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Find vacation rentals that suit your style
Our top choices for Talbot County cottages




1. Private 4BR Guest Cottage part of Estate, Magothy River Views, Near Annapolis
Private 4BR Guest Cottage part of Estate, Magothy River Views, Near AnnapolisArnold
10.0 out of 10, Exceptional, (5 reviews)
10/10
Exceptional
(5 reviews)
"Great location, excellent quality accommodations. Host communication was quick and helpful."
"Great location, excellent quality accommodations. Host communication was quick and helpful."Carl




2. Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly
Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-FriendlyAnnapolis
9.8 out of 10, Exceptional, (45 reviews)
9.8/10
Exceptional
(45 reviews)
"Second year staying here and absolutely love this place! The private beach is fantastic for all our grandchildren to play and swim."
"Second year staying here and absolutely love this place! The private beach is fantastic for all our grandchildren to play and swim."Gregg L.




3. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.Benedict
9.0 out of 10, Wonderful, (16 reviews)
9.0/10
Wonderful
(16 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"ed r.
$248 nightly
The price is $274
$274 total
Nov 10 - Nov 11
Total with taxes and fees




4. Lovely 2-bedroom waterfront cottage in charming Wittman
Lovely 2-bedroom waterfront cottage in charming WittmanWittman
9.8 out of 10, Exceptional, (8 reviews)
9.8/10
Exceptional
(8 reviews)
"This lovely cottage was just perfect for us! The house is newly updated & located on a beautiful property right on the water. We loved the firepit, seeing all the stars at night & watching the wildlife on the water. The kayaks were a nice surprise too! We visit MD often & will definitely stay here again!"
"This lovely cottage was just perfect for us! The house is newly updated & located on a beautiful property right on the water. We loved the firepit, seeing all the stars at night & watching the wildlife on the water. The kayaks were a nice surprise too! We visit MD often & will definitely stay here again!"Beth H.




5. Firefly Cottage at the Cape, USNA Football, Hot Tub, Com. beach, dogs, holidays,
Firefly Cottage at the Cape, USNA Football, Hot Tub, Com. beach, dogs, holidays,Cape Saint Claire
10.0 out of 10, Exceptional, (129 reviews)
10/10
Exceptional
(129 reviews)
"Patricia was excellent—literally one of the best VRBO hosts we've had. The goody bags were thoughtful, the hot tub was nice and the house was clean. We loved the community beach."
"Patricia was excellent—literally one of the best VRBO hosts we've had. The goody bags were thoughtful, the hot tub was nice and the house was clean. We loved the community beach."Leslie S.




6. John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!Downtown St. Michaels
9.6 out of 10, Exceptional, (136 reviews)
9.6/10
Exceptional
(136 reviews)
"A beautiful, historic home perfectly situated in the heart of St. Michael’s."
"A beautiful, historic home perfectly situated in the heart of St. Michael’s."Laura C.




7. Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Location, Location, Location! - W Melson House - Beautiful - In Town St MichaelsDowntown St. Michaels
9.6 out of 10, Exceptional, (143 reviews)
9.6/10
Exceptional
(143 reviews)
"Great location in St Michaels at a fun historical house."
"Great location in St Michaels at a fun historical house."Adam




8. Soul Oasis - home on the Chesapeake Bay
Soul Oasis - home on the Chesapeake BayLusby
10.0 out of 10, Exceptional, (67 reviews)
10/10
Exceptional
(67 reviews)
"Nice, clean, and would absolutely stay here again."
"Nice, clean, and would absolutely stay here again."Dusty S.
$264 nightly
The price is $280
$280 total
Dec 1 - Dec 2
Total with taxes and fees




9. Relaxing Waterfront Cottage Near St Michaels, Maryland
Relaxing Waterfront Cottage Near St Michaels, MarylandWittman
9.8 out of 10, Exceptional, (264 reviews)
9.8/10
Exceptional
(264 reviews)
"We had a great time at a great place."
"We had a great time at a great place."Jeffrey F.




10. Charming Waterfront Cottage Retreat near St. Michaels
Charming Waterfront Cottage Retreat near St. MichaelsBozman
10.0 out of 10, Exceptional, (13 reviews)
10/10
Exceptional
(13 reviews)
"This was a great stay for my wife and I on our mini moon. Everything was perfect. The property was well equipped with everything we needed, a great location that was private but not too far from town. We will be back!"
"This was a great stay for my wife and I on our mini moon. Everything was perfect. The property was well equipped with everything we needed, a great location that was private but not too far from town. We will be back!"Nick G.
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.
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.
Top reviews in Talbot County




