Winter Park Villas - Vacation Rentals in Heritage Square
House
10.0
(
34 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1500 ft²
-
Parking -
Balcony/Terrace -
Kitchen -
Air Conditioner
US $220
/Night
7 Nights - $1,541
House
10.0
(
1 Review
)
3 Bedrooms
3 Bathrooms
6 Guests
1625.35 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $263
/Night
7 Nights - $1,841
US $111
/Night
7 Nights - $775
House
10.0
(
17 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $208
/Night
7 Nights - $1,454
House
9.7
(
3 Reviews
)
2 Bedrooms
2 Bathrooms
10 Guests
1087.15 ft²
-
Balcony/Terrace
-
Air Conditioner
-
Internet
-
Pet Friendly
US $283
/Night
7 Nights - $1,981
House
10.0
(
14 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $301
/Night
7 Nights - $2,104
House
9.3
(
3 Reviews
)
3 Bedrooms
1 Bathroom
7 Guests
1011.81 ft²
-
Skiing -
Balcony/Terrace
-
Restaurant -
Bedding/Linens
US $262
/Night
7 Nights - $1,834
Cabin
10.0
(
12 Reviews
)
6 Bedrooms
6 Bathrooms
20 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $481
/Night
7 Nights - $3,367
House
10.0
(
11 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Hot Tub -
Air Conditioner
-
Internet
-
Child Friendly
US $217
/Night
7 Nights - $1,519
House
10.0
(
10 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
2800 ft²
-
Balcony/Terrace
-
View -
Kitchen
-
Internet
US $310
/Night
7 Nights - $2,172
House
10.0
(
8 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
1308 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $351
/Night
7 Nights - $2,460
House
10.0
(
7 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
2400 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $399
/Night
7 Nights - $2,795
House
10.0
(
7 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1036 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $342
/Night
7 Nights - $2,397
Condo
10.0
(
7 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $289
/Night
7 Nights - $2,020
Ski Chalet
10.0
(
5 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
1200 ft²
-
Parking
-
Spa -
Balcony/Terrace
-
Kitchen
US $684
/Night
7 Nights - $4,791
House
10.0
(
5 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
2100 ft²
-
Hot Tub
-
Balcony/Terrace
-
Kitchen
-
Internet
US $623
/Night
7 Nights - $4,358
House
10.0
(
5 Reviews
)
2 Bedrooms
2 Bathrooms
8 Guests
3000 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $338
/Night
7 Nights - $2,366
House
10.0
(
5 Reviews
)
2 Bedrooms
1 Bathroom
3 Guests
-
Balcony/Terrace
-
View
-
Kitchen
-
Air Conditioner
US $192
/Night
7 Nights - $1,341
House
10.0
(
4 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
411 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $307
/Night
7 Nights - $2,148
House
10.0
(
3 Reviews
)
4 Bedrooms
2 Bathrooms
11 Guests
2400 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $687
/Night
7 Nights - $4,811
House
10.0
(
3 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1393 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $401
/Night
7 Nights - $2,808
House
10.0
(
3 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
536 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $394
/Night
7 Nights - $2,759
Condo
10.0
(
3 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
980 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $343
/Night
7 Nights - $2,401
New
House
10.0
(
3 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1543 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $340
/Night
7 Nights - $2,378
★ Pro Tip: Winterparkvillas makes it easy to compare the best listings on Winterparkvillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Winterparkvillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Heritage Square.
Weather in Heritage Square
View the weather forecast for Heritage Square before booking your Heritage Square Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Heritage Square Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Heritage Square?
There are a lot of options in Heritage Square. If you plan on staying in the Heritage Square area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Heritage Square:
- Cheerful Newly remodeled 3-bedroom farmhouse
- Cozy little cabin in the heart of Hells Canyon, with boat parking.
- Family friendly Bowling Alley booking!
- Exclusive Mountain Grandeur! Back door to the Seven Devils Mountain range
- House right on Pine Creek, only one mile from the Snake.
- Wallowa River House Retreat
- Riverview | Riverfront Wallowa Lake Retreat
- House on the Hill
- Chimney Lake on the River at Wallowa Lake
- Upper Lewis Lodge Condo at Wallowa Lake
How many vacation rentals are available in Heritage Square?
Currently, the total number of properties listed in 2026 is over 194 in the Heritage Square area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Heritage Square.
