Talbot County Holiday Rentals
House
10.0Exceptional
(163 Reviews)
2 Bedrooms
2 Baths
4 Guests
1425 ft²
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $357/Night
7 Nights - US $2,496
Bed & Breakfast
10.0Exceptional
(89 Reviews)
23 Bedrooms
24 Baths
60 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
Internet
US $281/Night
7 Nights - US $1,966
Bed & Breakfast
10.0Exceptional
(96 Reviews)
1 Bedroom
1 Bath
Breakfast- Parking
- Balcony/Terrace
- Kitchen
US $374/Night
7 Nights - US $2,617
Cottage
- Maryland
- ·
- St. Michaels
- 0.37 mi to center
10.0Exceptional
(153 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
Private Pool
Oceanfront- Parking
Pool
US $516/Night
7 Nights - US $3,614
House
- Maryland
- ·
- St. Michaels
- 2.58 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
2 Baths
4 Guests
Hot Tub- Parking
- Pool
- Air Conditioner
US $636/Night
7 Nights - US $4,454
Cottage
10.0Exceptional
(48 Reviews)
1 Bedroom
1 Bath
2 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $556/Night
7 Nights - US $3,892
Apartment
- Maryland
- ·
- St. Michaels
- 0.23 mi to center
10.0Exceptional
(41 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $383/Night
7 Nights - US $2,680
New
Apartment
- Maryland
- ·
- St. Michaels
- 0.45 mi to center
10.0Exceptional
(41 Reviews)
1 Bedroom
1 Bath
2 Guests
480 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $333/Night
7 Nights - US $2,332
House
- Maryland
- ·
- St. Michaels
- 0.91 mi to center
10.0Exceptional
(26 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $582/Night
7 Nights - US $4,071
Luxury Holiday Rentals in Talbot County
Over 320+ Luxury Holiday Rentals in or Near Talbot County
House
25 Bedrooms
20 Baths
40 Guests
11000.72 ft²
- Parking
- Pool
View- Air Conditioner
Unlock the Best Price
House
1 Bedroom
1 Bath
50 Guests
17000 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
Unlock the Best Price
House
10.0Exceptional
(1 Review)
8 Bedrooms
7 Baths
16 Guests
6000 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $3,169/Night
7 Nights - US $22,183
New
House
10.0Exceptional
(2 Reviews)
6 Bedrooms
6 Baths
12 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $2,757/Night
7 Nights - US $19,299
House
10.0Exceptional
(1 Review)
5 Bedrooms
5 Baths
10 Guests
6800 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $2,753/Night
7 Nights - US $19,273
House
1 Bedroom
6 Baths
10 Guests
6802.79 ft²
- Parking
- Pool
- View
- Air Conditioner
US $2,655/Night
7 Nights - US $18,582
House
6 Bedrooms
4 Baths
12 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $2,078/Night
7 Nights - US $14,547
House
4 Bedrooms
4 Baths
8 Guests
3905 ft²
- Private Pool
- Parking
- Pool
- View
US $2,025/Night
7 Nights - US $14,173
House
10.0Exceptional
(39 Reviews)
8 Bedrooms
9 Baths
12 Guests
12000 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,771/Night
7 Nights - US $12,395
Top-Rated Holiday Rentals with a Pool in Talbot County
Over 142+ The Best Private Villas and Holiday Rentals in Talbot County with a Pool
House
- Maryland
- ·
- St. Michaels
- 2.35 mi to center
10.0Exceptional
(89 Reviews)
5 Bedrooms
4 Baths
8 Guests
5000 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,164/Night
7 Nights - US $8,149
Villa
10.0Exceptional
(76 Reviews)
6 Bedrooms
4 Baths
12 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $961/Night
7 Nights - US $6,729
New
House
10.0Exceptional
(54 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $1,089/Night
7 Nights - US $7,623
Cottage
10.0Exceptional
(32 Reviews)
3 Bedrooms
2 Baths
6 Guests
1350 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $438/Night
7 Nights - US $3,064
House
10.0Exceptional
(26 Reviews)
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $813/Night
7 Nights - US $5,694
House
10.0Exceptional
(25 Reviews)
6 Bedrooms
4 Baths
12 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,379/Night
7 Nights - US $9,651
House
10.0Exceptional
(24 Reviews)
5 Bedrooms
4 Baths
10 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $983/Night
7 Nights - US $6,882
House
10.0Exceptional
(19 Reviews)
5 Bedrooms
4 Baths
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,071/Night
7 Nights - US $7,497
House
10.0Exceptional
(14 Reviews)
5 Bedrooms
4 Baths
10 Guests
6000 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,268/Night
7 Nights - US $8,877
Pet-Friendly Holiday Rentals in Talbot County
Over 127+ Pet-Friendly Holiday Rentals in or Near Talbot County
Cottage
10.0Exceptional
(24 Reviews)
2 Bedrooms
1 Bath
4 Guests
650 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $334/Night
7 Nights - US $2,339
House
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
1119.45 ft²
- Parking
- Kitchen
- Internet
Pet Friendly
US $175/Night
7 Nights - US $1,225
Hotel
9.0Exceptional
(105 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
Spa
