Beachfront holiday rentals in Talbot County

Find and book unique beachfront homes on Airbnb

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Popular amenities for beachfront rentals in Talbot County

Pet-friendly beachfront home rentals

Guest favourite
Home in Easton
5 out of 5 average rating, 8 reviews

Ferry Bridge House

ColleenRating, 5 stars4 months ago
Beautiful property - everything was just as advertised and more. Spacious bedrooms with comfortable beds. Quiet, private location with gorgeous views. The hosts were exceptional - very gracious, thoughtful and accommodating to any possible need. We were delighted to find the house so beautifully decorated for Christmas. It made for a very special stay. Thank you!
Top guest favourite
Home in Cambridge
4.95 out of 5 average rating, 21 reviews

Charming Craftsman -Iron/EagleMan Start 2 Blocks

BrentleyRating, 5 stars2 months ago
Nice 100yr old house. Everything was great with our stay.
Cottage in 5, Bay Hundred
5 out of 5 average rating, 3 reviews

The Bayside Cottage STRN 23-3

BryanRating, 5 stars2 months ago
Nice, cozy place for two and a pup. Gorgeous views directly on the bay, especially from the bedroom. Very clean and stocked with everything one would need - nice furniture and the gas fireplace was lovely. Perfect spot for a quiet winter getaway.
Top guest favourite
Houseboat in Stevensville
4.94 out of 5 average rating, 52 reviews

Chesapeake Houseboat Getaway

RichardRating, 5 stars2 months ago
The houseboat was everything and more than the description. If you are looking for a great winter get away this is a perfect place to go to. You can kick back and relax or stay busy shopping and seeing the historical towns in the are. St Michaels and Easton are a short ride away. The restaurants are very good no matter what price range you are looking for. The shopping is great with many interesting small shops. I will certainly be back to the houseboat later this year.
Guest favourite
Cottage in Cambridge
4.98 out of 5 average rating, 43 reviews

Cozy 3-bedroom cottage steps away from the water.

AdamRating, 5 stars1 week ago
Beautiful, clean home ! Nice new appliances and comfortable stay !
Townhouse in Cambridge
4.77 out of 5 average rating, 22 reviews

Cozy Townhouse on Cambridge Marina

KellyRating, 5 stars7 months ago
Perfect location. Amazing host. We will 100% be back!
Top guest favourite
Home in Oxford
5 out of 5 average rating, 41 reviews

Stewart Ave Retreat

AbbieRating, 5 stars3 weeks ago
Our stay was wonderful. Nanette, was an amazing host and extremely accommodating. The house is beautiful and great for dogs. The town of Oxford is stunning and the locals are very friendly. We definitely would stay here again!

Beachfront home rentals with a pool

Home in Stevensville
5 out of 5 average rating, 3 reviews

Waterfront Escape with Pool Nature Lover Paradise

KarenRating, 5 stars3 weeks ago
This property has a breathtakingly beautiful view of the water that has a fully fenced in yard…so you don’t have to worry about little ones getting into the water. The master bedroom and master bath was amazing. My extended family and I traveled from 4 different states to stay at this property and all of us were comfortable. The house had plenty of spaces to kit be on top of each other. I highly recommend booking this property. The host is very responsive and helpful. I will keep this property in mind for future stays.
Resort in Saint Michaels
4.4 out of 5 average rating, 5 reviews

St. Michaels Harbour Inn - Premium King WF Suite

MonicaRating, 5 stars53 months ago
If you’re looking for a getaway that is quiet and has a great view, this is a great place for you. Our suite was spacious. Loved the fireplace and the jacuzzi tub. Views of the sunrise/sunset on our balcony facing the marina was spectacular. It’s a very short drive and 10 min walk to the town’s Main Street. Local restaurants are fabulous! With it being off-season, the restaurants have varying hours so be flexible on what’s open and what you’d like to eat. This made for a great long weekend getaway.
Superhost
Private room in Trappe
5 out of 5 average rating, 38 reviews

The Anchorage Bed & Breakfast

TaashiRating, 5 stars31 months ago
I'm super picky but this place was exceptional. The space was immaculate. Wonderful stay. Beautiful property. Bright, spacious apartment complete with a kitchen, dining table and even washer and dryer. The bed was super comfortable and the shower had great water pressure. Breakfast was yummy! Very kind hosts who accepted a last-minute booking. Enjoyed sitting around the fire pit watching a beautiful sunset over the Choptank River. Easy access to various small towns in the area. Great experience and would definitely stay again!
Superhost
Home in Saint Michaels
4.5 out of 5 average rating, 10 reviews

10 Minutes to St. Michaels with a Private Pool

JoyRating, 5 stars4 months ago
We had a great weekend a gain. Enjoying Christmas in St Michaels. Your home is beautiful. We ate at Ava’s, Limoncello, Carpenters and Talbots. Shopped on Sunday. Highly recommend the house tour. She you again soon.🥰
Cottage in Neavitt
4.87 out of 5 average rating, 23 reviews

