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10 Oct - 12 Oct
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31 Oct - 2 Nov
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Vacation Homes in Chesapeake Beach

Riverfront Retreat 7mil from MD Renaissance Fest!
Exterior

Riverfront Retreat 7mil from MD Renaissance Fest!

9.2 out of 10, Wonderful, (17)
"It was a beautiful and private setting for a family reunion."
Riverfront Retreat 7mil from MD Renaissance Fest!
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
Dining

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

10.0 out of 10, Exceptional, (26)
"Wow, what a homerun of a vacation house - it had everything we needed and more. We had the best time and hope to be back soon."
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
Cozy Home in Beautiful Annapolis
Exterior

Cozy Home in Beautiful Annapolis

10.0 out of 10, Exceptional, (13)
"Great property and very clean!"
Cozy Home in Beautiful Annapolis
Beautiful 2-bedroom water view house in Annapolis
Fridge, microwave, oven, stovetop

Beautiful 2-bedroom water view house in Annapolis

10.0 out of 10, Exceptional, (2)
"Very nice rental. Very clean and easy to access"
Beautiful 2-bedroom water view house in Annapolis
4BDRM River front house with Private Beach in Hollywood
Property grounds

4BDRM River front house with Private Beach in Hollywood

2.0 star property
9.8 out of 10, Exceptional, (15)
"This house was just what we needed for our business associates. "
4BDRM River front house with Private Beach in Hollywood
25-50% Off~Private Beach~Hot Tub~Fire Table~
Terrace/patio

25-50% Off~Private Beach~Hot Tub~Fire Table~

10.0 out of 10, Exceptional, (29)
"Excellent property, great communication with the hosts. Quite and relaxing"
25-50% Off~Private Beach~Hot Tub~Fire Table~
Dollhouse in Central Historic St Michaels
Exterior

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (54)
"This is a lovely historic home that is close to town. It's nicely decorated, has a screened deck out back, and makes for a comfortable stay."
Dollhouse in Central Historic St Michaels
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
Beach nearby, sun loungers, beach towels

Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis

10.0 out of 10, Exceptional, (94)
"Great property and great time in Oyster Harbour!"
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis
Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More
Smart TV, printers

Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More

10.0 out of 10, Exceptional, (3)
"My first thought was "gorgeous", when i walked through the door. This was just the weekend I needed. The screened in porch was relaxing. Be ready to take pictures of the sunrise! "
Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More
Beautiful Waterfront Retreat in Cambridge!
Interior

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (47)
"Beautifully decorated home, clean and spacious. We really enjoyed the private waterfront and kayak. Would love to come back. "
The price is AED 826
AED 1,643 total
includes taxes & fees
1 Oct - 2 Oct
Beautiful Waterfront Retreat in Cambridge!
Private Waterview Estate with 4 Suites, Hot Tub, Gourmet Kitchen and Game Room
Fridge, microwave, oven, stovetop

Private Waterview Estate with 4 Suites, Hot Tub, Gourmet Kitchen and Game Room

9.8 out of 10, Exceptional, (29)
"Spacious and clean home! Great communication! Every amenity possible! Highly recommend!"
Private Waterview Estate with 4 Suites, Hot Tub, Gourmet Kitchen and Game Room
Welcoming 3-bedroom townhome with AC in Waldorf
3 bedrooms, iron/ironing board, WiFi, bed sheets

Welcoming 3-bedroom townhome with AC in Waldorf

The price is AED 641
AED 1,205 total
includes taxes & fees
2 Oct - 3 Oct
Welcoming 3-bedroom townhome with AC in Waldorf
Relax on Kent Island in 3 Bedroom Home w/Waterview
Marina

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (40)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
The price is AED 289
AED 957 total
includes taxes & fees
2 Oct - 3 Oct
Relax on Kent Island in 3 Bedroom Home w/Waterview
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Outdoor dining

The Cozy Crab- Your Charming Haven in Lovely North Beach!

9.6 out of 10, Exceptional, (9)
"Great place. Just a short drive to town with shops, restaurants, and boardwalk."
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Fridge, microwave, oven, stovetop

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (43)
"Wonderful home in excellent location!!"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Exterior

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

10.0 out of 10, Exceptional, (2)
"The property is newly renovated and very comfortable. Property owner is responsive to any questions, and we enjoyed our stay here. Would recommend it for anyone staying in Shady Side."
The price is AED 529
AED 1,549 total
includes taxes & fees
30 Sep - 1 Oct
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Thorneton Point Estate
Interior

Thorneton Point Estate

9.6 out of 10, Exceptional, (20)
"Beautiful, well-maintained property in a gorgeous waterside setting. "
Thorneton Point Estate
Walk to Everything House
Fridge, microwave, oven, stovetop

Walk to Everything House

10.0 out of 10, Exceptional, (83)
"Clean and nice place to stay"
Walk to Everything House
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Terrace/patio

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

10.0 out of 10, Exceptional, (10)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is AED 863
AED 1,964 total
includes taxes & fees
28 Oct - 29 Oct
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Private Cottage on gated estate
Property grounds

Private Cottage on gated estate

10.0 out of 10, Exceptional, (29)
"Convenient and great price. If you have you have younger children they will love the play area."
Private Cottage on gated estate
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 Chesapeake Beach Hotel Reviews

Holiday Inn Express Waldorf by IHG

Holiday Inn Express Waldorf by IHG

10/10 Excellent
"It was a pleasurable stay"
Kianda 1-night trip
Posted 4 days ago
Holiday Inn Express Waldorf by IHG