Holiday Rentals in Pittsville

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Our top choices for Pittsville holiday rentals

Coconut Malorie Resort Ocean City, Ascend Collection Hotel

Coconut Malorie Resort Ocean City, Ascend Collection Hotel
3.0 star property
Midtown Ocean City
7.4 out of 10, Good, (1297)
"Scenic area with wonderful wooden bridges and view of water. There was no hot water to shower, but not a deal breaker."
United States
Isolda
The price is €83
includes taxes & fees
25 Jan - 26 Jan 2026
Coconut Malorie Resort Ocean City, Ascend Collection Hotel

"FENWICK ISL. WATERFRONT VACATION HOME AT THE BEACH W / BOAT DOCK, RAMP & POOL""

"FENWICK ISL. WATERFRONT VACATION HOME AT THE BEACH W / BOAT DOCK, RAMP & POOL""
Selbyville
9.2 out of 10, Wonderful, (118)
"Plenty of room, and everything you need for a few nights."
United States
Michael A.
The price is €243
includes taxes & fees
27 Dec - 28 Dec
"FENWICK ISL. WATERFRONT VACATION HOME AT THE BEACH W / BOAT DOCK, RAMP & POOL""

Comfortable cottage in gated community, 5 mins to OC and Assateague

Comfortable cottage in gated community, 5 mins to OC and Assateague
Assateague Pointe
9.8 out of 10, Exceptional, (43)
"This was the perfect little home for our stay. Everything was clean and comfortable and “cozy”. The location was wonderful with easy access to both Assateague Island and Ocean City. Everything needed for a great stay was provided. We are already planning our vacation for next year and will definitely book again. "
United States
Alecia C.
The price is €266
includes taxes & fees
4 Jan - 5 Jan 2026
Comfortable cottage in gated community, 5 mins to OC and Assateague

Boardwalk One

Boardwalk One
3.0 star property
Downtown Ocean City
7.4 out of 10, Good, (170)
"Close to boardwalk, beach, shopping and dining. Also it was very affordable."
United States
ANGELA
Boardwalk One

Mallard Lakes Waterfront Beach Condo in Fenwick Island with Two Pools

Mallard Lakes Waterfront Beach Condo in Fenwick Island with Two Pools
Selbyville
9.8 out of 10, Exceptional, (39)
"Loved this property! Owners were very responsive! "
United States
Michelle K.
The price is €265
includes taxes & fees
27 Dec - 28 Dec
Mallard Lakes Waterfront Beach Condo in Fenwick Island with Two Pools

BeachParadise1208-Charming 4BR Townhouse•DOWNTOWN•Short walk to Beach&Boardwalk

BeachParadise1208-Charming 4BR Townhouse•DOWNTOWN•Short walk to Beach&Boardwalk
2.0 star property
Downtown Ocean City
10.0 out of 10, Exceptional, (1)
"Great place to stay!"
United States
Joseph D.
The price is €261
includes taxes & fees
5 Jan - 6 Jan 2026
BeachParadise1208-Charming 4BR Townhouse•DOWNTOWN•Short walk to Beach&Boardwalk

Bethany Beach and Close by Marinas! Family and Pet Friendly!!

Bethany Beach and Close by Marinas! Family and Pet Friendly!!
Ocean View
9.2 out of 10, Wonderful, (79)
"The house and property was very spacious and comfortable. We enjoyed our stay and visit to the area very much."
United States
gisela j.
The price is €319
includes taxes & fees
29 Dec - 30 Dec
Bethany Beach and Close by Marinas! Family and Pet Friendly!!

Shore Point Cottages

Shore Point Cottages
3.0 star property
Berlin
9.4 out of 10, Exceptional, (300)
"Was a great place to bring kids and dogs! "
United States
AMANDA
Shore Point Cottages

Oceanside Haven -Steps to Sand + Indoor Pool + Game Rm - Perfect Beach Getaway

Oceanside Haven -Steps to Sand + Indoor Pool + Game Rm - Perfect Beach Getaway
North Ocean City
10.0 out of 10, Exceptional, (18)
"The condo is beautifully decorated and only steps from the beach! "
United States
Pamela H.
The price is €219
includes taxes & fees
29 Dec - 30 Dec
Oceanside Haven -Steps to Sand + Indoor Pool + Game Rm - Perfect Beach Getaway

Ocean calling & country concert availability!

Ocean calling & country concert availability!
North Ocean City
9.0 out of 10, Wonderful, (35)
"We really enjoyed our stay here! Close to the beach and in walking distance of a lot of activities but also very quiet! Loved it!"
United States
Renee P.
The price is €170
includes taxes & fees
29 Dec - 30 Dec
Ocean calling & country concert availability!

EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!

EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!
Georgetown
9.8 out of 10, Exceptional, (47)
"Very thoughtful and hospitable hosts. We had a lovely time!"
United States
Eve S.
The price is €171
includes taxes & fees
5 Jan - 6 Jan 2026
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!

Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo

Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo
Downtown Ocean City
9.8 out of 10, Exceptional, (62)
"The condo was very convenient to get to the beach. Beautiful view of the bay. Plenty of room for everyone to enjoy the stay. "
United States
David H.
The price is €308
includes taxes & fees
4 Jan - 5 Jan 2026
Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo

On Main Street - Apartment C - Berlin, MD

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.4 out of 10, Exceptional, (28)
"We loved everything about our stay! This place is adorable and the location is awesome!"
United States
kelly K.
The price is €194
includes taxes & fees
1 Jan - 2 Jan 2026
On Main Street - Apartment C - Berlin, MD

#1 Rated Condo, Oceanfront, with Bay View Too

#1 Rated Condo, Oceanfront, with Bay View Too
North Ocean City
10.0 out of 10, Exceptional, (317)
"Great location"
United States
Joshua I.
The price is €246
includes taxes & fees
29 Dec - 30 Dec
#1 Rated Condo, Oceanfront, with Bay View Too

BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!

BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!
North Ocean City
9.8 out of 10, Exceptional, (135)
"Very lovely pkace!! Would def book again!!"
United States
Brenda F.
The price is €269
includes taxes & fees
4 Jan - 5 Jan 2026
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!

Beach Paradise VII-Brand New Luxury Townhouse with Pool, Garage, and Water View

Beach Paradise VII-Brand New Luxury Townhouse with Pool, Garage, and Water View
Downtown Ocean City
9.2 out of 10, Wonderful, (19)
"Really nice place,had everything we needed very elegant and relaxing,tvs nice and updated will come back again "
United States
George H.
The price is €263
includes taxes & fees
20 Jan - 21 Jan 2026
Beach Paradise VII-Brand New Luxury Townhouse with Pool, Garage, and Water View

Charming 2-Bed Condo Steps From the Beach!

Charming 2-Bed Condo Steps From the Beach!
North Ocean City
10.0 out of 10, Exceptional, (32)
"We were very happy with our stay. "
United States
Stefanie N.
The price is €290
includes taxes & fees
27 Dec - 28 Dec
Charming 2-Bed Condo Steps From the Beach!

Quiet street in midtown that is close enough to walk to restaurants & shopping.

Quiet street in midtown that is close enough to walk to restaurants & shopping.
North Ocean City
10.0 out of 10, Exceptional, (14)
"The property was small but was perfect for what we needed it for , it had all the amenities and was cozy and quiet …short walk to the beach and restaurants …perfect location "
United States
Kirsten d.
The price is €245
includes taxes & fees
27 Dec - 28 Dec
Quiet street in midtown that is close enough to walk to restaurants & shopping.

⭐️203 Bimini Large Direct Oceanfront Epic Views⭐️

⭐️203 Bimini Large Direct Oceanfront Epic Views⭐️
North Ocean City
9.6 out of 10, Exceptional, (24)
" Fantastic property. Great ocean view, clean, close to many different restaurants. Excellent amenities. We will be back. "
United States
Damian J.
The price is €360
includes taxes & fees
27 Dec - 28 Dec
⭐️203 Bimini Large Direct Oceanfront Epic Views⭐️

Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews

Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews
North Ocean City
9.6 out of 10, Exceptional, (93)
"Nice place. Great views"
United States
Jill M.
The price is €383
includes taxes & fees
3 Jan - 4 Jan 2026
Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews
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 Pittsville Hotel Reviews

Find out more about Pittsville

Everything you need to know about Pittsville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pittsville holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Pittsville holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pittsville. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pittsville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pittsville holiday rentals we have selected for you start as low as €83 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pittsville rentals

At Expedia, we put the best Pittsville holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Pittsville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pittsville holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pittsville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Pittsville?

Yes, there are holiday rentals close to the most popular sights in Pittsville, 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 Pittsville has to offer?

DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15: This holiday home rental outside of Pittsville is located on the waterfront, and has an outdoor pool, a patio and air conditioning to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Pittsville?

While exploring the area, visit family-friendly sights like Salisbury Zoo, or get outside and enjoy nature at Assawoman Bay. Centre at Salisbury and Wicomico Youth and Civic Center are a couple of places you'll find in the wider area.

What are holiday rentals like in Pittsville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pittsville. Holiday rentals feature extras like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for a family trip.