US $397/Night
7 Nights - US $2,776
House
- Maryland
- ·
- St. Michaels
- 0.23 mi to center
10.0Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $744/Night
7 Nights - US $5,208
Bed & Breakfast
9.9Exceptional
(34 Reviews)
6 Bedrooms
6 Baths
17 Guests
376.74 ft²
- Hot Tub
- Breakfast
EV Charge Station- Parking
US $341/Night
7 Nights - US $2,384
House
10.0Exceptional
(9 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $441/Night
7 Nights - US $3,085
Apartment
- Maryland
- ·
- St. Michaels
- 0.08 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $498/Night
7 Nights - US $3,489
House
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $345/Night
7 Nights - US $2,418
Cottage
- Maryland
- ·
- St. Michaels
- 0.07 mi to center
9.8Exceptional
(208 Reviews)
2 Bedrooms
2 Baths
5 Guests
1400 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $413/Night
7 Nights - US $2,891
Large Holiday Rentals and Private Villas in Talbot County
Over 50+ Large Holiday Rentals and Private Villas in or Near Talbot County
House
10.0Exceptional
(103 Reviews)
5 Bedrooms
4 Baths
10 Guests
3400 ft²
- Oceanfront
- Parking
Ocean View- Balcony/Terrace
US $488/Night
7 Nights - US $3,416
House
- Maryland
- ·
- St. Michaels
- 2.31 mi to center
10.0Exceptional
(1 Review)
5 Bedrooms
4 Baths
8 Guests
5005.22 ft²
- Oceanfront
- Hot Tub
- Breakfast
- Parking
US $1,016/Night
7 Nights - US $7,110
House
- Maryland
- ·
- St. Michaels
- 0.83 mi to center
10.0Exceptional
(11 Reviews)
5 Bedrooms
4 Baths
10 Guests
2729 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,555/Night
7 Nights - US $10,884
Cabin
6.9Good
(64 Reviews)
47 Bedrooms
2 Baths
16 Guests
333.68 ft²
- Parking
- Air Conditioner
- Internet
Laundry
US $126/Night
7 Nights - US $882
House
10.0Exceptional
(6 Reviews)
5 Bedrooms
4 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,052/Night
7 Nights - US $7,364
House
10.0Exceptional
(3 Reviews)
5 Bedrooms
5 Baths
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,507/Night
7 Nights - US $10,546
House
9.8Exceptional
(46 Reviews)
4 Bedrooms
2 Baths
17 Guests
2121 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $985/Night
7 Nights - US $6,895
House
9.6Exceptional
(24 Reviews)
5 Bedrooms
5 Baths
10 Guests
48438 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $857/Night
7 Nights - US $6,000
House
9.6Exceptional
(10 Reviews)
5 Bedrooms
4 Baths
10 Guests
3408 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $1,450/Night
7 Nights - US $10,153
Wheelchair Accessible Holiday Homes in Talbot County
Over 20+ Wheelchair Accessible Holiday Homes in or Near Talbot County
House
9.8Exceptional
(56 Reviews)
2 Bedrooms
1 Bath
4 Guests
1100 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $392/Night
7 Nights - US $2,744
Hotel
9.4Exceptional
(110 Reviews)
5 Baths
374.05 ft²
Private Beach- Oceanfront
- Breakfast
- EV Charge Station
US $331/Night
7 Nights - US $2,315
Hotel
- Maryland
- ·
- St. Michaels
- 0.29 mi to center
9.6Exceptional
(401 Reviews)
1 Bath
- Hot Tub
- Breakfast
- Parking
- Pool
US $737/Night
7 Nights - US $5,159
House
9.4Exceptional
(18 Reviews)
4 Bedrooms
4 Baths
8 Guests
2827 ft²
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $681/Night
7 Nights - US $4,765
Hotel
9.2Exceptional
(102 Reviews)
5 Baths
10.76 ft²
- Private Pool
- Hot Tub
- Breakfast
- Parking
US $154/Night
7 Nights - US $1,078
Hotel
9.6Exceptional
(387 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $149/Night
7 Nights - US $1,041
House
4.5Average
(59 Reviews)
8 Bedrooms
5 Baths
12 Guests
5700 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $1,000/Night
7 Nights - US $7,000
Hotel
- Maryland
- ·
- St. Michaels
- 0.30 mi to center
9.2Exceptional
(57 Reviews)
9 Baths
431.53 ft²
- Oceanfront
- Breakfast
- EV Charge Station
- Parking
US $670/Night
7 Nights - US $4,690
Hotel
- Maryland
- ·
- St. Michaels
- 0.09 mi to center
9.1Exceptional
(130 Reviews)
7 Baths
299.85 ft²
- Parking
- Balcony/Terrace
- View
- Kitchen
US $502/Night
7 Nights - US $3,516
Talbot County Private Villas and Holiday Homes Under $200
Over 24+ Talbot County Private Villas and Holiday Homes Under $200
House
3 Bedrooms
2 Baths
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $172/Night
7 Nights - US $1,202
Bed & Breakfast
9.8Exceptional
(182 Reviews)
2 Bedrooms
2 Baths
6 Guests
398.26 ft²
- Breakfast
- Parking
- Balcony/Terrace
- View
US $155/Night
7 Nights - US $1,085
Hotel
9.4Exceptional
(389 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $165/Night
7 Nights - US $1,155
Cottage
9.8Exceptional
(35 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Kitchen
- Internet
TV
Security/Safety
US $163/Night
7 Nights - US $1,139
House
9.7Exceptional
(4 Reviews)
1 Bedroom
1 Bath
4 Guests
850.35 ft²
- Parking
- View
- Air Conditioner
- Internet
US $153/Night
7 Nights - US $1,071
House
10.0Exceptional