Marvel's on the Creek
Marvel's on the CreekEast New Market
10/10 Excellent
This was my first time @ a bed and breakfast. The owners, Debbie and Allen are amazing. Being an introvert and there for an Ironman race, I was concerned about having to interact too much with other people. Debbie struck the perfect balance of being available but also giving people space to hide away. The property is gorgeous and clean. Her breakfasts are amazing (eggs cooked to order, bacon, biscuits, quiche, homefries, etc). She goes above and beyond to make people feel welcomed. She woke up...
This was my first time @ a bed and breakfast. The owners, Debbie and Allen are amazing. Being an introvert and there for an Ironman race, I was concerned about having to interact too much with other people. Debbie struck the perfect balance of being available but also giving people space to hide away. The property is gorgeous and clean. Her breakfasts are amazing (eggs cooked to order, bacon, biscuits, quiche, homefries, etc). She goes above and beyond to make people feel welcomed. She woke up...
Joseph




The Oaks Waterfront
The Oaks WaterfrontEaston
10/10 Excellent
Absolutely perfect little 3 day get away. The entire atmosphere was excellent, great complementary breakfast from menu, beautiful modern rooms, perfectly manicured landscaping with lots of seating for relaxing by the water. The entire staff were so friendly and helpful. We made an excellent choice and would definitely go back. 10+ out of 10.
Absolutely perfect little 3 day get away. The entire atmosphere was excellent, great complementary breakfast from menu, beautiful modern rooms, perfectly manicured landscaping with lots of seating for relaxing by the water. The entire staff were so friendly and helpful. We made an excellent choice and would definitely go back. 10+ out of 10.
William




Inn at Huntingfield Creek
Inn at Huntingfield CreekRock Hall
10/10 Excellent
Quaint property - very laid-back. Exactly what we were looking for.
Quaint property - very laid-back. Exactly what we were looking for.
George




Hummingbird Inn
Hummingbird InnEaston
10/10 Excellent
My wife and I were celebrating our 15th anniversary and the Hummingbird Inn was the perfect relaxing and romantic getaway. Eric and Michael are gracious and accommodating hosts. The Inn is gorgeous. Our room was elegant yet comfortable. There are plenty of restaurants within walking distance and lots of cool shops to check out. I also want to throw a shout out to Storm and Daughters Ice Cream which we walked to after dinner because it’s maybe the best ice cream we’ve ever had. Then back to the...
My wife and I were celebrating our 15th anniversary and the Hummingbird Inn was the perfect relaxing and romantic getaway. Eric and Michael are gracious and accommodating hosts. The Inn is gorgeous. Our room was elegant yet comfortable. There are plenty of restaurants within walking distance and lots of cool shops to check out. I also want to throw a shout out to Storm and Daughters Ice Cream which we walked to after dinner because it’s maybe the best ice cream we’ve ever had. Then back to the...
Robert




Fairfield Inn & Suites by Marriott Easton
Fairfield Inn & Suites by Marriott EastonEaston
10/10 Excellent
The Fairfield Inn on US50 has become our go-to mid-range hotel in Easton. We have stayed here several times in recent years, and once again had a great experience during this Christmas stay. The facilities are clean and in good condition. The staff is friendly, welcoming, and accommodating. When I booked our stay this time through a third-party, I got a little confused about room options, and took the only king-bed room that I saw. The manager didnt know I had any concerns, and when the staff...
The Fairfield Inn on US50 has become our go-to mid-range hotel in Easton. We have stayed here several times in recent years, and once again had a great experience during this Christmas stay. The facilities are clean and in good condition. The staff is friendly, welcoming, and accommodating. When I booked our stay this time through a third-party, I got a little confused about room options, and took the only king-bed room that I saw. The manager didnt know I had any concerns, and when the staff...
Richard




Inn at Perry Cabin
Inn at Perry CabinDowntown St. Michaels
10/10 Excellent
This is an elegant old hotel with lovely gardens and a great view of the bay. Restaurant was very nice with fantastic views and excellent food. Best crab cakes ever! The main part of the hotel is original with low ceilings and uneven floors, and has several nice sitting rooms, nooks and alcoves. Reminds me of some European hotels I have visited.
This is an elegant old hotel with lovely gardens and a great view of the bay. Restaurant was very nice with fantastic views and excellent food. Best crab cakes ever! The main part of the hotel is original with low ceilings and uneven floors, and has several nice sitting rooms, nooks and alcoves. Reminds me of some European hotels I have visited.
Norm




134 Prince - Luxury Boutique Hotel
134 Prince - Luxury Boutique HotelAnnapolis
10/10 Excellent
Lovely room, comfy bed, great bathroom! Only complaint was that it was SO hot in the room and it was challenging to adjust that even after receiving instructions. Breakfast and coffee was excellent!
Lovely room, comfy bed, great bathroom! Only complaint was that it was SO hot in the room and it was challenging to adjust that even after receiving instructions. Breakfast and coffee was excellent!
Reyna




