Estia Villas - Vacation Rentals in Princess Anne
House
10.0
(
40 Reviews
)
5 Bedrooms
3 Bathrooms
10 Guests
3100 ft²
-
Private Pool -
Oceanfront -
Parking -
Pool
US $934
/Night
7 Nights - $6,541
House
10.0
(
12 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1248.61 ft²
-
Parking
-
View -
Air Conditioner -
Internet
US $383
/Night
7 Nights - $2,681
Bed & Breakfast
10.0
(
122 Reviews
)
1 Bedroom
1 Bathroom
-
Breakfast -
Parking
-
Balcony/Terrace -
View
US $195
/Night
7 Nights - $1,365
House
10.0
(
39 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
-
Oceanfront
-
Parking
-
Ocean View -
Balcony/Terrace
US $384
/Night
7 Nights - $2,686
House
10.0
(
22 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $370
/Night
7 Nights - $2,590
House
10.0
(
13 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Oceanfront
-
Hot Tub -
Parking
-
Ocean View
US $595
/Night
7 Nights - $4,166
New
House
10.0
(
5 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
-
Kitchen -
Air Conditioner
-
Internet
-
Pet Friendly
US $333
/Night
7 Nights - $2,332
House
10.0
(
3 Reviews
)
5 Bedrooms
3 Bathrooms
11 Guests
3684 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $777
/Night
7 Nights - $5,437
See More Princess Anne Vacation Rentals
Luxury Places to Stay in Princess Anne
Over 79+
Luxury Places to Stay in or Near Princess Anne
New
House
10.0
(
1 Review
)
7 Bedrooms
7 Bathrooms
14 Guests
-
Air Conditioner
-
Internet
-
Child Friendly -
Bedding/Linens
US $920
/Night
7 Nights - $6,441
House
9.8
(
7 Reviews
)
5 Bedrooms
4 Bathrooms
12 Guests
3785 ft²
-
Hot Tub
-
Parking
-
Kitchen
-
Air Conditioner
US $805
/Night
7 Nights - $5,636
Cottage
4 Bedrooms
2 Bathrooms
8 Guests
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $620
/Night
7 Nights - $4,337
House
10.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
4 Guests
1256 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $596
/Night
7 Nights - $4,174
Hotel
8.7
(
206 Reviews
)
204.51 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
US $498
/Night
7 Nights - $3,484
House
8.6
(
4 Reviews
)
4 Bedrooms
2 Bathrooms
7 Guests
2068 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $458
/Night
7 Nights - $3,209
House
7.5
(
2 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
2658.69 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
View
US $439
/Night
7 Nights - $3,071
House
4 Bedrooms
3 Bathrooms
10 Guests
2098.96 ft²
-
Private Beach -
Oceanfront
-
Parking
-
Ocean View
US $432
/Night
7 Nights - $3,024
Find More Princess Anne Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Princess Anne
Over 9+
Top-Rated Vacation Rentals with a Pool in or Near Princess Anne
Hotel
10.0
(
39 Reviews
)
-
Breakfast
-
Parking
-
Pool
-
Internet
US $166
/Night
7 Nights - $1,163
US $403
/Night
7 Nights - $2,824
Hotel
9.7
(
34 Reviews
)
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $320
/Night
7 Nights - $2,241
US $128
/Night
7 Nights - $894
Hotel
8.8
(
236 Reviews
)
3767.37 ft²
-
Private Pool
-
Breakfast
-
Parking
-
Pool
US $149
/Night
7 Nights - $1,045
Hotel
8.0
(
2 Reviews
)
1144.05 ft²
-
Private Beach
-
Oceanfront
-
Parking
-
Pool
US $425
/Night
7 Nights - $2,975
US $95
/Night
7 Nights - $664
Cabin
5.9
(
193 Reviews
)
52 Bedrooms
1 Bathroom
22 Guests
301.39 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $103
/Night
7 Nights - $723
Pet-Friendly Vacation Rentals in Princess Anne
Over 19+
Pet-Friendly Vacation Rentals in or Near Princess Anne
New
Cottage
10.0
(
1 Review
)
2 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $235
/Night
7 Nights - $1,644
House
4 Bedrooms
2 Bathrooms
7 Guests
2066.67 ft²
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
US $413
/Night
7 Nights - $2,890
Cottage
9.8
(
17 Reviews
)
2 Bedrooms
1 Bathroom
7 Guests
1152 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $329
/Night
7 Nights - $2,301
Cottage
9.6
(
60 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1550 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
View
US $280
/Night
7 Nights - $1,959
New
Cottage
2 Bedrooms
1 Bathroom
4 Guests
-
Air Conditioner
-
Internet
-
Pet Friendly
-
Child Friendly
US $373
/Night
7 Nights - $2,608
Apartment
10.0
(
13 Reviews
)
3 Bedrooms
1 Bathroom
4 Guests
750 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $337
/Night
7 Nights - $2,362
New
House
10.0
(
11 Reviews
)
3 Bedrooms
2 Bathrooms
12 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $347
/Night
7 Nights - $2,430
New
Apartment
1 Bedroom
1 Bathroom
4 Guests
-
Balcony/Terrace
-
Kitchen
-
Pet Friendly
-
Child Friendly
US $141
/Night
7 Nights - $987
See More Pet-Friendly Vacation Rentals in Princess Anne on PetFriendly.io
Large Vacation Homes & Villas in Princess Anne
Over 12+
Large Vacation Homes & Villas in or Near Princess Anne
House
3 Bedrooms
2 Bathrooms
11 Guests
1200 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $369
/Night
7 Nights - $2,581
House
10.0
(
1 Review
)
5 Bedrooms
4 Bathrooms
11 Guests
3681.26 ft²
-
Parking
-
Internet
-
Child Friendly
-
Sports/Activities
US $403
/Night
7 Nights - $2,819
House
10.0
(
1 Review
)
7 Bedrooms
4 Bathrooms
17 Guests
3143 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $922
/Night
7 Nights - $6,457
House
9.8
(
6 Reviews
)
4 Bedrooms
2 Bathrooms
10 Guests
2100 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $498
/Night
7 Nights - $3,485
House
7 Bedrooms
4 Bathrooms
15 Guests
3800 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $927
