Easton Holiday Rentals

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Holiday Rentals in Easton

Pool
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
10.0 out of 10, Exceptional, (1)
"This was the most peaceful and perfect property. I felt like I was on vacation and able to relax! We would definitely return if we are in the area again."
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
Outdoor pool
New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks.
10.0 out of 10, Exceptional, (126)
"While we wished for weather that was slightly better, we still enjoyed every minute of our 3 days. The weather didn't stop us from using the Kayaks or trying to catch a crab or two. the yard was perfect for exercising the kids and the puppies. It was a short easy drive into town, for some shopping, eating and even a visit to a rum distillery. The wineries were all closed at the beginning of the week this time of year. The house was supplied with everything we needed. The listing was spot on,...
New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks.
Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (3)
"Wonderful place to stay and Erin was great. Asked about a Grill on the property and the next day we had a grill. The young adults loved the pool and water activities while the older adults enjoyed sitting on the docks watching the sunrise with a cuppa coffee. Would highly recommend this property."
The price is NZ$2,315
includes taxes & fees
4 Jun - 5 Jun
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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Fridge, microwave, oven, stovetop
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (180)
"Charming spot in the heart of Annapolis, just a few moments walk from anything you might need."
Directly Across from Gate One & Steps from the Waterfront
Exterior
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (186)
"The cottage is fully stocked, clean, and cozy. We thoroughly enjoyed sitting on the deck and watching all the wildlife."
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (26)
"My family and I enjoyed our stay at the Carpenter Alley Cottage in Saint Michaels! The location was perfect -- walking distance from everything! Appreciated that there was a ground floor bedroom for my parents so they didn't have to climb the stairs and my daughter loved having her own bunk bed room! I did have a few questions about the cottage and the check-in process and my inquiries were all met with a prompt response. Would love to stay here again! (One note though is that it is a smaller,...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Property grounds
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
10.0 out of 10, Exceptional, (60)
"We had a great stay here for my husband’s birthday. Pat and Ken were fantastic hosts and even decorated for this birthday. They provided everything we would need for our toddler and if the weather had cooperated we’d have spent hours and hours in the backyard. Really appreciative of all the attention to detail and would highly recommend this listing if you’re looking for a low-key, relaxing stay where you don’t need to worry about the details."
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
Fridge, microwave, oven, stovetop
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, (44)
"This house was perfect for a group of friends celebrating a 50th birthday! The house was so clean and well cared for! The front porch and outdoor backyard space provided even more room for us to gather together. We will be back!"
Recently Renovated Annapolis Home - Conveniently Located
Interior
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
9.8 out of 10, Exceptional, (14)
"We really enjoyed our (much too short) stay at this waterfront gem!! The property was very clean, had all the amenities that we needed for our time away.... the only complaint is that we didn't have enough time to enjoy it all!! : ) thank you so much, we will be back!"
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Outdoor pool
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, (21)
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (104)
"Loved this historic house! Perfect location, peaceful neighborhood and walking distance to entire town."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Fridge, microwave, oven, stovetop
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (80)
"This is an absolutely fantastic place to stay!! The host Liz was so easy to work with and quick to respond to any inquiries we had. We booked for the Herndon climb (#plebenomore) and cannot say enough about how perfect this house was for us. It was an easy walk to DTA and gate #1. The kitchen was well stocked and had everything needed to make several home cooked meals for our son and his friends. The sun room is beautiful and the perfect spot to enjoy a cup of coffee or breakfast! The pool was...
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Property grounds
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (107)
"VRBO link hasn’t enabled me to communicate with property manger/owner as I’m unable to access account via the VRBO link. I’ve re-registered multiple times now."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Property grounds
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (43)
"Beautiful house and views. Amenities and grounds were great. Loved the playground and beach. Peace and quiet at its finest in nature."
The price is NZ$1,104
includes taxes & fees
28 May - 29 May
Charming Annapolis WaterVIEW Home
Fridge, microwave, stovetop, dishwasher
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, (4)
"We extremely enjoyed our stay. The house was beautiful, kitchen was well equipped and the view was spectacular, especially with the Eagles that have nested on the 32 acre property. However was disappointed in the fact that the fire places were not in working conditions and rooms should have been number. We enjoy kayaking up and down the bay and taking it all in. I would definitely stay again."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Beach nearby, sun-loungers, beach umbrellas, beach towels
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (39)
"It was clean and had everything we needed. We had a very comfortable stay. There are one or two steps between many of the rooms so keep that in mind."
The Blue Crab Beach House - Free beach passes
Property grounds
Chesapeake Houseboat Getaway on Kent Island, Maryland
10.0 out of 10, Exceptional, (7)
"My husband and I and our dog had a lovely getaway on "Julia's Arc". This was our first time on a Houseboat and it was a wonderful experience. So much light! And the movement of the boat was just enough to be comforting. The home was very clean and beautifully adorned with great attention to detail. Julia, the host, was very responsive and very generous in doing all she could to make our trip as comfortable and pleasurable as possible. The views over the water were gorgeous and we really...
Chesapeake Houseboat Getaway on Kent Island, Maryland
Property grounds
The Lazy Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (24)
"My husband and I moved from the area two years ago and so are in town frequently to visit friends and family. Weve stayed at the Lazy Crab and the owner's other property next door at the Blue Crab multiple times. The properties are located in a quiet neighborhood within easy walking distance of restaurants and shopping, and plenty of parking is provided. The houses are well appointed and provisioned, nicely decorated and comfortable, and always beautifully clean. Danielle is very easy to work...
The Lazy Crab Beach House - Free beach passes
Fridge, microwave, oven, stovetop
Waterfront Cottage on the Eastern Shore
8.0 out of 10, Very good, (1)
"Check-in was seamless, my family enjoyed the accommodations even though the weather outside was dismal. Parked by at times was challenging but we dealt with it. I must admit NO dishwasher at a vacation rental came as a surprise. None of us cared to deal with that chore. Septic issues cut bathroom access and shower access down significantly. But the biggest concern to me as the Mimi(Grandmother) was that someone had downstairs access while my two granddaughters were sleeping. They saw lights,...
The price is NZ$1,852
includes taxes & fees
17 Jun - 18 Jun
Waterfront Cottage on the Eastern Shore
Outdoor spa tub
Bay View Studio Apartment
10.0 out of 10, Exceptional, (25)
"If you are looking for a very spacious well-appointed one bedroom apt. style accommodation in a residential setting with lovely waterfront bay views, I highly recommend this place!"
Bay View Studio Apartment
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See all available properties in Easton
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.

