Princess Anne Holiday Rentals

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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Princess Anne holiday rentals

1 bedroom, premium bedding, individually decorated

Cottage in Downtown Chincoteague

Key West Cottages
3.0 star property
9.8 out of 10, Exceptional, (512 reviews)
"This was a Wonderful place to stay!! So much charm a the staff was wonderful! "
United States
CHRISTIE
Key West Cottages
Exterior

Holiday Home in Down the Marsh

Blufin Bungalows & Marina
3.0 star property
9.6 out of 10, Exceptional, (211 reviews)
"yesss amazing stay "
United States
EDA
Blufin Bungalows & Marina
Front of property

Cottage in Parsonsburg

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
The price is HK$719
HK$2,010 total
includes taxes & fees
10 Mar - 11 Mar
6 Mi to Salisbury: Forest-view Sanctuary!
Interior

Cottage in Up the Neck

Cozy cottage w/ creekside patio & fire pit
9.4 out of 10, Exceptional, (137 reviews)
"House was exactly as advertised. Everything worked as expected. This house is one of the few in this town that offered linens, a big selling point for us."
United States
Kato A.
The price is HK$1,065
HK$2,283 total
includes taxes & fees
8 Mar - 9 Mar
Cozy cottage w/ creekside patio & fire pit
2 bedrooms, individually decorated, individually furnished

Apartment in Salisbury

Salisbury Riverfront Lofts
3.0 star property
9.4 out of 10, Exceptional, (23 reviews)
"It was a great stay nice comfortable place "
United States
Adam
The price is HK$557
HK$1,988 total
includes taxes & fees
16 Mar - 17 Mar
Salisbury Riverfront Lofts
Terrace/patio

Holiday Home in Down the Marsh

Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
9.8 out of 10, Exceptional, (25 reviews)
"Loved that it was right on the bay. "
United States
Debra
The price is HK$1,087
HK$1,396 total
includes taxes & fees
15 Mar - 16 Mar
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
Exterior

Holiday Home in Fishing Creek

Riverside Lodge Bed & Breakfast on the Honga River UNIT C
10.0 out of 10, Exceptional, (11 reviews)
"Peggy and Gary are the perfect hosts: welcoming, friendly, attentive and respectful of your preferences. Wonderful views of the Bay and River via the lodge -- including the cupola -- and walking around the majestic property."
United States
Thomas S.
The price is HK$2,111
HK$2,560 total
includes taxes & fees
7 Mar - 8 Mar
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Fridge, microwave, oven, stovetop

Cottage in Deal Island

Deal Island Bay Cottage
9.6 out of 10, Exceptional, (58 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is HK$1,091
HK$2,034 total
includes taxes & fees
7 Mar - 8 Mar
Deal Island Bay Cottage
Interior

Holiday Home in Delmar

3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind
10.0 out of 10, Exceptional, (9 reviews)
"House was as described and just was great. 5 stars all the way around!!! "
United States
Julius D.
The price is HK$1,321
HK$5,386 total
includes taxes & fees
7 Mar - 8 Mar
3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind
Interior

Holiday Home in Crisfield

Cottage near the Bay
8.8 out of 10, Excellent, (52 reviews)
"Great little place "
United States
Eric R.
The price is HK$633
HK$1,458 total
includes taxes & fees
12 Mar - 13 Mar
Cottage near the Bay
Exterior

Holiday Home in Captain's Cove

The purple door at the bay.
9.2 out of 10, Wonderful, (54 reviews)
"Price and location was the primary reason the purple door works for us!"
United States
Patrick O.
The price is HK$1,231
HK$3,522 total
includes taxes & fees
7 Mar - 8 Mar
The purple door at the bay.
TV, DVD player

Condo in Chincoteague Island

Assateague Inn 104 by Seaside Vacations & Sales
9.6 out of 10, Exceptional, (22 reviews)
"Convenient location with everything we needed"
United States
John S.
The price is HK$787
HK$1,475 total
includes taxes & fees
8 Mar - 9 Mar
Assateague Inn 104 by Seaside Vacations & Sales
Interior

Cottage in Captain's Cove

1 Mi to Resort Marina! Greenbackville Retreat
3.0 star property
The price is HK$1,673
HK$4,350 total
includes taxes & fees
19 Mar - 20 Mar
1 Mi to Resort Marina! Greenbackville Retreat
Exterior

