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Hoopers Island Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Hoopers Island vacation rentals

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.
$309 nightly
The price is $328
Jul 8 - Jul 9
Total with taxes and fees
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.
$309 nightly
The price is $328
Jul 8 - Jul 9
Total with taxes and fees
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Exterior

'The Bayside Escape' Remote Chesapeake Bay Estate

'The Bayside Escape' Remote Chesapeake Bay Estate
Fishing Creek
$842 nightly
The price is $927
Jul 29 - Jul 30
Total with taxes and fees
'The Bayside Escape' Remote Chesapeake Bay Estate
House (6 Bedrooms) | Front of property

'the Bayside Escape' Remote Chesapeake Bay Estate

'the Bayside Escape' Remote Chesapeake Bay Estate
3.0 star property
Fishing Creek
$823 nightly
The price is $914
Jul 29 - Jul 30
Total with taxes and fees
'the Bayside Escape' Remote Chesapeake Bay Estate
Cottage (2 Bedrooms) | Interior

Pet-friendly Smith Island Cottage w/ Golf Cart!

Pet-friendly Smith Island Cottage w/ Golf Cart!
3.0 star property
Smith Island
10.0 out of 10, Exceptional, (1 review)
"We had a lovely 2 night stay. The owners and host were wonderful. We were so happy to have use of the golf cart and bicycles. The cottage is adorable with beautiful touches all around."
United States
Karl
$211 nightly
The price is $235
Jul 9 - Jul 10
Total with taxes and fees
Pet-friendly Smith Island Cottage w/ Golf Cart!
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, (1 review)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
$235 nightly
The price is $250
Jul 13 - Jul 14
Total with taxes and fees
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
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.
$279 nightly
The price is $296
Jul 20 - Jul 21
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay
Beach

Tangier Escape, great place get away from it all on Deal Island, MD.

Tangier Escape, great place get away from it all on Deal Island, MD.
Deal Island Historic District
10.0 out of 10, Exceptional, (1 review)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
$232 nightly
The price is $246
Jul 14 - Jul 15
Total with taxes and fees
Tangier Escape, great place get away from it all on Deal Island, MD.
Private kitchen

Saltwater Serenity Waterfront Cottage

Saltwater Serenity Waterfront Cottage
Deal Island Historic District
$356 nightly
The price is $377
Jul 12 - Jul 13
Total with taxes and fees
Saltwater Serenity Waterfront Cottage
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, (23 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
$474 nightly
The price is $502
Jul 28 - Jul 29
Total with taxes and fees
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Fridge, microwave, oven, stovetop

Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (59 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
$246 nightly
The price is $261
Jul 24 - Jul 25
Total with taxes and fees
Deal Island Bay Cottage
Private kitchen

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (35 reviews)
"Lovely place, huge rooms, definitely recommend it. "
United States
Lee P.
$239 nightly
The price is $253
Jul 9 - Jul 10
Total with taxes and fees
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
7.8 out of 10, Good, (7 reviews)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
$373 nightly
The price is $395
Jul 20 - Jul 21
Total with taxes and fees
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (61 reviews)
"Great place, will stay again"
United States
Matt S.
$263 nightly
The price is $279
Jul 15 - Jul 16
Total with taxes and fees
Waterfront Getaway with Dock
Marina

Summer is here on Smith Island! Come out and enjoy a great season on the Bay

Summer is here on Smith Island! Come out and enjoy a great season on the Bay
Smith Island
9.8 out of 10, Exceptional, (15 reviews)
"Visiting with locals, fresh steamed crabs, simply enjoying the quiet island life"
United States
Samantha J.
$326 nightly
The price is $360
Jul 8 - Jul 9
Total with taxes and fees
Summer is here on Smith Island! Come out and enjoy a great season on the Bay
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
$303 nightly
The price is $321
Aug 3 - Aug 4
Total with taxes and fees
Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
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, (10 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.
$427 nightly
The price is $430
Jul 20 - Jul 21
Total with taxes and fees
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
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)
"Great space. Great location for exploring Cambridge on foot. Check-in easy. Everything clean. Everything works."
United States
Peter G.
$469 nightly
The price is $497
Jul 28 - Jul 29
Total with taxes and fees
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.
$460 nightly
The price is $487
Jul 21 - Jul 22
Total with taxes and fees
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Exterior

Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
$415 nightly
The price is $458
Jul 8 - Jul 9
Total with taxes and fees
Plum Point Cottage #17
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 Hoopers Island Hotel Reviews

Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge

10/10 Excellent
"We appreciated the hotel's quiet location where we got restful sleep but could easily access what we needed/wanted along the Route 50 corridor. The staff were TOP NOTCH - so kind, informative, helpful, caring (especially Michelle at the front desk). Our room with a king bed and sleeper sofa was huge - we had room to spread out and keep our stuff organized. The bed was comfy; the AC was cold. The decor/facilities are slightly outdated, but that's easy enough to ignore when you have such a pleasant stay. We were able to easily park our truck with kayaks hanging off the bed and noticed two smaller boats that were also parked (with trailers *detached* from the towing vehicle). If you have an RV or a large truck towing a trailer, I'd recommend calling for parking advice because it can be limiting for larger vehicles. Overall, I'd happily stay here again because it's clean, it is affordable (and includes breakfast), and the staff are incredible."
Bobbi 4-night trip
Posted 8 hours ago
Comfort Inn & Suites Cambridge

Find out more about Hoopers Island

Everything you need to know about Hoopers Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Hoopers Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Hoopers Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Hoopers Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hoopers Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Hoopers Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $296 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Hoopers Island rentals

At Expedia, we put the best Hoopers Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Hoopers Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Hoopers Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Hoopers Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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