Easton Holiday Rentals

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Holiday Rentals in Easton

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

10.0 out of 10, Exceptional, (133)
"Great location and property. And epic crabbing to top it off!"
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

10.0 out of 10, Exceptional, (88)
"6 women for the 6 bedroom home. The house was great for our weekend. The only complaint was that the weather did not allow for more outdoor activities, though we had plenty of space inside to enjoy ourselves. The house has all the amenities and more. "
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (73)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is AU$716
includes taxes & fees
16 July - 17 July
Waterfront Oasis of Annapolis Star

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (227)
"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (48)
"This was our 2nd time at the house and it was just as relaxing as we hoped. Nice, quiet location and beautiful home!"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Quiet Relaxing Waterfront Suisse Chalet

9.6 out of 10, Exceptional, (76)
"Overall this was the most amazing experience from the location and the house itself to the property manager. The property manager was so amazing and made sure that if you needed anything in your stay they would make it happen. They were also very good about communication and responding quickly. On top of all of this the house itself is amazing and in the perfect location. Whether you want to have a chill getaway or explore Annapolis and the other amazing locations around it is the perfect house."
Quiet Relaxing Waterfront Suisse Chalet

Floating 2 bed 2 bath condo stunning views of the bay

2.0 star property
8.0 out of 10, Very good, (4)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
Floating 2 bed 2 bath condo stunning views of the bay

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (33)
"Such a cute and unique place to stay. Very peaceful. "
Chesapeake Houseboat Getaway on Kent Island, Maryland

Spacious 4 Bedroom Home w/ Hot Tub

9.8 out of 10, Exceptional, (19)
"We had a wonderful experience with our latest stay. They were flexible on arrival time, beds were very comfortable and the house was very comfortable! Will definitely stay again!"
The price is AU$837
includes taxes & fees
23 July - 24 July
Spacious 4 Bedroom Home w/ Hot Tub

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.6 out of 10, Exceptional, (10)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is AU$810
includes taxes & fees
14 July - 15 July
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (37)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is AU$520
includes taxes & fees
23 July - 24 July
Relax on Kent Island in 3 Bedroom Home w/Waterview

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

9.8 out of 10, Exceptional, (10)
"Very clean beautiful house! We stayed there for a wedding weekend and it was perfect. Great location. The hosts were wonderful and got back to us right away! Would love to go back one day."
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

9.8 out of 10, Exceptional, (127)
"We had a wonderful long weekend here. Perfect weather let us swim and kayak and fish all weekend. House was spacious enough for two families of five plus our dog. The views were perfect!"
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

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

9.6 out of 10, Exceptional, (28)
"Nice and peaceful stay for a quick local getaway. "
The price is AU$587
includes taxes & fees
4 Aug - 5 Aug
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (183)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (64)
"The property was well- maintained and the kitchen was well-equipped for our needs. Short walk to North Beach for dining and Boardwalk strolls. Nice and toasty for our winter stay - really enjoyed the trip."
The Blue Crab Beach House - Free beach passes

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

10.0 out of 10, Exceptional, (38)
"Loved the location and the pristine condition of the house. "
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (249)
"Our stay was great and Rob and Clarissa were very welcoming!"
Family and Pet-Friendly, Waterfront with Pier

Updated North Beach Cottage: Pet Friendly!

10.0 out of 10, Exceptional, (16)
"Awesome house a very short walk from Herrington Harbour."
Updated North Beach Cottage: Pet Friendly!

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (30)
"Great place for gathering. Plenty of space to hang out. Kitchen is big, well stocked and great for a large crowd. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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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Frequently asked questions

Can I find holiday rentals in Easton?

Yes, there are holiday rentals in Easton close to Easton Cycle and Sport, or you can select a more secluded option if you're looking for a relaxing stay. Travellers who like culture and the arts say Easton is known for its festivals and theatre scene. Allow some time to check out the shops during your trip.

What are some of the best holiday rentals that Easton has to offer?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : This holiday home rental outside of Easton is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Easton?

Choose from 35 Expedia holiday rentals in Easton for a memorable holiday.

What can I see and do in Easton?

Cultural attractions include Avalon Theatre and Historical Society of Talbot County, whereas Bruffs Island is one spot to enjoy nature. Other places in town to visit include Academy Art Museum and Academy of the Arts.

What are holiday rentals like in Easton?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Easton. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll feel right at home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a small group gathering.