Beachfront holiday rental in Talbot County

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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 stars2 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.
Guest favourite
Cottage in Cambridge
4.98 out of 5 average rating, 44 reviews

Cozy 3-bedroom cottage steps away from the water.

AdamRating, 5 stars1 month ago
Beautiful, clean home ! Nice new appliances and comfortable stay !
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 stars6 days 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.
Top Guest favourite
Home in Cambridge
4.83 out of 5 average rating, 40 reviews

Cambridge home in historic west end

NikkiRating, 5 stars1 week ago
Had a fabulous stay at this house. Came down for Eagleman 70.3 and loved the proximity to the water, the race and restaurants. House was perfect for our group, walkable, well equipped and everything as depicted no surprises. Holly was super communicative and accommodating and made us feel welcome and comfortable. Loved this house. Ava’s of course if looking for Italian and had a pretty good crab cake at Blue Ruin. Wished we were there longer to try some other places. Would love to return to Cambridge sometime.

Beachfront home rentals with a pool

Home in Stevensville
5 out of 5 average rating, 7 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.
Top Guest favourite
Home in Cambridge
5 out of 5 average rating, 16 reviews

Turtle's Nest - Hist. Cambridge

CoreyRating, 5 stars6 days ago
David and Wendy’s home was the perfect place for our family participating in and supporting the Cambridge Ironman with an easy walk to the course and to the Main Street. They went above and beyond accommodating our requests, since we were traveling with a two month old and a two year old. We were very comfortable and loved our evenings in the screened in porch and pool. We would love to stay at David and Wendy’s again.
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.
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.
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!
Guest favourite
Cottage in Neavitt
4.88 out of 5 average rating, 24 reviews

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

HeatherRating, 5 stars4 weeks ago
A cozy and quiet cottage right along the water. The kitchen is very well stocked. You can find any pot or utensil you may need. The best part of the cottage is the sun room, it was a great place to enjoy a glass of wine in the evening or enjoy a cup of coffee in the morning and soak in the sparkling water and peaceful surroundings. A peaceful spot away from everything, but a short 15 minute drive into St. Michaels. The road to the cottage is a bit rough, a small car has to navigate it with some care.

Private beachfront home rentals

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 stars2 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 stars6 days 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.
Guest favourite
Cabin in Saint Michaels
4.75 out of 5 average rating, 80 reviews

Cottage #4 Chesapeake Blue down the drive way.

DavidRating, 5 stars10 months ago
I recently had the pleasure of staying at Alexander and his wife's charming cottage, and we couldn't be happier with the experience. From the moment we arrived, Alex and his wife were incredibly accommodating and helpful, ensuring we had everything needed for a comfortable stay. The cottage itself was cozy and well-maintained, offering everything we required for a relaxing getaway. One of the highlights of our stay was the breathtaking sunset views. Watching the sun dip below the horizon from the dock was simply mesmerizing. The location is also ideal—just a short 10-minute drive to downtown St. Michaels, where we enjoyed exploring the local shops and restaurants. The hosts truly go above and beyond to make their guests feel welcome, and it shows in every aspect of their hospitality. I highly recommend this place for anyone looking for a peaceful and memorable retreat.
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 stars2 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, 18 reviews

High Water Guest House

LisaRating, 5 stars4 weeks ago
This was a beautiful stay right on the water in Cambridge. We walked from the house to RAR brewing and it’s such an easy drive to downtown Easton and St. Michael’s. Highly recommend Matti’s space for your next getaway!

Destinations to explore