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Our top choices for Taylors Island holiday rentals

1. 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, (6 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is £199
includes taxes & fees
31 Aug - 1 Sept
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

2. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (58 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is £233
includes taxes & fees
8 Sept - 9 Sept
Soul Oasis - home on the Chesapeake Bay

3. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (38 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is £186
includes taxes & fees
31 Aug - 1 Sept
Sailwinds Loft at Cambridge Creek

4. 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 £391
includes taxes & fees
27 Sept - 28 Sept
Sunset Breezes - quiet waterfront retreat

5. The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford
9.6 out of 10, Exceptional, (35 reviews)
"Really comfortable house, plenty of space. Lovely surroundings for a low-key quiet getaway. *Note, the nearby general store has closed permanently as of 30Apr2026"
United States
Rochelle K.
The price is £574
includes taxes & fees
1 Sept - 2 Sept
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

6. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (22 reviews)
"Lovely ! "
United States
Ellen B.
The price is £257
includes taxes & fees
30 Aug - 31 Aug
Beachside Oasis with Beach Passes & King Suite by A Haven Away

7. 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, (25 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 £302
includes taxes & fees
1 Sept - 2 Sept
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

8. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (15 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is £429
includes taxes & fees
2 Sept - 3 Sept
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

9. 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 £848
includes taxes & fees
1 Sept - 2 Sept
Lakefront Cabin Near Solomons Island w/ Hot Tub

10. 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, (14 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveller
The price is £624
includes taxes & fees
31 Aug - 1 Sept
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

11. Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is £334
includes taxes & fees
2 Sept - 3 Sept
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

12. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is £529
includes taxes & fees
8 Sept - 9 Sept
4-BR Waterfront Turret Home

13. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (37 reviews)
"Such a great house! "
United States
Stephanie V.
The price is £320
includes taxes & fees
30 Aug - 31 Aug
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

14. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
3.0 star property
Lusby
The price is £838
includes taxes & fees
1 Sept - 2 Sept
Lakefront Cabin Near Solomons Island w/ Hot Tub

15. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is £343
includes taxes & fees
28 Aug - 29 Aug
Plum Point Cottage #17

16. Brand New Waterfront Home • Pool • Walk Downtown & Events • Sleeps 8

Brand New Waterfront Home • Pool • Walk Downtown & Events • Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our weekend getaway at the beautiful gated community. Great water views and a walkable community. The townhouse met all our needs. Fully stocked with essential items. The added bonus is a the workout room with top of the line equipment. A nice touch! Two great decks overlooking the marina. The owners are very responsive."
United States
Melissa
The price is £504
includes taxes & fees
31 Aug - 1 Sept
Brand New Waterfront Home • Pool • Walk Downtown & Events • Sleeps 8
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 Taylors Island Hotel Reviews

Find out more about Taylors Island

Everything you need to know about Taylors Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Taylors Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 Taylors Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Taylors Island holiday rentals: An excellent choice for every season

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Taylors Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Taylors Island holiday rentals we have selected for you start as low as £199 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Taylors Island rentals

At Expedia, we put the best Taylors Island holiday 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 Taylors 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 Taylors Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Taylors 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. 

Frequently asked questions

Can I find holiday rentals in Taylors Island?

Yes, there are holiday rentals close to the most popular sights in Taylors Island, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Taylors Island has to offer?

Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly: This holiday home rental outside of Taylors Island is located on a river, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Taylors Island?

Expedia has 5 holiday rentals for your stay in Taylors Island.

What’s there to see and do in Taylors Island?

Blackwater National Wildlife Refuge and Northern Chesapeake Bay are a couple of lovely local spots to get outside and enjoy nature. Chesapeake Bay and Cove Point Lighthouse are a couple of places you'll find in the wider area.

What’s a holiday rental in Taylors Island like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Taylors Island. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for family trips or small group gatherings.