Talbot County Rentals

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77 Houses

Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

Wittman log cabin

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$1,112

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$350

Waterfront Property, Kayaks, Private Dock, Near Town

St. Michaels house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$855

Waterview Cottage In St. Michaels!

St. Michaels cottage

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

Price per night from

$380

Tranquil Easton Waterfront Property

Easton house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Price per night from

$6,841

St. Michael's Premier in Town Summer Cottage now with private pool!

St. Michaels house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$713

TRUE ST MICHAELS 6 ACRE WATERFRONT

St. Michaels house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 38 minutes

Price per night from

$2,281

CHESAPEAKE MANSION - NEW POOL/12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Sherwood house

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 12

Responds fast! avg. 38 minutes

Price per night from

$2,851

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Responds fast! avg. 38 minutes

Price per night from

$2,281

Ship's Cove Inn and Resort in St. Michaels, MD

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Price per night from

$1,882

Ferry Bridge House

Easton house

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 6

Price per night from

$793

Luxury Waterfront - 40 Acre Estate - Swimming, Boating, Activities

Royal Oak manor house

  • 25 bedrooms
  • 25 bathrooms
  • sleeps 50

Price per night from

$9,976

Great rentals within 20 miles that match your search

Love Point Waterfront

Kent Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

“Love Point Retreat” I stayed at Paula's property 3 times so far. We stayed once in October 2014 and twice in April 2015. Here is how I would break it up: Owner: Paula is very nice, accommodating and extremely responsive. She was easy to deal with, answered all of our questions and concerns timely. Property (Interior): The property is really clean and very well maintained considering its age. I also feel that it is properly stocked with all the necessities. Property (Outdoor Space / View): We spend the majority of our time there outside. The deck / backyard area is very well maintained and stocked with adequate furniture. We used the gas grill every day of our stay. The dock is set up nicely for fishing including rod holders and a light for night fishing. The view from the dock is to die for, the Bay is so wide and the Bay Bridge is a nice backdrop to the view specially during sunset. Fishing: Fishing is the best I have ever experienced (compared to all other rentals I tried). I caught numerous species from the dock including Spot, White Perch and of course Striped Bass (Rockfish). I caught my biggest Rockfish ever from the dock there (39 inch fish, roughly 30 pounds) in April. Overall, I love the property, the view and the peaceful surroundings. A great bonus for me is the short one hour commute to get there. We will definitely be back to Love Point for an encore.

Price per night from

$456

“Unbelievable value” We were a family group of 3 couples plus an infant traveling to a wedding at the Usna chapel. The home was just wonderful, had a great view, was very clean, and was well equipped for the cooking being planned. Stores, restaurants, and liquor store were close by. Easy on and off the freeway into annapolis. Scott was very personable and worked with us to make our visit just right from the moment we first contacted him about renting.

Price per night from

$451

Vintage Bungalow-cozy, walk to shops, water, free pkg.

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$474

KENT ISLAND-OCEAN VIEW Home for rent-4 bedrooms EASTERN SHORE sleeps 10-12

Kent Island house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Price per night from

$1,939

DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12

Chester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$1,939

Eat..Sleep..Fish..Repeat! Who needs a desk (there is one upstairs) when you can

Stevensville house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Price per night from

$798

The Heart of Historic Cool in Annapolis

Annapolis house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$1,140

Quiet Home Close to Downtown Annapolis and Parks

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$398

Great deal 4 Bedroom House Near the Ferry Park

Rock Hall house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 11

Price per night from

$274

Waterfront Condo Amazing Views with Resort Amenities

Annapolis condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$439

Gourmet Kitchen, Family and Pet Friendly Residence!

Mayo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$399

Waterfront Getaway, Dock Your Boat and Play!

Mayo camper van

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Price per night from

$341

Captain Quarters - Eastport!

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$569

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Annapolis apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$223

Fisher House - Downtown Annapolis!

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$679

Kent Island Luxury Waterfront

Stevensville house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 14

Price per night from

$797

Abay Palace of Kent Narrows in a King Bed

Grasonville apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Price per night from

$189

Cozy Downtown Annapolis Apartment

Annapolis apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$247

Ann House Getaway

Annapolis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$439

Annapolis Woodland Retreat

Cape Saint Claire house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$342

Charming 3 bdrm cottage with lovely front porch

Rock Hall house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

Price per night from

$227

King George Downtown Annapolis Getaway

Annapolis apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$428

Price per night from

$456

Private setting, enjoy nature, kayaking and total relaxation

Bethlehem house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$342

Annapolis Charm™ Waterfront Chesapeake Bay Getaway - Private Pier - Near USNA

Cape Saint Claire house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$397

Charming Annapolis Waterview home

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$797

Viewing 38 of 77
rentals in Talbot County

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Top Destination reviews

Location Location! St Michaels-- In Town Cottage!
Stepping back in history with today's amenities

This cottage was very nicely restored to capture the historic feel of colonial times, yet equipped with the modern conveniences. Since we visited during the winter, we especially enjoyed the fireplace. The location was convenient--within walking distance to shops and restaurants. It was tough to leave such a relaxing and comfortable cottage, we will definitely be back!see more

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