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Bear Holiday Rentals

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Holiday Rentals in Bear

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Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, 36 reviews
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Oaxaca, a private room with private entrance
9.0 out of 10, Wonderful, 8 reviews
"Ms Laura is such a great hostess. The room is so comfy and clean. We hope to stay again.. :)"
The price is AU$176
includes taxes & fees
2 June - 3 June
Oaxaca, a private room with private entrance
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Historic Chesapeake City Stay
8.0 out of 10, Very good, 1 review
"The place overall is very simple and nice. The bed was a little uncomfortable And decided to not stay the extra night and come home and use my own bed. Overall, very clean very nice."
The price is AU$367
includes taxes & fees
2 June - 3 June
Historic Chesapeake City Stay
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10.0 out of 10, Exceptional, 19 reviews
"Cozy & elegant ☀️ a clean bright space."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
9.8 out of 10, Exceptional, 27 reviews
"This location was perfect for our stay during a bass tournament on the upper bay. boa parking was great and very secure compared to hotels. SAhelly was very accomadating"
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Homey Retreat in Historic Kennett Square!!
10.0 out of 10, Exceptional, 44 reviews
"My friends and I stayed here for a girl's weekend. It was really a perfect stay. The location is great for walking to shops and restaurants. The house is so cute and beautifully decorated. There were so many little details that made us feel we were somewhere special--the kitchen had coffee, tea, and snacks set out for us. The bathroom had nice toiletries and we had plenty of towels for our group of five. The backyard patio looked very cozy and is set up for relaxing in privacy. We loved it!"
The price is AU$475
includes taxes & fees
6 June - 7 June
Homey Retreat in Historic Kennett Square!!
Family-Friendly Cottage, Walk to the Beach!
10.0 out of 10, Exceptional, 14 reviews
"Great location "
Family-Friendly Cottage, Walk to the Beach!
The Lodge at Cricklewood...where time melts away....
10.0 out of 10, Exceptional, 56 reviews
"14 of us stayed here for a secluded bachelorette weekend in nature and it was truly a dream come true. The home is beautiful and comfortable for a large group, it didn’t even matter that it rained the entire time! We even canceled some of our day plans to stay and enjoy the house. The only minor down side was the water heater struggled keeping up with 14 woman’s daily hygiene needs. Overall, everything was so wonderful and Eric was very pleasant and accommodating. If you stay here you will never...
The Lodge at Cricklewood...where time melts away....
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
9.2 out of 10, Wonderful, 10 reviews
"This was my second time to the houseboat and it was wonderful! It is conveniently located and many small shops, restaurants, brewery/bars are walking distance, and a short drive to wineries. Also a park right across from the marina."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
10.0 out of 10, Exceptional, 66 reviews
"We had a great get-away for a few days with our friends. The cabin was in a quiet neighborhood with amazing views. We especially enjoyed using the fire pit while sitting in the comfortable Adirondack chairs overlooking the Chesapeake Bay. The owners were friendly and great to work with. Highly recommend!"
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Waterfront house with amazing views. Top of the Chesapeake
10.0 out of 10, Exceptional, 89 reviews
"Our Family decided to take a last minute Spring Break trip and had a fantastic time. Matt was a great host and easy to communicate with. We were pleasantly surprised by all of the local dining options. Despite terrible weather that we experienced, we made the best of our trip and had a great time."
Waterfront house with amazing views. Top of the Chesapeake
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
9.8 out of 10, Exceptional, 34 reviews
"Great view awesome living space and easy access. Thank you."
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Quarry Landing - Center of Town & River View - 3 Bedroom
10.0 out of 10, Exceptional, 5 reviews
"What a beautiful home. The host was attentive to the small details in the house, and my friend and I greatly enjoyed our stay."
The price is AU$574
includes taxes & fees
17 June - 18 June
Quarry Landing - Center of Town & River View - 3 Bedroom
Riverfront Retreat: Panoramic water views with Hot Tub. Sleeps 16.
9.6 out of 10, Exceptional, 154 reviews
"The property was beautiful and just as described. The property managers were quick to respond and very helpful. We truly enjoyed our stay."
Riverfront Retreat: Panoramic water views with Hot Tub. Sleeps 16.
Entire place with private parking
7.8 out of 10, Good, 6 reviews
"Overall great location, space and with secure parking."
The price is AU$228
includes taxes & fees
4 June - 5 June
Entire place with private parking
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
9.8 out of 10, Exceptional, 87 reviews
"Very nice"
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
Stylish Private Suite in the heart of Brandywine Valley
10.0 out of 10, Exceptional, 148 reviews
"Very warm welcoming and great place to stay at mostly definitely recommend if you come down to Delaware!! My friends and I enjoyed it , we are planning to stay there again soon !!!"
The price is AU$274
includes taxes & fees
15 June - 16 June
Stylish Private Suite in the heart of Brandywine Valley
Hidden Gem! - Downtown
2.0 out of 10, 1 review
"Small AC that would not cool the upstairs, where bedrooms are. Receptacles were hazardous. Check the street view on Google Maps."
Hidden Gem! - Downtown
Newly renovated in the heart of Kennett Square. 3 miles from Longwood Gardens
10.0 out of 10, Exceptional, 7 reviews
"We couldn't have had a more positive experience! The apartment was extremely well equipped with lots of little extras and spotlessly clean. Very comfortable. The neighborhood is very enjoyable, good restaurants, galleries, shops, and an awesome little ice cream place across the street. An easy drive to Longwood Gardens, Brandywine Museum and other interesting places. Our hosts were fabulous. One evening a smoke detector battery ran low and started beeping and they were here in minutes to replace...
The price is AU$527
includes taxes & fees
2 June - 3 June
Newly renovated in the heart of Kennett Square. 3 miles from Longwood Gardens
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See all available properties in Bear
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.

