Hot Winter Garden Cottage Rates

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Cottages in Winter Garden

Orlando Lakefront Tiny House Community

Orlando Lakefront Tiny House Community

4.5 out of 5
3405 N Orange Blossom Trail, Orlando, FL
The price is AU$249 per night from 9 Apr to 10 Apr
AU$249
per night
9 Apr - 10 Apr
When you stay at Orlando Lakefront Tiny House Community in Orlando, you'll be on the waterfront, within a 10-minute drive of Kia Center and Camping World ...
Orlando Lakefront Tiny House Community
High Hedges Cottage  - Close to downtown Mt Dora in quiet neighborhood

High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood

Mt Dora
Located in Mount Dora, this cottage is within a 5-minute drive of Lake Dora and Mount Dora Center for the Arts.
High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood
Private Cottage 10 Minutes To Disney And 15 To Universal!  In- house laundry!!

Private Cottage 10 Minutes To Disney And 15 To Universal! In- house laundry!!

Kissimmee
With a stay at this cottage in Kissimmee, you'll be a 3-minute drive from Old Town and 9 minutes from Walt Disney World® Resort.
Private Cottage 10 Minutes To Disney And 15 To Universal! In- house laundry!!
Save an average of 15% on thousands of hotels when you're signed in
The Hidden Gem Cottage 4 miles from Disney Family Friendly 4 Star RV Park

The Hidden Gem Cottage 4 miles from Disney Family Friendly 4 Star RV Park

Kissimmee
The price is AU$315 per night from 21 Apr to 22 Apr
AU$315
per night
21 Apr - 22 Apr
With a stay at this cottage in Kissimmee, you'll be a 3-minute drive from Old Town and 10 minutes from Walt Disney World® Resort.
The Hidden Gem Cottage 4 miles from Disney Family Friendly 4 Star RV Park
Beautiful, Modern Home W/private Pool! Near WDW

Beautiful, Modern Home W/private Pool! Near WDW

4 out of 5
4825 Dedication Street, Kissimmee, FL
With a stay at this cottage in Kissimmee, you'll be a 5-minute drive from Old Town and 9 minutes from Disney Springs™.
Beautiful, Modern Home W/private Pool! Near WDW
Salty Parrot | 5 mins from Disney!

Salty Parrot | 5 mins from Disney!

Kissimmee
With a stay at this cottage, you'll be centrally located in Kissimmee, within a 10-minute drive of Walt Disney World® Resort and Old Town.
Salty Parrot | 5 mins from Disney!
Quiet 1 bedroom Guest House with pool & WiFi Lake May, Florida

Quiet 1 bedroom Guest House with pool & WiFi Lake May, Florida

Lake Mary
With a stay at this cottage in Lake Mary, you'll be within a 5-minute drive of Lake Mary Farmer's Market and Spring Hammock Preserve.
Quiet 1 bedroom Guest House with pool & WiFi Lake May, Florida
Contemporary Home w/ Hot Tub: 4 Mi to Disney Magic

Contemporary Home w/ Hot Tub: 4 Mi to Disney Magic

Kissimmee
With a stay at this cottage in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club.
Contemporary Home w/ Hot Tub: 4 Mi to Disney Magic
Margaritaville Cottages Orlando

Margaritaville Cottages Orlando

4 out of 5
2975 Castaway Ln, Kissimmee, FL
When you stay at this cottage in Kissimmee, you'll be in a shopping district, a 5-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® ...
Margaritaville Cottages Orlando
Don't see what you're looking for?
See all available properties in Winter Garden
View all properties
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.

Winter Garden Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Winter Garden will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Winter Garden definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Winter Garden, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Winter Garden Cottages essential information

Accommodation
1408 Cottages
Lowest Price
AU$183
Highest Price
AU$413
Popular accommodation
Orlando Lakefront Tiny House Community , High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood, Private Cottage 10 Minutes To Disney And 15 To Universal! In- house laundry!!, The Hidden Gem Cottage 4 miles from Disney Family Friendly 4 Star RV Park, Beautiful, Modern Home W/private Pool! Near WDW, Salty Parrot | 5 mins from Disney!, Quiet 1 bedroom Guest House with pool & WiFi Lake May, Florida, Contemporary Home w/ Hot Tub: 4 Mi to Disney Magic, Margaritaville Cottages Orlando

Top trending hotels in Winter Garden

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
Fully refundableReserve now, pay when you stay
The price is AU$413 per night from 7 Apr to 8 Apr
AU$413
per night
7 Apr - 8 Apr
Located in Four Corners, The Grove Resort & Water Park Orlando is on a lake, a 1-minute drive from Surfari Water Park and 11 minutes from Orange County National ...
The Grove Resort & Water Park Orlando
Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

3 out of 5
341 Flagler Ave, Winter Garden, FL
Fully refundableReserve now, pay when you stay
The price is AU$194 per night from 8 Apr to 9 Apr
AU$194
per night
8 Apr - 9 Apr
With a stay at Home2 Suites by Hilton Orlando at Flamingo Crossings in Winter Garden (Bay Lake), you'll be within a 15-minute drive of Walt Disney World® Resort ...
Home2 Suites by Hilton Orlando at Flamingo Crossings
Liki Tiki Village

Liki Tiki Village

3.5 out of 5
17777 Bali Blvd, Winter Garden, FL
Fully refundableReserve now, pay when you stay
The price is AU$183 per night from 16 Apr to 17 Apr
AU$183
per night
16 Apr - 17 Apr
Located in Four Corners, Liki Tiki Village is within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club.
Liki Tiki Village
Save an average of 15% on thousands of hotels when you're signed in
Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings

3 out of 5
411 Flagler Ave, Winter Garden, FL
Fully refundableReserve now, pay when you stay
The price is AU$219 per night from 8 Apr to 9 Apr
AU$219
per night
8 Apr - 9 Apr
With a stay at Homewood Suites by Hilton Orlando at Flamingo Crossings in Winter Garden (Bay Lake), you'll be within a 15-minute drive of Walt Disney World® ...
Homewood Suites by Hilton Orlando at Flamingo Crossings
Don't see what you're looking for?
See all available properties in Winter Garden
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.