Vacation Homes in Talbot County

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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Talbot County vacation homes

Fridge, microwave, oven, stovetop

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Historic District
10.0 out of 10, Exceptional, (32 reviews)
"Perfect location. Host was very responsive lots of shopping and restaurants nearby."
United States
Michelle B.
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Exterior

Private 2 Acre Waterfront Family Retreat with Pool & Pier

Private 2 Acre Waterfront Family Retreat with Pool & Pier
Cambridge
9.6 out of 10, Exceptional, (89 reviews)
"The host, Virgina, was amazing, so accommodating. Beautiful property. Looking forward to hopefully booking next year. "
United States
Susan B.
Private 2 Acre Waterfront Family Retreat with Pool & Pier
Terrace/patio

Historic Annapolis Home 1.5 blocks from center of town.

Historic Annapolis Home 1.5 blocks from center of town.
Historic District
9.8 out of 10, Exceptional, (46 reviews)
"We had another great stay! Great location and great host!"
United States
Liz D.
Historic Annapolis Home 1.5 blocks from center of town.
Property grounds

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Easton
10.0 out of 10, Exceptional, (98 reviews)
"Overall the stay was very good."
United States
Gregg S.
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Fridge, microwave, oven, stovetop

Sweet Bamboo Beach Cottage

Sweet Bamboo Beach Cottage
north beach
9.8 out of 10, Exceptional, (84 reviews)
"Cute, clean, pet friendly, even a full fenced in yard for the doggies. Great walking area. "
United States
kathy c.
Sweet Bamboo Beach Cottage
Property grounds

Mid-Century Modern Lake House – Gorgeous Fall Views, Fire pit, Sauna, 4BR

Mid-Century Modern Lake House – Gorgeous Fall Views, Fire pit, Sauna, 4BR
Lusby
9.6 out of 10, Exceptional, (8 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveler
Mid-Century Modern Lake House – Gorgeous Fall Views, Fire pit, Sauna, 4BR
Exterior

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Eastport
10.0 out of 10, Exceptional, (133 reviews)
"Great property and location. "
United States
Steve N.
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Interior

Waterfront Wildlife Retreat on the Patuxent River

Waterfront Wildlife Retreat on the Patuxent River
Lusby
10.0 out of 10, Exceptional, (177 reviews)
"Amazing location! Host is equally amazing and the home was perfect with everything we needed for a long relaxing weekend. Views are stunning and home was very comfortable. "
United States
Jenna G.
Waterfront Wildlife Retreat on the Patuxent River
Smart TV

Charming Historic Townhouse Steps From USNA

Charming Historic Townhouse Steps From USNA
Historic District
10.0 out of 10, Exceptional, (39 reviews)
"The beds were incredibly comfortable and the location simply perfect! Easy to get to the Yard and Downtown. "
United States
Jennifer H.
Charming Historic Townhouse Steps From USNA
Fridge, microwave, oven, stovetop

Historic Home with Parking Steps From Capital & USNA

Historic Home with Parking Steps From Capital & USNA
Historic District
9.8 out of 10, Exceptional, (18 reviews)
"Great place and only minutes form DTA."
United States
john c.
Historic Home with Parking Steps From Capital & USNA
Dining

Walking distance to Navy Stadium! No cleaning fees!

Walking distance to Navy Stadium! No cleaning fees!
West Annapolis
10.0 out of 10, Exceptional, (11 reviews)
"Great communication, easy access, and home had everything we needed!"
United States
laura j.
Walking distance to Navy Stadium! No cleaning fees!
Interior

Historic Downtown House with Off Street Parking

Historic Downtown House with Off Street Parking
Historic District
10.0 out of 10, Exceptional, (17 reviews)
"Place was nicely decorated, clean, and a GREAT location to downtown . You can walk to everything ! My only recommendation would be to put some motion lights on the side of the house as you need to walk through the alley to get to the side entrance . I would definitely recommend Christopher’s place! We hope to be back soon. "
United States
sandy l.
Historic Downtown House with Off Street Parking
Interior

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

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Cape Saint Claire
10.0 out of 10, Exceptional, (43 reviews)
"Everything was perfect for a large family gathering over the holiday. "
United States
daniel h.
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Exterior

Private Resort! 100" Home Theater, HotTub, Pool, Basketball Court, extra games

Private Resort! 100" Home Theater, HotTub, Pool, Basketball Court, extra games
Bowie
10.0 out of 10, Exceptional, (1 review)
"The hosts were responsive to all my questions. The house was beautiful; the pictures didn’t fully give it justice. It was the perfect place to hold an epic sweet 16 sleepover for my daughter. Highly recommend!"
United States
Cheryl L.
Private Resort! 100" Home Theater, HotTub, Pool, Basketball Court, extra games
Smart TV, printers

Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More

Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More
Mechanicsville
10.0 out of 10, Exceptional, (10 reviews)
"Clean, comfortable home! Beautiful property, well stocked with everything you will need. Excellent, one of the best we have stayed at. Will book again! "
United States
Brian H.
Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More
Outdoor dining

Back Creek Villa Covered Deck

Back Creek Villa Covered Deck
Solomons
Back Creek Villa Covered Deck
Fridge, microwave, oven, stovetop

Sophisticated Charmer with Parking & Views of the USNA Chapel Dome

Sophisticated Charmer with Parking & Views of the USNA Chapel Dome
Historic District
9.8 out of 10, Exceptional, (62 reviews)
"Great house and perfect location in town! "
United States
Sarah G.
Sophisticated Charmer with Parking & Views of the USNA Chapel Dome
Outdoor dining

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (65 reviews)
"Easy check in, always clean and we had a power outage and Andrea ho back to us immediately! Great kitchen and living area!"
United States
Regina L.
Charming Annapolis WaterVIEW Home
Dining

Spacious Luxe USNA Home - Pool, Hot Tub, Grill

Spacious Luxe USNA Home - Pool, Hot Tub, Grill
Murray Hill
9.8 out of 10, Exceptional, (26 reviews)
"Great location, great host! "
United States
Katie J.
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
Exterior

Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (35 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is AED 440
AED 1,129 total
includes taxes & fees
8 Apr - 9 Apr
Charming Coastal/Country Home w/3 Acres & Sauna!
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 Talbot County Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Julie is amazing!"
Cynthia 2-night trip
Posted less than an hour ago
DoubleTree by Hilton Hotel Annapolis