A stone church with a pointed steeple and arched windows.

Talbot County Holiday Rentals

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Our top choices for Talbot County holiday rentals

TV, fireplace

Marblehead Farm I Swing set, Hot tub * Indoor Pickleball court

Marblehead Farm I Swing set, Hot tub * Indoor Pickleball court
Ridgely
Marblehead Farm I Swing set, Hot tub * Indoor Pickleball court
Smart TV, books

Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
9.8 out of 10, Exceptional, (30 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveller
The price is HK$1,961
HK$3,021 total
includes taxes & fees
9 Jul - 10 Jul
Newly restored apartment in the heart of Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (116 reviews)
"Hosts were extremely friendly and helpful!Parking was within feet of entrance. Studio and bathroom were spotless. Nice touches like coffee and accoutrements in the shower. Beautiful surroundings, everything was in bloom and spring beauty was everywhere!Washer and dryer in studio with soap and softener. Charming location!"
United States
Rob C.
The price is HK$776
HK$1,246 total
includes taxes & fees
7 Jul - 8 Jul
First Floor Studio Apartment in Historic Chestertown
Exterior

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (55 reviews)
"Cute, sweet spot with a peaceful vibe and lovely view!"
United States
Melinda S.
The price is HK$1,176
HK$2,461 total
includes taxes & fees
20 Jul - 21 Jul
Soul Oasis - home on the Chesapeake Bay
Outdoor pool

Annapolis Garden Suite

Annapolis Garden Suite
Epping Forest
10.0 out of 10, Exceptional, (17 reviews)
"We had a quick overnight stay to attend an event at the Naval Academy! This was the perfect spot!! The accommodations were exactly what we needed!! Thanks for a great stay!!! "
United States
Mary S.
The price is HK$1,955
HK$3,731 total
includes taxes & fees
7 Jul - 8 Jul
Annapolis Garden Suite
Property grounds

Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"The house was lovely, very comfortable and hosts were very responsive! We will be back for another stay. "
United States
Diana S.
The price is HK$2,855
HK$4,330 total
includes taxes & fees
8 Jul - 9 Jul
Wren Retweet- Country Estate in Center of C’Town
Exterior detail

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (57 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is HK$1,412
HK$2,170 total
includes taxes & fees
20 Jul - 21 Jul
BAYSIDE BUNGALOW
Outdoor pool

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Owings
10.0 out of 10, Exceptional, (52 reviews)
"We love this place!"
United States
Joan K.
The price is HK$1,569
HK$3,192 total
includes taxes & fees
28 Jul - 29 Jul
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Interior

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
Lusby
The price is HK$4,972
HK$9,726 total
includes taxes & fees
7 Jul - 8 Jul
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
Sun-loungers

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (43 reviews)
"Second time here and we love the convenience to Prince Frederick and the comfort offered by the hosts. "
United States
RACHEL S.
The price is HK$2,365
HK$2,831 total
includes taxes & fees
7 Jul - 8 Jul
Cottage Located on the Patuxent River!
Exterior

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is HK$727
HK$2,137 total
includes taxes & fees
7 Jul - 8 Jul
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Beach nearby, sun-loungers, beach towels

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (16 reviews)
"Very nice property with plenty of room and a nice outdoor space. The hot tub was a great bonus. Close enough to visit USNA but the location feels like a vacation spot!"
United States
Gail S.
The price is HK$2,965
HK$5,651 total
includes taxes & fees
12 Jul - 13 Jul
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Smart TV

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, (15 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is HK$3,059
HK$5,404 total
includes taxes & fees
14 Jul - 15 Jul
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (38 reviews)
"Great place to stay, very private. Plenty of room for big groups. Would definitely book again, when in the area. "
United States
Handy M.
The price is HK$992
HK$2,547 total
includes taxes & fees
9 Jul - 10 Jul
Charming Coastal/Country Home w/3 Acres & Sauna!
Interior

Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (40 reviews)
"Just was very responsive to all requests and inquiries."
United States
Vesta M.
The price is HK$1,447
HK$3,089 total
includes taxes & fees
8 Jul - 9 Jul
Large 2 bedroom house with private parking in a nice neighborhood
Beach

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (24 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is HK$924
HK$2,249 total
includes taxes & fees
7 Jul - 8 Jul
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Smart TV

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, (13 reviews)
"Clean, cozy, and lovely - a winter cabin stay to remember. Kids already wanted to go back 5 days later. 10 out of 10 stars! "
United States
Mr.
The price is HK$3,510
HK$6,139 total
includes taxes & fees
13 Jul - 14 Jul
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Property grounds

Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.6 out of 10, Exceptional, (20 reviews)
"Sophia was an amazing host and the place was exactly as advertised. I couldn't recommend the place enough!"
United States
William N.
The price is HK$1,804
HK$3,026 total
includes taxes & fees
8 Jul - 9 Jul
Bright and airy waterfront getaway
Property grounds

Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (13 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is HK$2,823
HK$4,814 total
includes taxes & fees
7 Jul - 8 Jul
Turnbridge Manor
Property grounds

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, (13 reviews)
"The home was lovely and very quiet location. My sister and I were caring for our mom after discharge from hospital and it was very convenient. Would stay there again. "
United States
Tova A.
The price is HK$3,623
HK$6,734 total
includes taxes & fees
7 Jul - 8 Jul
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Great location. Friendly staff. Nice property."
Eric 1-night trip
Posted less than an hour ago
Graduate by Hilton Annapolis