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Vacation rentals in Bear

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Top-rated vacation rentals in Bear

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Villa in Paradise

4.98 out of 5 average rating, 124 reviews

Hilltop Mansion: Farm Views+HotTub+Pool+GameRoom.

This gorgeous home is located at the very top of a hill in one of the most central locations in Lancaster County. You'll be surrounded by breathtaking views of the nearby farmland and the interior has been beautifully decorated in calming, neutral tones. No amenity has been spared for your stay some of which include a spacious master suite, stunning kitchen, Nespresso machine, large game room, a kid's toy room, a firepit, yard games and a patio with outdoor seating, a hot tub, pool and a grill.

Home in Paradise

4.92 out of 5 average rating, 217 reviews

Vacation Home in Paradise, Lancaster County PA!

The Vacation Home in Paradise is located in central Lancaster County just a short drive from the most popular Lancaster attractions. We're located just 8 min. from the Sight & Sound Theater, 13 min. from Dutch Wonderland & 10 min. from the village of Bird in Hand. Enjoy watching the Amish buggies roll by this quiet family getaway. There are three bedrooms with queen beds, & one with a full size bed. Three of the bedrooms are on the ground floor & one is in the basement. We also have central AC.

Guesthouse in Christiana

5 out of 5 average rating, 167 reviews

The Loft at Jackson Farm-Your Relaxing Destination

The Loft at Jackson Farm- Come experience the hospitality that so many 5 Star reviews talk about! This luxury loft apartment is your next relaxing getaway! It features spectacular views of Amish farmland. Built with old world craftsmanship, from the field stone walls to the walnut counters. While this property is private and secluded, we are close to many of Lancaster and Chester Counties abundant attractions. Shopping, Hiking, Entertainment, and Restaurants are all in the local area.

Guesthouse in Chesapeake City

5 out of 5 average rating, 161 reviews

High-End Cottage, Water View, Chesapeake City, MD

"Fairwinds Cottage" is a newly renovated coastal themed guest cottage with a water view on the quiet side of the canal in Chesapeake City, Maryland. Enjoy watching the ships pass through the canal, take a walk on the beautiful 17-mile Ben Cardin/Mike Castle Recreational Trail just steps from the house. Walk to Schaefer's Canal House for their amazing crab cakes and libations. Stay with us and learn why Chesapeake City was voted the #1 most charming town in Maryland in 2018.

Townhouse in Havre de Grace

4.99 out of 5 average rating, 152 reviews

Historic Victorian just a block from the water!

*If you are in need of additional bedrooms or just more space, inquire about adding our 2Br/1Ba first floor unit to your rental* Welcome to Millard’s Rest! While retaining much of the original Victorian millwork and architecture, contemporary conveniences make this home a comfortable retreat for guests of all ages. Whether in town for a wedding, business trip, sports tournament, or just some R&R - "Millard's Rest" is a conveniently located home away from home!

Rental unit in Gordonville

4.93 out of 5 average rating, 484 reviews

“Buy the ticket, take the ride” - Luxury retreat

Welcome to an inspirational and relaxing getaway in the heart of Amish country. My goal was to create a relaxing and comfortable space that reflected my love of travel and design. I’ve included some of my personal style along with an aesthetic that matches the heritage of Lancaster. I’ve included artwork and many books that reflect some of my favorite places from around the world. I truly hope that you enjoy your stay and leave feeling rested and inspired.

Home in Elkton

4.83 out of 5 average rating, 341 reviews

Cozy Cottage Elkton North East 3bed 2 bath Patio

Hacienda on the Hill! Perfect country & city location! Close to North East activities, fishing tournaments & shows. Newark & UofDE(20min). Sandy Cove & North Bay(20 min). Quiet, end of gravel road location. Offering 3 bedrooms 2 full baths & stocked kitchen. Backyard patio t w/seating, & fire pit. The best part, just 1 mile to quaint downtown North East with free parking!! 1 mile from seafood, mexican, steak house, coffee shops, grocer, convenience store etc.

