Find a Bed and Breakfast in Deep Hole from CA $285

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Check prices for these dates

Next weekend
Apr 11 - Apr 13
In two weeks
Apr 18 - Apr 20
In one month
May 2 - May 4
In two months
May 30 - Jun 1

Browse Select Deep Hole B&B

Garden and Sea Inn
Front of property

Garden and Sea Inn

3.5 star property
9.6 out of 10, Exceptional, (25)
" Nice place, owner genuinely nice. Had a really great breakfast, served in our room each morning, interesting area, all and all great long weekend getaway- recommended. Place just needs an ice machine. "
The price is CA $285
CA $314 total
includes taxes & fees
Apr 1 - Apr 2
Garden and Sea Inn
Chanceford Hall Bed & Breakfast - The Chadwick
Outdoor pool

Chanceford Hall Bed & Breakfast - The Chadwick

10.0 out of 10, Exceptional, (4)
"Perfect location for our stay (2 adults) while we were touring nearby locations. Place was in clean and top condition and building has great touch of history. Owners are super nice and we felt very welcomed. After the first day of breakfast we felt we were part of their family. Breakfast: Top of the line breakfast which included 4 courses and met all our dietary needs (my spouse is gluten free and vegetarian). Bedroom comfort: comfortable/clean and had all needed amenities (extra pillows,...
Chanceford Hall Bed & Breakfast - The Chadwick
River House Inn Bed & Breakfast
Building design

River House Inn Bed & Breakfast

3.0 star property
9.8 out of 10, Exceptional, (17)
"Beautiful & scenic views, pool was refreshing, Complimentary wine was unexpected, Dwayne was helpful & breakfast was delicious & made to order by Rick! Food & fun within walking distance and just a short drive to other sites. Some basic updates & repairs needed on the property but that’s expected for the age of the house. We’ll be back!"
River House Inn Bed & Breakfast
Chanceford Hall Bed & Breakfast - The Conway
Outdoor pool

Chanceford Hall Bed & Breakfast - The Conway

10.0 out of 10, Exceptional, (7)
"Character "
Chanceford Hall Bed & Breakfast - The Conway
Chanceford Hall Bed & Breakfast
Grand Room, 1 King Bed

Chanceford Hall Bed & Breakfast

3.0 star property
10.0 out of 10, Exceptional, (3)
"A great experience! The home is historical, the owners are a delight, it was very clean and the food was delicious!!!! Highly recommend "
Chanceford Hall Bed & Breakfast
Chanceford Hall Bed & Breakfast - The Chanceford
Outdoor pool, a lap pool

Chanceford Hall Bed & Breakfast - The Chanceford

10.0 out of 10, Exceptional, (3)
"We thoroughly enjoyed ourv stay at Chanceford. The historic house is absolutely beautiful and Shae was an amazing host. The room was spotless and every detail was thought of. And the breakfasts! Oh my. Delicious 3-course breakfast that were different and delicious each day. We will stay again. "
Chanceford Hall Bed & Breakfast - The Chanceford
Chanceford Hall Bed & Breakfast - The Cliveden
Outdoor pool

Chanceford Hall Bed & Breakfast - The Cliveden

10.0 out of 10, Exceptional, (2)
"Very nice Bed and Breakfast. Well appointed. The hostess was fantastic and the breakfast was to die for"
Chanceford Hall Bed & Breakfast - The Cliveden
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 property types in Deep Hole

Oyster Bay Hideaway on Chincoteague Island!
Fridge, microwave, oven, stovetop

Oyster Bay Hideaway on Chincoteague Island!

10.0 out of 10, Exceptional, (8)
"It was great!"
Oyster Bay Hideaway on Chincoteague Island!
Sunrise Shore - Waterfront; Private pool & hot tub!
Fridge, microwave, oven, stovetop

Sunrise Shore - Waterfront; Private pool & hot tub!

8.8 out of 10, Excellent, (32)
"Our family had a wonderful stay at Sunrise Shore. The house had a great location with beautiful views. The kitchen was well appointed and met all of needs. Our children really enjoyed the hot tub. There was plenty of room for our family of five. We hope to return someday soon!"
Sunrise Shore - Waterfront; Private pool & hot tub!
Waterfowl Watch Chincoteague Island Great Rates Quiet area, 2 night stays, bikes
Miscellaneous

Waterfowl Watch Chincoteague Island Great Rates Quiet area, 2 night stays, bikes

10.0 out of 10, Exceptional, (11)
"Cozy and clean cottage with all the amenities. Close to everything!"
Waterfowl Watch Chincoteague Island Great Rates Quiet area, 2 night stays, bikes
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

Searching for B&Bs in Deep Hole?
Whether you’re on a romantic trip and want to stay somewhere quiet and intimate, or you’re traveling solo and hoping to make some connections, B&Bs can be a great choice for many types of vacationers. When you want to explore some of the destination’s attractions, Oyster Bay is worth a visit.
How do you know if a B&B is the best choice for your stay?
Every B&B has a unique charm. Whether it’s a garden for guests to admire or a sunlit breakfast nook to enjoy your morning cup of coffee, the tiny details are what make bed and breakfasts a home away from home.
What are the top B&Bs in Deep Hole?
Here are some well-liked B&Bs in the surrounding area: Garden and Sea Inn: 4 rooms. 10.2 mi (16.4 km) from the heart of Deep Hole. Enjoy the free full breakfast and designer toiletries. Chanceford Hall Bed & Breakfast - The Chadwick: 16.4 mi (26.4 km) from the downtown core. Enjoy the arcade game room and in-room fireplace. River House Inn Bed & Breakfast: 8 rooms. Situated 16.7 mi (26.9 km) from the heart of Deep Hole. Enjoy the free cooked breakfast and outdoor pool. Chanceford Hall Bed & Breakfast - The Conway: 16.4 mi (26.4 km) from the heart of downtown. Enjoy the in-room pools and in-room fireplace. Chanceford Hall Bed & Breakfast: 4 rooms. Located 16.4 mi (26.4 km) from the core of Deep Hole.
What's the best time of year to book my B&B in Deep Hole?
When you’re planning your escape to Deep Hole, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 43°F. Average annual precipitation for Deep Hole is 48 inches.
What is there to do in Deep Hole?
When you want to explore some things to do in Deep Hole, consider a visit to Oyster Bay. You might also consider a trip to sites like Captain Timothy Hill House or Maui Jack’s Waterpark if you have time to see more of the area.
How can I get to and around Deep Hole?
Mapping out your trip in and around Deep Hole is easy with these transportation options. Fly into Ocean City, MD (OCE-Ocean City Municipal), which is located 28.7 mi (46.2 km) away from the city center. Otherwise, you can search for flights to Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional), which is 29.4 mi (47.3 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.