Pittsville Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Pittsville

Deluxe Cottage | Private kitchen | Fridge, microwave, stovetop, toaster
Shore Point Cottages

Cottage in Berlin

3.0 star property
9.4 out of 10, Exceptional, (300)
"Was a great place to bring kids and dogs! "
United States
AMANDA
Shore Point Cottages
Outdoor pool
Comfortable cottage in gated community, 5 mins to OC and Assateague

Cottage in 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 ￥13,980
￥47,415 total
includes taxes & fees
Dec 9 - Dec 10
Comfortable cottage in gated community, 5 mins to OC and Assateague
Pool
"FENWICK ISL. WATERFRONT VACATION HOME AT THE BEACH W / BOAT DOCK, RAMP & POOL""

Mobile Home in 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 ￥8,108
￥34,603 total
includes taxes & fees
Dec 21 - Dec 22
"FENWICK ISL. WATERFRONT VACATION HOME AT THE BEACH W / BOAT DOCK, RAMP & POOL""
Exterior
Coconut Malorie Resort Ocean City, Ascend Collection Hotel

Aparthotel in Midtown Ocean City

3.0 star property
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 ￥11,881
￥15,053 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Coconut Malorie Resort Ocean City, Ascend Collection Hotel
Apartment (2 Bedrooms) | Interior
2 Mi to Beach: Gem w/ Enclosed Patio in Selbyville

Apartment in Selbyville

3.5 star property
10.0 out of 10, Exceptional, (3)
"We had a great couple of days here. The community is well located to get to and from the beaches (Fenwick and Bethany) and yet away from the crowds and in a really scenic part of Selbyville. We loved our stay and enjoyed the pool (there are 2). The place itself felt like home from the start, owner is really responsive and friendly, and it exceeded our expectations. Would definitely stay again. Felt like home away from home. "
United States
Lauren
The price is ￥12,892
￥47,534 total
includes taxes & fees
Dec 8 - Dec 9
2 Mi to Beach: Gem w/ Enclosed Patio in Selbyville
Beach nearby
Bethany Beach and Close by Marinas! Family and Pet Friendly!!

Vacation Home in Ocean View

9.2 out of 10, Wonderful, (78)
"Location was great, very spacious. Quiet neighborhood and perfect for us to enjoy our stay. Plenty of utensils and seasonings in the kitchen to use. Check in and check out process was very smooth and easy. We did bring our own linens as requested, but the pillows we put our pillow covers on, were dirty so if you are picky on that matter, bring your own. "
United States
Nick R.
The price is ￥11,650
￥58,153 total
includes taxes & fees
Dec 8 - Dec 9
Bethany Beach and Close by Marinas! Family and Pet Friendly!!
Apartment D: Riverfront Grand | In-room dining
Salisbury Riverfront Lofts

Apartment in Salisbury

3.0 star property
9.4 out of 10, Exceptional, (23)
"It was a great stay nice comfortable place "
United States
Adam
The price is ￥11,198
￥39,663 total
includes taxes & fees
Dec 11 - Dec 12
Salisbury Riverfront Lofts
Property grounds
BeachParadise1208-Charming 4BR Townhouse•DOWNTOWN•Short walk to Beach&Boardwalk

Vacation Home in Downtown Ocean City

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great place to stay!"
United States
Joseph D.
The price is ￥7,611
￥47,759 total
includes taxes & fees
Dec 8 - Dec 9
BeachParadise1208-Charming 4BR Townhouse•DOWNTOWN•Short walk to Beach&Boardwalk
Outdoor pool, a heated pool
Mallard Lakes Waterfront Beach Condo in Fenwick Island with Two Pools

Condo in Selbyville

9.8 out of 10, Exceptional, (39)
"Loved this property! Owners were very responsive! "
United States
Michelle K.
The price is ￥19,572
￥47,946 total
includes taxes & fees
Dec 10 - Dec 11
Mallard Lakes Waterfront Beach Condo in Fenwick Island with Two Pools
TV, fireplace, video games, DVD player
Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo

Condo in 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 ￥7,611
￥54,828 total
includes taxes & fees
Dec 14 - Dec 15
Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo
Property grounds
Beach Paradise 105 - Beach Home at Broad Marsh OC

Vacation Home in North Ocean City

9.8 out of 10, Exceptional, (9)
"Lovely rental! Would stay again!"
United States
Kelly W.
The price is ￥6,990
￥47,070 total
includes taxes & fees
Dec 8 - Dec 9
Beach Paradise 105 - Beach Home at Broad Marsh OC
Outdoor pool
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!

