Beachfront holiday rental in Talbot County

Find and book unique beachfront homes on Airbnb

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Popular amenities for Talbot County beachfront rentals

Pet-friendly beachfront home rentals

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

Ferry Bridge House

ColleenRating, 5 stars5 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
4.96 out of 5 average rating, 25 reviews

Spacious Historic Craftsman only 3 blocks to water

HeidiRating, 5 stars3 weeks ago
Great location, very responsive and helpful host, and warm feel to the home. We particularly appreciated the openness of the first floor which was nice for our group to gather. Very clean, all the necessities, great decor reflecting the location. We would stay here again and recommend to others.
Cottage in 5, Bay Hundred
5 out of 5 average rating, 4 reviews

The Bayside Cottage STRN 23-3

AnnaRating, 5 stars1 week ago
Most peaceful, relaxing and beautiful place, most responsive host and a comfortable house. We had a great time swimming, exploring the surroundings and watching sunsets from the porch.
Top Guest favourite
Houseboat in Stevensville
4.94 out of 5 average rating, 53 reviews

Chesapeake Houseboat Getaway

RomaRating, 5 stars1 month ago
I loved Julia’s Arc. First time I Airbnb’d in a houseboat; won’t be my last. I loved this experience! Julia’s was inviting, comfortable, well appointed. I enjoyed sitting on the upper deck but even sitting inside with the blinds up and the windows open afforded the sounds of the water while enjoying the view of the marina and boats. I wish I had more time here to explore more. This was exactly what I needed for some time alone.
Guest favourite
Cottage in Cambridge
4.98 out of 5 average rating, 45 reviews

Cozy 3-bedroom cottage steps away from the water.

ZackRating, 5 stars1 week ago
Stayed for a weekend and it was a perfect place. Very clear and easy instructions for getting in and very clean. Had everything we needed. Would highly recommend.
Townhouse in Cambridge
4.77 out of 5 average rating, 26 reviews

Cozy Townhouse on Cambridge Marina

FredRating, 5 stars2 weeks ago
The house is right on the main street that goes along the marina and the waterfront. There are many old historic houses within one to two blocks. It is a convenient walk to some nearby restaurants that offer great menus and seafood. This reservation is very compatible with walks along the waterfront and great dining.
Cabin in Saint Michaels
5 out of 5 average rating, 3 reviews

Serene Waterfront Retreat – Chesapeake Bay Escape

JamesRating, 5 stars1 week ago
Elizabeth's house was perfect for our weekend stay in St. Michael's. The house sits right on the water about a 5 minute drive from the center of town. It was the perfect home base for the Ironman event we were attending in Cambridge. Elizabeth was incredibly responsive and provided thoughtful recommendations for our stay. If we are in the area again we will certainly stay again.
Top Guest favourite
Home in Oxford
5 out of 5 average rating, 46 reviews

Stewart Ave Retreat

JeffreyRating, 5 stars1 week ago
Nanette’s place was extremely cozy and as described. It was a wonderful stay with everything you would need. She is also very responsive and helpful.

Beachfront home rentals with a pool

Home in Stevensville
4.88 out of 5 average rating, 8 reviews

Waterfront Escape with Pool Nature Lover Paradise

AnaRating, 5 stars2 weeks ago
Hosted my intimate wedding at Nancy’s home and we had an amazing weekend! My family & closest friends loved the home, location, amenities & the coziness of the house. Perfect for a lil vacation with friends & family and very kid friendly. Absolutely loved my stay. Thanks for letting us stay at your place, view was incredible and so much space for a big group. Will definitely come back and recommend 100%
Top Guest favourite
Campervan/RV in Stevensville
5 out of 5 average rating, 9 reviews

Charming RV With A Water View

CodyRating, 5 stars20 months ago
Andy was an awesome host! He checked in with us in the mornings to see if we needed anything (via text). They also had some great recommendations for us since we were out-of-towners. Would not hesitate to book with Alice and Andy again if we are ever in the area!
Resort in Saint Michaels
4.4 out of 5 average rating, 5 reviews

St. Michaels Harbour Inn - Premium King WF Suite

MonicaRating, 5 stars54 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, 26 reviews

The Anchorage Bed and Breakfast

SusanRating, 5 stars36 months ago
Hosts are awesome and take excellent care of their property and guests.
Home in Saint Michaels
4.71 out of 5 average rating, 7 reviews

Bankors Aweigh | an ESVR property

CaitlinRating, 5 stars9 months ago
I wanted a vacation where the house I stayed in was my vacation. The pool and hot tub were crystal clear, both of which overlooked the beautiful water. I went crabbing and fishing on the private dock, soaked in the private hot tub, roasted s'mores in the private firepit, and cooked my food on the grill overlooking the water. It was a vacation in small paradise. I cannot wait to return next year, or who knows, maybe sooner!
Superhost
Cottage in Trappe
4.87 out of 5 average rating, 30 reviews

