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Pittsville Vacation Rentals

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Our top choices for Pittsville vacation rentals

1. Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (28 reviews)
"I loved the location, the cleanliness and how good I felt being there. Thank you"
United States
Carmen
The price is CA $96
CA $352 total
includes taxes & fees
Oct 28 - Oct 29
Salisbury Riverfront Lofts

2. Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
Salisbury
9.8 out of 10, Exceptional, (25 reviews)
"Great location with plenty of space to relax."
United States
Doug R.
The price is CA $105
CA $262 total
includes taxes & fees
Nov 8 - Nov 9
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

3. On Main Street - Apartment C - Berlin, MD

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.4 out of 10, Exceptional, (43 reviews)
"Had great mini vac . The vrbo was right down town lots great shops and good choices for meals. All ready thinking about going back"
United States
Jeffry C.
The price is CA $106
CA $332 total
includes taxes & fees
Nov 3 - Nov 4
On Main Street - Apartment C - Berlin, MD

4. Pet-Friendly Cottage on 1.5 Acres Near Beaches!

Pet-Friendly Cottage on 1.5 Acres Near Beaches!
Selbyville
The price is CA $75
CA $282 total
includes taxes & fees
Oct 27 - Oct 28
Pet-Friendly Cottage on 1.5 Acres Near Beaches!

5. Salisbury Hideaway

Salisbury Hideaway
Salisbury
10.0 out of 10, Exceptional, (24 reviews)
"Perfect for our weekend away watching college softball!!!"
United States
Michelle S.
The price is CA $196
CA $491 total
includes taxes & fees
Oct 26 - Oct 27
Salisbury Hideaway

6. Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (40 reviews)
"Super convenient to campus and everything was clean and worked perfectly. Overall, a great stay and met all of our expectations."
United States
Matthew B.
The price is CA $195
CA $488 total
includes taxes & fees
Oct 27 - Oct 28
Salisbury Cottage

7. Retro Hipster: Close to downtown, dining and fun

Retro Hipster: Close to downtown, dining and fun
Salisbury
9.2 out of 10, Wonderful, (20 reviews)
"Great alternative to a hotel!"
United States
Courtney L.
The price is CA $101
CA $263 total
includes taxes & fees
Oct 28 - Oct 29
Retro Hipster: Close to downtown, dining and fun

8. 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, (63 reviews)
"The suite was very clean and our two children greatly enjoyed the pool!"
United States
Kay Lorelle R.
The price is CA $88
CA $256 total
includes taxes & fees
Oct 26 - Oct 27
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!

9. On Main Street - Apartment B - Berlin, MD

On Main Street - Apartment B - Berlin, MD
Downtown Berlin
8.8 out of 10, Excellent, (47 reviews)
"Great location and the place was clean and spacious. Nice little surprise seeing the farmers market right out front Sunday morning."
United States
April M.
The price is CA $106
CA $332 total
includes taxes & fees
Nov 3 - Nov 4
On Main Street - Apartment B - Berlin, MD

10. Spacious Riverfront Loft Close to Downtown and Dining

Spacious Riverfront Loft Close to Downtown and Dining
Salisbury
9.0 out of 10, Wonderful, (13 reviews)
"Great location, great restaurants below the loft."
United States
Pamela F.
The price is CA $101
CA $320 total
includes taxes & fees
Nov 1 - Nov 2
Spacious Riverfront Loft Close to Downtown and Dining

11. Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!

Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!
Newark
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful, clean, well appointed house in a peaceful setting. Easy & quick (20 minute) access to Assateague & Ocean City beaches without the chaos of staying in OC. Berlin and Snow Hill are fun historic eastern shore towns to explore. Take a day trip south to Pokomoke State Park for a calming non-beach nature experience. So nice we booked it again on our first day there."
United States
David M.
The price is CA $166
CA $574 total
includes taxes & fees
Nov 9 - Nov 10
Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!

12. Dog Friendly: Pool, Game Room, Near Bethany Beach

Dog Friendly: Pool, Game Room, Near Bethany Beach
Dagsboro
The price is CA $181
CA $670 total
includes taxes & fees
Oct 26 - Oct 27
Dog Friendly: Pool, Game Room, Near Bethany Beach

13. Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
3.0 star property
Midtown Ocean City
7.4 out of 10, Good, (1,331 reviews)
"Our room.seemed to be all new and we loved how there was a separate living room and bedroom with privacy doors. We had a beautiful view of the bay too from the second floor and we loved being on the sunset side of OC:)"
United States
cara
The price is CA $146
CA $163 total
includes taxes & fees
Oct 26 - Oct 27
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

14. 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, (58 reviews)
"The cottage location is great for golf, less than 20 minutes ride to most courses. Also dining in Berlin is better than traffic to Oean City."
United States
Joe
The price is CA $189
CA $510 total
includes taxes & fees
Oct 27 - Oct 28
Comfortable cottage in gated community, 5 mins to OC and Assateague

15. 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, (51 reviews)
"Ideal location and very nice accommodations!"
United States
Jeff A.
The price is CA $170
CA $421 total
includes taxes & fees
Oct 26 - Oct 27
Mallard Lakes Waterfront Beach Condo in Fenwick Island with Two Pools

16. Luxury Home 3 Mi to Bethany Beach Boardwalk!

Luxury Home 3 Mi to Bethany Beach Boardwalk!
3.0 star property
Ocean View
The price is CA $253
CA $1,113 total
includes taxes & fees
Oct 31 - Nov 1
Luxury Home 3 Mi to Bethany Beach Boardwalk!

17. "BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE

"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE
North Ocean City
9.6 out of 10, Exceptional, (143 reviews)
"We had a good stay"
United States
Nicole G.
The price is CA $50
CA $411 total
includes taxes & fees
Nov 1 - Nov 2
"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE

18. Dagsboro Retreat

Dagsboro Retreat
2.0 star property
Dagsboro
10.0 out of 10, Exceptional, (1 review)
"I loved it"
United States
Alexandra
The price is CA $334
CA $334 total
includes taxes & fees
Nov 1 - Nov 2
Dagsboro Retreat

19. Getaway on 1/2 Acre w/ Deck in Georgetown

Getaway on 1/2 Acre w/ Deck in Georgetown
Georgetown
10.0 out of 10, Exceptional, (8 reviews)
"Fantastic property for our trip. We are looking forward to staying there again next year. Great owners!"
United States
Charles M.
The price is CA $154
CA $483 total
includes taxes & fees
Nov 9 - Nov 10
Getaway on 1/2 Acre w/ Deck in Georgetown

20. Ocean Pines Retreat with Beach Club

Ocean Pines Retreat with Beach Club
Ocean Pines
10.0 out of 10, Exceptional, (46 reviews)
"This is our family's second year staying here and we loved it just as much!"
United States
Ashleigh N.
The price is CA $233
CA $561 total
includes taxes & fees
Oct 26 - Oct 27
Ocean Pines Retreat with Beach Club
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Pittsville. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Quiet Beachfront Retreat with Private Balcony: This vacation home near Pittsville is located by the ocean and has a balcony, a selection of books, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

What can I see and do in Pittsville?

While exploring the area, visit family-friendly sights like Frontier Town Water Park and Golf, or get outside and enjoy nature at Ocean City Beach. Wicomico Youth and Civic Center and Henry S. Parker Athletic Complex 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.