Holiday Rentals in Upper Hooper Island

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Holiday Rentals in Upper Hooper Island

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (73)
"Absolutely perfect location to get away for the weekend. It was so peaceful and we saw osprey and deer in the back yard. You have access to a dock which is fantastic at night to see the stars. The house has everything you could need. They have 2 kayaks we intended to use but ran out of time. The best part was sitting outside at night with a fire. Would absolutely stay again! "
Waterfront Cottage in Beautiful Hoopers Island

A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

10.0 out of 10, Exceptional, (116)
"It was a great stay!"
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.8 out of 10, Exceptional, (11)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is €458
includes taxes & fees
24 Aug - 25 Aug
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

9.8 out of 10, Exceptional, (69)
"Property was exactly as advertised. Charming Farmhouse with plenty of space situated on a large property with a private beach. We even enjoyed some of the local restaurants, Captain Pat's Seafood and Tacos Haciendas."
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

9.8 out of 10, Exceptional, (128)
"We had a wonderful long weekend here. Perfect weather let us swim and kayak and fish all weekend. House was spacious enough for two families of five plus our dog. The views were perfect!"
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Waterfront Solomons Apartment

9.4 out of 10, Exceptional, (9)
"The location is great with amazing views of the docks and very walkable to the boardwalk, restaurants, and the Solomon museum. Apartment was cozy with great communication from the hosts. Would recommend to anyone! "
The price is €230
includes taxes & fees
11 Aug - 12 Aug
Waterfront Solomons Apartment

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

10.0 out of 10, Exceptional, (49)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (166)
"The Waterfront Retreat on the Patuxent River is better than advertised. Our whole family stayed -- everyone loved it! It was clean, comfortable, with everything needed to stay comfortably, sleep, eat, relax and use as a home base for exploring. Solomons Island and the surrounding area was filled with lots of fun things to do (restaurant's, museums, history, boating, walking, etc.). "
Waterfront Wildlife Retreat on the Patuxent River

Terrace Suite · Terrace Suite - Private Flat in Historic Manor.

9.8 out of 10, Exceptional, (30)
"Great stay, clean & owner gave great local suggestions!"
Terrace Suite · Terrace Suite - Private Flat in Historic Manor.

Hays Beach House - Hot Tub - Private Beach

9.6 out of 10, Exceptional, (8)
"Stayed with two other families for the State Swim Championships. Property is spacious, clean and well appointed. Even the kitchen knives were sharp!"
Hays Beach House - Hot Tub - Private Beach

Waterfront property with private boat ramp and new dock!

9.8 out of 10, Exceptional, (11)
"Thoroughly enjoyed our stay! Cottage was comfortable and very clean with everything we could have needed! "
Waterfront property with private boat ramp and new dock!

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

2.0 star property
9.8 out of 10, Exceptional, (9)
"This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. "
The price is €454
includes taxes & fees
24 Aug - 25 Aug
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (250)
"Our stay was great and Rob and Clarissa were very welcoming!"
Family and Pet-Friendly, Waterfront with Pier

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (42)
"The house was so cute and the fact that we were able to do early check in was amazing!"
The price is €425
includes taxes & fees
3 Aug - 4 Aug
Beautiful Waterfront Retreat in Cambridge!

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (70)
"If you want to relax by the water and getaway from the hustle and bustle, this is the place. The cottage is updated and cozy with amazing views. Just step off the patio onto the sand. Cottage was stocked with essentials and extra goodies to make it feel like home."
Private Beach Front Getaway at The Sunshine Beach Cottage.

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

10.0 out of 10, Exceptional, (5)
"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Screened Patio, Deck & Grill: Saint Inigoes Home!

9.8 out of 10, Exceptional, (6)
"great location relative to smc for a campus visit"
Screened Patio, Deck & Grill: Saint Inigoes Home!

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (45)
"Fit all of our needs. Clean,well furnished, nice kitchen. Stayed there twice and will probably go back."
The price is €244
includes taxes & fees
30 Jul - 31 Jul
Waterfront Getaway with Dock

Cozy Cottage with access to and partially obstructed views of the bay.

9.2 out of 10, Wonderful, (25)
"Enjoy our time there"
Cozy Cottage with access to and partially obstructed views of the bay.

Your private beach retreat in historic St. Mary's

10.0 out of 10, Exceptional, (25)
"This was the perfect house for our family trip to St. Mary's -- nicely upgraded, well stocked and beautiful views. Will definitely return."
Your private beach retreat in historic St. Mary's
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