Holiday Rentals in Massey

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Holiday Rentals in Massey

Guest Lodge | Private Pool | Outdoor Dining | Game Room

Guest Lodge | Private Pool | Outdoor Dining | Game Room

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (44)
"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!"
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Newly renovated single family home with attached guest suite

Newly renovated single family home with attached guest suite

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

9.8 out of 10, Exceptional, (13)
"The house was beautiful. We enjoyed the pool. The kitchen was wonderful. We did wish we could warm up the house a little more. We loved that the house had so many bathrooms. The only improvement would be to state that there are 5 bedrooms with en-suites."
Stunning waterfront villa with indoor pool and kids swing set and play area.

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (78)
"Very clean, excellent communications,"
The price is €155
includes taxes & fees
4 Mar - 5 Mar
First Floor Studio Apartment in Historic Chestertown

Country Get Away 1 Bedroom Apartment

9.8 out of 10, Exceptional, (29)
"We were attending my niece's wedding. Our stay was located in the beautiful countryside yet quick access to places to eat. Our apartment was decorated so cute and for the season. Very, Very clean and I would stay again!"
The price is €111
includes taxes & fees
3 Mar - 4 Mar
Country Get Away 1 Bedroom Apartment

Chesapeake Retreat with hot tub. Charming 2 Bed, 1 Bath Home in Chesapeake City

2.0 star property
10.0 out of 10, Exceptional, (2)
"Our stay was an abundant blessing. The hot tub was just the added bonus for those chilly winter evenings. Communication with Jon was superb and his kindness and consideration go above and beyond a 5 Star review!!! Thanks for allowing our family an awesome Christmas!! We can’t wait to be back!!"
Chesapeake Retreat with hot tub. Charming 2 Bed, 1 Bath Home in Chesapeake City

Newly restored apartment in the heart of Chestertown

9.8 out of 10, Exceptional, (19)
"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 "
Newly restored apartment in the heart of Chestertown

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

10.0 out of 10, Exceptional, (78)
"We had a wonderful stay! Really enjoyed the eagles and osprey. The hot tub was amazing and the fire pit was nice to enjoy in the cold weather. All amenities were there that we needed, the location is great and the town is really cute. We will be back! "
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

Saybrook Hall | Pickleball + Pool + Hot Tub

Saybrook Hall | Pickleball + Pool + Hot Tub

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (13)
"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). "
Chesapeake City Quiet Overlook

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (4)
"An absolute stunning view from the four season enclosed porch. This beautiful home is well equiped and a perfect location for Fall and Winter hunting trips near Chestertown/Kennedyville. Plenty of rooms/bathrooms/beds. Highly recommend!!!"
Pet-Friendly Home on Chester River w/ Dock!

Waterfront Home & Dock,Remodel Kitchen,Eastern shore, Betterton,Chestertown MD.

9.8 out of 10, Exceptional, (87)
"The house and location on Still Pond Maryland was great!! House was clean and tiddy. Caught perch, catfish and bass off their dock!! Area is beautiful and quiet! "
Waterfront Home & Dock,Remodel Kitchen,Eastern shore, Betterton,Chestertown MD.

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

10.0 out of 10, Exceptional, (34)
"Great location, wonderful place and fantastic owner. Recommendations on restaurants and things to do were perfect. We had a great time and Betty Ann was very kind and responsive in communications. Will definitely visit again!"
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

Spring Season in Chesapeake City, MD Old Lock View @ C&D Canal

10.0 out of 10, Exceptional, (65)
"The place was great!!"
Spring Season in Chesapeake City, MD Old Lock View @ C&D Canal

Dover Home - 2 Mi to Delaware State University!

9.2 out of 10, Wonderful, (5)
"We attended a program at the college "
Dover Home - 2 Mi to Delaware State University!

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

10.0 out of 10, Exceptional, (75)
"Spacious, extremely well maintained and appointed home on the Chester River. We would definitely stay here again. "
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (8)
"Property was clean and close to everything in Chesapeake City"
The price is €284
includes taxes & fees
7 Mar - 8 Mar
Historic Chesapeake City Stay

Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

9.8 out of 10, Exceptional, (16)
"From the moment we entered the property the relaxation began!! The location and history of the area was interesting. The rooms were comfortable and homey. The screened porch was the central space and the reading knook was never empty. All enjoyed kayaking and paddle boarding in the calm river water. All agreed we would like to revisit the property again. Communication with the owners was prompt and courteous. Thank you"
The price is €1,088
includes taxes & fees
21 Feb - 22 Feb
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

9.8 out of 10, Exceptional, (80)
"Beautiful location on the river. We were visiting family in the fall so did not use the kayaks available—maybe next time! Nice to have a dog-friendly place too. Great and prompt communication with the hosts."
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
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, (2269)
"Great staff, welcoming and helpful. Overall amazing experience. Would suggest softer tissue and a microwave even if its in the vending area. But we had a great stay."
The price is €84
includes taxes & fees
26 Feb - 27 Feb
Bally's Dover Casino Resort

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (197)
"Everything "
The price is €103
includes taxes & fees
9 Mar - 10 Mar
Fairfield Inn & Suites by Marriott Middletown

Comfort Inn & Suites

2.5 star property
8.8 out of 10, Excellent, (1000)
"Pool and Hot tub were great "
The price is €86
includes taxes & fees
9 Mar - 10 Mar
Comfort Inn & Suites
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?

Guest Lodge | Private Pool | Outdoor Dining | Game Room: This holiday home rental outside of Massey is equipped with an arcade/games room, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 Crow Farm and Vineyard and Tilmon's Island Winery.

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.