Talbot County Vacation Rentals

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Top cities in Talbot County

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St. Michaels

St. Michaels
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Easton

Easton
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Oxford

Oxford

Talbot County Vacation Rentals

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

St Michaels MD
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Pool
Kitchen
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St Michaels MD
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Pool
Kitchen
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)

Royal Oak MD
Guests staying at this vacation home enjoy an outdoor pool, an arcade/game room, and laundry facilities. Other amenities at this family-friendly vacation home include a garden and barbecue grills.
Pool
Kitchen
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Cambridge MD
Guests staying at this vacation home enjoy an outdoor pool, an arcade/game room, and laundry facilities. Additional amenities include barbecue grills and a garden.
Pool
Kitchen
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cambridge MD
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Stevensville MD
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Floating 2 bed 2 bath condo stunning views of the bay

Floating 2 bed 2 bath condo stunning views of the bay

2 out of 5
Stevensville MD
At this houseboat, guests have access to barbecue grills.
Kitchen
Pet friendly
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Chester MD
Guests staying at this vacation home enjoy free WiFi in public areas, laundry facilities, and barbecue grills. This family-friendly vacation home also has a garden.
Kitchen
Washer
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Port Republic MD
At this cabin, guests have access to a garden.
Pool
Kitchen
Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat

Grasonville MD
This houseboat is a smoke-free houseboat.
Kitchen
Free WiFi
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Cambridge MD
Guests of this vacation home enjoy features like an outdoor pool, a hot tub, and an arcade/game room. Other amenities at this family-friendly vacation home include laundry facilities, local meal delivery service, and barbecue grills.
Pool
Hot Tub
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

stevensville MD
Guests of this vacation home enjoy access to a water park, laundry facilities, and a garden. This beach vacation home also has barbecue grills.
Kitchen
Washer
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Annapolis MD
$1,019 nightly
The price is $1,161 total per night
$1,161 total
Dec 21 - Dec 22
Total with taxes and fees
This vacation home offers an arcade/game room, laundry facilities, and local meal delivery service. Friendly staff can provide concierge services, and also offer advice about sightseeing. Additional amenities include a water dispenser, a garden, and barbecue grills.
Kitchen
Washer
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Annapolis MD
At this vacation home, guests have access to features like laundry facilities.
Kitchen
Washer
Luxury Waterfront Executive Family Home Annapolis with All Amenities

Luxury Waterfront Executive Family Home Annapolis with All Amenities

Annapolis MD
Guests of this vacation home enjoy features like a gym, a hot tub, and laundry facilities. This smoke-free vacation home also has barbecue grills.
Hot Tub
Washer
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Annapolis MD
At this vacation home, guests have access to a gym, laundry facilities, and barbecue grills. Transportation is made easy with limo/town car service. Friendly staff can provide concierge services, and also offer advice about sightseeing. This smoke-free vacation home also has a garden.
Pool
Kitchen
BAYSIDE BUNGALOW

BAYSIDE BUNGALOW

Rock Hall MD
$285 nightly
The price is $302 total per night
$302 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Guests of this vacation home enjoy sun loungers and beach towels.
Free WiFi
Air conditioning
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown MD
$144 nightly
The price is $159 total per night
$159 total
Dec 23 - Dec 24
Total with taxes and fees
Guests of this apartment have access to an outdoor pool, a gym, and a hot tub. Other amenities at this golf apartment building include laundry facilities and barbecue grills.
Pool
Hot Tub
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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.

Hotel Options in Talbot County

    Inn at Perry Cabin

    Inn at Perry Cabin

    308 Watkins Ln St. Michaels MD
    $574 nightly
    The price is $632 total per night from Dec 21 to Dec 22
    $632 total
    Dec 21 - Dec 22
    Total with taxes and fees
    9.4/10 Exceptional! (371 reviews)
    St Michaels Inn

    St Michaels Inn

    1228 S Talbot Street St. Michaels MD
    $95 nightly
    The price is $105 total per night from Jan 4 to Jan 5
    $105 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    8/10 Very Good! (1,000 reviews)
    Quality Inn

    Quality Inn

    8523 Ocean Gtwy Easton MD
    $81 nightly
    The price is $89 total per night from Dec 28 to Dec 29
    $89 total
    Dec 28 - Dec 29
    Total with taxes and fees
    7.6/10 Good! (824 reviews)

Orbitz makes it easy to find vacation rentals in Talbot County 

🏠 What is the best price for a Talbot County vacation rental?


Talbot County rentals range between $89 and $1,161 per night. At Orbitz, we have a vacation rental for every budget.


🏠 What types of vacation rentals in Talbot County can I rent?


Choose from apartments to beautifully decorated vacation homes, condo resorts or even B&Bs or motels for your next Talbot County getaway. Orbitz filters your search results so you can find the best Talbot County vacation rental for you. We have tons of options.


🏠 Are cancellations free on Talbot County vacation rentals with Orbitz?


You may be able to cancel or amend your Talbot County vacation rental booking free of charge before a pre-agreed deadline. Make sure to check the terms of cancellation before you book—so you know exactly where you stand. 


🏠 How do I find the best vacation rental deals in Talbot County?


Enter your travel dates, and we’ll do the rest. You can then browse our exciting deals and all the tempting vacation rentals we have on offer in Talbot County by filtering your search by amenities, prices, and property types and look at customers ratings to help you pick.


🏠 How do I cancel my vacation rental booking through Orbitz


Vacation rentals have slightly different rules to other bookings on Orbitz. Usually, you need to contact your property manager, you may be able to get a full refund before the cancellation date. Click My TripsOpens in a new window on your Orbitz account page to find the right information contact. If you need more help, visit our Customer ServiceOpens in a new window page. 


🏠 What are the advantages of booking a vacation rental in Talbot County?


When you book a Talbot County vacation rental, you have the privacy of home and can add on those luxury amenities of a hotel. Filter your vacation rental results to find a place with a hot tub or pool, games rooms or large patio with a barbecue. With so much choice on offer, it’s easy to plan the perfect trip with Orbitz. 


🏠 Where can I find vacation rentals in Talbot County?


Escape back to nature and check out some of the smaller towns. You’ll find great vacation rentals right across Talbot County—with plenty of hidden gems. We also have plenty of inventory in Talbot County main cities and near popular attraction spots.


🏠 Why should I book my Talbot County vacation rental with Orbitz?


At Orbitz, we search the market for the best accommodation, flights, and car rental deals, so you don’t have to. We’ll help you build your dream Talbot County vacation. With plenty of vacation rentals on offer, you can be sure to find the one that’s right for you in just a few clicks. 


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