Default HTG hotel image

Whaleyville Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Whaleyville holiday rentals

1. Snowbird Bay Cottage | Playground + Community Pool

Snowbird Bay Cottage | Playground + Community Pool
Ocean Pines
9.2 out of 10, Wonderful, (15 reviews)
"nice little place."
United States
Dwayne C.
The price is NZ$966
includes taxes & fees
25 Aug - 26 Aug
Snowbird Bay Cottage | Playground + Community Pool

2. Majestic Hotel & Apartments

Majestic Hotel & Apartments
2.0 star property
Downtown Ocean City
5.8 out of 10, (478 reviews)
"Great location--Very close to the steps and boardwalk!"
United States
ALEXIS
The price is NZ$161
includes taxes & fees
1 Sept - 2 Sept
Majestic Hotel & Apartments

3. 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, (1,316 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 NZ$130
includes taxes & fees
14 Sept - 15 Sept
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

4. CANAL FRONT - GREAT VIEWS - 5 BDRM, 3&1/2 BATHS, 2 KINGS, GOLF, RELAX...

CANAL FRONT - GREAT VIEWS - 5 BDRM, 3&1/2 BATHS, 2 KINGS, GOLF, RELAX...
Ocean Pines
10.0 out of 10, Exceptional, (65 reviews)
"We had a great time. The house was nice, clean and was in a great location. We had a wonderful time! "
United States
Kim c.
CANAL FRONT - GREAT VIEWS - 5 BDRM, 3&1/2 BATHS, 2 KINGS, GOLF, RELAX...

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

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.4 out of 10, Exceptional, (39 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 NZ$479
includes taxes & fees
2 Sept - 3 Sept
On Main Street - Apartment C - Berlin, MD

6. NEW! Sleeps 23 Mins to OCMD w/Gym-Game Room-Firepit

NEW! Sleeps 23 Mins to OCMD w/Gym-Game Room-Firepit
Berlin
NEW! Sleeps 23 Mins to OCMD w/Gym-Game Room-Firepit

7. Shore Point Cottages

Shore Point Cottages
3.0 star property
Berlin
9.2 out of 10, Wonderful, (357 reviews)
"Perfect space!"
United States
Brandi
The price is NZ$188
includes taxes & fees
13 Sept - 14 Sept
Shore Point Cottages

8. 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, (110 reviews)
"Great hosting by Laurie"
United States
Jim C.
The price is NZ$642
includes taxes & fees
13 Sept - 14 Sept
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

9. 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 NZ$406
includes taxes & fees
1 Sept - 2 Sept
Dagsboro Retreat

10. Ocean Pines Dog Friendly Cottage

Ocean Pines Dog Friendly Cottage
Ocean Pines
9.0 out of 10, Wonderful, (12 reviews)
"It was nice& quiet…The yard was wonderful for our dog…Kelly our host was great in communication checkin was easy it was keyless…"
United States
Shelly P.
The price is NZ$934
includes taxes & fees
23 Aug - 24 Aug
Ocean Pines Dog Friendly Cottage

11. Ocean Pines Retreat with Beach Club

Ocean Pines Retreat with Beach Club
Ocean Pines
10.0 out of 10, Exceptional, (43 reviews)
"The place is beautiful and very, very clean. We had so much space. My 13 year old daughter loved the room she stayed in and having her own bathroom. Our dog quickly learned where the basket of toys was. The location was very close to the boardwalk and in town there were a lot of good restaurants.Bill made it easy to communicate with and gave immediate responses to any questions we had.We will definitely stay here again!"
United States
Anna A.
The price is NZ$835
includes taxes & fees
15 Sept - 16 Sept
Ocean Pines Retreat with Beach Club

12. 8 Mi to Ocean City: Warm & Cozy 3BR Family Home

8 Mi to Ocean City: Warm & Cozy 3BR Family Home
3.0 star property
Ocean Pines
The price is NZ$1,022
includes taxes & fees
21 Aug - 22 Aug
8 Mi to Ocean City: Warm & Cozy 3BR Family Home