/Night
7 Nights - $6,486
House
10.0
(
66 Reviews
)
8 Bedrooms
3 Bathrooms
24 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $990
/Night
7 Nights - $6,928
House
10.0
(
6 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
2500 ft²
-
Air Conditioner
-
Internet
-
Child Friendly
-
Laundry
US $469
/Night
7 Nights - $3,281
House
5.0
(
57 Reviews
)
8 Bedrooms
4 Bathrooms
20 Guests
3500 ft²
-
Oceanfront
-
Ocean View
-
Balcony/Terrace
-
View
US $1,100
/Night
7 Nights - $7,700
See More Family Vacation Rentals in Princess Anne on FVR
Wheelchair Accessible Vacation Homes in Princess Anne
Over 1+
Wheelchair Accessible Vacation Homes in or Near Princess Anne
Hotel
8.7
(
172 Reviews
)
226.05 ft²
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Air Conditioner
US $83
/Night
7 Nights - $581
Princess Anne Vacation Rentals and Airbnb Places to Stay Under $200
Over 12+
Princess Anne Vacation Rentals and Airbnb Places to Stay Under $200
Cottage
2 Bedrooms
1 Bathroom
2 Guests
732 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $179
/Night
7 Nights - $1,251
Apartment
2 Bedrooms
2 Bathrooms
8 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
View
US $164
/Night
7 Nights - $1,148
Hotel
7.0
(
65 Reviews
)
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $83
/Night
7 Nights - $583
House
2 Bedrooms
2 Bathrooms
6 Guests
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $128
/Night
7 Nights - $897
Bed & Breakfast
1 Bedroom
1 Bathroom
2 Guests
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Air Conditioner
US $158
/Night
7 Nights - $1,106
Bed & Breakfast
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Air Conditioner
-
Internet
-
Bedding/Linens
US $158
/Night
7 Nights - $1,106
Apartment
10.0
(
4 Reviews
)
1 Bedroom
1 Bathroom
5 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $177
/Night
7 Nights - $1,237
Condo
4.7
(
13 Reviews
)
2 Bedrooms
3 Bathrooms
1179 ft²
-
Oceanfront
-
Ocean View
-
Balcony/Terrace
-
View
US $125
/Night
7 Nights - $875
See More Princess Anne Vacation Rental Deals
Instantly Bookable Vacation Homes in Princess Anne
Over 10+
Instantly Bookable Vacation Homes in or Near Princess Anne
House
9.4
(
11 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
2660 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $393
/Night
7 Nights - $2,752
Apartment
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
2 Guests
450 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $227
/Night
7 Nights - $1,586
House
9.8
(
9 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $334
/Night
7 Nights - $2,336
House
9.6
(
7 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
1550 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $422
/Night
7 Nights - $2,953
House
9.2
(
9 Reviews
)
4 Bedrooms
3 Bathrooms
6 Guests
1460 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $214
/Night
7 Nights - $1,496
House
8.8
(
3 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $237
/Night
7 Nights - $1,657
Cabin
8.0
(
11 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
-
Hot Tub
-
Parking
-
Spa -
Kitchen
US $276
/Night
7 Nights - $1,929
House
4.9
(
15 Reviews
)
4 Bedrooms
3 Bathrooms
9 Guests
1500 ft²
-
Oceanfront
-
Ocean View
-
Balcony/Terrace
-
View
US $350
/Night
7 Nights - $2,450
About Princess Anne Vacation Rentals
With more than 88 Princess Anne vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Princess Anne.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Princess Anne, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Princess Anne. Places to stay near Princess Anne are 949.06 ft² on average, with prices averaging US $371 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Princess Anne with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Princess Anne
| Type | Count |
|---|---|
| Vacation Homes | 53 |
| Hotels | 12 |
| Cottages | 8 |
| Holiday Apartments | 6 |
| B&B | 4 |
| Cabin Rentals | 3 |
| Others | 1 |
Use these Quick Filters to Find a Vacation Rental in Princess Anne
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Princess Anne.
Weather in Princess Anne
View the weather forecast for Princess Anne before booking your Princess Anne 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 Princess Anne, MD
Estiavillas offers a large selection of top attractions around Princess Anne. Research things to do on your vacation before you visit Princess Anne.
University of Maryland Eastern Shore
Chesapeake Health Care
Salisbury University
Chincoteague National Wildlife Refuge
Wicomico Youth and Civic Center
Wallops Flight Facility
Smith Island
Salisbury Zoo
Assateague Point
Blackwater National Wildlife Refuge
Tangier Island
Wor-Wic Community College
Centre at Salisbury
Coco's Funhouse
Poplar Hill Mansion
Skydive Delmarva
Ward Museum of Wildfowl Art
Pocomoke River State Park
Pocomoke River Canoe Company
Layton's Chance Vineyard and Winery
Other Places to Stay Near Princess Anne, MD
Princess Anne Vacation Rental Frequently Asked Questions
Which vacation homes in Princess Anne are best for families?
If you are looking for a family-friendly vacation home in Princess Anne, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Princess Anne:
How many vacation rentals are available in Princess Anne?
Currently, the total number of properties listed in 2026 is over 88 in the Princess Anne area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Princess Anne.