86 State Circle - Luxury Boutique Hotel
86 State Circle - Luxury Boutique HotelHistoric District
10/10 Excellent
The property was immaculate! The room we stayed (Chase suite) was gorgeous!!
The staff were so wonderful and helpful and the location was perfect. Loved everything about this property
The property was immaculate! The room we stayed (Chase suite) was gorgeous!!
The staff were so wonderful and helpful and the location was perfect. Loved everything about this property
MARA




Sandaway Suites & Beach
Sandaway Suites & BeachOxford
10/10 Excellent
I took a solo trip and picked the perfect spot. This family owned inn is great for a family trip, a romantic getaway, or for a quiet escape by yourself. The owners are such a welcoming family and made me feel very like VIP. I will be going back and recommend Sandaway to anyone looking for that getaway in the Eastern Shore. Thank you Gibson Family for a wonderful experience!
I took a solo trip and picked the perfect spot. This family owned inn is great for a family trip, a romantic getaway, or for a quiet escape by yourself. The owners are such a welcoming family and made me feel very like VIP. I will be going back and recommend Sandaway to anyone looking for that getaway in the Eastern Shore. Thank you Gibson Family for a wonderful experience!
joseph




Knapps Narrows Marina & Inn
Knapps Narrows Marina & InnSherwood
10/10 Excellent
We had a wonderful two night stay at the hotel. The marina is beautiful with nightly rentals if needed. Our first stay and we will return. Great staff very helful. If you are looking for a peacefull,tranquil location you will like it.
We had a wonderful two night stay at the hotel. The marina is beautiful with nightly rentals if needed. Our first stay and we will return. Great staff very helful. If you are looking for a peacefull,tranquil location you will like it.
Stan and Joan




Haven Point Inn and Gallery
Haven Point Inn and GalleryRock Hall
10/10 Excellent
Host is fantastic. Great room with garden view. Breakfast made to order. Beautiful art gallery.
Host is fantastic. Great room with garden view. Breakfast made to order. Beautiful art gallery.
Joe




Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
10/10 Excellent
Loved it
Loved it
Joe




The Inn at Tacaro Estate
The Inn at Tacaro EstateTracys Landing
10/10 Excellent
It was a spectacular location, beautiful rooms and restoration of a stunning property, the owners Luciano and Susan are superstars, the staff amazing the breakfast was unbelievably and the ambiance was amazing! I was in Maryland for a wedding, I never thought I would return but I MUST come back and stay again!
It was a spectacular location, beautiful rooms and restoration of a stunning property, the owners Luciano and Susan are superstars, the staff amazing the breakfast was unbelievably and the ambiance was amazing! I was in Maryland for a wedding, I never thought I would return but I MUST come back and stay again!
ian




The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach ClubStevensville
10/10 Excellent
Beautiful place, quiet and clean.
Beautiful place, quiet and clean.
Chuck




Anchored Inn at Hidden Harbour Marina
Anchored Inn at Hidden Harbour MarinaDeale
10/10 Excellent
We needed overnight accommodations before heading out for a day of sailing on the bay and Hidden Harbour popped up as the closest venue geographically and we're glad it did. The accommodations are new, with quality and fixtures and bathrooms that you wouldn't mind taking home with you. The price seemed fair and as we watched the full moon rising from our deck we wished that we were spending a week.
We needed overnight accommodations before heading out for a day of sailing on the bay and Hidden Harbour popped up as the closest venue geographically and we're glad it did. The accommodations are new, with quality and fixtures and bathrooms that you wouldn't mind taking home with you. The price seemed fair and as we watched the full moon rising from our deck we wished that we were spending a week.
Rico




Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
10/10 Excellent
The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...
The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...
Christina




Laurel Grove Inn on the South
Laurel Grove Inn on the SouthAnnapolis
10/10 Excellent
We really loved everything, but Guinness the dog topped everything. There was a miscommunication about dinner reseservations but it worked out. Would have appreciated more whole food at breakfast. Neither of these would keep me away. In fact, we would love to see the property in the spring.
We really loved everything, but Guinness the dog topped everything. There was a miscommunication about dinner reseservations but it worked out. Would have appreciated more whole food at breakfast. Neither of these would keep me away. In fact, we would love to see the property in the spring.
Marti




Kent Island Resort
Kent Island ResortStevensville
10/10 Excellent
I stayed here for a quick overnight and did not utilize many of the amenities however, the staff was incredibly kind overall and with tips on dinner. This place is historic, which is a nice way of saying old but classic. Don’t expect a huge room, the photos portray the room accurately. Some things were a little rickety, but everything was clean. Overall I recommend this if you’re solo or a couple looking for a place as you enjoy the bay.
I stayed here for a quick overnight and did not utilize many of the amenities however, the staff was incredibly kind overall and with tips on dinner. This place is historic, which is a nice way of saying old but classic. Don’t expect a huge room, the photos portray the room accurately. Some things were a little rickety, but everything was clean. Overall I recommend this if you’re solo or a couple looking for a place as you enjoy the bay.
John