Holiday Home in Salisbury

Salisbury Hideaway
10.0 out of 10, Exceptional, (20 reviews)
"This property was wonderful for our trip to Salisbury for my daughter's travel softball tournament. It was only 30-45 minutes from Ocean City (give or take traffic), and very close to many shopping areas and restaurants. The property itself was very clean and provided many necessities. "
United States
Lisa H.
The price is HK$1,188
HK$2,854 total
includes taxes & fees
8 Mar - 9 Mar
Salisbury Hideaway
Interior

Holiday Home in Salisbury

Salisbury Cottage
10.0 out of 10, Exceptional, (35 reviews)
"My family and I had a great stay was a comfy and safe space to relax and enjoy our Halloween weekend would definitely recommend!"
United States
Mackenzie N.
The price is HK$1,345
HK$2,996 total
includes taxes & fees
29 Mar - 30 Mar
Salisbury Cottage
Exterior

Condo in Chincoteague Island

Bella's Beach Retreat by Seaside Vacations & Sales
8.0 out of 10, Very good, (8 reviews)
"What a lovely little space! Everything was clean and just as described. We loved the dock out over the marsh grasses and used it every day - especially since the beach was closed we could still feel close to the water. The staff were super friendly and helpful. "
United States
Mary Kalbach E.
The price is HK$787
HK$1,483 total
includes taxes & fees
9 Mar - 10 Mar
Bella's Beach Retreat by Seaside Vacations & Sales
Fridge, microwave, oven, stovetop

Holiday Home in Pocomoke City

Cozy Barn Loft: Country Views & Central to Beaches
10.0 out of 10, Exceptional, (19 reviews)
"Was wonderfully comfortable and clean. Would definitely recommend. "
United States
Joy D.
The price is HK$1,048
HK$2,093 total
includes taxes & fees
7 Mar - 8 Mar
Cozy Barn Loft: Country Views & Central to Beaches
Interior

Holiday Home in Downtown Chincoteague

The Neigh-Neigh - Location! Location! Location!
10.0 out of 10, Exceptional, (4 reviews)
"Loved staying at this house…plenty of room for everyone."
United States
ashley b.
The price is HK$1,016
HK$3,459 total
includes taxes & fees
7 Mar - 8 Mar
The Neigh-Neigh - Location! Location! Location!
TV, DVD player

Condo in Chincoteague Island

Only 5 min. from the Beach!
9.2 out of 10, Wonderful, (9 reviews)
"Close to everything, quiet, clean"
United States
Eileen D.
The price is HK$936
HK$1,667 total
includes taxes & fees
8 Mar - 9 Mar
Only 5 min. from the Beach!
Terrace/patio

Holiday Home in Smith Island

Historic home on Smith Island w/ dock!
9.6 out of 10, Exceptional, (46 reviews)
"Very nice property! Spacious rooms, great host"
United States
Sara L.
The price is HK$1,556
HK$2,353 total
includes taxes & fees
31 Mar - 1 Apr
Historic home on Smith Island w/ dock!
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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Top Princess Anne Hotel Reviews

Waterside Inn

Waterside Inn

10/10 Excellent
"Yes"
Valarie 1-night trip
Posted 4 days ago
Waterside Inn

Find out more about Princess Anne

Search for holiday rentals in Princess Anne on Expedia! You can easily find your home rentals, villas, holiday apartments in Princess Anne using one of the methods below:

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Look no further and take a look at our great range of rental properties in Princess Anne!

Frequently asked questions

Can I find a holiday rental in Princess Anne?

Yes, there are holiday rentals close to the most popular sights in Princess Anne, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Princess Anne has a good selection of restaurants. Make sure you have time to check out the beaches and shopping during your trip.

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

Blufin Bungalows & Marina: This holiday home rental outside of Princess Anne is on the beach, and equipped with free WiFi and a TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave.

What can I see and do in Princess Anne?

Mount Vernon Beach and Ballards Island are a couple of lovely local spots to get outside and enjoy nature. Somerset County Library and Princess Anne Town Hall are other places to visit while you're in town.

What are holiday rentals like in Princess Anne?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Princess Anne. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for family trips.