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Pomona Holiday Rentals

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Our top choices for Pomona holiday rentals

1. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (124 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is NZ$269
includes taxes & fees
2 Sept - 3 Sept
First Floor Studio Apartment in Historic Chestertown

2. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (28 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is NZ$481
includes taxes & fees
1 Sept - 2 Sept
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

3. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is NZ$474
includes taxes & fees
1 Sept - 2 Sept
Secluded Cottage in Middle of Chestertown

4. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveller
The price is NZ$579
includes taxes & fees
1 Sept - 2 Sept
Newly restored apartment in the heart of Chestertown

5. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
The price is NZ$477
includes taxes & fees
8 Sept - 9 Sept
Cozy 1-bedroom in-law suite in lovely Chestertown with AC

6. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
The price is NZ$837
includes taxes & fees
2 Sept - 3 Sept
Wren Retweet- Country Estate in Center of C’Town

7. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (64 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is NZ$518
includes taxes & fees
1 Sept - 2 Sept
BAYSIDE BUNGALOW

8. Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (27 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is NZ$211
includes taxes & fees
10 Sept - 11 Sept
Guest Suite for up to 2 in a Victorian on the Chester River

9. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is NZ$681
includes taxes & fees
29 Sept - 30 Sept
Bayside Cottage steps from Rock Hall Harbor

10. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (27 reviews)
"Everything was lovely! The dock was beautiful and the accommodations were comfortable.Thanks!"
United States
Max G.
The price is NZ$633
includes taxes & fees
1 Sept - 2 Sept
Waterfront Retreat with Private Dock and Beach

11. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (46 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is NZ$506
includes taxes & fees
2 Sept - 3 Sept
Charming Coastal/Country Home w/3 Acres & Sauna!

12. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (12 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
The price is NZ$617
includes taxes & fees
2 Sept - 3 Sept
Family Retreat at Lansdowne Manor

13. Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
The price is NZ$330
includes taxes & fees
14 Sept - 15 Sept
Beachcomber Suite

14. Turtle Cove Room

Turtle Cove Room
Kent County
The price is NZ$295
includes taxes & fees
14 Sept - 15 Sept
Turtle Cove Room

15. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (16 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is NZ$710
includes taxes & fees
1 Sept - 2 Sept
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

16. FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
10.0 out of 10, Exceptional, (2 reviews)
"FLOHOM 14 did not disappoint!!! This was my first stay on a houseboat. Now I know why babies fall asleep when rocked. The boat is beautifully appointed & well equipped. Bring a good book. I’m already missing it!!!"
United States
Maria D.
The price is NZ$860
includes taxes & fees
15 Sept - 16 Sept
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
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 Pomona Hotel Reviews

Find out more about Pomona

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 Pomona 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 Pomona. 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 Pomona. Seeing all the best attractions is bound to make you fall in love with Pomona. 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 Pomona short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Pomona?

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

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Pomona offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 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 Pomona?

Explore the area and family-friendly sights such as Paul Reed Smith Guitars, or get out into nature at a spot like Eastern Neck National Wildlife Refuge. Chestertown Historic District and Washington College are a couple of places you'll find in the wider area.

What’s a holiday rental in Pomona like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Pomona. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for a family getaway.