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Red Point Holiday Rentals

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Our top choices for Red Point holiday rentals

1. 5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (163 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
The price is NZ$929
includes taxes & fees
13 Oct - 14 Oct
5-bedroom vacation home 5 minutes from historic Charlestown

2. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (30 reviews)
"The rental was perfect for what we needed. The bed and living room furniture were very comfortable and the kitchen well stocked. The host was quick to respond to questions I had. I will definitely see if this rental if available the next time I’m in the area."
United States
Martha J.
The price is NZ$482
includes taxes & fees
19 Oct - 20 Oct
Historic Chesapeake City Stay

3. Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure

Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
Chesapeake City
9.2 out of 10, Wonderful, (5 reviews)
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure

4. Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Port Deposit
9.8 out of 10, Exceptional, (57 reviews)
"Very unique property, with lots of history. We enjoyed our short stay."
United States
Terry R S.
The price is NZ$370
includes taxes & fees
11 Oct - 12 Oct
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

5. Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge

Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
Charlestown
10.0 out of 10, Exceptional, (5 reviews)
"This property was amazing! The perfect spot to relax and recharge. It has such a cozy feel. The decor was perfection. We’ll definitely be back. And Dave was super quick to respond to all questions. Thank you!"
United States
Sandy B.
The price is NZ$833
includes taxes & fees
18 Oct - 19 Oct
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge

6. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (50 reviews)
The price is NZ$199
includes taxes & fees
26 Oct - 27 Oct
Country Get Away Studio Apartment

7. Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Elkton
10.0 out of 10, Exceptional, (13 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is NZ$324
includes taxes & fees
11 Oct - 12 Oct
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

8. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is NZ$658
includes taxes & fees
19 Oct - 20 Oct
Bohemia Manor Farm

9. Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland

Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
Port Deposit
10.0 out of 10, Exceptional, (3 reviews)
"Renee & Pat were excellent hosts and we will definitely try to book again when in the area. Everything was as advertised and much more. Being pet friendly was a plus. We enjoyed two restaurants in the area while there, Lee's Landing and Old South Smokehouse, highly recommend!"
United States
Don S.
The price is NZ$343
includes taxes & fees
19 Oct - 20 Oct
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland

10. Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (33 reviews)
"This is a very nice apt. The owner was very receptive to any questions we had, even allowed an early checkin."
United States
Kathleen B.
The price is NZ$590
includes taxes & fees
13 Oct - 14 Oct
Private 3 room Queen Suite w/Kitchenette

11. Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.6 out of 10, Good, (19 reviews)
"Nice place"
United States
christine
The price is NZ$174
includes taxes & fees
19 Oct - 20 Oct
Charming 2-bedroom house in Aberdeen with WiFi and AC

12. Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Elkton
9.8 out of 10, Exceptional, (6 reviews)
The price is NZ$679
includes taxes & fees
20 Oct - 21 Oct
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

13. WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
10.0 out of 10, Exceptional, (11 reviews)
"The host was incredibly friendly and communicative. The place was a lot bigger than I expected, and it was beautiful to sit out by the fire pit and look at the river nearby. And, she left us snacks and smores for the stay! A nice quiet spot to spend a night."
United States
Matthew
The price is NZ$274
includes taxes & fees
4 Nov - 5 Nov
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

14. Amish Countryside Escape at Forest Edge Farm

Amish Countryside Escape at Forest Edge Farm
Nottingham
9.0 out of 10, Wonderful, (4 reviews)
"Property was close enough to stores and restaurants if needed. House is located in the rural area of the county (very peaceful). Property had all of the necessary kitchen utensil, pots, pans, and dishes that was needed for this trip. "
United States
jckglss6 G.
The price is NZ$368
includes taxes & fees
3 Nov - 4 Nov
Amish Countryside Escape at Forest Edge Farm

15. Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Bear
9.8 out of 10, Exceptional, (6 reviews)
"My boyfriend and I had a fantastic night on the yacht. We arrived right on time and found the AC and the lights on and ready for our arrival. I sunbathed on the front of the yacht and danced on the back after dinner at Grain H2O. The restaurant is located at the top of the hill on the marina . There was a band and we could hear the music from the boat. The marina was clean and everyone is friendly. At night it was very peaceful and easy to fall asleep. The morning we enjoyed our last couple of...
United States
Karen
The price is NZ$522
includes taxes & fees
16 Oct - 17 Oct
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

16. 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$376
includes taxes & fees
9 Nov - 10 Nov
Beachcomber Suite

17. Turtle Cove Room

Turtle Cove Room
Kent County
The price is NZ$353
includes taxes & fees
9 Nov - 10 Nov
Turtle Cove Room

18. Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses

Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
Nottingham
9.6 out of 10, Exceptional, (29 reviews)
"Relaxing place to stay! Winery was great, had fun!"
United States
Anonymous traveller
The price is NZ$415
includes taxes & fees
12 Oct - 13 Oct
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses

19. Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Great place to relax after a while on the go. Karin was very friendly and informative about places to see in the area. Everything was great "
United States
Maxwell
The price is NZ$406
includes taxes & fees
8 Nov - 9 Nov
Nature's Haven Tiny Home

20. Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
10.0 out of 10, Exceptional, (2 reviews)
"This was a stop over on our way to the beach- it was a convenient comfy space for our family."
United States
Erin C.
The price is NZ$467
includes taxes & fees
10 Oct - 11 Oct
Tiny Home Tranquil Oasis
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 Red Point Hotel Reviews

Find out more about Red Point

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

Frequently asked questions

Are there holiday rentals in Red Point?

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

Sailor's Sunrise Cottage - Chesapeake Bay: This holiday home rental outside of Red Point is located on a lake, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

What can I see and do in Red Point?

Northern Chesapeake Bay and Chesapeake Bay are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find North East Beach Area and Elk Neck State Park.

What are holiday rentals like in Red Point?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Red Point. Holiday rentals feature amenities such as patios, hot tubs and fire pits so your stay will be comfortable. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for family gatherings.