Private Waterfront Cottage on Bolingbroke Creek

IsaiahRating, 5 stars10 months ago
Our stay Rick/Kevin’s place was fantastic. The property and setting exceeded our expectations. Everything was extremely well maintained. We loved staying in the lovely guest house which had everything we could possibly want. There were so many wonderful places to relax, from the screened porch to the pool and the amazing outdoor kitchen in the open air beach house. We loved floating in the pool while watching the big screen TV. The best of both worlds! We highly recommend Rick/Kevin’s place.
Superhost
Home in Royal Oak
4.67 out of 5 average rating, 3 reviews

Waterfront, Pool, Dock, Hot Tub.Stunning Views! A

HeatherRating, 5 stars3 weeks ago
We had a fantastic stay at this Chesapeake Bay home for our annual family trip! The outdoor space is a total standout—beautiful views, a great pool, and everything we needed for kayaking, crabbing, and making memories by the water. We especially loved the roomy layout, the well-stocked kitchen, and the big dining table that made family dinners a highlight each night. The house is full of personality, with tons of unique decor and interesting items throughout—definitely made for a fun and memorable stay, though we did find ourselves having to keep a very close eye on the kids around all the treasures! Overall, it was a wonderful trip and we’d absolutely book again!
Home in Cambridge

Sunny Home in Cambridge w/ Pool - Close to Ironman

BeckyRating, 5 stars8 months ago
This house is perfect for Ironman Maryland. The pool was refreshing and the house was pristine. Ryan and Phil were wonderful host with great communication!

Private beachfront home rentals

Apartment in Cambridge
5 out of 5 average rating, 12 reviews

SUPER WATER-VIEW 1 BEDROOM APT/CAMBRIDGE MARYLAND

AmandaRating, 5 stars1 week ago
Larry's place was perfect. We were able to book with him last minute for the Eagleman and he was able to accommodate our needs. It was a pleasure to meet Larry and have him give us a tour of the home. He was a great host. Would recommend to anyone!
Cottage in Cambridge
4.6 out of 5 average rating, 30 reviews

River Light Cottage-Cheerful three bedroom Cottage

VictoriaRating, 5 stars8 months ago
My brothers, sisters and I spent a weekend. It was wonderful, the house was just as we remembered it. Some changes, we lived in this house for almost 20 years and it was fun to stay there and reminisce. It was very well stocked and I highly recommend it.
Guest favourite
Home in Cambridge
5 out of 5 average rating, 16 reviews

"Riverside Retreat"

MeganRating, 5 stars3 weeks ago
We enjoyed a long weekend here with our kids and their grandparents! We were very comfortable, the house was clean, and the area is walkable and lovely. We would very happily stay again.
Guest favourite
Home in Tilghman Island
4.98 out of 5 average rating, 40 reviews

Tilghman Retreat: A house on the Chesapeake Bay.

TroyRating, 5 stars1 week ago
Sarah and Andrew were always available and responded to all questions and needs immediately. Their home was awesome, well appointed kitchen for cooking, beautiful grounds, quiet, peaceful and relaxing. We were in the area for a family wedding and didn’t get to spend as much time enjoying the dock and water as we would have liked, so we now have an excuse for a return visit. Thank you Sarah and Andrew for your local recommendations and for being so quick to respond to any and all needs.
Apartment in Oxford
5 out of 5 average rating, 3 reviews

Town Creek Hideaway +Boat Slip

DarylRating, 5 stars7 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.
Superhost
Home in Annapolis

Cozy Cottage with Beach Access

SharonRating, 5 stars5 months ago
This was a very comfortable place to stay beautiful inside and out quiet neighborhood. beautiful to walk along the bay
Guest favourite
Cottage in Oxford
4.97 out of 5 average rating, 31 reviews

Historic Home in Heart of Oxford, MD

MatthewRating, 5 stars3 weeks ago
Our stay at Matt’s house was perfect. The location is unbeatable, right behind the Market and creamery in Oxford. The house is charming and had thoughtfully been stocked with everything we needed for our stay.
Top Guest favourite
Guesthouse in Cambridge
5 out of 5 average rating, 19 reviews

High Water Guest House

LeighRating, 5 starstoday
My family had a wonderful stay at this beautiful cottage. It is beautifully furnished and modern. The screened in porch was so wonderful to sit and look out on the river. Everything was so organized from check in and check out- and everything in between!

Destinations to explore