Massey Holiday Rentals
10.0
Exceptional
(89 Reviews)
650 ft²
5 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $152/Night
For 7 Nights US $1,061
New
7997.59 ft²
18 Guests
5 Bedrooms
6 Bathrooms
Free Cancellation
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $1,163/Night
For 7 Nights US $8,139
9.2
Exceptional
(669 Reviews)
- Wilmington
- Middletown
- 0.87 mi to center
1 Bathroom
Family Friendly
Hotel
- Pool
- Breakfast
- Kitchen
US $121/Night
For 7 Nights US $847
10.0
Exceptional
(16 Reviews)
- Maryland
- Chestertown
- 8.68 mi to center
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $234/Night
For 7 Nights US $1,640
New
1797.57 ft²
8 Guests
4 Bedrooms
2 Bathrooms
House
- Hot Tub
- Fireplace/Heating
- View
US $1,162/Night
For 7 Nights US $8,134
New
1798 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $348/Night
For 7 Nights US $2,436
10.0
Exceptional
(2 Reviews)
- Maryland
- Sudlersville
- 3.88 mi to center
3887 ft²
25 Guests
7 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $1,308/Night
For 7 Nights US $9,153
10.0
Exceptional
(2 Reviews)
9 Guests
3 Bedrooms
2 Bathrooms
Group Friendly
House
- Fireplace/Heating
- Parking
- Air Conditioner
US $401/Night
For 7 Nights US $2,804
10.0
Exceptional
(1 Review)
1798 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $557/Night
For 7 Nights US $3,898
Luxury Holiday Rentals in Massey
Over 73+ Luxury Holiday Rentals in or Near Massey
10.0
Exceptional
(61 Reviews)
- Maryland
- Chestertown
- 5.92 mi to center
8 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $1,974/Night
For 7 Nights US $13,817
9.6
Exceptional
(23 Reviews)
10000 ft²
16 Guests
7 Bedrooms
6 Bathrooms
Family Friendly
Villa
- Hot Tub
- Fireplace/Heating
- Pool
US $1,548/Night
For 7 Nights US $10,833
New
- Maryland
- Sudlersville
- 3.88 mi to center
3885.77 ft²
25 Guests
1 Bedroom
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Parking
US $1,539/Night
For 7 Nights US $10,771
10.0
Exceptional
(28 Reviews)
- Maryland
- Chestertown
- 5.36 mi to center
6000 ft²
13 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $1,265/Night
For 7 Nights US $8,858
8.0
Excellent
(1 Review)
15 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $897/Night
For 7 Nights US $6,280
10.0
Exceptional
(4 Reviews)
7998 ft²
18 Guests
5 Bedrooms
6 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
US $873/Night
For 7 Nights US $6,111
New
- Maryland
- Chesapeake City
- 2.33 mi to center
7104.18 ft²
38 Guests
14 Bedrooms
8 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- View
US $748/Night
For 7 Nights US $5,234
9.8
Exceptional
(25 Reviews)
12 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $647/Night
For 7 Nights US $4,526
10.0
Exceptional
(1 Review)
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $589/Night
For 7 Nights US $4,123
Top-Rated Holiday Rentals with a Pool in Massey
Over 13+ The Best Private Villas and Holiday Rentals in Massey with a Pool
9.8
Exceptional
(81 Reviews)
2270 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $434/Night
For 7 Nights US $3,038
9.2
Exceptional
(354 Reviews)
- Wilmington
- Middletown
- 1.33 mi to center
1 Bathroom
Couples Retreat
Hotel
- Pool
- Breakfast
- Air Conditioner
US $110/Night
For 7 Nights US $769
9.1
Exceptional
(200 Reviews)
- Wilmington
- Middletown
- 0.87 mi to center
333.68 ft²
10 Bathrooms
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $152/Night
For 7 Nights US $1,062
8.9
Fabulous
(250 Reviews)
- Wilmington
- Middletown
- 1.32 mi to center
1 Bathroom
Family Friendly
Hotel
- Private Pool
- Pool
- Balcony/Terrace
US $238/Night
For 7 Nights US $1,664
8.8
Fabulous
(883 Reviews)
- Wilmington
- Middletown
- 0.73 mi to center
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Pool
- Breakfast
US $106/Night
For 7 Nights US $739
8.3
Excellent
(185 Reviews)
- Wilmington
- Middletown
- 0.73 mi to center
322.92 ft²
1 Bathroom
Ocean View
Hotel
- Private Pool
- Oceanfront
- Hot Tub
US $255/Night
For 7 Nights US $1,783
10.0
Exceptional
(61 Reviews)
- Maryland
- Chestertown