Other types of properties in Easton you may be interested in

Exterior
Quality Inn
2.5 star property
7.6 out of 10, Good, (613)
"Staff was lovely and beds were decent and floors are redone. Bathroom has seen better days and walls need to be renovated. "
The price is NZ$159
includes taxes & fees
2 Jun - 3 Jun
Quality Inn
Exterior
Best Western Plus Easton Inn & Suites
2.5 star property
9.4 out of 10, Exceptional, (1005)
"Very nice stay. Could have used a hair dryer and there was only one small facial bar of soap in the room. Never bothered to mention this with staff. Otherwise, a very nice and clean room."
The price is NZ$232
includes taxes & fees
28 May - 29 May
Best Western Plus Easton Inn & Suites
Room, 1 King Bed, Non Smoking
Days Inn by Wyndham Easton
2.5 star property
5.8 out of 10, (739)
"It seemed as if we got a “new” room which was kind of nice but they forgot to install the toilet paper holder and supply a roll. Also, fridge was off and we had to peel the new tv film off and get assistance to get volume. It’s ok for the price but the pics online are not a true representation of what it looks like inside or outside. "
The price is NZ$135
includes taxes & fees
28 May - 29 May
Days Inn by Wyndham Easton
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Easton holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Easton. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Easton. Seeing all the best attractions is bound to make you fall in love with Easton. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Easton short-term rentals, that won’t be hard to do.

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?

Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F: This highly rated holiday home rental in Easton is equipped with a fireplace, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Easton?

Choose from 36 Expedia holiday rentals in Easton for a memorable holiday.

What can I see and do in Easton?

Cultural attractions include Avalon Theatre and Pickering Creek Audubon Center, whereas Easton Cycle and Sport is just one of the family-friendly sights. Other places in town to visit include Historical Society of Talbot County and Customs House.

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.

Recent reviews of Easton properties
Expedia verified reviews