Woolford Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Woolford

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Smart TV, books, printers
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
10.0 out of 10, Exceptional, 5 reviews
"We had a lovely stay at The Blue Heron. We had a retreat scheduled with friends that we had to relocate last minute due to snow in western Maryland. We stumbled upon this listing, and the home was perfect for our needs. Plenty of beds, fully stocked kitchen, several rooms and couches for those who wanted to read, others to play games, and others to watch football playoffs on tv. The best part of the house was the dining room table that could seat up to 18 (?). It was nice to be able to not have...
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Lake
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
9.8 out of 10, Exceptional, 67 reviews
"Wonderful house. Well stocked with supplies. Great open floor plan along with a couple separate spaces on the main floor. Our group had 7 adults and our eight grandchildren six and under. Pool has gated access which was a key feature with all our little ones. The owner provided much info regarding things to do in the area. The bedroom spaces worked out great with our mix. We really enjoyed the crab traps and the dock for fishing. It was mostly casting practice but the kids loved it. We enjoyed...
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Waterfront Getaway with Dock
Fridge, microwave, oven, stovetop
Waterfront Getaway with Dock
10.0 out of 10, Exceptional, 25 reviews
"We loved the proterty! House was set up with pleanty of room for 4 of us. It was clean and comfortable. Out back was very private. Would definitely stay here again. We had a blast!"
The price is CA $300
CA $361 total
includes taxes & fees
Jun 10 - Jun 11
Waterfront Getaway with Dock
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Waterfront Cottage in Beautiful Hoopers Island
Property grounds
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, 54 reviews
"We have stayed at this property twice and love it. Very peaceful, clean, and comfortable."
Waterfront Cottage in Beautiful Hoopers Island
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
3 bedrooms, desk, iron/ironing board, free WiFi
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
10.0 out of 10, Exceptional, 102 reviews
"Loved the house!"
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
The Schultz Estate
Outdoor dining
The Schultz Estate
9.6 out of 10, Exceptional, 5 reviews
"Had a great stay! Beautiful location! House was clean roomy, overall had a great time! The only thing I would say is work on the doors closing. In restrooms."
The Schultz Estate
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, 105 reviews
"This is our third visit. You can’t have a better location! We love St. Michael’s and this historical cottage."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Maryland Vacation Rental w/ Private Pool & Dock
Property grounds
Maryland Vacation Rental w/ Private Pool & Dock
10.0 out of 10, Exceptional, 4 reviews
"Had a great time fishing from the dock while we got out of the city for a weekend."
Maryland Vacation Rental w/ Private Pool & Dock
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Beach
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
10.0 out of 10, Exceptional, 4 reviews
"We were in town for a friends wedding. This was the perfect location as it was right in between the Catholic Church for the nuptial mass and the reception site. This place certainly did not disappoint. There was plenty of space for our large family, the home was well equipped and stocked with the necessary items. It was a relatively short stay, but I wish we had a bit more time and better weather to enjoy the use of kayaks - our one free morning was a bit chilly for us Florida folks, and we had...
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Fridge, microwave, stovetop, dishwasher
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, 4 reviews
"We extremely enjoyed our stay. The house was beautiful, kitchen was well equipped and the view was spectacular, especially with the Eagles that have nested on the 32 acre property. However was disappointed in the fact that the fire places were not in working conditions and rooms should have been number. We enjoy kayaking up and down the bay and taking it all in. I would definitely stay again."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Waterfront House with Dock, Kayaks, & Sailboat!
View from property
Waterfront House with Dock, Kayaks, & Sailboat!
9.4 out of 10, Exceptional, 23 reviews
"The house was nice and the property is spacious. Great views from the dining room table. A little steep heading down to the dock but not terrible. Very private setting, but also only 5 mins away from pretty much anything you could need. Some nice restaurants just across the bridge in Solomons Island. Would love to return in warmer weather to take advantage of the kayaks and water."
Waterfront House with Dock, Kayaks, & Sailboat!
Soul Oasis - home on the Chesapeake Bay
Sun loungers, beach towels
Soul Oasis - home on the Chesapeake Bay
10.0 out of 10, Exceptional, 6 reviews
"Pleasant relaxing time. We were pleased and impress to locate this property"
The price is CA $177
CA $389 total
includes taxes & fees
Jun 11 - Jun 12
Soul Oasis - home on the Chesapeake Bay
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Smart TV, fireplace
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, 29 reviews
"👍👍"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Property grounds
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, 108 reviews
"VRBO link hasn’t enabled me to communicate with property manger/owner as I’m unable to access account via the VRBO link. I’ve re-registered multiple times now."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Property grounds
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
10.0 out of 10, Exceptional, 152 reviews
"Cute, quaint, conveniently located home. Lovely stay!"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, 197 reviews
"We had our boat with us. Split out time between being on the water and going into St Michaels"
Relaxing Waterfront Cottage Near St Michaels, Maryland
Beautiful Waterfront Retreat in Cambridge!
Fridge, microwave, oven, stovetop
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, 16 reviews
"We had a very enjoyable and relaxing stay here for Mother's Day weekend, coming in from DC. The property is in a great spot on the water and is a short ride into town. The house itself is cozy, clean, and welcoming with everything you need (including the crab house out back, which our four year old loved!) Rebecca is a thoughtful and accommodating host, too. She gave us several recommendations for food in the area and we really enjoyed her suggested restaurants in Cambridge and in Easton on the...
The price is CA $398
CA $689 total
includes taxes & fees
Jun 17 - Jun 18
Beautiful Waterfront Retreat in Cambridge!
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
Fridge, microwave, oven, stovetop
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
10.0 out of 10, Exceptional, 31 reviews
"One of the best properties I have stayed at. With all the amenities, you never need to leave the home. We enjoyed the views, the quietness of the area, and the wildlife. We nicknamed two beautiful ducks…Sonny and Cher! The house is very clean, the checkin checkout procedures were very easy. The host communicated all the details plus additional suggestions. We are definitely returning very soon."
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
Waterfront, Pool, Dock, Hot Tub.Stunning Views! A Luxury VIP Vacation Rental
Interior
Waterfront, Pool, Dock, Hot Tub.Stunning Views! A Luxury VIP Vacation Rental
9.2 out of 10, Wonderful, 15 reviews
"We were pleasantly surprised that the house is the end of the small road with several private acres. The layout offered main floor bed/bath for my parents, 2nd floor 3b/3b for my brother and his teens, and an attached garage apartment for my husband and I. The pool was fun and well kept. The dock was protected and allowed us to rent a boat and the guys to fish. The kitchen had everything a gourmet chef could imagine. Our main difficulty was that there was no easy place/way to launch kayaks or...
Waterfront, Pool, Dock, Hot Tub.Stunning Views! A Luxury VIP Vacation Rental
Lakefront Maryland Cabin w/ Fire Pit, Grill & Deck
Beach umbrellas, beach towels
Lakefront Maryland Cabin w/ Fire Pit, Grill & Deck
9.4 out of 10, Exceptional, 9 reviews
"The cabin itself was lovely with a southwestern feel. Very clean when we arrived and met our expectations. The outside space was the best! Even though it was a rainy weekend, we were able to take the kayaks out on the lake during a break in the rain. Unfortunately the weather prohibited us from visiting the beach but the property was close to Solomon's Island where there is plenty of shopping and dining. My only complaint was the mattress in the master bedroom. It felt wore out and we kind of...
Lakefront Maryland Cabin w/ Fire Pit, Grill & Deck
Don't see what you're looking for?
See all available properties in Woolford
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.