13. Ocean City Paradise, Large Outside Deck, Bar&Grill

Ocean City Paradise, Large Outside Deck, Bar&Grill
West Ocean City
9.2 out of 10, Wonderful, (18 reviews)
"This is our 4th year staying here. We love it it's perfect for our needs."
United States
Joe S.
Ocean City Paradise, Large Outside Deck, Bar&Grill

14. Pool, Trail Access! Dog-Friendly Ocean Pines Haven

Pool, Trail Access! Dog-Friendly Ocean Pines Haven
Ocean Pines
9.6 out of 10, Exceptional, (24 reviews)
"We enjoyed our stay and the house was perfect for our family and my kids loved it. "
United States
Vannessa H.
The price is NZ$751
includes taxes & fees
27 Aug - 28 Aug
Pool, Trail Access! Dog-Friendly Ocean Pines Haven

15. 5 Bed/3.5 Bath in Bayside near West Ocean City

5 Bed/3.5 Bath in Bayside near West Ocean City
Bayside
10.0 out of 10, Exceptional, (25 reviews)
"This was our 3rd year of staying here & it really works for our family of 12. It is always clean & well keep & the hosts have been great to work with"
United States
Brent S.
5 Bed/3.5 Bath in Bayside near West Ocean City

16. Ocean City MD waterfront rental with skyline views, canal access, bring your boat or jet ski!

Ocean City MD waterfront rental with skyline views, canal access, bring your boat or jet ski!
Ocean Pines
10.0 out of 10, Exceptional, (20 reviews)
"This rental property is in a very nice location and is well maintained and furnished. Everyone in our group, ages 10 to 77, enjoyed the stay. "
United States
Eric D.
Ocean City MD waterfront rental with skyline views, canal access, bring your boat or jet ski!

17. BeachParadise107-DOWNTOWN OCEANVIEW Luxury Townhome 3BR-Steps to Beach&Boardwalk

BeachParadise107-DOWNTOWN OCEANVIEW Luxury Townhome 3BR-Steps to Beach&Boardwalk
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
BeachParadise107-DOWNTOWN OCEANVIEW Luxury Townhome 3BR-Steps to Beach&Boardwalk

18. Beautiful 4 bedroom apartment in Ocean City perfect for families

Beautiful 4 bedroom apartment in Ocean City perfect for families
North Ocean City
9.0 out of 10, Wonderful, (75 reviews)
"We had such a wonderful time at this location. The place and all the amenities were perfect for our family. We would highly recommend! "
United States
Jason E.
The price is NZ$1,328
includes taxes & fees
14 Sept - 15 Sept
Beautiful 4 bedroom apartment in Ocean City perfect for families

19. 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, (52 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 NZ$711
includes taxes & fees
1 Sept - 2 Sept
Comfortable cottage in gated community, 5 mins to OC and Assateague

20. Boho Beach Cottage- Quiet, Deck, Private parking, Bikes- 1 mi to Beach & Boards!

Boho Beach Cottage- Quiet, Deck, Private parking, Bikes- 1 mi to Beach & Boards!
West Ocean City
10.0 out of 10, Exceptional, (9 reviews)
"Clean with easy check in/ check out. Good location."
United States
Aaron T.
The price is NZ$658
includes taxes & fees
25 Aug - 26 Aug
Boho Beach Cottage- Quiet, Deck, Private parking, Bikes- 1 mi to Beach & Boards!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Whaleyville Hotel Reviews

Find out more about Whaleyville

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Whaleyville holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Whaleyville. 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 Whaleyville. Seeing all the best attractions is bound to make you fall in love with Whaleyville. Who knows, you may even be tempted to extend your 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 holiday 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 Whaleyville short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Whaleyville?

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

Beach comfort-lovely home, beach, pools, pet friendly!: This holiday home rental outside of Whaleyville is located near the beach, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What’s there to see and do in Whaleyville?

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. Maryland Beach and Main Street Berlin are a couple of places you'll find in the wider area.

What’s a holiday rental in Whaleyville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Whaleyville. Holiday rentals offer extras such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and busy concierge desks 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 families.