- 5.57 mi to center
4000 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
US $1,025/Night
For 7 Nights US $7,173
9.6
Exceptional
(35 Reviews)
2416 ft²
16 Guests
5 Bedrooms
6 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $849/Night
For 7 Nights US $5,945
5.0
Average
(1 Review)
18 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
US $1,295/Night
For 7 Nights US $9,065
Pet-Friendly Holiday Rentals in Massey
Over 13+ Pet-Friendly Holiday Rentals in or Near Massey
9.8
Exceptional
(60 Reviews)
1000 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
US $207/Night
For 7 Nights US $1,447
New
1001.04 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Spa
- Fireplace/Heating
US $217/Night
For 7 Nights US $1,519
8.6
Fabulous
(4 Reviews)
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $186/Night
For 7 Nights US $1,299
New
4 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Fireplace/Heating
- Pet Friendly
- Parking
US $246/Night
For 7 Nights US $1,725
8.6
Fabulous
(4 Reviews)
- Maryland
- Kennedyville
- 0.14 mi to center
1600 ft²
7 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $243/Night
For 7 Nights US $1,699
New
- Wilmington
- Middletown
- 0.99 mi to center
7 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $224/Night
For 7 Nights US $1,568
10.0
Exceptional
(18 Reviews)
1000 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
US $283/Night
For 7 Nights US $1,981
New
8 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $255/Night
For 7 Nights US $1,783
10.0
Exceptional
(2 Reviews)
1743 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $677/Night
For 7 Nights US $4,738
Large Holiday Rentals and Private Villas in Massey
Over 10+ Large Holiday Rentals and Private Villas in or Near Massey
9.8
Exceptional
(53 Reviews)
10 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $384/Night
For 7 Nights US $2,686
New
3196.88 ft²
10 Guests
7 Bedrooms
4 Bathrooms
House
- Hot Tub
- Fireplace/Heating
- Parking
US $537/Night
For 7 Nights US $3,757
9.8
Exceptional
(9 Reviews)
3200 ft²
10 Guests
7 Bedrooms
4 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Kitchen
US $532/Night
For 7 Nights US $3,724
10.0
Exceptional
(6 Reviews)
8 Guests
7 Bedrooms
4 Bathrooms
Family Friendly
Other
- Hot Tub
- Fireplace/Heating
- Kitchen
US $451/Night
For 7 Nights US $3,154
10.0
Exceptional
(1 Review)
- Maryland
- Chesapeake City
- 2.33 mi to center
30 Guests
12 Bedrooms
10 Bathrooms
Group Friendly
House
- Child Friendly
US $3,689/Night
For 7 Nights US $25,822
New
- Maryland
- Chesapeake City
- 2.11 mi to center
16 Guests
9 Bedrooms
7 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Kitchen
Unlock the Best Price
9.0
Exceptional
(2 Reviews)
- Wilmington
- Middletown
- 0.29 mi to center
1 ft²
2 Guests
8 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $175/Night
For 7 Nights US $1,226
4.8
Average
(4 Reviews)
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Kitchen
- Air Conditioner
- Internet
US $199/Night
For 7 Nights US $1,393
New
16 Guests
7 Bedrooms
6 Bathrooms
Family Friendly
Villa
- Private Pool
- Hot Tub
- Spa
US $4,257/Night
For 7 Nights US $29,796
Massey Private Villas and Holiday Homes Under $200
Over 18+ Massey Private Villas and Holiday Homes Under $200
9.6
Exceptional
(11 Reviews)
- Wilmington
- Middletown
- 0.87 mi to center
1550 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $187/Night
For 7 Nights US $1,306
New
2 Guests
1 Bedroom
1 Bathroom
Bed & Breakfast
- Fireplace/Heating
- Balcony/Terrace
- View
US $95/Night
For 7 Nights US $662
9.8
Exceptional
(52 Reviews)
3 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
US $143/Night
For 7 Nights US $1,003
9.8
Exceptional
(9 Reviews)
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $165/Night
For 7 Nights US $1,156
9.6
Exceptional
(20 Reviews)
- Maryland
- Millington
- 0.14 mi to center
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $125/Night
For 7 Nights US $876
New
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $186/Night
For 7 Nights US $1,305
9.4
Exceptional
