Easton Holiday Rentals

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Holiday Rentals in Easton

Thorneton Point Estate
9.6 out of 10, Exceptional, (21)
"The house and property were beautifully maintained. We had 3 generations and everyone was able to get quiet moments and yet be able to be all together. The dining table was well used with lunches/dinner/games. "
United States
Natalia R.
Thorneton Point Estate
St. Michaels Waterfront Home
9.8 out of 10, Exceptional, (31)
"What a great place to stay!! Close to town and very well equipped. We’ll be back!!"
United States
Craig W.
St. Michaels Waterfront Home
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
10.0 out of 10, Exceptional, (95)
"Gorgeous views and surroundings"
United States
Robin P.
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
10.0 out of 10, Exceptional, (14)
"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."
United States
Tammy S.
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Floating 2 bed 2 bath condo stunning views of the bay
2.0 star property
7.0 out of 10, Good, (6)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
United States
Natalia F.
Floating 2 bed 2 bath condo stunning views of the bay
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
10.0 out of 10, Exceptional, (31)
"The location is fabulous. We could walk wherever we wanted to go. The room to bathroom ration was also great. We would stay here again. "
United States
Diana L.
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Cass-N-Reel Luxury Houseboat
10.0 out of 10, Exceptional, (43)
"If you’re looking for a great view sitting on the water, with a modern look, convenient to everything, you need to stay on the Cass-and-Reel Luxury Houseboat!!"
United States
Karen B.
Cass-N-Reel Luxury Houseboat
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
10.0 out of 10, Exceptional, (17)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
United States
Tracy S.
The price is NZ$509
includes taxes & fees
8 Nov - 9 Nov
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
9.4 out of 10, Exceptional, (17)
"The gigantic house was perfect for our quick Army-Navy Football game weekend. We hope to come back when it’s warm to take advantage of the great gathering spaces outdoors. Go Navy! Beat Army!!"
United States
Elizabeth B.
The price is NZ$2,029
includes taxes & fees
9 Nov - 10 Nov
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Waterfront Getaway, Dock Your Boat & Play!
10.0 out of 10, Exceptional, (3)
"Great place to stay. It is clean, comfortable, and not lacking convenience.Quick communication with the host. We would definitely recommend!"
United States
Daniel K.
The price is NZ$537
includes taxes & fees
5 Nov - 6 Nov
Waterfront Getaway, Dock Your Boat & Play!
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
10.0 out of 10, Exceptional, (14)
"Really nice property. Relaxing weekend. Stayed here with my daughter for two nights. We had a great time. "
United States
Dara M.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (38)
"Fabulous week! Our family of 3 generations had a blast and appreciated the outstanding accommodations. House and outdoor areas are beautiful and well-maintained. Excellent location close to amenities and just minutes from Annapolis. Everything was great!"
United States
Melissa K.
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (122)
"The house and location was perfect for a girls weekend with my mom and 2 daughters! The 1/2 bathrooms in each bedroom were nice to have upstairs!"
United States
Kimberly L.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
9.8 out of 10, Exceptional, (7)
"The property was perfect for our family get together. We had a baby, toddler, preschooler, elementary and teens, moms, dads and grandparents. There was a place for everyone. Having a pack n’ play available would have been nice, but we procured one elsewhere. The property was large and felt very private, but Cambridge was just a quick drive."
United States
Jacqueline M.
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Family and Pet-Friendly, Waterfront with Pier
10.0 out of 10, Exceptional, (262)
"Our stay was great and Rob and Clarissa were very welcoming!"
United States
Allison L.
Family and Pet-Friendly, Waterfront with Pier
Charming townhome with AC and WiFi in delightful Annapolis
3.0 out of 10, (2)
"So this was the very definition of a flophouse. It is not the whole house, it is not even a secluded room. It was a mattress in the middle of the foyer/entering the kitchen area. The pictures show a nice kitchen - this is where the mattress abuts and again also used by the host. In the pictures the kitchen is clean - in reality there were dirty dishes piled up with some bugs within them; there was also food left on the stove. The area around the house was somewhat sketchy - admittedly we...
United States
Jason
The price is NZ$119
includes taxes & fees
5 Nov - 6 Nov
Charming townhome with AC and WiFi in delightful Annapolis
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
9.6 out of 10, Exceptional, (21)
"The house was very nice, the host was very responsive! The outside was nice, only down side lots of mosquitos but that’s expected. "
United States
Elizabeth M.
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (41)
"This is a great place for a small family and friends' weekend reunion."
United States
Paul G.
The price is NZ$503
includes taxes & fees
16 Nov - 17 Nov
Relax on Kent Island in 3 Bedroom Home w/Waterview
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
10.0 out of 10, Exceptional, (79)
"Good stay overall"
United States
Bill C.
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
10.0 out of 10, Exceptional, (55)
"My wife and I have stayed at many different places over the years but this may be one of the most well maintained properties I've ever seen. It was a great place for us to unwind with our dog and we would certainly recommend this location for anyone looking to stay in the area"
United States
Nick B.
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
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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Top Easton Hotel Reviews

Find out more about Easton

Everything you need to know about Easton holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Easton holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Easton holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Easton holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Easton. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Easton holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Easton holiday rentals we have selected for you start as low as NZ$119 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Easton rentals

At Expedia, we put the best Easton holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Easton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Easton holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Easton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres. : This holiday home rental outside of Easton is located next to a golf course, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, 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 pool table.

How many holiday rentals are there in Easton?

Choose from 34 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.