Rental unit in Bryn Mawr

4.93 out of 5 average rating, 238 reviews

+Restaurants Coffee Colleges+ Bryn Mawr Has It All

Welcome to Bryn Mawr, Pennsylvania! This comfortable 2nd floor apartment layout is cozy whether you are by yourself or in town with a large family of 8. It has an eat in kitchen for enjoying takeout or preparing a meal yourself. Each bedroom comfortably fits 2 people for sleeping, and the living room sofa doubles as a pull out couch. With ROKU on the TV you have an instant entertainment center. Wake up to free hot coffee prepared in the Keurig coffee maker.

Home in Gap

4.91 out of 5 average rating, 117 reviews

Dream View

Welcome to our beautiful 3 bedroom,2 bath home with an attached 1 bedroom,1 bath apartment that’s perfect for families or groups who value privacy and convenience. Enjoy breathtaking views of the picturesque surroundings right from the comfort of your home or bask in the serene atmosphere of the big backyard where you will possibly see wildlife. The hot tub is an added bonus,perfect for a relaxing evening under the stars.

Home in Gordonville

4.93 out of 5 average rating, 142 reviews

Prime Location:Spacious Renovated Gordonville Home

This home is all about location! Located on a quiet back road surrounded by Amish farms and fields, but just off of Route 30 which means you'll be close to endless shopping, restaurants, and attractions. It's decorated in a warm, cozy style with plenty of neutrals which makes it the perfect place to relax after a long day of exploring. In the summer, you be able to enjoy a large backyard and back porch area as well.

Guest suite in Darlington

4.97 out of 5 average rating, 275 reviews

Syd Acres

Unplugged retreat. Great for birders, piano players, gardening fans, antiquers. Twenty minutes from historic Havre de Grace. Nearby gardens include: Longwood Gardens; Chanticleer Garden; Winterthur Museum, Garden, and Library; and LaDew Topiary Gardens. Small kitchen with microwave, sink, fridge, and coffee maker. Private entrance. Smoke detectors, hair dryer. No WiFi. No stove.

Cottage in Port Deposit

4.93 out of 5 average rating, 216 reviews

The River Cottage

Take it easy in this unique cottage built in the 1800s nestled upon the Granite Cliffs of Port Deposit Maryland. While enjoying your tranquil get away you’re minutes from local shops, local dining, local wineries, local breweries and a local marina. There is plenty of sightseeing and wildlife. If you enjoy fishing and kayaking it’s just a short distance away.

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Popular amenities for Bear vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Bear

Cabin in North East

4.96 out of 5 average rating, 165 reviews

Waterfront Cabin on the Chesapeake

Home in Elkton

4.92 out of 5 average rating, 52 reviews

Waterfront Sunset River Cottage -perfect getaway

Townhouse in Elkton

4.91 out of 5 average rating, 56 reviews

Bright and airy townhome with outdoor seating

Home in North East

5 out of 5 average rating, 38 reviews

Boho River Cottage

Farm stay in Christiana

4.96 out of 5 average rating, 223 reviews

See Wild Deer From The Front Porch! *With Hot-Tub*

Home in Quarryville

4.85 out of 5 average rating, 428 reviews

Camargo Inn - Farm Stay Feel

Farm stay in Atglen

4.95 out of 5 average rating, 338 reviews

Lavender Farm Retreat.Home of Peace an Relaxation.

Home in Gordonville

4.91 out of 5 average rating, 118 reviews

The BREEO House: An Outdoor Living Experience.

Quick stats about vacation rentals in Bear

Total rentals
30 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
630 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi

Frequently Asked Questions

How much does it cost to stay in house rentals in Bear?
Experience the best of Bear with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Bear?
Bear has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Where should I stay in Bear?
Make yourself at home in Bear by choosing from our most frequently booked neighborhoods. We have over 70 vacation rentals in Becks Woods, and over 70 vacation rentals in Glendale.
Are there vacation rentals with a dedicated workspace in Bear?
Yes! Work meets play with ease at over 10 vacation rentals in Bear featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore