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Upper Hooper Island Holiday Rentals

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Upper Hooper Island holiday rentals

Exterior

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (55 reviews)
"Cute, sweet spot with a peaceful vibe and lovely view!"
United States
Melinda S.
The price is HK$1,263
HK$2,511 total
includes taxes & fees
24 Aug - 25 Aug
Soul Oasis - home on the Chesapeake Bay
Exterior

Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Fishing Creek
10.0 out of 10, Exceptional, (11 reviews)
"Peggy and Gary are the perfect hosts: welcoming, friendly, attentive and respectful of your preferences. Wonderful views of the Bay and River via the lodge -- including the cupola -- and walking around the majestic property."
United States
Thomas S.
The price is HK$2,117
HK$2,552 total
includes taxes & fees
7 Aug - 8 Aug
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Exterior

Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Fishing Creek
10.0 out of 10, Exceptional, (1 review)
"We stayed Sunday - Wednesday at Riverside Lodge. The Lodge was beautiful. Breakfast was absolutely fantastic and Hooper Island was breath taking. We were able to take a boat ride to tour around the island and grad a little history and enjoy the stories. If you looking for a place to relax and renew... this is the place. "
United States
Robin E.
The price is HK$2,117
HK$2,552 total
includes taxes & fees
7 Aug - 8 Aug
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Front of property

'the Bayside Escape' Remote Chesapeake Bay Estate

'the Bayside Escape' Remote Chesapeake Bay Estate
3.0 star property
Fishing Creek
The price is HK$3,576
HK$7,164 total
includes taxes & fees
29 Jul - 30 Jul
'the Bayside Escape' Remote Chesapeake Bay Estate
Exterior

'The Bayside Escape' Remote Chesapeake Bay Estate

'The Bayside Escape' Remote Chesapeake Bay Estate
Fishing Creek
The price is HK$3,004
HK$7,214 total
includes taxes & fees
29 Jul - 30 Jul
'The Bayside Escape' Remote Chesapeake Bay Estate
TV, fireplace

3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Saint Leonard
10.0 out of 10, Exceptional, (3 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is HK$1,129
HK$2,244 total
includes taxes & fees
6 Aug - 7 Aug
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Coffee/tea maker, fridge, microwave, oven

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (63 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
The price is HK$1,803
HK$2,111 total
includes taxes & fees
23 Aug - 24 Aug
Waterfront Getaway with Dock
Interior

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Lexington Park
10.0 out of 10, Exceptional, (11 reviews)
"We had a wonderful stay! Beautiful waterfront home with a brand new pier overlooking the river and a perfect sunset. Quiet location, perfectly appointed and great location next to parks, St Mary’s City and campus. Highly recommend!"
United States
Kurt O.
The price is HK$1,372
HK$2,985 total
includes taxes & fees
27 Jul - 28 Jul
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Private kitchen

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (37 reviews)
"Can’t wait to come back!"
United States
Tiffany K.
The price is HK$1,215
HK$1,995 total
includes taxes & fees
9 Aug - 10 Aug
Sailwinds Loft at Cambridge Creek
Marina

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Downtown Cambridge
8.4 out of 10, Very good, (9 reviews)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is HK$1,608
HK$3,092 total
includes taxes & fees
25 Aug - 26 Aug
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
1 bedroom, iron/ironing board, WiFi, bed sheets

Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing

Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
Downtown Cambridge
The price is HK$1,067
HK$2,003 total
includes taxes & fees
28 Jul - 29 Jul
Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
Marina

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, (24 reviews)
"Lovely terrace style town house in a lovely location in close proximity to the Marina and other amenities. Beautiful place to relax."
United States
Robert
The price is HK$2,078
HK$3,940 total
includes taxes & fees
28 Jul - 29 Jul
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Property grounds

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lusby
9.6 out of 10, Exceptional, (13 reviews)
"The home was lovely and very quiet location. My sister and I were caring for our mom after discharge from hospital and it was very convenient. Would stay there again. "
United States
Tova A.
The price is HK$3,623
HK$6,675 total
includes taxes & fees
26 Jul - 27 Jul
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Marina

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Downtown Cambridge
10.0 out of 10, Exceptional, (12 reviews)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
The price is HK$2,352
HK$4,106 total
includes taxes & fees
5 Aug - 6 Aug
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Marina

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Downtown Cambridge
9.8 out of 10, Exceptional, (13 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is HK$2,039
HK$3,899 total
includes taxes & fees
28 Jul - 29 Jul
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Interior

Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"Very much enjoyed our stay. The host was very kind and responsive and the property very comfortable. Hot tub and quiet location were great!"
United States
Tanya S.
The price is HK$3,395
HK$9,014 total
includes taxes & fees
10 Aug - 11 Aug
Lakefront Cabin Near Solomons Island w/ Hot Tub
Smart TV, books

4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is HK$3,137
HK$6,466 total
includes taxes & fees
5 Aug - 6 Aug
4-BR Waterfront Turret Home
Interior

Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
3.0 star property
Lusby
The price is HK$4,007
HK$8,972 total
includes taxes & fees
5 Aug - 6 Aug
Lakefront Cabin Near Solomons Island w/ Hot Tub
Smart TV, fireplace, ping pong, books

Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!

Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!
Point Lookout
10.0 out of 10, Exceptional, (135 reviews)
"The property was very clean and well-stocked. Beds were comfortable and pictures matched reality. Jocelyn was so kind to leave us ingredients for smores and Easter eggs for my kids to have a hunt in the backyard. Overall, we had a wonderful stay and hope to make it back again some time!"
United States
Allie P.
Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!
Outdoor dining

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (45 reviews)
"Comfortable, roomy, awesome views!"
United States
John C.
The price is HK$3,803
HK$4,786 total
includes taxes & fees
29 Jul - 30 Jul
Sunset Breezes - quiet waterfront retreat
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 Upper Hooper Island Hotel Reviews

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

8/10 Good
"Room was clean, amenities were cool for the kids."
Justin 2-night trip
Posted 13 hours ago
Hyatt Regency Chesapeake Bay

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