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Holiday Rentals in Bear

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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
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
9.4 out of 10, Exceptional, 11 reviews
"Great"
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
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House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
9.8 out of 10, Exceptional, 90 reviews
"Myself, mom, sister, and friend came down for the weekend to participate in the Mammoth March held at the Fair Hill Park. The house was nice and close, clean, and comfortable."
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
The Lodge at Cricklewood...where time melts away....
10.0 out of 10, Exceptional, 57 reviews
"This was perfect for our needs. Great place. Very big, lots of space to spread out. Hot tub was a nice addition. Eric was great to work with"
The Lodge at Cricklewood...where time melts away....
Stylish Private Suite in the heart of Brandywine Valley
10.0 out of 10, Exceptional, 152 reviews
"We had a great time staying here for one night. The suite is super clean and comfortable. The hosts made us feel welcome. The beds were cozy with plenty of blankets of needed. The baked goods were an extra special touch and were a great breakfast before checkout. We would definitely stay here again."
The price is €173
includes taxes & fees
2 Jul - 3 Jul
Stylish Private Suite in the heart of Brandywine Valley
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10.0 out of 10, Exceptional, 20 reviews
"Thoroughly enjoyed our stay! Betty is such a great host. Beautiful area...GREAT sunsets and close to the beach! Very comfortable weekend stay! Also close to some great wineries and Alpaca farms!"
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Cozy home with fenced in yard-Pet Friendly. 2 block walk to historic downtown!
9.6 out of 10, Exceptional, 45 reviews
"Owner very helpful to anything we needed. Was within walking distance to everything in town which has wonderful shops and places to eat."
Cozy home with fenced in yard-Pet Friendly. 2 block walk to historic downtown!
Chesapeake City Overlook: Breathtaking View!
10.0 out of 10, Exceptional, 5 reviews
"Lovely home and hostess! Very clean and responsive. Beautiful water views. Excellent vacation home"
Chesapeake City Overlook: Breathtaking View!
Cozy Spring House in Gorgeous Chadds Ford!
10.0 out of 10, Exceptional, 43 reviews
"So much to do in Brandywine Valley and this home was a perfect home base. The location was close to everything - historic sites, antique shops, wineries, great restaurants and Longwood Gardens. It’s advertised as “cozy” and we found it charming and comfortable. Loved the excellent communication, ease of entry and departure, and warm welcome from our hostess. It was a perfect weekend getaway."
The price is €307
includes taxes & fees
15 Jul - 16 Jul
Cozy Spring House in Gorgeous Chadds Ford!
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
Beachfront Sunsets on the Water at Oakwood Beach
10.0 out of 10, Exceptional, 20 reviews
"This was the perfect house for 3 Dads and their 14-15 yr olds for a weekend lacrosse tournament. The house was clean and spacious. The owner went over and above to welcome us and make us feel at home. The boys loved the kayaks, swimming and the beach. The Dads enjoyed the outdoor area, fire pit and grilling. All the beach supplies were on hand. Easy and quick communications with the owner."
Beachfront Sunsets on the Water at Oakwood Beach
Homey Retreat in Historic Kennett Square!!
10.0 out of 10, Exceptional, 45 reviews
"We had a lovely stay and hope to return. The house was exactly what we want in a vacation rental. It had charm and personality, was located within walking distance of cafes and restaurants and was very comfortable for the four of us. Communication with Ivanna was seamless. Our family has a wonderful stay."
The price is €323
includes taxes & fees
8 Jul - 9 Jul
Homey Retreat in Historic Kennett Square!!
Relaxing 5BR Family Home w/ Fire Pit & Pool Table
10.0 out of 10, Exceptional, 2 reviews
"We had a wonderful stay at this house. The managers were gracious enough to allow for an early check-in and everything was as mentioned. It really helped to have the house layout on the website description so that we could plan (we had multiple family units). Communication with the managers was fantastic from before booking until after checkout. I'd highly recommend staying at this property."
Relaxing 5BR Family Home w/ Fire Pit & Pool Table
Clean and Cozy 2 BR home blocks away from downtown
10.0 out of 10, Exceptional, 15 reviews
"Great house, very clean. Only a short few minute walk to restaurants and shops and parks."
Clean and Cozy 2 BR home blocks away from downtown
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
9.8 out of 10, Exceptional, 36 reviews
"House was very clean and in an excellent location. However the grounds were in need of weeding to the point that the advertised upper bay view was blocked or partially blocked from many areas. Host was prompt in responding when I reached out."
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Top of the Chesapeake - Minutes from Historic Charlestown
9.8 out of 10, Exceptional, 128 reviews
"Three generations from PA, CO and VT all converged on the "Top of the Chesapeake" and had a lovely time. This is a stellar place for bird watching since it's between a creek and the upper Bay ("river".) Kayaks were a hit with 12 year olds and their parents. The owner's very reasonable rules and guidelines were so easy and he was available for help. Highly recommend this place!"
The price is €626
includes taxes & fees
8 Jul - 9 Jul
Top of the Chesapeake - Minutes from Historic Charlestown
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
9.8 out of 10, Exceptional, 28 reviews
"Pretty house with plenty of room. Easy check in and out."
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Riverfront Retreat: Panoramic water views with Hot Tub. Sleeps 16.
9.6 out of 10, Exceptional, 155 reviews
"This River property is a little bit of Paradise away from home! It is everything and more as advertised! My husband and I leased the property for 5 nights for a family reunion, ages 1 to 89 years old! My family of 5, my Mom, Dad and Grandmother, my brothers family of 4 and my nieces family of 3. The house was big enough for all of us to be together or everyone could have their own space. We enjoyed the pool, the hot tub, the playground and the sunsets across the river were amazing. My...
Riverfront Retreat: Panoramic water views with Hot Tub. Sleeps 16.
Family-Friendly Cottage, Walk to the Beach!
10.0 out of 10, Exceptional, 14 reviews
"Great location "
Family-Friendly Cottage, Walk to the Beach!
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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.

Other types of properties in Bear you may be interested in

Best Western Plus Newark/Christiana Inn
2.5 star property
7.0 out of 10, Good, 1,002 reviews
"Very quiet environment Enjoyed our stay"
The price is €104
includes taxes & fees
30 Jun - 1 Jul
Best Western Plus Newark/Christiana Inn
Sheraton Suites Wilmington Downtown
3.5 star property
8.2 out of 10, Very good, 1,000 reviews
"Location."
The price is €139
includes taxes & fees
14 Jul - 15 Jul
Sheraton Suites Wilmington Downtown
Brandywine Plaza Hotel
3.5 star property
7.6 out of 10, Good, 1,005 reviews
"Convenient location. friendly staffs. "
The price is €93
includes taxes & fees
1 Jul - 2 Jul
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, apart-hotels, 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 favorite 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 depends 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 €173 per night. Entering your travel dates in the search wizard you might find 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?

Waterfront house with amazing views. Top of the Chesapeake: This holiday home rental outside of Bear is located on the beach, and has a fireplace, a balcony and a BBQ 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. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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, 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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