Holiday Rentals in Woolford

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Check prices for these dates

Our top choices for Woolford holiday rentals

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 €258
includes taxes & fees
16 Nov - 17 Nov
Waterfront Getaway with Dock

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 €293
includes taxes & fees
16 Nov - 17 Nov
Cambridge Apt in Walkable Neighborhood

3. 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 €276
includes taxes & fees
28 Nov - 29 Nov
Cambridge Apt in Walkable Neighborhood

4. 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 €332
includes taxes & fees
15 Dec - 16 Dec
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

5. 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 €221
includes taxes & fees
16 Nov - 17 Nov
Sailwinds Loft at Cambridge Creek

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 €328
includes taxes & fees
15 Dec - 16 Dec
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

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 €226
includes taxes & fees
28 Nov - 29 Nov
2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

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 €517
includes taxes & fees
16 Nov - 17 Nov
Marina Views | 3BR Downtown Townhouse, Heated Decks, Pool & Gym

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

More, than just a place to sleep - welcome home!
Cambridge
The price is €353
includes taxes & fees
16 Nov - 17 Nov
More, than just a place to sleep - welcome home!

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, (16 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 €421
includes taxes & fees
16 Nov - 17 Nov
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

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 €416
includes taxes & fees
19 Nov - 20 Nov
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

12. Lusby 3BD Family Beach House - Steps to the Sand!

Lusby 3BD Family Beach House - Steps to the Sand!
Lusby
The price is €429
includes taxes & fees
17 Nov - 18 Nov
Lusby 3BD Family Beach House - Steps to the Sand!

13. 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 €276
includes taxes & fees
13 Dec - 14 Dec
Soul Oasis - home on the Chesapeake Bay

14. 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, (9 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is €269
includes taxes & fees
16 Nov - 17 Nov
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

15. Covenant Cove - Cove Point Beach

Covenant Cove - Cove Point Beach
Lusby
The price is €388
includes taxes & fees
28 Nov - 29 Nov
Covenant Cove - Cove Point Beach

16. 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 €349
includes taxes & fees
2 Dec - 3 Dec
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

17. 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 €840
includes taxes & fees
17 Nov - 18 Nov
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

18. 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)
"Beautiful home. Great fishing and kayaking."
United States
Alexander B.
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

19. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is €640
includes taxes & fees
22 Nov - 23 Nov
4-BR Waterfront Turret Home

20. 1BR Solomons Island Home with Private Deck

1BR Solomons Island Home with Private Deck
Solomons
The price is €277
includes taxes & fees
13 Dec - 14 Dec
1BR Solomons Island Home with Private Deck
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.

Find holiday rentals that suit your style

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, 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 Woolford holiday rental for you by simply entering your desired dates. Then check your favorite 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 depends 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 €292 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 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.