Bear Holiday Home Travel Info

Other types of properties in Bear you may be interested in

Best Western Plus Newark/Christiana Inn
2.5 star property
7.2 out of 10, Good, 1,002 reviews
"Hotel was clean, halls well lite, room was a good size for 4 people. Pool looked inviting. Housekeeping very accommodating I asked for extra towels and they were brought to my room within 5 minutes. "
The price is AU$170
includes taxes & fees
12 June - 13 June
Best Western Plus Newark/Christiana Inn
Sonesta Select Newark Christiana Mall
3.0 star property
7.8 out of 10, Good, 1,003 reviews
"I had a little stupid something happen in regards to my room (a self caused issue), that left me locked out of my room. The staff was nothing but understanding & even offered me a side room until the problem was resolved. Thanks so much for everything!"
The price is AU$183
includes taxes & fees
1 July - 2 July
Sonesta Select Newark Christiana Mall
Brandywine Plaza Hotel
3.5 star property
7.6 out of 10, Good, 1,004 reviews
"The place is priced properly. It’s a low cost, nice place to stay for up to a few nights. Breakfast buffet options are pretty simple and typical. The people complaining about the breakfast options and amenities need to be realistic and go somewhere else and spend $200 a night."
The price is AU$150
includes taxes & fees
1 July - 2 July
Brandywine Plaza Hotel
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.

Everything you need to know about Bear holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Bear holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Bear holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Bear holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Bear. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Bear holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Bear holiday rentals we have selected for you start as low as AU$176 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Bear rentals

At Expedia, we put the best Bear holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Bear rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Bear holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Bear. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Bear?

Yes, there are holiday rentals in Bear close to Delaware Rock Gym, or you can select a more secluded option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Bear. Make sure you have time to check out the football matches while you're in the area.

What are some of the best holiday rentals that Bear has to offer?

Oaxaca, a private room with private entrance: This holiday home rental outside of Bear is located in the city centre, and offers a garden, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and a coffee maker.

How many holiday rentals are there in Bear?

Expedia has 6 holiday rentals for your stay in Bear.

What can I see and do in Bear?

Family-friendly attractions include Delaware Rock Gym and Hullabaloo Amusement Center, whereas Lums Pond State Park is a spot to enjoy the outdoors. In the wider area, you’ll find Mansion House Paintball and Kirkwood Soccer Complex.

What are holiday rentals like in Bear?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Bear. Holiday rentals provide amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and busy front desks 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 popular choice for small groups.

Recent reviews of Bear properties
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