Woodbury Vacations from $193

Book a Hotel + Flight or Car together to unlock savings

Your Woodbury Vacation

Reserving a tailor-made Woodbury vacation package is an excellent way to get to know this neighborhood. From its well-known places to its lesser-known treasures, you'll be sure to uncover something new. Eager to sightsee? Nancy Lopez Legacy Golf & Country Club and Glenview Champions Country Club are top nearby attractions to check out during your trip to Woodbury. Expedia will help you turn your dream Woodbury vacation into reality, no matter your travel plans or budget.

The Latest Woodbury Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $584, price is now $193 per person
$193
per person
Jan 17 - Jan 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.2/10 Very Good! (5,145 reviews)
The beauty inside and out

Reviewed on Dec 3, 2025

Residence Inn by Marriott Daytona Beach Oceanfront

Residence Inn by Marriott Daytona Beach Oceanfront

3 out of 5
Price was $1,463, price is now $605 per person
$605
per person
Jan 27 - Feb 3
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
The outside of the building could use some tlc but inside was clean and updated. Staff was attentive, polite, & helpful. Breakfast was surprisingly better than I anticipated with hot options outside of the traditional continental options. Furniture around pool was pressure washed every morning and plentiful. There are no seating options for the beach however we would definitely stay here again.

Reviewed on Nov 30, 2025

Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Price was $596, price is now $266 per person
$266
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9.2/10 Wonderful! (2,232 reviews)
Visited the Florida Black Friday weekend. The proximity to the Florida mall makes it a great location for shopping. This is a huge mall with a large assortment of shops. We were impressed with the cleanliness in the hotel and the mall. Our room was clean and quiet. The bed was very comfortable. Crickets restaurant is in the hotel. They have a good assortment of meal and drink options. The waiters were very accommodating and attentive. The sun shone the afternoon we were there so we enjoyed the beautiful outdoor pool and hot tub. We would definitely stay at the Florida hotel again in the future.

Reviewed on Dec 3, 2025

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $1,770, price is now $837 per person
$837
per person
Jan 7 - Jan 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (500 reviews)
No Beach view but beach is an10m walk so not too bad. Beach chairs falling apart. The pools and tiki bar were awesome. The two room suite was okay and for the most part pretty clean. But there were some dead bugs which is not what I expected for the price point.

Reviewed on Nov 6, 2025

Mi Casa Hotel

Mi Casa Hotel

2.5 out of 5
Price was $892, price is now $427 per person
$427
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
6/10 (1,003 reviews)
It was awesome and their Pizza is excellent

Reviewed on Dec 2, 2025

Where to stay in Woodbury

Find the best Woodbury areas and neighborhoods for the activities you enjoy most. Learn more about Woodbury
Default Image

Lake Sumter Landing

1 out of top 10 points of interest in this area
4.5/5(30 area reviews)

Though Lake Sumter Landing might not have many top sights, you can venture to the surrounding area to see attractions like The Villages Market Square and Cane Garden Country Club.

Find hotels in Lake Sumter Landing

Woodbury Hotel Deals

Equus Inn Ocala

Equus Inn Ocala

2.5 out of 5
3434 Sw College Rd Ocala FL
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $90 total per night from Dec 7 to Dec 8
$90 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (1,738 reviews)
The room was spotless, Free Breakfast was amazing, heated pool!

Reviewed on Dec 1, 2025

Equus Inn Ocala
The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
$129 nightly
The price is $138 total per night from Dec 11 to Dec 12
$138 total
Dec 11 - Dec 12
Total with taxes and fees
9/10 Wonderful! (1,273 reviews)
Great hotel

Reviewed on Dec 1, 2025

The Waterfront Inn
Microtel Inn & Suites by Wyndham Leesburg/Mt Dora

Microtel Inn & Suites by Wyndham Leesburg/Mt Dora

2 out of 5
9700 Us Highway 441 Leesburg FL
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $80 total per night from Dec 9 to Dec 10
$80 total
Dec 9 - Dec 10
Total with taxes and fees
8.4/10 Very Good! (1,000 reviews)
Excellent budget friendly hotel!! I can't say enough good things about our stay here! The room was clean and super comfortable and quiet. I slept so well! The staff was friendly and nice and we had all the little things that make a difference like good shampoo/conditioner/body wash bottles in the ...

Reviewed on Dec 1, 2025

Microtel Inn & Suites by Wyndham Leesburg/Mt Dora
See all 2,361 properties in Woodbury
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Woodbury

The Villages Market Square

4.5/5(174 reviews)

You can enjoy retail therapy at The Villages Market Square during your visit to The Villages. Wander the lakeside in this quaint area.

The Villages Market Square

Nancy Lopez Legacy Golf & Country Club

Enjoy a round of golf in The Villages at Nancy Lopez Legacy Golf & Country Club. While in this family-friendly area, you can savor the top-notch restaurants.

Nancy Lopez Legacy Golf & Country Club

Glenview Champions Country Club

Enjoy a round of golf in The Villages at Glenview Champions Country Club. While in this family-friendly area, you can savor the top-notch restaurants.

Glenview Champions Country Club

Things to do

King William, a Gypsy Vanner Horse Stallion

Gypsy Gold Horse Farm Tour

$55
per adult
100% of travellers recommend
Gypsy Gold Horse Farm Tour
See all activities in The Villages
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.