Massey Holiday Rentals

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Holiday Rentals in Massey

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
10.0 out of 10, Exceptional, (73)
"A hidden gem! Beautiful location on the bay with the cutest town!!! "
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Captivating Chesapeake experience
10.0 out of 10, Exceptional, (250)
"We had a wonderful stay at this beautiful property. The water views are amazing and it was so relaxing! The house was very clean and well maintained. Everything we expected it to be from the listing, actually more charming and comfortable than the pictures show. Thank you. "
Captivating Chesapeake experience
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10.0 out of 10, Exceptional, (29)
"What a great location, practically on the water! Betty Ann was very responsive and everything about this place was easy!"
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (71)
"Just what we needed for the night! Thank you "
The price is AU$226
includes taxes & fees
9 Oct - 10 Oct
First Floor Studio Apartment in Historic Chestertown
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (43)
"We really enjoyed the water views & walking by the water. It was a very enjoyable and relaxing stay."
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
9.4 out of 10, Exceptional, (32)
"We had a great time in the pool, fishing off dock, paddle boarding, kayaking and swimming. The kids (5 under 8) loved playing in the bAsement."
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
Sunset River Cottage encapsulates nautical romance.
8.8 out of 10, Excellent, (10)
"Great view and cute cottage"
Sunset River Cottage encapsulates nautical romance.
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
9.6 out of 10, Exceptional, (35)
"This house had the most amazing views and was clean and tidy. It was perfect for us and the dogs. The yard was clean and mowed and provided plenty of room for frisbee play which is part of my german shepherd's job. The kitchen was very adequate for our needs! As expected, the upstairs bedrooms were "historic" and the staircase was steep also "historic". The showers were perfect. We had a great visit and would love to come back here!"
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Stunning waterfront villa with indoor pool and kids swing set and play area.
10.0 out of 10, Exceptional, (8)
"The house is very impressive! We loved many things about it. It was very clean. The pool and porches were very good. . The setting is impressive. We were 11 family members ranging from 62-82. For us, getting in and out of the tall beds was a challenge. Besides that all was good . Thank you for sharing your beautiful home"
Stunning waterfront villa with indoor pool and kids swing set and play area.
Hidden gem with water and golf course views! Bike ride to downtown!
10.0 out of 10, Exceptional, (29)
"We had a wonderful time! The house was described perfectly. It was clean and comfortable and everything we needed it to be to enjoy our time! "
Hidden gem with water and golf course views! Bike ride to downtown!
Chesapeake City Quiet Overlook
10.0 out of 10, Exceptional, (11)
"My wife and I booked Jane’s house for our wedding weekend in Chesapeake city. Jane allowed us to use her property for our wedding of 40 ppl. She could not have been nicer or more accommodating for this special occasion. She responded to all of our questions quickly and even made special offers to make our wedding weekend even more special. I cannot say enough nice things about Jane. The house and property were gorgeous in a really great location along the canal in Chesapeake city. The views...
Chesapeake City Quiet Overlook
BEACH WITHOUT THE BUSTLE
10.0 out of 10, Exceptional, (25)
"Good time and the condo was super."
BEACH WITHOUT THE BUSTLE
Guest Suite for up to 2 in a Victorian on the Chester River
10.0 out of 10, Exceptional, (8)
"The apartment is charming, very clean and tastefully decorated. Pus the en suite private bathroom, which must be new, is beautiful. The owner also included thoughtful touches, such as coffee and tea. Check-in was straightforward and the owner is super responsive. We'll be back. We had a wonderful stay. "
The price is AU$187
includes taxes & fees
21 Oct - 22 Oct
Guest Suite for up to 2 in a Victorian on the Chester River
Harbor View Haven | Waterfront w/ HOT TUB + Dock!
10.0 out of 10, Exceptional, (12)
"Everything about our stay was delightful. Not even tropical storm Debby could put a damper on our stay and visit with family in Chestertown. The property is remarkable and the setting incomparable. Stunning sunsets on the Chester River were equaled by the comfort and style of Harbor View Haven."
Harbor View Haven | Waterfront w/ HOT TUB + Dock!
Be persuaded to experience this vintage cottage by the Sassa
9.4 out of 10, Exceptional, (8)
"We had one of the best vacations ever. Our 9 and 7 year old grandchildren wanted to live there forever! We had a beautiful house and access to the outdoor spaces including a dock for gishing, crabbing and swimming. We were able to make smores over a great fire pit and enjoyed phenominal sunsets from a sitting area overlooking the river. Gene and Suzie, the hosts were on-site and so warm and welcoming. Our every need was met immediately. We will definitely be vacationing at Gregg Neck Cottage...
Be persuaded to experience this vintage cottage by the Sassa
Country Get Away 1 Bedroom Apartment
9.8 out of 10, Exceptional, (28)
"I was there for 10 days in September. Very clean accommodations. Very quiet. I will definently go back if I need to stay in the area!"
The price is AU$167
includes taxes & fees
5 Nov - 6 Nov
Country Get Away 1 Bedroom Apartment
Circa 1900 Home in the Heart of Historic Downtown Chestertown
10.0 out of 10, Exceptional, (62)
"Enjoyed the stay and house very comfortable."
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Historic Downtown Garden Oasis with Private Patio
10.0 out of 10, Exceptional, (22)
"We love this place and would stay here again in a heartbeat. Beautifully decorated with so many details and touches that make it extra special. Such a well done lovely property!!!"
Historic Downtown Garden Oasis with Private Patio
Peaceful country home away in the wilderness
10.0 out of 10, Exceptional, (13)
"So comfortable and prefect. I woken in the early morning and I went to outside and get some fresh air, and chickens around the backyard it was so beautiful. Very cute decorated house! There’s adorable animals made me so happy. Thank you for let us stay! What the wonderful people!"
Peaceful country home away in the wilderness
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (60)
"Great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
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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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Other types of properties in Massey you may be interested in

Bally's Dover Casino Resort
4.0 star property
8.8 out of 10, Excellent, (1773)
"Casino very convenient and clean"
The price is AU$137
includes taxes & fees
10 Oct - 11 Oct
Bally's Dover Casino Resort
Comfort Inn & Suites
2.5 star property
8.8 out of 10, Excellent, (1000)
"Everything was great"
The price is AU$128
includes taxes & fees
21 Oct - 22 Oct
Comfort Inn & Suites
Wyndham Garden Dover
3.0 star property
6.6 out of 10, (985)
"It’s nice"
The price is AU$138
includes taxes & fees
10 Oct - 11 Oct
Wyndham Garden Dover
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.

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?

Captivating Chesapeake experience: This holiday home rental outside of Massey is located on the waterfront, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of books.

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 Bohemia Vista Marina and Elk Neck State Park.

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.