Massey Holiday Rentals from AU$253: Search Short-Term Rentals

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Holiday Rentals in Massey

"Very clean, excellent communications,"

includes taxes & fees

29 Jan - 30 Jan

"It is a beautiful place. It was a perfect fit for our family. The game room and the pool were a huge hit with everyone we made tons of memories that will last a lifetime. The cleaning crew is amazing. The place was spotless. My wife accidentally misplaced her diamond wedding ring and the host contacted us immediately to let us know the cleaning crew had found it. My wife was absolutely relieved to hear that they found it. We already booked our stay for next year!! Thank you!!"

"We all had a great time at the cottage. It was very cozy, well cared for and loaded with personality. The kitchen was well-stocked and easy to navigate. The beds were very comfortable. We really enjoyed the wood burning fireplace that was all ready to be lit upon arrival. It was the perfect spot to have cocktails, watch football, play games and catch up! The view of the bay was lovely while having morning coffee, watching the birds and admiring the sunsets. I highly recommend a visit!"

"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"

"Property was clean and close to everything in Chesapeake City"

Beach nearby, sun-loungers, beach towels

"We had a great time at the house with friends from our apartment building and neighborhood for the long Thanksgiving weekend. Debbie and Bob had everything we needed to cook with, the porch overlooking the Bay was amazing, and the living room, TV room and dining room were all used frequently. We also played games, and had a nice fire in the portable fire pit outside. Weather got coooold but the house was always warm and cozy. It was a really fun stay. The bedrooms were great, too. They've taken...

"This home was amazing. Nicely decorated for the holiday. Labels on kitchen cavinets. Host was easy to communicate with. Fast responses. doors made it easy to find things (huge kitchen). "

"Great!"

"Everything was nice enough space for everyone to sleep comfortably."

"This is the cutest place! Super clean and equipped to the max, everything we could possibly need was provided. The beds/linens are extremely comfortable. And our hostess was quick to respond to a problem with the heat. Highly recommend!"

"This home had to have been the most perfect VRBO we have stayed in. The home was clean, comfortable, stocked with amenities that made the stay incredibly pleasant and in a fantastic location. We particularly enjoyed the built in speakers in the dining room. I would highly recommend this home for a visit to Chestertown. "

"We fell in love with Chestertown and are so glad we stayed in the heart of downtown at this charming vrbo. Everything was perfect. Will return and recommend "

"This home is beautifully decorated, making it most inviting and pleasant. The view of the bay was magical! Sitting on the sun porch was so wonderful! The kitchen was the most well equipped kitchen I’ve had the pleasure to use! Thank you for an amazing stay!!"

"We enjoyed our Thanksgiving get away at this very cute waterfront cottage. Our stay was a extremely relaxing and enjoyable time. 😊👌👍"

"We had an unforgettable stay at this property! The house and two bungalows exceeded all expectations. The entertainment/living room is massive—one of the largest I’ve ever seen—and offers incredible views of the river from almost every angle. Watching the sunrise and sunset through the large windows was absolutely breathtaking. The kitchen was impressively well-stocked, making meal prep a breeze. There are two dining areas: one table that seats ten and another that seats six, offering...

"This was the best Christmas yet and on top of that, the home was amazing, great amenities, great view, great time. Thank you to the host! "

"The home was nice - great to fit our group of 12, good room for sitting and dining and sleeping, and a nice open layout with the kitchen opening up to the living room. The host also was quite communicative. Overall, this was a good stay.Cons:The biggest offense lacking was that there were no real kitchen knives (one utensil mostly resembled a knife) which made preparing a meal for 12 quite difficult. There also was not shampoo/conditioner/body wash provided in the bathrooms.The hot tub also...

"The Lark's Nest is in a nice location. The home decor is pleasant to the eyes and well-arranged. The host provided us with all the necessities (towels, cooking supplies, cleaning supplies, and toiletries). The cons were dirty ceiling fans, the sofa needed cleaning, and the outside lighting needed to be brightened. A mouse was found in the house. The host was apologetic, accommodated us financially, and sent out an exterminator to handle the rodent issue. Overall, the actual place was a good stay...

"Really comfortable and in a great neighborhood."

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Other types of properties in Massey you may be interested in

"Excellent for the price. Most of the workers were friendly and helpful. "

includes taxes & fees

30 Jan - 31 Jan

"I really like this hotel! VERY COMFORTABLE!!! I booked this hotel based on price. After booking I read reviews and was really put off. I read multiple "bad reviews" that made me a little worried. When I arrived, I was greeted immediately. Very quick and easy check-in process! I walker to my room, so that I had a point of reference where I should park and was happy to see that I had a spot right outside of my rooms window. I opened the door of my room and caught the wonderful "clean smell. No...

includes taxes & fees

2 Feb - 3 Feb

"Cleanliness and friendly staff . Updated premises with nice decor. "

includes taxes & fees

2 Feb - 3 Feb

Find out more about Massey

Everything you need to know about Massey 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 Massey 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 Massey holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Massey holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Massey. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Massey 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 Massey holiday rentals we have selected for you start as low as AU$253 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Massey rentals

At Expedia, we put the best Massey 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 Massey 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 Massey 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 Massey. 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 Massey?

Yes, there are holiday rentals close to the most popular sights in Massey, or you can select a more secluded option if you're looking for a relaxing stay.

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

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach: This holiday home rental outside of Massey is located on a river, and has a garden, a selection of games and a BBQ to put you at ease in your new surroundings. 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.

What’s there to see and do in Massey?

Explore the area and family-friendly sights such as Crumpton Auction, or get out into nature at a spot like Betterton Beach. In the wider area, you’ll find Skipjack Cove Yachting Resort and Crow Farm and Vineyard.

What’s a holiday rental in Massey like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Massey. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for small groups.

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Massey Holiday Rentals

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Holiday Rentals in Massey

First Floor Studio Apartment in Historic Chestertown

Stunning waterfront villa with indoor pool and kids swing set and play area.

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Historic Chesapeake City Stay

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Chesapeake City Quiet Overlook

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

Right in the center of everywhere in Dover

Circa 1900 Home in the Heart of Historic Downtown Chestertown

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

Newly restored apartment in the heart of Chestertown

Upper Chesapeake Getaway - Newly Renovated

Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!

Private Peaceful Waterfront House with Pool & Hot Tub

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Home away from home

Saybrook Hall | Pickleball + Pool + Hot Tub

Other types of properties in Massey you may be interested in

Bally's Dover Casino Resort

Wyndham Garden Dover

Fairfield Inn & Suites by Marriott Middletown

Find out more about Massey

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