Woolford Vacation Rental Travel Info

Popular accommodation
Woolford private vacation homes
Known landmarks
Great Marsh Park, Choptank River Lighthouse and Long Wharf Park
International airport
Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)

Other types of properties in Woolford you may be interested in

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Lake
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
9.8 out of 10, Exceptional, 67 reviews
"Wonderful house. Well stocked with supplies. Great open floor plan along with a couple separate spaces on the main floor. Our group had 7 adults and our eight grandchildren six and under. Pool has gated access which was a key feature with all our little ones. The owner provided much info regarding things to do in the area. The bedroom spaces worked out great with our mix. We really enjoyed the crab traps and the dock for fishing. It was mostly casting practice but the kids loved it. We enjoyed...
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Hyatt Regency Chesapeake Bay
Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers
Hyatt Regency Chesapeake Bay
4.0 star property
8.8 out of 10, Excellent, 1,009 reviews
"It's the second time I've gone and I love it! What I like most is that they close the jacuzzi very late sometimes until 3 am!"
The price is CA $290
CA $387 total
includes taxes & fees
Jun 6 - Jun 7
Hyatt Regency Chesapeake Bay
St Michaels Inn
Front of property
St Michaels Inn
2.5 star property
8.2 out of 10, Very good, 1,004 reviews
"Toilet seat was pealing. Bathroom floor needed a scrub."
The price is CA $188
CA $206 total
includes taxes & fees
Jun 24 - Jun 25
St Michaels Inn
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 Woolford vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Woolford vacation rental for you. At Expedia, you can take your pick from private vacation 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 Woolford vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Woolford vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Woolford. 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 Woolford vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Woolford vacation rentals we have selected for you start as low as CA $177 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Woolford rentals

At Expedia, we put the best Woolford vacation 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 Woolford 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 Woolford vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Woolford. 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

Can I find a vacation rental in Woolford?

Yes, we offer vacation rentals near well known sights in Woolford, or you can choose a more secluded option if you're looking for a relaxing stay.

What's the top vacation rental in Woolford?

Bay view from Calvert Cliffs, Solomons Island & State Park nearby: You might like this vacation home rental near Woolford. It is located on a lake and has a fireplace, a patio, and air-conditioning 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 you can cook with friends or family.

How many vacation rentals will I find in Woolford?

With 6 Expedia vacation rentals, you're sure to find just the right place for your Woolford stay.

What can I see and do in Woolford?

While exploring the area, visit family-friendly sights like Richardson Maritime Museum, or get outside and enjoy nature at Blackwater National Wildlife Refuge. In the larger area, you’ll find Harriet Tubman Underground Railroad National Historical Park and Harriet Tubman Museum and Educational Center.

What’s a vacation rental in Woolford like?

A vacation rental is a private property where you can stay for a couple of days or more in Woolford. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for a family getaway.

Recent reviews of Woolford properties
Expedia verified reviews

The Tilghman Island Inn

The Tilghman Island Inn

5/5 Excellent
"Really nice Inn. The staff wad super friendly and accommodating. The view from the property is fantastic and the whole experience is very calming and relaxing."
A verified traveller from Washington stayed at The Tilghman Island Inn
Posted 2 days ago
The Tilghman Island Inn