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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, (27 reviews)
"Excellent choice for the price, recommended for larger groups."
United States
Marcos
The price is CA $90
CA $347 total
includes taxes & fees
Oct 25 - Oct 26
Salisbury Riverfront Lofts

2. Salisbury Hideaway

Salisbury Hideaway
Salisbury
10.0 out of 10, Exceptional, (23 reviews)
"Perfect for our weekend away watching college softball!!!"
United States
Michelle S.
The price is CA $181
CA $444 total
includes taxes & fees
Sep 27 - Sep 28
Salisbury Hideaway

3. 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 $98
CA $239 total
includes taxes & fees
Sep 30 - Oct 1
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

4. 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 $218
CA $516 total
includes taxes & fees
Oct 19 - Oct 20
Salisbury Cottage

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

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.4 out of 10, Exceptional, (42 reviews)
"A perfect location if you want to explore downtown Berlin. It’s right in the heart of Main Street walking distance to everything.The apartment had everything we needed and was very cozy and clean . Would definitely book this spot again."
United States
Sarah V.
The price is CA $109
CA $335 total
includes taxes & fees
Oct 7 - Oct 8
On Main Street - Apartment C - Berlin, MD

6. Pool + Bay Access! Home 13 Mi to Ocean City Beach

Pool + Bay Access! Home 13 Mi to Ocean City Beach
3.0 star property
Ocean Pines
The price is CA $134
CA $603 total
includes taxes & fees
Sep 27 - Sep 28
Pool + Bay Access! Home 13 Mi to Ocean City Beach

7. 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, (1,323 reviews)
"The hotel did not disappoint. The room, the tub and especially the shower was the best. We also loved the view. Would come back again and get the same room. We had the presidential suite."
United States
Nichole
The price is CA $102
CA $115 total
includes taxes & fees
Oct 16 - Oct 17
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

8. 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 $98
CA $246 total
includes taxes & fees
Sep 27 - Sep 28
Retro Hipster: Close to downtown, dining and fun

9. BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen
Berlin
9.8 out of 10, Exceptional, (111 reviews)
"Great hosting by Laurie"
United States
Jim C.
The price is CA $281
CA $540 total
includes taxes & fees
Sep 29 - Sep 30
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

10. "The Hive"-Downtown Berlin, 4 BR, Sleeps 8, 2 Bath

"The Hive"-Downtown Berlin, 4 BR, Sleeps 8, 2 Bath
Downtown Berlin
10.0 out of 10, Exceptional, (6 reviews)
"My friends and I were absolutely thrilled with this place! It is clean, spacious and perfectly located in a cute little town with shops and restaurants.We all said we could live ve here. Very homey and comfortable."
United States
Bonni R.
"The Hive"-Downtown Berlin, 4 BR, Sleeps 8, 2 Bath

11. 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, (56 reviews)
"Convenient amenities at Assateague Point, easy access to Assateague Island and OCMD. Everything in the unit was clean, in proper working order, and we had everything we needed for our family with young children. Would definitely stay here again."
United States
Alexandra
The price is CA $190
CA $509 total
includes taxes & fees
Sep 27 - Sep 28
Comfortable cottage in gated community, 5 mins to OC and Assateague

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

On Main Street - Apartment B - Berlin, MD
Downtown Berlin
8.8 out of 10, Excellent, (47 reviews)
"The location was perfect for our travel purpose!! Other than the couch seeming to be a little dingy, the place was well kept and comfy. We would love to stay here again."
United States
Lori A.
The price is CA $109
CA $332 total
includes taxes & fees
Oct 5 - Oct 6
On Main Street - Apartment B - Berlin, MD

13. Game Room! Waterfront Group Haven in Ocean Pines

Game Room! Waterfront Group Haven in Ocean Pines
Ocean Pines
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful views, quiet neighborhood close to the beach. "
United States
James C.
The price is CA $316
CA $1,238 total
includes taxes & fees
Sep 27 - Sep 28
Game Room! Waterfront Group Haven in Ocean Pines

14. 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, (62 reviews)
"We stayed at this property for 6 nights, everything was exactly like the pictures and very clean. We were just far enough to many shopping areas and grocery stores. It was very quiet and peaceful. Ed and Cindy are amazing hosts, we will be returning next year!"
United States
Haileigh
The price is CA $141
CA $286 total
includes taxes & fees
Oct 13 - Oct 14
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!

15. 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)
"This place was perfect. Beds were comfy, it had everything i needed in the kitchen, secluded enough to feel like you were alone with nature but close enough to drive to tourist attractions. Literally everything we we looking for. Added bonus was napping in the screened in porch."
United States
Jackie P.
The price is CA $230
CA $661 total
includes taxes & fees
Oct 5 - Oct 6
Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!

16. Game Room! Waterfront Group Haven in Ocean Pines

Game Room! Waterfront Group Haven in Ocean Pines
3.0 star property
Ocean Pines
The price is CA $392
CA $1,210 total
includes taxes & fees
Sep 27 - Sep 28
Game Room! Waterfront Group Haven in Ocean Pines

17. BeachParadise107-OCEANVIEW Townhome-Steps to BEACH and BOARDWALK-LINENS INCLUDED

BeachParadise107-OCEANVIEW Townhome-Steps to BEACH and BOARDWALK-LINENS INCLUDED
Downtown Ocean City
10.0 out of 10, Exceptional, (4 reviews)
"The house was as listed, it was an enjoyable stay. Ann was easy to work with. Thanks VRBO."
United States
Anonymous traveller
The price is CA $134
CA $520 total
includes taxes & fees
Sep 28 - Sep 29
BeachParadise107-OCEANVIEW Townhome-Steps to BEACH and BOARDWALK-LINENS INCLUDED

18. Studio Charm w/ Deck, Fireplace & Fooseball!: Walk to Beach, Boardwalk & Dining!

Studio Charm w/ Deck, Fireplace & Fooseball!: Walk to Beach, Boardwalk & Dining!
Midtown Ocean City
9.8 out of 10, Exceptional, (18 reviews)
"Very friendly and helpful host! The room was lovely and very clean when we arrived. We would stay with this host again."
United States
Hannah
The price is CA $95
CA $341 total
includes taxes & fees
Sep 28 - Sep 29
Studio Charm w/ Deck, Fireplace & Fooseball!: Walk to Beach, Boardwalk & Dining!

19. "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, (140 reviews)
"Great place to stay. There was plenty of room, easy access to close shopping."
United States
Rebecca D.
The price is CA $107
CA $484 total
includes taxes & fees
Sep 28 - Sep 29
"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE

20. Ocean Pines Retreat with Beach Club

Ocean Pines Retreat with Beach Club
Ocean Pines
10.0 out of 10, Exceptional, (44 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 $282
CA $613 total
includes taxes & fees
Oct 25 - Oct 26
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.