(2 Reviews)
11 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $173/Night
7 Nights - US $1,211
Hotel
9.2Exceptional
(106 Reviews)
1 Bath
- Parking
- Pool
- Balcony/Terrace
- Air Conditioner
US $170/Night
7 Nights - US $1,191
House
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
7 Guests
- Air Conditioner
- Internet
- Laundry
Bedding/Linens
US $154/Night
7 Nights - US $1,076
Cottage
2 Bedrooms
2 Baths
4 Guests
1800 ft²
- Kitchen
- Air Conditioner
- Internet
Child Friendly
US $171/Night
7 Nights - US $1,197
Instantly Bookable Holiday Homes in Talbot County
Over 131+ Instantly Bookable Holiday Homes in or Near Talbot County
Apartment
- Maryland
- ·
- St. Michaels
- 0.03 mi to center
10.0Exceptional
(13 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $694/Night
7 Nights - US $4,859
Cottage
10.0Exceptional
(11 Reviews)
1 Bedroom
1 Bath
2 Guests
800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $434/Night
7 Nights - US $3,041
House
10.0Exceptional
(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
1120 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $287/Night
7 Nights - US $2,011
Bed & Breakfast
- Maryland
- ·
- St. Michaels
- 0.07 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
603 ft²
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $336/Night
7 Nights - US $2,350
Bed & Breakfast
- Maryland
- ·
- St. Michaels
- 0.07 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
205 ft²
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $239/Night
7 Nights - US $1,671
House
- Maryland
- ·
- St. Michaels
- 0.08 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
817 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $473/Night
7 Nights - US $3,308
Cottage
9.8Exceptional
(22 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $536/Night
7 Nights - US $3,751
House
- Maryland
- ·
- St. Michaels
- 2.58 mi to center
9.8Exceptional
(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $713/Night
7 Nights - US $4,993
House
9.8Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $531/Night
7 Nights - US $3,715
Book a Last Minute Place to Stay in Talbot County
About Casai's Private Villas and Holiday Rentals in Talbot County
Discover more than 329 vacation rentals available in Talbot County. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Talbot County.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Talbot County, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Talbot County. On average, places to stay near Talbot County offer 1563.18 ft², with nightly prices averaging US $815.
With Casai, finding and comparing holiday rentals in Talbot County is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Talbot County
| Type | Count |
|---|---|
| Vacation Homes | 226 |
| Cottages | 37 |
| Holiday Apartments | 14 |
| Villas | 2 |
Use these Quick Filters to Find a Holiday Rental in Talbot County
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Talbot County.
Weather in Talbot County, MD
View the weather forecast for Talbot County before booking your Talbot County Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Talbot County, MD
Casai offers a large selection of top attractions around Talbot County . Research things to do on your vacation before you visit Talbot County.
Other Places to Stay in Talbot County, MD
Frequently Asked Questions About Talbot County?
What are the top holiday rentals in Talbot County?
With numerous options available in Talbot County, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Talbot County:
- Overlook on Dun's Cove - Luxury waterfront hideaway minutes from St. Michaels
- St. Michael's Premier In-Town Rental with heated pool. Pool closes 10/27
- We still have availability for August to October 2026 STR #22-30
- Hummingbird Inn
- Baydream Believer
- Wades Point Inn on the Bay
- Breathtaking Waterfront Estate
- Secluded Waterfront Property on 3 acres with swimming pool and dock.
- Cottage at Goose Neck Point
- Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets
How many holiday rentals have private pools in Talbot County?
Discover a selection of holiday rentals with private pools near Talbot County with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- The B&B of Anchorage - Skipjack
- Hampton Inn Easton
- Saint Michaels Summer Retreat with Pool & Hot Tub
- St. Michaels Escape | Pool, Hot Tub & Fire Pit
Which holiday homes in Talbot County are best for families?
If you're searching for a family-friendly holiday home in Talbot County, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Talbot County:
How many Casai.com holiday rentals are available in Talbot County?
As of 2026, Casai boasts over 329 properties listed in the Talbot County area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Talbot County.
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