Vacation Home in 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 ￥13,980
￥30,142 total
includes taxes & fees
Dec 19 - Dec 20
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!
Property grounds
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!

Vacation Home in North Ocean City

9.8 out of 10, Exceptional, (134)
"Very lovely pkace!! Would def book again!!"
United States
Brenda F.
The price is ￥7,611
￥47,759 total
includes taxes & fees
Dec 8 - Dec 9
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!
Fridge, microwave, oven, stovetop
Beach Paradise VII-Brand New Luxury Townhouse with Pool, Garage, and Water View

Vacation Home in 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 ￥7,611
￥47,759 total
includes taxes & fees
Dec 8 - Dec 9
Beach Paradise VII-Brand New Luxury Townhouse with Pool, Garage, and Water View
Fridge, microwave, oven, stovetop
"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE

Vacation Home in North Ocean City

9.8 out of 10, Exceptional, (119)
"Great property in a great location. Host was quick to get ahold of and the instructions were incredibly easy. Highly recommend this property for a family or large group. We would stay here again!"
United States
Joseph G.
The price is ￥6,850
￥46,916 total
includes taxes & fees
Dec 8 - Dec 9
"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE
Fridge, microwave, oven, stovetop
Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!

Vacation Home in Downtown Ocean City

10.0 out of 10, Exceptional, (17)
"All amenities available, perfect location and plenty of room for a large group. Would stay again!"
United States
Trish K.
The price is ￥7,611
￥47,759 total
includes taxes & fees
Dec 8 - Dec 9
Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!
Smart TV
On Main Street - Apartment C - Berlin, MD

Apartment in 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 ￥10,764
￥35,225 total
includes taxes & fees
Dec 16 - Dec 17
On Main Street - Apartment C - Berlin, MD
Interior
Ocean calling & country concert availability!

Condo in North Ocean City

9.0 out of 10, Wonderful, (35)
"Everything was as stated. We had zero issues and everything was great. Perfect for a family getaway! "
United States
James R.
The price is ￥8,388
￥30,173 total
includes taxes & fees
Dec 8 - Dec 9
Ocean calling & country concert availability!
Fridge, microwave, stovetop, coffee/tea maker
Clean, modern and well-equipped Ocean City condo

Condo in Downtown Ocean City

10.0 out of 10, Exceptional, (15)
"Good overall stay."
United States
James S.
The price is ￥13,281
￥39,398 total
includes taxes & fees
Dec 8 - Dec 9
Clean, modern and well-equipped Ocean City condo
Coffee/tea maker
Newly Remodeled Condo - Steps to Beach & Boardwalk

Vacation Home in Downtown Ocean City

9.8 out of 10, Exceptional, (9)
"Beautiful condo and so close to the beach!"
United States
Kathryn L.
The price is ￥16,147
￥75,492 total
includes taxes & fees
Dec 8 - Dec 9
Newly Remodeled Condo - Steps to Beach & Boardwalk
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

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

10/10 Excellent
"Great place "
jeffrey 2-night trip
Posted 19 hours ago
Grand Hotel Ocean City Oceanfront

Find out more about Pittsville

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

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Frequently asked questions

Can I find vacation rentals in Pittsville?

Yes, we have vacation rentals near top local attractions in Pittsville, or you can go with a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation rentals in Pittsville?

BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!: This vacation home rental near Pittsville is located next to a golf course and has an outdoor pool, a balcony, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

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 larger area.

What are vacation rentals like in Pittsville?

Vacation rentals are private properties you can stay in for a short or long stay in Pittsville. Vacation rentals offer extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a small group gathering.