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Holiday Homes in Taylors Island

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Taylors Island holiday homes

A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

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, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is €233
includes taxes & fees
6 Oct - 7 Oct
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink.

2. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (66 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
The price is €220
includes taxes & fees
4 Oct - 5 Oct
Waterfront Getaway with Dock
A spacious living room with a large TV, blue sofa, and a ceiling fan.

3. 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)
"Great house for a large group! Very well equipped kitchen and comfortable home. Extra pillows and black out curtains would be the only thing I would add."
United States
Ximena G.
The price is €603
includes taxes & fees
5 Oct - 6 Oct
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

4. 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, (23 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is €307
includes taxes & fees
4 Oct - 5 Oct
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

5. 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 €352
includes taxes & fees
27 Oct - 28 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

6. 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)
"We enjoyed our stay in North Beach at this lovely residence. It was spacious, clean, nicely furnished and only a few minutes walk to the bay. The beds were so comfortable too!!"
United States
Penny N.
The price is €346
includes taxes & fees
29 Sept - 30 Sept
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

7. 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, (16 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is €532
includes taxes & fees
27 Oct - 28 Oct
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A spacious cabin interior with a wooden ceiling, a kitchen area, a living room with a sofa and a dining table, and a large window providing natural light.

8. 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 €1,055
includes taxes & fees
27 Oct - 28 Oct
Lakefront Cabin Near Solomons Island w/ Hot Tub
A pathway lined with trees and lights leading to a wooden building with a visible window.

9. 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 €748
includes taxes & fees
27 Oct - 28 Oct
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

10. 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 €384
includes taxes & fees
27 Oct - 28 Oct
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
A living room with two brown leather sofas, a wooden side table with a lamp, a small shelf with plants, and a painting of a tree.

11. More, than just a place to sleep - welcome home!

More, than just a place to sleep - welcome home!
Cambridge
The price is €354
includes taxes & fees
27 Sept - 28 Sept
More, than just a place to sleep - welcome home!
A spacious living room with a large sofa, a television, and a view of the ocean.

12. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is €628
includes taxes & fees
27 Oct - 28 Oct
4-BR Waterfront Turret Home
A single-story house with a gabled roof, a front porch, and a small front yard with a flag.

13. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is €414
includes taxes & fees
27 Sept - 28 Sept
Plum Point Cottage #17
A house with a large lawn and a dock extending into a calm lake.

14. 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 €299
includes taxes & fees
28 Sept - 29 Sept
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

15. 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, (2 reviews)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is €858
includes taxes & fees
27 Oct - 28 Oct
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
A lakeside property with a large house, a shed, and a dense forest in the background.

16. 'The Bayside Escape' Remote Chesapeake Bay Estate

'The Bayside Escape' Remote Chesapeake Bay Estate
Fishing Creek
10.0 out of 10, Exceptional, (2 reviews)
"We absolutely loved our stay. They house was beautiful, the amenities were excellent, and we loved the crabs!! We went for a family weekend (mix of 18 kids and adults) and it was very spacious and comfortable for everyone. The pergola in the back was an especially big hit! We highly recommend and would stay again."
United States
Bridget C.
The price is €812
includes taxes & fees
27 Sept - 28 Sept
'The Bayside Escape' Remote Chesapeake Bay Estate
A house with a large lawn and a dock extending into a calm lake.

17. 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 €269
includes taxes & fees
28 Sept - 29 Sept
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
A wooden interior with a dining area, sofas, and a table.

18. WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Cambridge
9.0 out of 10, Wonderful, (14 reviews)
"Very spacious home. 4 bedrooms and 4 baths. Great basement for watching TV with a large group. Home is about 15 minutes from downtown Cambridge."
United States
Anonymous traveller
The price is €587
includes taxes & fees
27 Sept - 28 Sept
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
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

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

10/10 Excellent
"My room was nice, clean and cozy"
jerria 2-night trip
Posted 11 hours ago
Hyatt Regency Chesapeake Bay

Find out more about Taylors Island

Taylors Island Holiday Homes information

Number of reviews
227
Accommodation
272 Holiday Homes
Lowest Price
€220
Highest Price
€1,055