Grandview - Cottage 1B, Queen Bed, Pool, Bay, WIFI

TyesRating, 5 stars7 months ago
A nice peaceful place to stay. Easy to get into town. A little tricky to find the first turn off the main road, but once you see the sign it makes sense. Would bring everything you need including ingredients to cook (sugar for coffee, salt, etc). But cleaning supplies are there and it's all very comfortable.
Guest favourite
Cottage in Neavitt
4.71 out of 5 average rating, 21 reviews

Grandview - Cottage 1A, King Bed, Pool, Bay, WIFI

SophiaRating, 5 stars1 week ago
This is a beautiful little gem right by the waterfront and very close to St. Michael. We loved it! So cosy, relaxing and peaceful. The overall property is amazing. We will be back!
Home in Tilghman
5 out of 5 average rating, 3 reviews

Clearview | an ESVR property

TomRating, 5 stars34 months ago
fantastic spot on the Island. incredible sunsets. very clean with stunning views of the Bay. everything you need to enjoy the Island is here with walking distance general store.

Private beachfront home rentals

Top guest favourite
Home in Annapolis
5 out of 5 average rating, 31 reviews

Peaceful Waterfront Home in Annapolis 3BR 2BA.

TolanRating, 5 stars1 week ago
We really enjoyed staying at this home. Such a beautiful view and extremely peaceful. Gwen was a great host. We would definitely stay here again.
Guest favourite
Home in Cambridge
5 out of 5 average rating, 14 reviews

"Riverside Retreat"

ValerieRating, 5 stars7 months ago
I had such a great stay at this property and Doug was a great host! The location is fantastic—it's in a friendly, welcoming community that's just a short walk to great restaurants and coffee shops, which was super convenient. The space itself was clean, comfortable, and had a cozy, inviting vibe that made me feel right at home. If you're visiting Cambridge, Maryland, I definitely recommend staying here—it’s the perfect spot for a relaxing getaway. Would stay again in a heartbeat!
Home in Cambridge
4.94 out of 5 average rating, 16 reviews

Charming Cambridge Home and Garden

LucRating, 5 stars19 months ago
We rented a week at Nancy’s house for Ironman Maryland. Wow, what a great place! This was by far the best house we rented for an Ironman, and we did a lot of renting. The house is just between the transition area and the Ironman village. Perfect for 2 couples. Plenty of space and privacy. You can park 2 and even 3 cars. You have a garage for your bike. Etc etc etc. I recommend this place any time. Luc
Guest favourite
Home in Cambridge
5 out of 5 average rating, 14 reviews

Outdoor fun for all ages biking canoeing crabbing

LisaRating, 5 stars9 months ago
This is the second time we've stayed at Copper Top. I love the location and it is a charming home. I also love that Michelle is so responsive to issues. We had a full house with 7 people, but there were plenty of towels and beds for everyone. It's helpful to know that when it is hot and humid (we were there during 4th of July week when the weather was in the 90's and very humid), the upstairs air conditioning struggles to get the front bedroom cool. There are plenty of fans for every room, which helped. The two back bedrooms were nice and cool. Downstairs stays nice and cool as well, as there is a separate AC unit for that floor.
Flat in Oxford
5 out of 5 average rating, 3 reviews

Town Creek Hideaway +Boat Slip

DarylRating, 5 stars5 months ago
There were a lot of thoughtful touches- the bathroom had everything I could have needed. The kitchen was fully stocked and everything I wanted for my morning coffee was all set. The apartment was comfortable and complete. The neighborhood is nice and quaint- I love the cottages and historic buildings of Oxford. Thank you for giving me extra time on Sunday before my performance.
Top guest favourite
Home in Cambridge
5 out of 5 average rating, 29 reviews

• Peaceful Point • A relaxing waterfront retreat

DarleneRating, 5 stars3 days ago
This property was wonderful. We were there with another couple. The home was well appointed including a lovely coffee area. Well designed, nicely decorated that was up to date and clean. The view was wonderful. We enjoyed the towns of Cambridge, St Micheals and the Blackwater Preserve.I would definitely come back again!
Top guest favourite
Home in Cambridge
5 out of 5 average rating, 84 reviews

In Town Waterfront Nature Retreat in Cambridge, MD

AshbyRating, 5 stars1 week ago
Lisa’s place is a beautiful home with a gorgeous view. She has thought of everything for their Airbnb guests. Everything you would need in the kitchen, lawn games for outside (we had some very competitive croquet games happening), solo fire pit with a s’mores kit, enough firewood for the year, long swing overlooking the pond, towels, toiletries, etc. I can’t recommend this house enough. The down town is a short drive away and had a couple great restaurants that we tried. Great visit all around.
Guest favourite
Guest house in Oxford
4.93 out of 5 average rating, 30 reviews

Newly Renovated Guest House

JaimieRating, 5 stars2 weeks ago
My daughter and I stayed here for a girls weekend and it was everything we wanted and more! As soon as you walked in the door, you felt relaxed and cozy. The place was very spacious. It is way bigger than I thought it was going to be and it just gives off a cozy comfy vibe. It’s beautifully decorated and the view outback was the cherry on top. Absolutely stunning! The home had everything you needed. The kitchen was completely stocked, tons of extra linens and towels, and they left a little gift basket filled with snacks on the counter. The host was also super friendly and accommodating. We really enjoyed our weekend and hope to go back soon! Thank so much!

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