Upper Hooper Island Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Apr 17 - Apr 19
In two months
May 29 - May 31
In three months
Jun 26 - Jun 28
In four months
Jul 24 - Jul 26

Our top choices for Upper Hooper Island vacation rentals

Exterior

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (43 reviews)
"House was very nice and tidy and exactly as described. The host had a small binder full of helpful info including local restaurants and attractions. There was so much to do and everything was close bye. "
United States
Mindy V.
The price is ￥20,118
￥44,174 total
includes taxes & fees
Apr 13 - Apr 14
Soul Oasis - home on the Chesapeake Bay
Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.6 out of 10, Exceptional, (20 reviews)
"Very nice place in a great location. We would definitely stay there again "
United States
Traci C.
The price is ￥30,337
￥64,992 total
includes taxes & fees
Apr 6 - Apr 7
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
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, (12 reviews)
"Host was personally accessible during stay, responded quickly, and went the extra mile with wonderful touches left around the place."
United States
John S.
The price is ￥28,741
￥62,961 total
includes taxes & fees
Apr 6 - Apr 7
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Private kitchen

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (24 reviews)
"Lovely place, huge rooms, definitely recommend it. "
United States
Lee P.
The price is ￥24,749
￥40,620 total
includes taxes & fees
Apr 7 - Apr 8
Sailwinds Loft at Cambridge Creek
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, (10 reviews)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
The price is ￥31,136
￥65,839 total
includes taxes & fees
Apr 6 - Apr 7
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
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, (6 reviews)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is ￥25,547
￥53,483 total
includes taxes & fees
Apr 20 - Apr 21
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
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 ￥43,111
￥51,960 total
includes taxes & fees
Apr 6 - Apr 7
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Outdoor dining

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (43 reviews)
"Clean, quiet, comfy"
United Kingdom
Deborah V.
The price is ￥48,220
￥60,125 total
includes taxes & fees
Apr 12 - Apr 13
Sunset Breezes - quiet waterfront retreat
Smart TV, books

4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is ￥55,885
￥124,312 total
includes taxes & fees
Apr 6 - Apr 7
4-BR Waterfront Turret Home
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 ￥16,526
￥33,596 total
includes taxes & fees
Apr 6 - Apr 7
Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (54 reviews)
"Great place, will stay again"
United States
Matt S.
The price is ￥36,724
￥42,312 total
includes taxes & fees
Apr 29 - Apr 30
Waterfront Getaway with Dock
House (3 Bedrooms) | Interior

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
Lusby
The price is ￥38,161
￥111,194 total
includes taxes & fees
Apr 13 - Apr 14
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
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, (7 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is ￥29,539
￥62,533 total
includes taxes & fees
Apr 6 - Apr 7
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
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 ￥43,111
￥51,960 total
includes taxes & fees
Apr 6 - Apr 7
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
TV, fireplace, video games, books

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Lusby
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is ￥52,691
￥132,299 total
includes taxes & fees
Apr 8 - Apr 9
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Upper Hooper Island Hotel Reviews

Days Inn & Suites by Wyndham Cambridge

Days Inn & Suites by Wyndham Cambridge

10/10 Excellent
"Love it here"
Jerri 2-night trip
Posted 5 hours ago
Days Inn & Suites by Wyndham Cambridge

Find out more about Upper Hooper Island

Search for holiday rentals in Upper Hooper Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Upper Hooper Island using one of the methods below:

  • View our selection of featured holiday rentals in Upper Hooper Island
  • Use the map to find apartments and other holiday homes in the Upper Hooper Island neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Upper Hooper Island while they last

Look no further and take a look at our great range of rental properties in Upper Hooper Island!