(8 Reviews)
- Wilmington
- Middletown
- 0.87 mi to center
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $187/Night
For 7 Nights US $1,312
4.0
Average
(1 Review)
- Wilmington
- Middletown
- 0.10 mi to center
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $101/Night
For 7 Nights US $709
New
3 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $172/Night
For 7 Nights US $1,207
Instantly Bookable Holiday Homes in Massey
Over 16+ Instantly Bookable Holiday Homes in or Near Massey
10.0
Exceptional
(2 Reviews)
- Maryland
- Chestertown
- 8.61 mi to center
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $360/Night
For 7 Nights US $2,523
New
2200 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $322/Night
For 7 Nights US $2,251
10.0
Exceptional
(19 Reviews)
6 Guests
3 Bedrooms
2 Bathrooms
House
- Child Friendly
US $208/Night
For 7 Nights US $1,454
10.0
Exceptional
(1 Review)
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $545/Night
For 7 Nights US $3,818
9.2
Exceptional
(11 Reviews)
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $348/Night
For 7 Nights US $2,436
9.2
Exceptional
(9 Reviews)
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $279/Night
For 7 Nights US $1,954
10.0
Exceptional
(4 Reviews)
2200 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $315/Night
For 7 Nights US $2,203
10.0
Exceptional
(4 Reviews)
1500 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $227/Night
For 7 Nights US $1,588
New
- Wilmington
- Middletown
- 1.24 mi to center
3240 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $393/Night
For 7 Nights US $2,753
Book a Last Minute Place to Stay in Massey
About Casai's Private Villas and Holiday Rentals in Massey
Discover more than 82 vacation rentals available in Massey. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Massey.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Massey, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Massey. On average, places to stay near Massey offer 1267.16 ft², with nightly prices averaging US $643.
With Casai, finding and comparing holiday rentals in Massey is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Massey
| Type | Count |
|---|---|
| Vacation Homes | 52 |
| Holiday Apartments | 8 |
| Cottages | 8 |
| Villas | 3 |
Use these Quick Filters to Find a Holiday Rental in Massey
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Massey.
Weather in Massey, MD
View the weather forecast for Massey before booking your Massey Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Massey, MD
Casai offers a large selection of top attractions around Massey . Research things to do on your vacation before you visit Massey.
Frequently Asked Questions About Massey?
What are the top holiday rentals in Massey?
With numerous options available in Massey, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Massey:
- Life is better at the RIVER!-Cozy waterfront cottage
- STONE RIVERSIDE COTTAGE is just a few steps from the SASSAFRAS RIVERS edge
- Eastern Shore Get Away
- Eagles Point Landing
- Historic Manor House on Beautiful Eastern Shore Estate
- Peaceful country home away in the wilderness
- Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
- Waterfront venue on secluded 60 acres with 2 homes great for a family retreat
- Waterfront Lodge packed with Amenities
- Guest Lodge | Private Pool | Outdoor Dining | Game Room
Which holiday homes in Massey are best for families?
If you're searching for a family-friendly holiday home in Massey, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Massey:
- STONE RIVERSIDE COTTAGE is just a few steps from the SASSAFRAS RIVERS edge
- Patio and Water Views Serene Bohemia River Escape!
- Life is better at the RIVER!-Cozy waterfront cottage
How many Casai.com holiday rentals are available in Massey?
As of 2026, Casai boasts over 82 properties listed in the Massey area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Massey.
People Also Ask
Finding the best prices in Massey
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