Woolford Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Woolford holiday rentals

A grassy area with a wooden dock extending into a calm body of water, surrounded by trees and greenery.

1. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (69 reviews)
"Excellent stay! Just as described! Very quiet, private location."
United States
Mills Family A.
The price is AU$367
includes taxes & fees
10 Nov - 11 Nov
Waterfront Getaway with Dock
A waterfront view with a pier extending into the water, a bridge in the background, and a clear sky.

2. Cambridge Apt in Walkable Neighborhood

Cambridge Apt in Walkable Neighborhood
3.0 star property
Cambridge
10.0 out of 10, Exceptional, (1 review)
"This apt was built in the 50’s, or back when fewer outlets were needed, and it has window air conditioners. It was just what we were looking for as we visited the ste for family reunions"
United States
LOIS
The price is AU$470
includes taxes & fees
14 Nov - 15 Nov
Cambridge Apt in Walkable Neighborhood
A brick building with a white porch and a well-maintained lawn.

3. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.4 out of 10, Exceptional, (26 reviews)
"Pet friendly!"
United States
Mary Beth S.
The price is AU$530
includes taxes & fees
30 Nov - 1 Dec
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

4. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (40 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is AU$350
includes taxes & fees
16 Nov - 17 Nov
Sailwinds Loft at Cambridge Creek
A living room with two grey sofas, a coffee table, and a ceiling fan.

5. Cambridge Apt in Walkable Neighborhood

Cambridge Apt in Walkable Neighborhood
Cambridge
8.0 out of 10, Very good, (4 reviews)
"great location."
United States
Anonymous traveller
The price is AU$451
includes taxes & fees
14 Nov - 15 Nov
Cambridge Apt in Walkable Neighborhood
A living room with a dark gray sofa, a small round table, and a green throw blanket. There is a brick accent wall and a ceiling fan.

6. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Downtown Cambridge
9.8 out of 10, Exceptional, (15 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is AU$542
includes taxes & fees
1 Dec - 2 Dec
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
A lakeside view from a deck with a wooden railing, a sandy area with a boat, and a dock extending into the water.

7. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.
Cambridge
The price is AU$373
includes taxes & fees
10 Nov - 11 Nov
2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.
A marina with boats docked, a water tower, and residential buildings with balconies.

8. Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym

Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym
Cambridge
10.0 out of 10, Exceptional, (2 reviews)
"We only stayed one night but wouldn't hesitate to come back and stay for a few days. Beautiful home overlooking the docks."
United States
mike
The price is AU$709
includes taxes & fees
10 Nov - 11 Nov
Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym
A dining area with a round table, chairs, and a decorative table runner.

9. More, than just a place to sleep - welcome home!

More, than just a place to sleep - welcome home!
Cambridge
The price is AU$560
includes taxes & fees
11 Nov - 12 Nov
More, than just a place to sleep - welcome home!
A wooden interior with a dining area, sofas, and a table.

10. WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Cambridge
9.0 out of 10, Wonderful, (15 reviews)
"Very spacious home. 4 bedrooms and 4 baths. Great basement for watching TV with a large group. Home is about 15 minutes from downtown Cambridge."
United States
Anonymous traveller
The price is AU$686
includes taxes & fees
10 Nov - 11 Nov
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

11. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (17 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is AU$714
includes taxes & fees
1 Dec - 2 Dec
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A triangular cabin with a wooden staircase leading to a door, surrounded by trees.

12. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (68 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is AU$424
includes taxes & fees
10 Nov - 11 Nov
Soul Oasis - home on the Chesapeake Bay
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

13. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Saint Leonard
10.0 out of 10, Exceptional, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is AU$417
includes taxes & fees
16 Nov - 17 Nov
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A house with a large lawn and a dock extending into a calm lake.

14. Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Fishing Creek
10.0 out of 10, Exceptional, (11 reviews)
"Peggy and Gary are the perfect hosts: welcoming, friendly, attentive and respectful of your preferences. Wonderful views of the Bay and River via the lodge -- including the cupola -- and walking around the majestic property."
United States
Thomas S.
The price is AU$452
includes taxes & fees
10 Nov - 11 Nov
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Downstairs living Space

15. Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Very clean and nice property"
United States
Ben W.
The price is AU$559
includes taxes & fees
2 Dec - 3 Dec
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
A house with a large lawn and a dock extending into a calm lake.

16. Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Fishing Creek
10.0 out of 10, Exceptional, (1 review)
"We stayed Sunday - Wednesday at Riverside Lodge. The Lodge was beautiful. Breakfast was absolutely fantastic and Hooper Island was breath taking. We were able to take a boat ride to tour around the island and grad a little history and enjoy the stories. If you looking for a place to relax and renew... this is the place. "
United States
Robin E.
The price is AU$409
includes taxes & fees
10 Nov - 11 Nov
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
A pathway lined with trees and lights leading to a wooden building with a visible window.

17. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lusby
9.8 out of 10, Exceptional, (16 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveller
The price is AU$1,175
includes taxes & fees
10 Nov - 11 Nov
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Living area

18. EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places

EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
Easton
10.0 out of 10, Exceptional, (1 review)
"Fabulous location in town location! It was much larger than we expected - 2 levels. Nice open layout on the main level with 2 BR/BA and a 3rd BR/BA on 2nd floor. Owners are very responsive before and during the trip. We could not connect to the TV, but owner quickly offered assistance. Bathrooms can use some towel racks and shelves. Beds/pillows were comfy! We were very happy with our stay."
United States
Lynn G.
The price is AU$579
includes taxes & fees
16 Nov - 17 Nov
EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
A spacious cabin interior with a wooden ceiling, a kitchen area, a living room with a sofa and a dining table, and a large window providing natural light.

19. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"Very much enjoyed our stay. The host was very kind and responsive and the property very comfortable. Hot tub and quiet location were great!"
United States
Tanya S.
The price is AU$1,563
includes taxes & fees
10 Nov - 11 Nov
Lakefront Cabin Near Solomons Island w/ Hot Tub
A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

20. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Lusby
10.0 out of 10, Exceptional, (4 reviews)
"Dude. This is what I always hope a rental property will be. Comfy beds, best stocked kitchen, working hot tub, beautiful waterfront area with kayaks and a dock. And our mini golden doodle could come too?! It was absolute perfection."
United States
Dani B.
The price is AU$1,347
includes taxes & fees
10 Nov - 11 Nov
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
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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Find holiday rentals that suit your style

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Top Woolford Hotel Reviews

A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.
St Michaels Inn

St Michaels Inn

St Michaels Inn
St. Michaels

10/10 Excellent

Good
Australia
Ashish
Reviewed November 10, 2025
St Michaels Inn

Find out more about Woolford

Everything you need to know about Woolford 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 Woolford 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 Woolford holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Woolford holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Woolford 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 Woolford holiday rentals we have selected for you start as low as AU$349 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Woolford rentals

At Expedia, we put the best Woolford 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 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 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 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 holiday rental in Woolford?

Yes, there are holiday rentals close to the most popular sights in Woolford, or you can select a more secluded option if you're looking for a relaxing stay.

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

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks: This highly rated holiday home rental in Woolford is located in a rural location, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Woolford?

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

What can I see and do in Woolford?

Blackwater National Wildlife Refuge and Woods Island are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Harriet Tubman Underground Railroad National Historical Park and Harriet Tubman Museum and Educational Center.

What’s a holiday rental in Woolford like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Woolford. Holiday rentals provide amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.