5 Aug - 6 Aug
Rooftop Deck Escape! Free Parking!
Exterior

14. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (49 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is AED 500
AED 1,210 total
includes taxes & fees
12 Aug - 13 Aug
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Lake

15. Awesome New Property/ CANAL RIVER RETREAT

Awesome New Property/ CANAL RIVER RETREAT
Cumberland
9.8 out of 10, Exceptional, (126 reviews)
"Very private remote place to stay."
United States
Chasity B.
Awesome New Property/ CANAL RIVER RETREAT
Interior

16. Delightful 4-Bed Whole House with Easy Parking

Delightful 4-Bed Whole House with Easy Parking
Catonsville
9.4 out of 10, Exceptional, (22 reviews)
"The house was great. Very spacious and the hosts are wonderful. It's a cute neighborhood with character. Thanks again! "
United States
Nathaniel B.
Delightful 4-Bed Whole House with Easy Parking
Smart TV, fireplace, books, offices

17. Stunning Chesapeake views from almost ever room, private 15 home community beach, fossils, 450 pier,crabbing,fishing

Stunning Chesapeake views from almost ever room, private 15 home community beach, fossils, 450 pier,crabbing,fishing
Port Republic
10.0 out of 10, Exceptional, (134 reviews)
"Great spot! Homeowner communicated great before, during, and after the stay. Would highly recommend. "
United States
Jeff M.
Stunning Chesapeake views from almost ever room, private 15 home community beach, fossils, 450 pier,crabbing,fishing
Smart TV

18. 3 Bedroom Ranch near Assateague

3 Bedroom Ranch near Assateague
Berlin
9.4 out of 10, Exceptional, (10 reviews)
"Beautiful property and it was very clean! I loved that it was so close to everything, yet extremely quiet and pet-friendly. So modern and nicely decorated. Would stay again!"
United States
Rebecca K.
3 Bedroom Ranch near Assateague
Terrace/patio

19. GORGEOUS Large Direct Ocean Front Boardwalk/Pool 2 parking

GORGEOUS Large Direct Ocean Front Boardwalk/Pool 2 parking
Downtown Ocean City
9.4 out of 10, Exceptional, (48 reviews)
"Great location on the Boardwalk!"
United States
Mary Beth J.
GORGEOUS Large Direct Ocean Front Boardwalk/Pool 2 parking
Exterior detail

20. Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Murray Hill
10.0 out of 10, Exceptional, (50 reviews)
"We loved the coziness of the house. It was perfect for our visit to Annapolis."
United States
Patrick C.
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"This is our 2nd visit here and primarily chosen for location, historical significance and cleanliness. Located directly in the hub of beautiful Annapolis, it is easy walking and convenient to all shops, restaurants and the harbor. The rooms are nicely decorated with all the amenities needed for a short stay. The tiny bathroom is much warmer than the room but this can be solved by leaving the door open to allow the cold AC in. Of note, the dehumidifier can fill up quickly but shuts off automatically so it doesn’t overflow. The bed was comfortable and a bonus bottle of Prosecco was available with 2 glasses. The rate was reasonable making this an inn worthy of repeat stays."
kevin 1-night trip
Posted less than an hour ago
Historic Inns of Annapolis

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