Taylors Island Vacation Rentals from $261: Search Short-Term Rentals

Q: What are some of the best vacation rentals in Taylors Island?

Private 2 Acre Waterfront Family Retreat with Pool & Pier : This vacation home near Taylors Island is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

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Our top choices for Taylors Island vacation rentals

1. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Saint Leonard

Nancy P.

$246 nightly

Sep 16 - Sep 17

Total with taxes and fees

2. Soul Oasis - home on the Chesapeake Bay

Lusby

Dusty S.

$281 nightly

Sep 30 - Oct 1

Total with taxes and fees

3. Sunset Breezes - quiet waterfront retreat

Dorchester County

John C.

$412 nightly

Oct 4 - Oct 5

Total with taxes and fees

4. 3-bedroom house in serene Lusby with refreshing AC, heat, outdoor fireplace

Lusby

$398 nightly

Oct 6 - Oct 7

Total with taxes and fees

5. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge

Robert

$370 nightly

Sep 28 - Sep 29

Total with taxes and fees

6. Sailwinds Loft at Cambridge Creek

Cambridge

Sharon D.

$239 nightly

Sep 7 - Sep 8

Total with taxes and fees

7. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Downtown Cambridge

Kristen S.

$338 nightly

Sep 8 - Sep 9

Total with taxes and fees

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

Woolford

Ramon A.

$709 nightly

Oct 6 - Oct 7

Total with taxes and fees

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Top Taylors Island Hotel Reviews

Hyatt Regency Chesapeake Bay

10/10 Excellent

"Would definitely return in the near future. My family had fun."

Wylder Tilghman Island

8/10 Good

"Beautiful large property by the water. I wish the pool and area around it was bigger (having all that land around....) . The view from our room was NOT what I expected. Sad to say that it overlooked to an area with working noisy compressors units. I had to keep the blinds close not to see this terrible view.. Staff was helpful when I expressed my disappointment and offered me resort fee waiver for the inconvenience. Thank you! We will come back again but will be more careful with room selection when booking.."

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

10/10 Excellent

"My family and I had a great stay at this LaQuinta location for a funeral . David was such a great help checking us in. There were lots of shopping and restaurants near by to choose from if needed. The rooms were roomy and clean."

Quality Inn Solomons - Beacon Marina

8/10 Good

"Everything was good, standard hotel/motel stuff: little coffee pot, mini-fridge, microwave, tv,a/c - everything worked as expected, furniture, carpeting, lights, bathroom all looked newish and everything was very clean. Desk folk were pleasant, didn’t have much interaction. The big plus is the location, right by a huge marina (if you like looking at boats) and the Calvert Marine Museum- combines natural history and the commercial history of the area, has the Drum Point lighthouse (you can tour) and a boat tour of Patuxent Harbor, plus fossils, river otters, fish. Calvert Cliffs / Flag Pond parks are a 10 minute drive if you want to dig for fossils yourself. So: comfortable place, very reasonably priced, close to all sorts of stuff; definitely worth it."

Find out more about Taylors Island

Everything you need to know about Taylors 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 Taylors 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 Taylors Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Taylors Island vacation 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 low season months. For more hustle and bustle, you may prefer to visit Taylors 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 $261 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 Taylors Island rentals

At Expedia, we put the best Taylors 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 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 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 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.

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Frequently asked questions

Can I find vacation rentals in Taylors Island?

Yes, there are vacation rentals near the most popular local attractions in Taylors Island, or you can select a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals in Taylors Island?

Private 2 Acre Waterfront Family Retreat with Pool & Pier: This vacation home near Taylors Island is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

How many vacation rentals will I find in Taylors Island?

Expedia has 5 vacation 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 larger area.

What’s a vacation rental in Taylors Island like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in Taylors Island. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a family getaway.

Taylors Island Vacation Rentals

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Check prices for these dates

Our top choices for Taylors Island vacation rentals

1. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

2. Soul Oasis - home on the Chesapeake Bay

3. Sunset Breezes - quiet waterfront retreat

4. 3-bedroom house in serene Lusby with refreshing AC, heat, outdoor fireplace

5. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

6. Sailwinds Loft at Cambridge Creek

7. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

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

9. Family Beach House: Spacious Deck, Grill & Views

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

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

12. Lakefront Cabin Near Solomons Island w/ Hot Tub

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

14. Lakefront Cabin Near Solomons Island w/ Hot Tub

15. 4-BR Waterfront Turret Home

16. Plum Point Cottage #17

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

18. Riverside Lodge Bed & Breakfast on the Honga River UNIT C

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

20. Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Find vacation rentals that suit your style

Top Taylors Island Hotel Reviews

Hyatt Regency Chesapeake Bay

Find out more about Taylors Island

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