Pomona Holiday Rentals

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Holiday Rentals in Pomona

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (21)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

10.0 out of 10, Exceptional, (51)
"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

10.0 out of 10, Exceptional, (21)
"Convenient to restaurants and a warm, comfortable place to gather and relax after a hard, cold waterfowl hunt"
The price is AU$404
includes taxes & fees
24 Feb - 25 Feb
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Guest Lodge | Private Pool | Outdoor Dining | Game Room

Guest Lodge | Private Pool | Outdoor Dining | Game Room

Grasonville Home w/ Private Pool on the Water

9.8 out of 10, Exceptional, (20)
"We started an annual tradition to rent this house with friends. Love the property, beautiful views and great location. Making great memories that will last a lifetime. Thank you for allowing us to use your beautiful home! :)"
Grasonville Home w/ Private Pool on the Water

Circa 1700 Chesapeake Colonial home on the National Register.

9.8 out of 10, Exceptional, (50)
"Very cool house with great host. Very spacious. Excellent kitchen and very cozy. It would have been helpful to know about the staircases. We had an 8 month pregnant woman and 2 year old that were not able to come but it would have been an issue as getting to the single bed rooms is challenging."
Circa 1700 Chesapeake Colonial home on the National Register.

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (24)
"Great place for gathering. Plenty of space to hang out. Kitchen is big, well stocked and great for a large crowd. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (46)
"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Beautiful Chesapeake Bay Views -pet friendly

9.6 out of 10, Exceptional, (114)
"The home accomodated"
Beautiful Chesapeake Bay Views -pet friendly

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (78)
"Very clean, excellent communications,"
The price is AU$251
includes taxes & fees
19 Mar - 20 Mar
First Floor Studio Apartment in Historic Chestertown

Waterfront Annapolis Home: Fire Pit & Fishing Pier

9.2 out of 10, Wonderful, (32)
"We immensely enjoyed our stay! The home is a peaceful retreat yet close enough to Annapolis and DC to visit! It was super clean! It was a joy to sit outside and watch the wildlife on the water during the day! Will definitely come back!"
Waterfront Annapolis Home: Fire Pit & Fishing Pier

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (33)
"The bay cottage's porch was a perfect spot to enjoy a bottle of wine and snacks provided by the thoughtful hosts. Clever decor , furnishings, and sauna made our stay special and warm. Had crab dinner viewing sunset over the bay at dockside suggested by hosts. we hope to return. "
The price is AU$421
includes taxes & fees
19 Mar - 20 Mar
BAYSIDE BUNGALOW

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

10.0 out of 10, Exceptional, (32)
"Beautiful home, beautiful property! My family meets up annually and the house fit us perfectly. Plenty of room to spread out and congregate together. The home also provides so much to do with all the amenities! Thanks for the memories "
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Waterfront CHeerful 2 with Private Pier

10.0 out of 10, Exceptional, (8)
"Quiet location on the water, well laid out. Very clean and very easy to work with. "
Waterfront CHeerful 2 with Private Pier

Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

9.8 out of 10, Exceptional, (28)
"The property was very nice. It felt so homey. Clean and nicely appointed, even decorated for Christmas! In 2 short days ther was so much laughter and memories made! We would definitely recommend this home for a family stay!and memories made!"
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

Kent Island Waterfront | New Construction | Pool | Hot Tub | Stunning View | Lux

10.0 out of 10, Exceptional, (5)
"This is a terrific property with tons of room and beautifully appointed. We had a great stay. Beautiful sunsets to the west over the water. "
Kent Island Waterfront | New Construction | Pool | Hot Tub | Stunning View | Lux

Waterfront family resort Lodge with private pier, game room and bar

9.8 out of 10, Exceptional, (24)
"We had a great time. Place was unique and good for group get together. "
Waterfront family resort Lodge with private pier, game room and bar

Stay in the landmark Lighthouse!

10.0 out of 10, Exceptional, (96)
"We stayed at the light house for three nights in celebration of the new year, 2025. It was a work vacation involving winter covering of our sailboats as well as celebrating the new year. We thoroughly enjoyed our time together and will come here again."
Stay in the landmark Lighthouse!

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

10.0 out of 10, Exceptional, (118)
"comfortable and very cozy. Wonderful crabbing and sunsets."
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (4)
"An absolute stunning view from the four season enclosed porch. This beautiful home is well equiped and a perfect location for Fall and Winter hunting trips near Chestertown/Kennedyville. Plenty of rooms/bathrooms/beds. Highly recommend!!!"
Pet-Friendly Home on Chester River w/ Dock!
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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Other types of properties in Pomona you may be interested in

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (486)
"Even thought staff were Eagle’s fans, visit was very enjoyable!"
The price is AU$222
includes taxes & fees
25 Feb - 26 Feb
Hyatt Place Kent Narrows & Marina

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very good, (1001)
"We have stayed at this Best Western on several occasions and always find it clean and affordable. The staff is always pleassnt and accommodating. "
The price is AU$143
includes taxes & fees
25 Feb - 26 Feb
Best Western Kent Narrows Inn

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (878)
"Love it great room settings."
The price is AU$192
includes taxes & fees
24 Feb - 25 Feb
Hilton Garden Inn Kent Island Marina
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.

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?

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.: This holiday home rental outside of Pomona is located on the waterfront, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of an arcade/games room in this rental home to help you unwind.

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. River Arts Chestertown and Rolphs Wharf Marina 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.